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  • βœ‡Keep Thrifty
  • 3 Tips for Making Your Freedom Dream a Reality
    Do you think your dreams are unattainable? In addition to 3 Steps To Get Financially Unstuck and 3 Ways To Live With Intention, we have come to realize a few other components that have made a huge difference in turning our dreams into a reality. Change Your Mindset For most of my life I told myself I couldn’t. Everything seemed out of reach or too complicated. Because of this, I didn’t even try to make my dreams a reality. One thing I really wanted to do was paint all the woodwork
     

3 Tips for Making Your Freedom Dream a Reality

19 February 2019 at 11:58

Do you think your dreams are unattainable? In addition to 3 Steps To Get Financially Unstuck and 3 Ways To Live With Intention, we have come to realize a few other components that have made a huge difference in turning our dreams into a reality.

Change Your Mindset

For most of my life I told myself I couldn’t. Everything seemed out of reach or too complicated. Because of this, I didn’t even try to make my dreams a reality. One thing I really wanted to do was paint all the woodwork in our first home white, but I wasn’t the best painter and there was a lot of woodwork. I didn’t even know the right way to go about it anyway.

In 2015 my confidence was at an all time low and my depression at an all time high. I needed to do something for me, to lift me up. I still wanted to paint the woodwork and finally decided to give it a try. I bought primer, paint, tape, and a paintbrush. I turned on the radio and got to work. I had no idea what I was doing, but I was doing it anyway. I figured I would learn along the way.

After two layers of primer and paint I pulled the tape away and found an uneven paint job. Instead of feeling defeated, I grabbed the wall paint to fix the mistakes. Then I noticed that the gaps between the wall and woodwork made it difficult to create an even look. I was determined to figure out how to get the look I wanted. I continued to tweak my approach. Eventually my process looked like this:

  1. Fill gaps between trim and wall with 3M Patch Plus Primer, using baby wipes to smooth the spackle before it dried
  2. Two coats of primer and paint on trim and spackle
  3. Tape woodwork, paint wall color just above the tape
  4. Finally, fix small mistakes with very thin paint brush

It took multiple tries and revisions to get to this point, but in the end I had really crisp lines! In the process I realized I had also changed my mindset from I can’t, to I can try, to I will figure it out!

Allow Yourself To Have A Beginning

Back when I told myself that I couldn’t, I spent a lot of time feeling that I wasn’t talented or financially successful. When I wanted to remodel our first home, I watched Fixer Upper in awe of their talent, knowing I didn’t have any of those skills. When a friend moved to Australia, we wished to visit, but felt we would never be able to save enough money to make it happen (cost $3,000). I truly believed that I was destined to float through life with dreams unfulfilled.

Then I read Capital Gaines and learned that their story didn’t start with a remodeled farmhouse and a TV show. Chip started with fixing up small homes he rented to college students. Joanna started by decorating their first home in various themes. With each small project they took on their knowledge and talent grew. Their first projects were imperfect. They faced roadblocks and struggles on their journey. What we see on TV is the culmination of all those experiences. They had a beginning.

When we wanted to travel to Australia, we had a hard time saving money. We made good money and spent freely in our day to day life. It never dawned on me to change how we spent our income. When we finally took our first family road trip (cost: $3,000) five years later, we didn’t magically have the funds to travel. In fact, our expenses with three kids had increased more than our income had. Instead, we started tracking our spending and tried to decrease our expenses one category at a time. We decreased our grocery bill, followed by spending less on clothes, and then eliminated our auto loan by selling our second vehicle. Accomplishing our dream of being able to save up for travel started with making small changes that led to many road trips, traveling to Hawaii and Costa Rica, and still on the wish list - Australia!

If you have a dream, don’t expect to be able to do it right away. Allow yourself to take small steps that build upon each other. Remember that everything has a beginning. You have to start somewhere to get to the next place.

Create Your Support System

My belief that we couldn’t accomplish our goals came from negative self talk and letting people convince me that we wouldn’t succeed. Creating a strong support system helped stop the negative self talk and build the confidence we needed to move forward.

I needed people in my day to day life that lifted me up. When my husband supported me in remodeling our home, his belief in my skills helped me to persevere. When I found a therapist that understood me, she helped me create the tools I needed to build my confidence and follow our dreams. And when I found friends who love me in the midst of my unconventional dreams, I found strength in following my values.

We’ve also found that reaching out to people who have more knowledge on the things we want to accomplish has helped us move forward. When we researched moving to Costa Rica for 9 months, we connected with a principal of an international school in Uvita who was willing to help us navigate challenges and answer any questions we had. When I decided to design our new home, The Little White Shack, I found a builder who was willing and had the experience to help me bring my vision to life. And when Chris wanted to take this blog to the next level, he reached out to the the personal finance community for support and advice. So many people freely lifted Chris up, including but not limited to: Grant, Jillian, Nick, The Groovys, J. Money, Fritz, Cait, Mystery Money Man, Jim, Jay, and Scott. Creating these support systems took stepping outside our comfort zone, but it was worth it.

We are so grateful to everyone who has supported and believed in us and we want to pay that kindness forward. Chris and I would be happy to be a part of your support system - just reach out!

  • βœ‡Keep Thrifty
  • Our 2019 Spending Plan
    So much has and is changing in our finances this year. Chris is back to having a regular paycheck. We will move out of our apartment this Summer, move into our new house, and be back to having a mortgage. While we aren’t excited about the mortgage, we are thankful to be able to build our dream home, the Little White Shack. We definitely want to pay off our mortgage as soon as possible. I know we will be tempted to take every extra cent and throw it at eliminating this debt. For some peop
     

Our 2019 Spending Plan

26 February 2019 at 11:58

So much has and is changing in our finances this year. Chris is back to having a regular paycheck. We will move out of our apartment this Summer, move into our new house, and be back to having a mortgage. While we aren’t excited about the mortgage, we are thankful to be able to build our dream home, the Little White Shack.

We definitely want to pay off our mortgage as soon as possible. I know we will be tempted to take every extra cent and throw it at eliminating this debt. For some people that is the right decision, but I want to make sure that we don’t neglect our other values, mental sanity, or relationships in the pursuit of debt freedom.

For us, this means contributing to charities we believe in, investing in travel, and spending money hosting dinner with friends. Sure we could postpone these things and pay off our mortgage crazy fast, but it would leave us feeling empty. That’s not what we want.

With those things in mind, we are creating a general spending plan for the year. To help wrap my mind around all the different types of spending that come up throughout the year, I divided each category into one of two groups: needs or wants. And since we have been tracking our spending in Thrifty for over 3 years, it was fairly easy to come up with spending estimates. Here is our plan:

Total planned needs: $52,640. Includes: Healthcare (insurance, bills, medication) - $8,400, Monthly Bills (utilities, rent/mortgage, life insurance) -  $14,600, Quarterly Bills (swim lessons, water bill) - $6,240, Yearly Bills (property tax, tax filing, home/car insurance) - $6,600, Food (all food for simplicity) - $12,000, Hygiene (consumables for wellbeing) - $2,400, and other (gasoline and other necessary spending) - $2,400

Total planned wants: $118,220. Includes: Giving (church and charities we support) - $12,000, Travel (multiple trips planned) - $12,000, Christmas (big spending holiday) - $500, Chores (kids can earn by helping around the house) - $120, Fun (all other non-necessary spending) - $3,600, Little White Shack down payment - $80,000, Little White Shack furnishings - $10,000

This brings our total spending plan to $170,860. This definitely isn’t a normal year for us, mostly because we are building our house. The $90,000 for the Little White Shack has already been saved up, so that won’t affect our bi-weekly paycheck. Along with that, some of our healthcare costs are covered via Chris’s employer ($3,240 healthcare premium) and an HSA account ($2,890 balance remaining as of January 2019). When you take these expenses out of our total, our spending plan is $74,730!

Halfway through the year, we’ll let you know how we are doing! We’ll tell you if we estimated any category wrong, over-spent, under-spent, and where we land on our mortgage!

  • βœ‡Keep Thrifty
  • Why You Should Totally Spend on Wants
    If you read enough personal finance articles, you’re bound to have come across numerous discussions about needs versus wants. If you take the messages at face value, you’ll come away with a sense that the majority of your financial issues come from an inability to minimize your wants. This sage advice comes from all over, whether it be from your favorite personal finance blogger or musicians from the 1990’s. It’s not having what you want It’s wanting what you
     

Why You Should Totally Spend on Wants

5 March 2019 at 11:58

If you read enough personal finance articles, you’re bound to have come across numerous discussions about needs versus wants.

If you take the messages at face value, you’ll come away with a sense that the majority of your financial issues come from an inability to minimize your wants.

This sage advice comes from all over, whether it be from your favorite personal finance blogger or musicians from the 1990’s.

It’s not having what you want
It’s wanting what you’ve got
Sheryl Crow

At the end of the day, most financial “wisdom” these days seems to tell you that wants are bad and you should get rid of those urges altogether.

Live like a caveman and you can retire in 3 years!

While I appreciate the sentiment, I think people often take this too far.

Money is a tool. A tool that is meant to be exchanged for things that are of value.

So, why are wants bad? If your wants are things that align with your values, aren’t they completely worth spending on?

Frivolous Wants

The problem is that unfortunately, for most people, the wants they spend are not in alignment with their values.

It’s the cute, but frivolous, serving tray from the Target Home Decor aisle that they didn’t even know existed until they entered the store.

It’s the awesome new thing on Kickstarter that is such a cool idea (and look awesome!) but solves a problem they don’t really have.

It’s habitual spending on in-app purchases, whether it’s a new outfit for a digital pet or a new gun to kill those pesky zombies.

These purchases are wants in the moment, but aren’t usually an accurate reflection or real values.

How do I know? Because Jaime and I have been there.

We have always wanted to travel. But despite making a decent income, we never seemed to find the money.

Disappointed that we couldn’t afford to travel, we’d blow our money on ice cream treats, carry-out dinners, revolving household decor, and kitchen gadgets.

And, because we blew our money on these, we never had the money to travel.

It was a vicious cycle.

But once we started tracking our spending, everything changed.

We started to see how much we spent on ice cream. How much we spent on carry-out. How much on decor, and how much on gadgets.

And when we saw the totals, it was staggering.

Values-Based Wants

Seeing the big picture of our spending helped us understand the crazy amount of money we were spending on frivolous purchases. When we saw those numbers rolled up, we knew we could shrink our frivolous spending without feeling any real pain.

Cooking six nights a week instead of four would save us hundreds in our food bill.

Cutting Target and Costco out of our shopping altogether would eliminate even more in impulse buys.

And with these thousands of dollars, we could afford to travel. We could afford to increase our charitable giving. We could prepay our mortgage and save for retirement.

Once we were able to look at our spending at a high level, we quickly saw that we had more than enough to spend on our wants - at least the wants that really added value to our lives.

It wasn’t about foregoing wants, it was about prioritizing wants based on our values. (Tweet this )

Over the last three years, we’ve refined this practice year-over-year:

  • In 2016, we spent $104,000 total
  • In 2017, we spent $92,000 total
  • In 2018, we spent $83,000 total
  • In 2019, we’ve budgeted $80,000 (not including our house down payment and initial furnishing)

And all the while, we’ve steadily increased our spending on value-adding wants:

  • In 2016, we spent $4,400 on travel and $6,700 in charity
  • In 2017, we spent $5,300 on travel and $2,750 in charity
  • In 2018, we spent $19,000 on travel and $4,000 in charity
  • In 2019, we’ve budgeted $12,000 for travel and $12,000 for charity

This is the spending that gives us joy. The spending that we feel aligns with our values, and I wouldn’t eliminate this at all. These aren’t bad wants - these are the wants that are most important.

What’s Next

Jaime’s going through the exercise of recategorizing all of our entries in Thrifty into value-based wants, “fun” (aka frivolous wants), and needs.

Once we get through that, We’re going to take a look at how our proportion between these has changed over time and we’ll share the results year.

Without seeing the numbers in front of me, I can tell you that we feel so much better about how we budget and spend today.

Having money carved out for our priorities make me completely comfortable saying “yes” to a last-minute family trip to Nevada. It makes us happy to increase our giving to great causes like The Hope Effect and World Vision.

This process has changed our lives. And I bet it can change yours too.

So, I challenge you.

Track your spending for three months. Measure how much you’re actually spending on those frivolous wants and see what real wants you could afford if you cut the frivolous ones in half.

  • βœ‡Keep Thrifty
  • 5 Lessons From Our Buy Nothing New Challenge
    Back in 2017, we took on the challenge to buy nothing new for a full calendar year. We wanted to break away from the consumerism that surrounds us on a daily basis. Our hope was that if we could get through an entire year of buying nothing new that it would help us become more intentional with our money. We came up with five strategies to help us avoid buying new items: Wear out - don’t replace items until they no longer perform their function Fix - where possible, fix broken/torn
     

5 Lessons From Our Buy Nothing New Challenge

12 March 2019 at 11:58

Back in 2017, we took on the challenge to buy nothing new for a full calendar year. We wanted to break away from the consumerism that surrounds us on a daily basis. Our hope was that if we could get through an entire year of buying nothing new that it would help us become more intentional with our money.

We came up with five strategies to help us avoid buying new items:

  1. Wear out - don’t replace items until they no longer perform their function
  2. Fix - where possible, fix broken/torn items instead of replacing
  3. Repurpose - do we already have something that can fulfill that item’s usage?
  4. Self-provision - can we make it ourselves from other materials?
  5. Buy used - can we find what we need used instead of new

While those strategies were useful, we knew that there were going to be exceptions. Chris and I thought hard and came up with 4 exceptions that we felt were in line with our values:

  • Underwear, Socks, and Shoes
  • Photo prints (school pictures and for our road trip map)
  • Car maintenance parts (we know we need new tires next year)
  • Home remodeling (we needed to wrap up current projects)

Our Experience

Chris and I were really optimistic when we started January 1, 2017. We even stayed within the rules! We did buy new carbon monoxide detectors, which weren’t on the exception list. But it was a safety issue for our family and deemed a necessary new purchase. The following two months we stayed focused and never broke our challenge rules. We went into month four thinking this challenge was going to be easy for our minimalist family.

Then my computer’s power cord finally gave out. We debated buying used, but we had already done that and it had not lasted long. So we broke the challenge for a good cause, buying a brand spanking new mac laptop power cord! It was a justified purchase. But that’s the problem right? Once you make one excuse, a few more follow. I bought one of our kids a costume as a birthday present. I told myself it was an experience, but let’s be honest - it was an item! And either way it was new.

The following month I bought some stainless steel straws. I still love them to this day, but it honestly was an impulse purchase. A week later I found myself having a pity party. My clothes all felt worn and frumpy. I felt worn and frumpy. I had errands to run and decided I would just have a look in one of my favorite shops. I walked out with an $80 summer dress from Title Nine. I felt a little guilty, but I came up with an excuse to justify my expensive buy. This is what I said to Chris when I showed him the dress:

“Our buy nothing new challenge is supposed to help us be more intentional with our spending. I want you to know that I very intentionally bought this dress!” (Tweet this )

I was really proud of myself for that statement! It was also the downfall of our experiment. The second half of the year was full of new purchases. We had multiple issues with buying second hand clothes for the girls. One was that we would later find holes in unfortunate places - so we gave up on buying used pants. I struggled with Sciatica and purchased a stability ball and foam roller to help. They were more or less impulse purchases that I used to delay going to a doctor. I now visit a chiropractor and don’t use those items.

Buying stuff in the second half of the year felt like binging on food after a miserable diet. In the following months we bought a lot of new items. We continued to try avoiding buying new, but our resolve wasn’t as strong. Buying used takes more time and patience (sifting through thrift stores). We were tired and buying new felt easier at times.

Trying to buy nothing new for a full year was tough. We finished the year with 90 new purchased items. This is far above our goal of zero, but the challenge did have an impact on how much new stuff we bought. In 2016 we had purchased 153 new items. We cut that by 40% in 2017. We also learned a few lessons along the way.

5 Lessons From Our Buy Nothing New Challenge

  1. There will be unexpected necessary purchases (carbon monoxide detectors)
  2. You will have a pity party at some point (my $80 dress, that I still love by the way)
  3. Be diligent when you purchase used (holes in pants we didn’t notice before)
  4. Don’t use purchases as solutions (stability ball)
  5. When taking on a new challenge, start small (a full year is a long time, a three month challenge would have been a better first step)

Have you ever taken a buy nothing new challenge? How did it go for you?

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  • The Awesomely Big Features of our Little White Shack
    I’ve been dreaming up different house plans for years. The square feet, number of bedrooms, and layout always varied, but the one thing that remained the same was my desire to create a functional compact home. For us, smaller square feet means a smaller mortgage and less to clean! This frees up financial resources to invest in other things we love to do (travel). It also frees up our time - I would rather spend my Saturday hiking than cleaning bathrooms! Now that we have taken the step t
     

The Awesomely Big Features of our Little White Shack

19 March 2019 at 11:58

I’ve been dreaming up different house plans for years. The square feet, number of bedrooms, and layout always varied, but the one thing that remained the same was my desire to create a functional compact home. For us, smaller square feet means a smaller mortgage and less to clean! This frees up financial resources to invest in other things we love to do (travel). It also frees up our time - I would rather spend my Saturday hiking than cleaning bathrooms!

Now that we have taken the step to build, all those different designs have melded together to become the floor plan below. While my focus has been on creating a small, multi-functional home, there are two areas that I loosened that focus in order to emphasize our values.

  1. The first area we wanted to focus on was our screened-in deck. While we could have kept it small or even delayed building this feature to save money, we dreamed of having a mosquito free outdoor sanctuary where we could relax and spend time with friends and family. So instead of limiting this space, we extended the deck to be 20x10 sq ft.

  2. The other area we extended was the kids’ bedroom. While we know the girls can survive in a 10x10 bedroom space together, I know that their need for privacy is growing. With that in mind, I created a 400 sq. ft. oasis with individual retreats (built in queen beds with shelf, outlet, light, and curtain) and an ensuite bathroom that maximizes privacy with three separate zones (toilet, sinks, shower).

    Note: You may wonder why we opt for a single bedroom instead of individual rooms for our girls: This has been an intentional choice. For Chris and I, the girls sharing a bedroom builds their friendship while also putting them in a situation where they have to learn to respect each other and resolve conflicts. Plus, the giggles we often hear after 7pm melt my heart - I wouldn’t want it any other way!

The remaining areas of the little white shack were designed to provide the biggest bang per square foot. For us, this meant creating multi-functional spaces that work for our family and lifestyle. This is how we made our decisions for each space:

  1. Our minimalist lifestyle shows itself in our kitchen - a small galley that leads to the screened-in deck! There’s little counter space, limited storage, no microwave, and no cooktop range. Chris and I prefer simple meals, stay away from single purpose gadgets, and focus on using up groceries instead of stocking up. We have just enough counter space and storage to match our needs, haven’t used a microwave in years, and are opting to use induction hot plates that can be stored when not in use. It is a kitchen that exactly meets our needs!

  2. We love our long narrow IKEA table and designed our dining space to fit it perfectly. This is where most of our life happens - family dinners, gathering with friends for pizza night, building puzzles, kids art projects, work, homework, and so much more. This table is at the center of our home, overlapping with the kitchen and open to the living room. It is the heart of our home, pulling us all together no matter what we are doing!

  3. Chris and I have always wanted a fireplace in our living room. Sure, it’s not necessary and would save us close to $5k if we eliminated this feature, but it provides an extra layer of coziness in the winter. And this is exactly what we want out of our living room - a cozy welcoming space that invites you to sink in and relax. We don’t need a large room to make this happen. Instead we’ll be focusing more on the decor to maximize seating and create an atmosphere that encourages family movie nights, snuggling up with a good book, and chatting with friends.

  4. We designed our bedroom to be useful day and night by installing a Murphy bed with a desk so Chris also has an office. We wanted to keep our room compact, yet comfortable. So when the bed is down, there is just enough space to comfortably walk around the bed and instead of nightstands, we each have our own 9 ft high cupboard that houses our minimalist wardrobe.

    Note: We love floor sleeping so much and don’t want to give it up with the Murphy bed. So the company making our bed is customizing our unit to accommodate our Japanese floor mat!

  5. I wanted a single bathroom on the main floor that functioned as an ensuite and main floor restroom. In order to do this, I added a door off the kitchen that opens to a small landing space. That landing space has a door to the bathroom and a separate door to our bedroom. This allows Chris to work privately in our room during the day while also allowing anyone to access the bathroom. At night, we can close the kitchen door to create an ensuite feel.

  6. In order to keep our home small, I needed to keep the mudroom simple. With five people in our family a large mudroom seems ideal, but I decided on a small hallway with hooks that just accommodate the current season. Off season shoes, jackets, etc will be stored in our unfinished basement where our laundry will also be located. In the end, it wasn’t worth the extra cost to us to make space for laundry and storage on the main floor.

  7. We love being a single car family and plan on sticking with this lifestyle choice. We don’t want a two car garage, but we do want extra space for bike storage and maneuverability around our van. With this vision, I designed a deep garage with a little extra width - 16x28 square feet.

We feel so blessed to be able to build a home that matches our minimalist lifestyle. Most places wouldn’t allow a 1,112 square foot home with a single car garage due to neighborhood ordinances and deed restrictions. So when a narrow lot with zero restrictions in the middle of our town came up for sale we knew it was a match made in heaven. We can’t wait to enjoy life in the Little White Shack - a childhood dream come true!

Here’s the Little White Shack Floor Plan:

Little White Shack front view - two story home with a single-car-width garage and a porch surrounding the front door.

Little White Shack rear view - two story home with a screened-in-deck at the back

Little White Shack South view - lots of windows and a stub out for a fireplace

Little White Shack North view - no windows

Little White Shack main floor - extra deep/wide single-car garage, bedroom and bathroom, small kitchen, dining, living room, front entry, garage entry, stairs, front porch rear screened-in deck

Little White Shack upper floor - landing that looks over living room, kids room with walk-in closet, bathroom and will have built-in beds

  • βœ‡Cait Flanders
  • What I’ve Been Doing, Consuming and Thinking About So Far in 2019
    Hello, my friend :) It’s been just over four months, since I sent my last newsletter. A lot has changed in that time, and there are also a lot of new people who are hearing from me for the first time. So I’m here to say: hello to all! A very belated “happy new year”. And before starting the next season of the newsletter, I thought it would be nice to share some of what I’ve been doing, consuming + thinking about so far this year. Future newsletters
     

What I’ve Been Doing, Consuming and Thinking About So Far in 2019

13 April 2019 at 14:00

The Year of Less in Paperback

Hello, my friend :)

It’s been just over four months, since I sent my last newsletter. A lot has changed in that time, and there are also a lot of new people who are hearing from me for the first time. So I’m here to say: hello to all! A very belated “happy new year”. And before starting the next season of the newsletter, I thought it would be nice to share some of what I’ve been doing, consuming + thinking about so far this year. Future newsletters may not make sense, without this info.

What I’ve Been Doing

Overall, the first few months of 2019 have generally been pretty quiet. I created a nice routine: writing first thing in the morning, going to the gym/hiking in the afternoon, visiting with friends (and spending many hours/days holding the new identical twin girls born to one of my oldest friends!) and having a night at home. As much as I like to challenge myself, I’ve also accepted that routine really does help me get things done—as well as supports my mental health.

What has made this a little more interesting is that I’ve done all of this in my hometown, Victoria, BC. Last summer, I began to wonder what it would be like to give up my apartment and travel full-time for a year. I knew it wouldn’t be easy, but it also seemed like a natural extension of how I’ve already been living. And so, after sitting on that question for some time, I ultimately decided to give it a go. I gave up my apartment in Squamish and left there at the end of 2018.

My idea, for this year anyway, is that I’ll spend a few months at my dad’s house in Victoria, and then spend the rest of the year travelling. I want to move fairly slowly, staying in places for at least one month at a time—and that’s both so I can maintain my routine and enjoy the new places I’m in. It’s not something everyone would enjoy, and I certainly won’t sell it as a dream, but it’s feeling quite natural, so far.

So, that’s a fairly big update on my personal life, I suppose! Aside from that, I’ve actually been working a lot. The paperback version of The Year of Less came out in January, and I did two events to support that: one at Powell’s in Portland, the other for a great group of people in Nashville. But most of the work I’ve been doing this year was on my proposal for book #2. And I’m so happy to share that it was acquired by Little, Brown Spark a few weeks ago!

I’ll be able to tell you a lot more about that, as time goes on. For now, I’m excited to share the title: ADVENTURES IN OPTING OUT. It should be ready for you in fall 2020. :)

What I’ve Been Consuming

Whew! Ok, that was a pretty massive update, haha. But oddly, I’m more excited to share what I’ve been consuming + thinking about so far this year. Because that’s the nitty gritty stuff, right? Some of the details that make up our days!

At the start of 2019, I still felt completely tapped out of nearly everything happening online—and in a lot of ways, that hasn’t changed. The general feeling I get when I look at most blogs/social media profiles is that everyone is an expert and they are all prescribing expertise I’ll never have or yet another long list of things I will never achieve, all of which, ultimately, just makes me feel worse about myself. And I can’t read it anymore.

I’ve been craving stories. Journeys to follow. Even just the “boring” (NOT BORING) updates we used to share on blogs. Like what are you thinking about right now? What have you been curious enough to actually learn more about? And where are the BEGINNERS!? Where are the people who are raising their hands and saying “I have no idea what I’m doing, but here’s what I’m attempting and my progress so far”? I miss those days. Blogging was actually fun, back then.

Books

In the absence of reading whatever is on the internet these days, I’ve picked up more books this year. Way more than usual. To date, I’ve read 14 (about 4 per month)! And aside from Company of One and Digital Minimalism (both of which I love), they have been memoirs and works of fiction. Stories. Real-life thoughts and lessons. Characters you are rooting for (or some you’re not). And my gosh, it has felt both indulgent, and like a really positive shift.

A few of my faves so far have been:

***THIS BOOK! UGH, so good! I read it after watching the movie (for the second time) and believe it is one I will read again and again. It’s written entirely in letters being sent between people, and has inspired an idea for this newsletter.

Podcasts

You might remember that last year I basically unsubscribed from everything, including most newsletters and podcasts. I also stopped using Twitter. Part of this was to help with the general sense of overwhelm re: how much content exists (reminder: you can’t read, watch and do everything). But I was also curious how my thoughts about them all might change. And change, they have! There were a few newsletters I missed (and a few more I unsubscribed from). And I kept experimenting with Twitter, but don’t think I’ll ever go back there. It’s simply too hostile.

The change with podcasts was a little bigger. First, I not only unsubscribed from them all but also deleted every episode I had downloaded. A little digital declutter, I suppose. Then, whenever I missed a show, I would download the latest episode that sounded interesting. Sometimes I enjoyed them, but I haven’t subscribed to any of them. Instead, I’ve taken recommendations from friends to listen to a specific episode of a podcast, and have found so many new voices and topics that way. I’ve also found a few people I enjoy and listened to many interviews they’ve done, so I can learn more.

This isn’t particularly helpful, I’m sure, but I’m sharing because it’s been yet another act of letting go. Releasing the expectation that you have to follow something entirely from beginning to end, and being ok with the fact that some things only come into your life for a reason or a season.

Anyway, here are the few podcasts I’ve listened to more than one episode of:

  • Climate One – candid conversations about energy, the economy and the environment. I started by devouring the episodes with Yvon Chouinard (who I’m fascinated with right now).
  • Front Burner – my new fave podcast by the CBC. Every weekday, Jayme Poisson takes one of the big stories in Canada and helps you understand what’s going on, what the impact is, etc.
  • Making Sense – Sam Harris changed the name of his podcast, which threw me off. I’ve listened to the eps with Jack Dorsey (Twitter) and Roger McNamee (Facebook). Also have the one on digital capitalism downloaded.
  • Real Talk Radio – Nicole has done TWENTY (20) seasons of this show now and I still love it! Have a few episodes from the new season downloaded for upcoming travel days. :)
  • The Slow Home Podcast – Brooke and Ben decided to change the format of the podcast and start doing it in seasons, which I am always in favour of (change is healthy). It was also lovely to hear about their journey home.

What I’ve Been Thinking About

The better question might be: what haven’t I been thinking about this year? As you can imagine, with giving up my home, selling another book, travelling full-time, there’s a lot on my mind. For the sake of keeping things simple, I’ll share two topics and some of the thoughts I’ve had around them both. I will preface this by saying there are no answers here. Just thoughts, questions, etc. :)

  1. A few months ago, I listened to this podcast called The Dream. It’s about the history of MLMs (multi-level marketing companies) and I devoured all 11 episodes within a week. There were so many interesting points shared throughout it (including people’s experiences with them) but there was one that really stood out for me: the fact that, yes, there are some people who make a lot of money with MLMs. But they are the 1%. The majority of the money they earn comes from the people they have recruited. And while MLMs haven’t disappeared, more and more people now see them for what they are and avoid them at all costs. While I was listening, the only thing I could think about was: wow, this sounds a lot like selling the dream of being a full-time blogger. Yes, some people make a lot of money doing it. But they are the 1%. The majority of the money they earn comes from people clicking on affiliate links, buying products, etc. And people can package up their tips, tricks and expertise, but they can’t sell their unique experiences, character traits, or skills that help them do what they do. A few questions I’ve pondered since: I wonder how long the “make money online” industry will continue to seem appealing? If this hasn’t happened already, I wonder when people will begin to avoid blogs that talk about ways to make money, the same way we avoid friends who join MLMs and try to sell us products we don’t need? And I wonder if/when the whole thing will crumble? Maybe never! Actually, probably never! But anyway, that one podcast series opened my eyes in a way I wasn’t expecting when I first started listening.
  2. How can I do more to help the planet? It’s the one question I’ve thought about more than anything else, this year. And it’s scary to start writing and sharing any of the thoughts that have come up for me, because I only know enough to know I don’t know much of anything yet lol. I am not an expert on the environment or climate change or consumption or waste or anything else. I’m also not interested in becoming an expert or trying to be “perfect”. But I’m standing in the place most of my other personal journeys have begun: where I’m starting to notice things and pay more attention, ask questions and figure out what feels right for me, before taking too many steps down a new and unknown path. One thing I have done is committed to donating 1% of my income to environmental causes via 1% For The Planet. I’ve also been looking for more podcasts on these topics, so I can find new people to learn from, books to read, etc. If you have any suggestions, I’m all ears! Please! Anything you want to share. :)

Ok, I’ll leave it there for today, my friend! I’ll be starting up my newsletter again, and have a fun idea for it that I’m excited to share with you. But now I’d love to hear from you. How has 2019 been so far? What’s on your mind? Is there anything you want to learn more about this year?

xx Cait

This was originally shared in my newsletter.

  • βœ‡Cait Flanders
  • 30 Honest Thoughts From My First Month Away
    Hello, my friend :) I’m writing from the kitchen table at a friend’s flat in London. It’s 9am, around 11°C (52°F) and looks like we’re in for yet another classic British forecast: some sun, some cloud, some rain, and a little wind to mix it all up and sprinkle it throughout the day. Note that I’m not complaining! This weather is similar to what I would be experiencing at home. I’m only talking about it because that’s what you do in the UK. ;) I
     

30 Honest Thoughts From My First Month Away

27 April 2019 at 14:00

30 Honest Thoughts From My First Month Away

Hello, my friend :)

I’m writing from the kitchen table at a friend’s flat in London. It’s 9am, around 11°C (52°F) and looks like we’re in for yet another classic British forecast: some sun, some cloud, some rain, and a little wind to mix it all up and sprinkle it throughout the day. Note that I’m not complaining! This weather is similar to what I would be experiencing at home. I’m only talking about it because that’s what you do in the UK. ;)

I’ve been in England for a month now, and it’s taken that long for me to feel like I can settle in and get some actual work done now. That’s not good or bad. It’s just something I’m going to have to think more about, as I continue to map out my travels. Because I’ve been here before, I assumed I would be able to quickly settle into a routine of writing, going for long walks, cooking, seeing some friends, etc. Of course, it’s never as simple as we want it to be, is it?

Within 5 days of being here, I reconnected with someone I met last year and our first conversation quickly opened my eyes and shifted one of my priorities. At the same time, it only took one trip to the grocery store for me to be faced with a new truth: that my thoughts and values around the consumption of single-use plastics have changed dramatically over the past year, and I feel really (read: really) uncomfortable shopping here now, where nearly everything is wrapped in it.

Before I left Victoria, I had coffee with an old friend I hadn’t seen in a few years. When we said goodbye, he hugged me and whispered, “you know you’re going to come back changed, right?” It hit me hard, and felt like the most honest thing someone had ever said to me. I said yes and, one month later, I can confirm that he was right. But it’s also true that I changed even before I left. I just didn’t know it, until I returned to somewhere I’d been before and saw it with new eyes.

Anyway, I still haven’t dug deep enough into those thoughts or feelings yet, to make more sense of them or figure out what’s next for me. What I have done is kept a detailed journal of everything I’ve done so far on this trip, along with little notes so I can remember what I was thinking while I was here. In flipping through the pages, I realized that some of my notes might actually be helpful for others. So I’ve compiled a list of 30 thoughts to share from my first 30 days away.

I hope at least one of them feels good for you. :)

  1. Sometimes meeting someone one time is good enough, and you should leave the memory at that.
  2. Sometimes meeting someone a second and third time proves to be better, and you realize you might have even more in common than you thought the first time.
  3. You won’t know who the “one time only” people are, until you see them a second or third time.
  4. You can change a lot in a year.
  5. Your values can change a lot in a year too.
  6. The people you can sit in silence with, or quietly read your own books together with, are special. It’s strange how being silent with someone can actually be more memorable than forcing your way through a conversation.
  7. When you’re unexpectedly in the same place as someone at the same time, make plans. The universe wants you to spend time together.
  8. It’s not always a good idea to meet your heroes. But sometimes, you meet them and are pleasantly surprised to discover they are exactly who you hoped they would be.
  9. If you don’t ask, the answer is always no. (I already knew this lesson, but have been reminded of it a few times.)
  10. There are people who understand you and people who never will. Don’t try to force the latter. It’s ok if only a few people really understand you. It’s a gift to have even one.
  11. You don’t owe anyone an interaction. Hard stop.
  12. Being a beginner sucks most of the time, until you’re no longer a beginner. When you start to see the early signs of your efforts paying off, you’ll be glad you tried something new.
  13. Being self-aware is exhausting. But it can also be a gift for you and everyone who comes into your life.
  14. You don’t have to always be right. One day, you will overhear a stranger from another country try to explain something silly/inconsequential about yours. And they will get it all wrong, but tell the story with such enthusiasm that you can’t bear to tell them the truth. So, don’t! Let them think they are right. Who is it really hurting?
  15. It can feel really good to do regular daily life things in new cities.
  16. Move at the pace that feels natural to you.
  17. “Treat everyone you meet like an old friend.” (I first read this quote in a book last year, and have thought about it almost every day since—especially when it comes to dating.)
  18. Rejection isn’t about you. Even if it seems like it is, it’s really not.
  19. A breakup won’t be the worst thing you go through. You’ve survived worse.
  20. The kindest thing you can do is let someone go on their own journey, even if it doesn’t include you.
  21. Don’t be afraid to tell people what positive impact they’ve had on you. We don’t do this enough, probably because it’s scary. But put yourself in their shoes. Wouldn’t it be nice to hear how you had helped someone?
  22. The thought of trying to do anything to help the planet is so overwhelming, because you quickly realize that basically everything you do is bad for the planet. Turn the dial back and remember what ONE thing sparked these spiralling thoughts. Start with that.
  23. All you can do is live according to your values.
  24. When someone invites you to go on an adventure, don’t ask too many questions. Say yes, pack water/snacks and go.
  25. The state of your space is the state of your mind.
  26. Decluttering is just a tool. You need to dig up the root(s) cause, so it doesn’t keep spreading and you aren’t clearing out the mess again every 5-10 years.
  27. There’s no point in earning more money or being successful if you aren’t sharing it with people/the world.
  28. Nothing matters more than the health of you and your loved ones.
  29. When it comes to big/tough decisions, take your ego out of the equation and then ask yourself what you should do.
  30. When in doubt, rent the pedal boat. You will laugh. A LOT.

xx Cait

PS – I wrote the intro to this newsletter in my journal, and am thinking about writing them all like that while I’m away and, of course, sharing them with you! It feels like I’m writing a letter to a friend (and who doesn’t love snail mail?). The tone will naturally be much more conversational, but I’m curious if my writing will get any better as time goes on and I can’t constantly self-edit? I won’t know, unless I try! Here’s to new experiments and being a beginner again. :)

Journal Entry

This was originally shared in my newsletter.

  • βœ‡Spencer H Fry
  • As the size of your team changes, so must processes
    At Podia, we ended 2018 at 10 people. By the end of April 2019, we were 17. Very quickly, as we were hiring more people, it became very apparent that we would need to update our processes. In principle, I hate processes. I think most of the time they just get in the way of doing real work and add unnecessary steps from whatever you’re trying to do. Having to double-check that you’re following company procedure or logging into yet another application to perform a task is frustrating
     

As the size of your team changes, so must processes

1 May 2019 at 15:58

At Podia, we ended 2018 at 10 people. By the end of April 2019, we were 17. Very quickly, as we were hiring more people, it became very apparent that we would need to update our processes.

In principle, I hate processes. I think most of the time they just get in the way of doing real work and add unnecessary steps from whatever you’re trying to do. Having to double-check that you’re following company procedure or logging into yet another application to perform a task is frustrating and brain draining to me.

But, the reality is, knowledge sharing and the general understanding of how things work at your company tend to break down as you grow.

As our company grew, we found this to be true for us, so we added a few new processes to help:

1. Hiring process

Before 2019, we were only hiring one person at a time, so managing the process was fairly straightforward. We had a job posting on our website, a link to a Typeform to submit the application, and we used Dropbox Paper to track candidates and share feedback between the people in charge of hiring.

In 2019, we started hiring for 3 positions at once (Creative Support Agent, Developer, and Creative Content Marketer) and trying to manage all of that with how we had things set up broke down, and quickly. The bottle neck was reviewing applications and taking feedback, so we moved to a “proper” Application Tracking System to smooth out our process.

2. File sharing and document sharing

As more people joined the team, it became unwieldy without proper permission settings, so we finally bit the bullet and upgraded our Dropbox setup from shared Personal folders to Dropbox Teams. The benefit is two-fold: it helps us now and protects us down the road when people eventually leave the team (though we’ve been very lucky to date 🤞).

Before, we’d just share a document with the relevant people as needed, but people having to request access to documents was a pain. This way, everything is super well-organized in our Dropbox account and we have it segmented by department.

One thing I kind of lament is the fact that Dropbox Teams is pretty expensive at $20/user/month. That adds up with 17 people where we’re now paying $340/month. 🤷‍♂️

3. 1-on-1s

We’ve never had a very formal process to our 1-on-1s. As a small team under 10, we were able to keep fairly up-to-date and engaged with people through Slack and our weekly calls. I’d do 1-on-1s every few months as things became quieter.

Now, as we’ve grown, we’re looking into 1-on-1 apps as a way to formalize the process and I also think we need to increase the frequency of 1-on-1s. At this time, I’m not in favor of weekly or even bi-weekly 1-on-1s, so we’ll likely consider monthly or every six weeks to test that out.

4. Company knowledge board

While we had just started using a company knowledge board to gather and document all of our internal notes, docs, processes, etc., as new people joined the team, it became very apparent that we’d need to do a better job of updating it.

This is one of the processes I think we’ve benefited the most from. For example, as new Customer Support Agents have joined, they’ve been able to see how we do things, answers to common questions, and guides on all sorts of things. Same goes with the Development, Design, and Marketing team.

And everyone benefits from our newly created “HR” folder that has everything from the payment schedule to our Family Leave Policy (also new).

5. Product management

Since hiring two new developers in 2019 — we’re now at seven — we’ve also spent time cleaning up the way we use Trello. Previously, we had two boards: one for things we were currently working on, and one for our backlog of do’s that included bugs and tasks.

Since then, we’ve added a third for bugs and other tasks and removed those from our backlog. Now, our customer support folks can add any reported bugs directly into the “Bugs and Tasks” board.

This helps keep things more organized. It may seem obvious in retrospect, but when you’re fewer people, it’s often not necessary to separate things so much.

What hasn’t changed?

Just about everything else I can think of hasn’t changed. For me, it’s important to not make too many changes too quickly. Change is good, adapting to having more people is important, but I don’t want to rock the boat and mess up everything that’s been working so well up until now.

Before Podia, the largest team I’ve led was thirteen people, so this is definitely different, but as you often hear from experienced founders who have grown larger teams, it doesn’t really get harder as long as you’re working with great people and you stay organized.

I’m excited to see how things continue to change as we grow in size.

  • βœ‡Keep Thrifty
  • How We Vacationed With Extended Family
    Have you ever vacationed with your entire family in a single house? I’ve always told Chris that I think the best time to spend with extended family would be in a neutral setting at a neutral time (no holidays please). This idea became a reality when my mom surprised us with an amazing gift. My mom and aunts recently sold my grandparents’ house. With my mom’s portion of the sale she decided to take her family on a vacation. We joined my parents, two sisters and their husbands
     

How We Vacationed With Extended Family

14 May 2019 at 11:58

Have you ever vacationed with your entire family in a single house? I’ve always told Chris that I think the best time to spend with extended family would be in a neutral setting at a neutral time (no holidays please). This idea became a reality when my mom surprised us with an amazing gift.

My mom and aunts recently sold my grandparents’ house. With my mom’s portion of the sale she decided to take her family on a vacation. We joined my parents, two sisters and their husbands and kiddos in a beautiful three story home with a pool right on Bradenton Beach, FL. My Nana loved nothing more than being with all of her family so it was a wonderful way to honor her and my grandpa.

Anna Maria Island, Florida

Our days in Florida were slow and relaxing. Mornings were filled with coffee, cartoons, and taking in the view of the waves. The rest of the day was spent between the pool, beach, and foosball table! Lunches were simple sandwiches and fresh fruit. My brother-in-law rocked the grill at dinner time. And as the sun was about to set we would head to the beach to absorb the last of the sun’s rays.

We rarely left the property - a few trips to the beach wear and grocery stores filled our needs. Halfway through the week we had a girlie with ear pain at 1AM. We didn’t realize that my dad (with the dog) and sister (with the baby) were up as well. Had we known, Chris could have brought the dog and our nephew in the car when he made his late night run to Walgreens.

Sharing this vacation with my family allowed all of our relationships grow. We all helped each other out. My sisters would take N to the beach when the twins wanted to stay in the pool. I grabbed the baby when he woke up from his nap so my sister could stay on the beach a bit longer. Chris taught our two year old nephew the potato fries fist bump. The girls cuddled on the couch with my niece when they watched movies. And on a few nights the adults would stay up with a glass of wine and chat!

Before the week was over my sisters and I agreed that we would love to vacation like this again! It was the most relaxing, fun time we’ve spent with family. And while this trip was free thanks to my parents, we would gladly split the cost in the future because a week in paradise with my family was priceless.

Family vacation collage

  • βœ‡Keep Thrifty
  • What Are You Optimizing For?
    Here’s a scenario I bet you’ve encountered: You’re on your way home. It’s a familiar route. You’ve done this trip hundreds or thousands of times. Your mind drifts to other parts of your day. You think about the grocery list, the latest challenge with work or the kids. The next thing you know, you’re home. You don’t remember the commute. You don’t remember the turns, the signs, or the stops. You know they happened and you feel like you were rea
     

What Are You Optimizing For?

11 June 2019 at 11:58

Here’s a scenario I bet you’ve encountered:

You’re on your way home. It’s a familiar route. You’ve done this trip hundreds or thousands of times.

Your mind drifts to other parts of your day. You think about the grocery list, the latest challenge with work or the kids.

The next thing you know, you’re home.

You don’t remember the commute. You don’t remember the turns, the signs, or the stops. You know they happened and you feel like you were reasonably safe, but you must admit that you were, in essence, on autopilot.

Why do we end up on autopilot? Certainly getting home safely is important to us. The last thing any of us wants is to get in a car accident or to hit a pedestrian.

Here’s my theory - subconsciously, we’re making a decision to optimize. We know we only have so many minutes in the day. We can’t avoid the commute, so we choose to optimize our time by balancing a “sufficient” amount of attention to the road with the rest on other priorities.

If we can give enough attention to driving, isn’t it the best of both worlds to be able to mentally prepare for other parts of our day as well?

Optimizing is a driving force in our day. We optimize our time. We optimize our money. We optimize our skills, our talents, and our relationships.

When Optimization Goes Wrong

But optimization has a dark side. When we let our optimization be subconscious (instead of conscious), we run the risk of optimizing for the wrong things and getting further away from the life we really want.

Optimizing your time on the road might be worth the safety tradeoff if you’re spending that time figuring out a cure to a debilitating disease. But is it worth getting into an accident because you were trying to decide whether your Instagram photo of tonight’s tacos would look better with white or orange cheddar?

You see, optimizing on autopilot is risky; especially when you’ve got celebrities, carefully curated social media profiles, and advertising telling you what you’re “supposed” to value.

When you start combining subconscious optimizing with “adopted” values from others, you can quickly find your life spinning in the wrong direction.

Modern Society’s Preferred Optimizations

So what do those celebs, influencers, and marketers tell you to optimize for?

Two big ones come to mind, both of which are recipes for failure.

First, they tell you to optimize for your “image”. You’re told to optimize for how others perceive you. Get this car and people will think X. Wear these clothes and you’ll give the appearance that you’re Y.

But if you optimize for your image, you’re optimizing on other peoples’ perceptions instead of your own. You’re inherently placing your personal value in what other people think of you, which is something you should never optimize for.

Your worth isn’t defined by what other people think. It’s not even defined by what you think. God loves you and no matter how poor your image (self or otherwise) is. God determined your worth a long time ago and no one can take that away.

Second, society will tell you to optimize for convenience.

Between fast food, internet shopping with 2-day delivery, on-demand streaming, and instant answers from your phone (or a digital assistant sitting in your living room), we’ve been trained to think that convenience is king.

But is our ultimate goal on this planet to “get things easily?” Is that what you want on your tombstone?

Here Lies Chris
Loving husband and father
Found innovative ways to avoid lifting a finger
Rest in peace

Come on! God made you for bigger and better things than finding the easiest and fastest way to satisfy your compulsions.

I had a beer with one of our readers the other week (BTW, this is something I’m highly for and would love to do with any of you that are swinging by Madison, WI) and he shared a great example of how he and his family flipped convenience on its head and found a much better thing to optimize for.

Here’s the rundown:

Their family has three kids (one college, one high school, one middle school) and two working parents. Their college-aged son is home for the summer and working a second-shift internship on the other side of town. With only 2 cars, transportation can get a little bit tricky.

The convenient solution would be to buy another car - even a junker - to help ensure that transportation is easy for everyone. But this family knows that convenient doesn’t necessarily mean best, so they came up with another approach.

Every morning, the dad drives to work. When the son needs to head to work in the afternoon, he rides his bike to his dad’s office. When he gets there, he drops off the bike and takes the car the rest of the way to his second-shift job. When the dad finishes work, he rides the bike home. When the son finishes work (late at night), he drives the whole way back.

Is this convenient? Definitely no. Biking is exercise and that’s hard work. But it’s also good for you. Rain and temperature could make for some pretty rough riding conditions. But those conditions aren’t impossible to tackle.

It’s not convenient, but it does align with this family’s values. They didn’t want to spend the extra money on a car, gas, and insurance. They didn’t want to add more pollution to the air or another set of rusted out parts in the landfill. So they got creative and found a better solution to the problem for their family.

Optimize for Your Values

I love that story - not because that situation and solution precisely matches us, but because it precisely matches them. This reader’s family thought hard about what was important to them and optimized on their values.

Over the last several years, we’ve worked to do the same in our own lives. Here’s a small example:

In our old house, we had four bedrooms. With three kids, that gave us precisely enough space to allow each child to have their own bedroom as they got older.

But as we build the little white shack, we are building with a floorplan that has just two bedrooms and two bathrooms. All three of our girls will share a single bedroom and a single bathroom.

Keep in mind, we’re going to have three teenage girls in our household in the not-so-distant future, so this definitely doesn’t sound convenient from most perspectives.

But convenient isn’t what we want here. We don’t want a situation where our daughters all shut themselves off in separate parts of the house. We don’t want our house to just be a place we all happen to live; we want to be present and supportive in one another’s days every day.

And we don’t want to let convenience drive our finances. More bedrooms and bathrooms mean a bigger mortgage, higher property taxes, and higher operating cost. That expense comes at the cost of other things we’d rather spend our money on - like charity and family travel.

Will sharing a room cause some extra sibling fighting? Maybe. Will there be times that they scream and tell us we’re ruining their lives for not giving them their own room? Probably. But will they be forced to confront issues, work through conflict, and connect as a family? Definitely.

This piece of our floorplan may sound massively inconvenient to some. But for us, it’s a reflection of the values we think are right for our family. And that’s the perfect thing to optimize for.

What are you optimizing for? How does your life reflect your values (or not)? What optimizations are you second-guessing?

  • βœ‡Spencer H Fry
  • Podia’s product process
    This article is inspired by a tweet I made back on July 16th. Gregg Blanchard on Twitter asked if I could turn the tweet into a post and elaborate more on each stage of our process at Podia, so that's what I've done. Thanks for the inspiration, Gregg! Yearly roadmap Between Christmas and New Years, I take a little downtime, but I also spend it writing up a Yearly Product Roadmap for Podia to present to the team during the first week back. Every Yearly Product Roadmap starts with a brief hist
     

Podia’s product process

2 August 2019 at 14:03

This article is inspired by a tweet I made back on July 16th. Gregg Blanchard on Twitter asked if I could turn the tweet into a post and elaborate more on each stage of our process at Podia, so that's what I've done. Thanks for the inspiration, Gregg!

Yearly roadmap

Between Christmas and New Years, I take a little downtime, but I also spend it writing up a Yearly Product Roadmap for Podia to present to the team during the first week back.

Every Yearly Product Roadmap starts with a brief history of what we did during that year. For us, it goes all the way back to 2014.

After the brief history (which only gets one additional line every year, but does provide context as to where we came from), I write out a reflection on the product work from the previous year.

While every year has a loose theme, I always cover the same topics: whether or not we hit our goals, if the goals shifted throughout the year because we learned new things, and what, if anything, we thought we were going to do, but didn't.

Then I write a bit about our KPIs and how well we performed for the year and wrap it up with a few FAQs.

After concluding the review of the past year, I start to write about what we want to do for the next year. As I mentioned above, every year has a loose theme, which is usually tied back to the major product ideas that we want to work on for the upcoming year.

After writing about the theme and the major product ideas, I write out the high-level new features and current product improvements that we want to do in a table and bucket them into themes.

From there, I take every high level feature and break it down one or two layers deeper to give more context as to how we might address it.

Lastly, I'll assign a specific “to do” to each developer and designer for them to focus on at the start of the year.

Quarterly roadmap

I don't create a Q1 Roadmap, because we just start by working off the Yearly Product Roadmap.

By Q2, we've learned more in Q1 than I knew back in December when planning for the year, so the Q2 Roadmap will have new things on it and some old things will be removed.

These Quarterly Roadmaps start off by reviewing the previous quarter by outlining what we released, what's in progress, and what we still want to do or not do.

From there, every feature is listed out with a few paragraphs on each with a high-level overview; the goal here is to give context around why we're building each one.

Accompanying the list of features is a table that shows the “Status” for every feature for the quarter, links to the specs, links to Trello, links to Figma, and who is working on it.

Some of the features in the table won't have anything listed out until it's time to start those features.

We don't write the specs until a few days or a week before we're going to start on a new feature because we want it to be fresh; we don't write specs for features we never build because what's the point in that?

Strategy doc

The strategy doc is short, concise, and it outlines the feature that we're planning to build. I write these to have a lot of context as to what we're building and why, what I think it should be, some example screenshots of where it could go, and what's unknown/still needs to be figured out.

These aren't supposed to include the entire spec, because for that, I want to spend time with a designer and/or developer to work it out exactly.

Specs collaboration with me/designer/dev

Once the strategy doc is done, and the time is right, I'll jump on a video call with a developer or designer to discuss the spec. We'll go over the strategy doc and talk about the specifics as to how we might implement this.

Design

If we need designs, the designer will go off and start designing it; we use Figma. Once there's a design to review, we'll start leaving comments and talking through everything in Figma.

Somewhere in the design process, we'll loop in a developer to review the designs to make sure we're all on the same page in terms of how this will get implemented.

If the screens require copy, we'll loop in our copywriter to write it.

Dev

Once the developers start working on the code, they’ll keep me and the designers up-to-date on their progress in Trello and Slack. If during that process they get stuck or if they have a concern as to how something was designed, they'll voice that.

Dev/design clean up

We'll then make any changes we need to make after we see how the feature is working on our staging servers.

Most of the time, we don't really have many changes to make on staging as we've been collaborating throughout the process.

Deploy feature flag

We'll then deploy the feature to product behind a feature flag where only we as the Podia Team can see it. If it's something critical like touching the checkout process, we'll let it run for 24 hours or so before removing the feature flag.

Write announcement / write help doc

While the feature is deployed behind a feature flag, I'll write the announcement and the developer who worked on the feature will write the help doc.

Once both are drafted, our copywriter will review both and make any necessary changes before going live.

Remove feature flag

Next, we remove the flag so that everyone has access. We’ll wait an hour or so to make sure everything is working okay.

Announce 🙌

Send the announcement!

We'll either opt for an email to all of our customers (on paid accounts and people on trial accounts) or we'll just send an in-app notification; the kind of notification really depends on how important the update is to our customers.

Feedback/recap/data

Once the feature is live, we'll gather up the feedback we got from customers and post them into our #product channel in Slack and review any data we're tracking in Metabase about how the feature is performing.

That's it. I hope you find this helpful and please let me know if any questions in the comments. 🙌

  • βœ‡Cait Flanders
  • Seeing the World Can Change Your World
    Another thoughtful guest post for slow travel week! This one is from my friend Amanda. Travel has been part of my life since I was nine years old, when my parents packed us up for a six-month motorhome trip around Europe. Thanks to Australia’s long service leave provisions, my dad could take six months off work and still get paid, so off we went. It was a low-budget trip with lots of simple meals and days spent playing in local parks, following the principles of slow travel long before
     

Seeing the World Can Change Your World

15 November 2017 at 12:00

Seeing the World Can Change Your World

Another thoughtful guest post for slow travel week! This one is from my friend Amanda.


Travel has been part of my life since I was nine years old, when my parents packed us up for a six-month motorhome trip around Europe. Thanks to Australia’s long service leave provisions, my dad could take six months off work and still get paid, so off we went. It was a low-budget trip with lots of simple meals and days spent playing in local parks, following the principles of slow travel long before anyone started to describe it that way.

To say that the travel bug bit me on that trip would be an understatement, and so much of my life—and let’s be honest, my money—has been spent on travel ever since. In my teens and early twenties, I couldn’t really explain my desire to travel more, I just knew I wanted to do it.

I grew up in Perth, Western Australia, which is a gorgeous city but is known to many as the most isolated city in the world. Even the next significant city is close to a two-day drive away. It’s improved a lot thanks to the internet age, but Perth in the past really lagged behind the rest of the world and it felt stifling growing up here; most people from my age group have moved away at least for a few years. Some come back; others never do.

It wasn’t until I finally left Perth, after several failed attempts, and moved to teach English in Japan at the age of 25, that I finally began to understand why I wanted to travel. When I’m travelling, I really and truly feel alive. Leaving behind the humdrum of daily home life and exploring cultural differences, meeting people who speak different languages, and taking in amazing landscapes and enticing cities—all of this gives me so much energy and inspiration.

But even more than making me feel properly alive, travelling has changed me and taught me so much. Most of my core values are thoughts I developed from my experiences living and travelling throughout Asia and Europe. Empathy for others—especially others who have a different background to me—is something I learnt when I had to understand why my Japanese friends were so worried about making a mistake speaking English; acknowledging and accepting different viewpoints was something I understood after chatting many times with friends in Slovakia about how their life had been different under socialism and capitalism.

Travelling also taught me confidence and the quiet ability to know that everything will work out okay, eventually. When I left Australia, I’d been suffering from bouts of severe anxiety since my late teens, and I had phobias of driving on highways, of flying, of being in elevators. But removing myself from the place where it all started, and opening myself up to these new experiences of the world, changed everything. I lived in buildings where I could only reach my apartment in an elevator, and doing that every day dissolved that phobia. I loved so much to see new countries, and flying was often the only way, so I kept doing it until I didn’t have a panic attack on take off. I still don’t love driving on highways, but I pushed myself enough that I managed to pass my German driving licence test, including a stint on the Autobahn.

I could go on, but suffice to say, when I think about what makes up my personality and outlook on the world, I know that all of it has been influenced oh-so-heavily by my travels.

And now I have a seven-year-old son and I’m back in Perth. It’s such a big responsibility, trying to shape the way a small human being thinks, but I’m trying to use what influence I have as effectively as possible. So far, I’ve raised him to love to travel, and to not really see differences but to see the similarities that we all have, because after all, we are all human. When he plays with his Lego, or his cars and trucks and planes, so often his games turn into experiences on a world-wide scale—his Lego car is driving some Lego guys to the airport to fly to Iceland and see the puffins; his trucks are carrying sumo wrestlers and taiko drums and sushi stands for a festival in Japan. It warms my heart.

As a single parent, I don’t have a huge budget, and remember, we live in Perth, the most isolated city on the planet. But travel is important, and I find ways to take my son travelling as often as possible—usually abroad once or twice a year, at least. It changes him every time.

Just before our most recent trip, to Malaysia and Singapore, he’d been getting stressed in school and was emotionally pretty worn down. By the first night of our trip, it was like a huge weight had lifted off him, and he was back being a happy-go-lucky seven-year-old. He brought that feeling back from our trip, and I saw him run so confidently into school, restored by the same inspirational feeling that travel gives me, too.

My son hasn’t even yet reached the age I was when I first travelled, and he’s been to a dozen different countries and experienced so many varied cultures and people. When I look at how much travelling has impacted my life, and to think that at his age, none of that had started, I feel proud that I’m able to give him these amazing lessons that are shaping his personality and thinking. And I look forward to travelling with him to many more places, and watching both of us continue to grow through travel.


Amanda blogs about travel at NotABallerina.com and hosts The Thoughtful Travel Podcast where she chats with fellow travel-lovers about all of the wonderful lessons travel provides.

  • βœ‡Cait Flanders
  • What My Dogs Taught Me About Slow Living
    May was not meant to be a month of silence. I did not intend to disappear. My plan with the slow technology experiment was only to take a break from social media, not the blog. I had planned to write a post about the role television plays in my life, these days. I had also planned to write a post about how I use technology, as a whole. Of course, as I continue to learn again and again, things don’t always go as planned. Life is not always in our control. In fact, I think it was Lauryn Hi
     

What My Dogs Taught Me About Slow Living

29 May 2017 at 16:00

What My Dogs Are Teaching Me About Slow Living

May was not meant to be a month of silence. I did not intend to disappear. My plan with the slow technology experiment was only to take a break from social media, not the blog. I had planned to write a post about the role television plays in my life, these days. I had also planned to write a post about how I use technology, as a whole. Of course, as I continue to learn again and again, things don’t always go as planned. Life is not always in our control. In fact, I think it was Lauryn Hill who said, “We can’t plan life. All we can do is be available for it.”

And that’s exactly what I did in May. I made myself available to the two creatures who needed me more than anyone or anything else: our family dogs.

The girls, as we call them, have been part of our family since shortly after I graduated from high school. We brought Molly home in 2004, and got Lexie in 2005. There is no doubt we spoiled them, the way many small dog owners do (and sometimes have to). But they loved the same things as every other dog: going on walks (especially at the beach), eating food and hanging out with their pack. And they each came with their own unique personality. Lexie is a brat who plays by her own rules, and Molly quickly became her protector.

In April, Molly started showing signs she was aging. She ate a little slower, took the stairs a little slower, walked a little slower. We had one scare with her in early May, where we had to leave her in the animal hospital overnight. She quickly recovered, though, and came home the next day. Unfortunately, just 2.5 weeks later, we had to bring her back in. Again, I thought we were going to bring her home the next day, but things don’t always go as planned. Her test results showed us we had to let her go. We said goodbye to Molly (age 13) on May 22nd.

Since then, I have spent almost every minute of every day with Lexie. She’s been adjusting to life without Molly fairly well (probably because I rarely leave her side). However, she started showing her own signs of aging a few weeks ago. While Molly was slowing down, Lexie started doing circles; and walking around like she was drunk; and even bumping into things. It was easy to assume she was just going blind—until she had two seizures. With all of that combined, our vet says it’s likely she has a brain tumor. We got this news on May 26th.

It’s fair to say I’ve been on an emotional roller coaster, this past week. The pain comes in waves. Lexie and I will have a great day, then I’ll crawl into bed and be so uncomfortable in the silence that I burst into tears. Sometimes, it’s just the little things: doing a routine that would have normally involved Molly and remembering she’s not here anymore. I’ve even missed hearing her bark at the mailman. To counter this, there have also been a lot of smiles and laughs in our family, as we share our favourite things about her. Molly was truly loved.

If Lexie does have a brain tumor, there’s no way to tell how long she will be here with us. My heart is broken at the thought of having to say goodbye to her too. So far, two things have helped me not have a breakdown about it: 1) knowing she’s not in pain, and 2) knowing she is blissfully unaware of her condition. That second point is something I think about many times each day, and comes with even more lessons of its own.

While I’ve been trying to figure out what slow living looks like, the girls have been exemplifying it their whole lives. And while they have needed me this month, Molly and Lexie have taught me lessons I will carry with me for a lifetime. <3

  • Live in the moment. Dogs have no concept of time. They live one day at a time, and enjoy each moment as it comes. Whether they are laying in the sun, playing with a toy or going for a walk, they are simply happy to be alive – and to be spending that moment with someone in their pack.
  • It’s ok to cry. That’s not to say they have no emotions. Molly was one of the most emotional dogs I’ve ever met, and wore her heart on her sleeve. But she didn’t sit around worrying all day. She simply had emotional reactions in the moments they were needed (like when something was wrong with Lexie).
  • Make sure your basic needs are met. Dogs only have a few basic needs: food and water, a place to sleep and access to a patch of grass. They don’t care what colour their leash is, how cute their toys and beds are, or anything else. They just need food, water, exercise and sleep. And a human. :)
  • Be grateful your basic needs are met. One of the best things about living in the moment is that dogs also have no concept of wanting more. They don’t care about getting the newest or best of anything. They are simply grateful to eat their food, lap up their water, soak up the sun and get some attention.
  • Give people your full attention. Speaking of attention, dogs are the one animal that give humans all of theirs. They greet you with pure love and joy. When you’re together, they look at you – not at their cell phones. And for as long as you are willing to give them your attention, they will give theirs to you.
  • Nature is therapy. I have never met a dog who didn’t jump at the words, “Do you want to go for a walk?” They don’t care about climbing mountains or running personal bests. And they really don’t care about the pictures you can take and share on social media. Dogs are simply excited to get some fresh air and spend more time with their pack. It also helps them release some energy and sleep better at night.
  • Don’t take life too seriously. There is always a reason to play. <3

None of this is to say I’ve put it all into practice and am high on life right now. I’ve spent much of the past week in a daze. While I’m present with Lexie, I have ignored my inbox and my client work. I dragged the vacuum out last Monday, but didn’t actually vacuum the house until yesterday. I even forgot about an important interview, and wrote down the wrong date for my nephew’s birthday party. Grief messes with us. It’s human. I’m human. But my four-legged family members are doing their best to bring me down to earth and remind me to be present.

I’ll do an update on the social media detox next week, but for now I will say this: I don’t know what was shared online, but I know it wasn’t important to me. I don’t care what news I missed, which trends became fashionable or who made the top 10 list of whatever. The only thing that mattered was taking care of the girls, starting to grieve the loss of Molly and making sure Lexie was living her best days. There is nothing more important than the people and animals in our lives. Please give yours an extra hug and cuddle today. xo

UPDATE: Lexie lost her fight on May 31st. My heart is broken, but I’m so grateful I got to spend all her final days with her. The girls are together again. <3

  • βœ‡Cait Flanders
  • Why Spending Time Outdoors Matters to Me
    There are a lot of posts out there that talk about why it’s important to spend time outdoors. It’s a natural remedy that offers a workout, lifts our spirits and helps us sleep better at night. It gives us the opportunity to disconnect from our constantly-connected world and take some time to be with ourselves and others. And it can come with beautiful views and show us parts of the worlds we might otherwise never see. All of those are factors in why I love spending time outdoo
     

Why Spending Time Outdoors Matters to Me

27 September 2017 at 19:00

Why Spending Time Outdoors Matters to Me

There are a lot of posts out there that talk about why it’s important to spend time outdoors. It’s a natural remedy that offers a workout, lifts our spirits and helps us sleep better at night. It gives us the opportunity to disconnect from our constantly-connected world and take some time to be with ourselves and others. And it can come with beautiful views and show us parts of the worlds we might otherwise never see.

All of those are factors in why I love spending time outdoors, but I don’t need—and don’t want—to write a post with that same list. Yes, I’ve found that even a 30-minute mindfulness walk around your neighbourhood can be a meditative experience that provides an immense amount of relief and clarity. That’s exactly why I go for a walk every day. But that’s not why spending time outdoors matters to me.

Growing up, I wasn’t good at much. I learned how to read even before I could ride a bike (and I learned that at age 5). So I read a lot and rode my bike around the different neighbourhoods I grew up in. I also loved to swim. But I wasn’t good at anything else.

I attempted to play basketball for a couple years but was lucky if I could make 15% of my shots. I usually walked away from volleyball games with sprained fingers. I still don’t understand how I was part of a relay team in track and field but that was short-lived. Soccer and softball were laughable. And I hated literally every other sport we had to play in gym class. I wasn’t lazy. I just wasn’t good.

Something I’ve only accepted and started to work through this year is the fact that I am a recovering perfectionist. This has manifested differently in all areas of my life, but when you’re a kid and you’re not immediately good at any sport, it means you basically always feel like a failure. It was like walking around with a sandwich board hanging over me that read, “DON’T PICK ME” on the front and, “I SUCK” on the back.

So, when I was done being forced to play these games I was terrible at in gym class, I would walk away feeling like a failure and run to the worlds of the things I was good at. Reading books, riding my bike and swimming. By age 13, I was also good at partying, and being drunk and high was my favourite world of all.

The irony of being a perfectionist who is “good” at partying is that it will ultimately lead to some kind of failure. If you’re lucky, that failure will lead you back to a sober life. I got sober when I was 27 and, while my self-worth still isn’t exactly where I would like it to be, I know I’m better in this world than in the party world. I know because it’s the first world where I have truly felt like I could be myself—and I have the outdoors to thank for that.

I have always loved* being outside. As soon as I got my driver’s license, I took my little old Hyundai Excel on as many adventures as she could handle. When we needed more space, my girlfriends and I would fill up the back of my dad’s truck with gear and set out to explore Vancouver Island and the Gulf Islands. We would hike, bike, swim, skimboard (and bail). We would camp in places that didn’t have much water, not shower for 4 or 5 days, and come home covered in dirt. And I loved it.

*Note: There are still things I don’t love. Like the heat. I’m as pale as a ghost and burn easily. The hot sun and I are not friends. But you learn how to manage (or avoid) these things!

Still, I never considered myself particularly outdoorsy. Then I spent two years with a guy who hated the outdoors and who I essentially melted into and shaped myself into whoever he wanted me to be. Not long after we broke up, I started going hiking and camping more regularly again, but I did it for some of the wrong reasons: to prove something, to spend time with certain people and to party. (And I’ll never forgot how proud I used to be when I could wake up without a hangover and do a sunrise hike. Pretty cool, Cait.)

I started spending time outdoors for better reasons in 2011, when I was maxed out with nearly $30,000 of debt and was also at my heaviest weight. It was a free workout, and a free activity I could do with friends where we could take in some beautiful views together. Also, the workout + the fresh air helped me sleep better at night, which was a rarity during a time when I was so stressed out by my financial situation. These were all wins.

I was still drinking at the time, but I was also doing these other things to better myself—and it was only a matter of time before the two worlds couldn’t work well together. After taking control of my finances and my health, I decided to take control of my drinking and completely opt out. It was the best decision I’ve ever made.

Living in this world and seeing it through sober eyes is such a gift, but it has also come with its own challenges. I had wrapped up so much of my identity in being “good” at partying and being the girl everyone wanted to party with. Since I let go of that girl, I’ve been left with an odd-shaped hole inside me that I still can’t seem to fill up.

Some days, I genuinely don’t understand why people would want to invite me places. And I don’t usually like to talk about this but a huge reason I don’t date is because of one particular story I tell myself: I won’t find a guy who is comfortable dating a girl who doesn’t drink. (On the surface, I know that’s not true. But there is so much power in the stories we tell ourselves that I’ve let that one stop me from even trying to find him.)

Remember when I said my self-worth still isn’t where I want it to be? That’s one example of what I’m working through—and I am working through it. Being sober means I am finally able to acknowledge and voice these things, rather than numb myself. So, I know I’m better in this world than in the party world, because it’s the first world where I have truly felt like I could be myself—and I also have the outdoors to thank for that.

The outdoors is the one place where I’ve never felt like I had to measure up to anyone else. Let’s look at hiking as an example. I love hiking. I love it because it’s not a race. It doesn’t matter how fast you complete a hike or if you even complete it at all. And it doesn’t demand you have any skills, other than wanting to go, then putting one foot in front of the other, and picking yourself up if you slip or fall.

Hiking also doesn’t demand you look a certain way. You don’t need to keep up with trends or wear name brands or be a certain height or weight. Comfort and sensibility are the only two things to consider (along with how much food and water you want to pack). And you should just start by expecting to get dirty. Use your hands to get up and sit down to rest when you need to. The rocks, trees, stumps, and your friends are happy to help.

Along the way, you can appreciate the scenery and even the work that’s gone into creating and maintaining the trails you’re on. And if you make it to the viewpoint, amazing! Soak it all in. If you’re in a time where things feel hard or the world feels like a bad place, taking in that view has a way of putting things into perspective—the most important perspective being that you didn’t need to be “good” at anything to get there.

You don’t have to be an athlete to spend time outdoors. You just have to be a human who appreciates the world and wants to see more of it.

So yes, I think it’s important to spend time outdoors. It’s a natural remedy that offers a workout, lifts our spirits and helps us sleep better at night. It gives us the opportunity to disconnect from our constantly-connected world and take some time to be with ourselves and others. And it can come with beautiful views and show us parts of the worlds we might otherwise never see. But that’s not why spending time outdoors matters to me.

I love the outdoors because it’s the one place where I can truly be myself. My beautiful, messy, happy, sad, sober, uncoordinated and hilarious self.


PS – This #atwildwoman image has been licensed from Amanda Sandlin. She also created my beautiful logo! To see more of her work, check out her shop and follow her on Instagram.

  • βœ‡Cait Flanders
  • How I Slowly Grew My Blog My Own Way
    It’s not hard to find posts/entire websites that can help you launch a blog; and launch a blog that gets a lot of attention and success early on; and then use that success to turn it into a blog that not only helps people see you as an expert but also makes you a lot of money. I can’t write a blog post like that. Some of my friends can! I have friends who are really smart and know everything it takes to build a successful blog with a huge mailing list that proves you are an expert
     

How I Slowly Grew My Blog My Own Way

11 October 2017 at 19:00

How I Slowly Grew My Blog My Own Way

It’s not hard to find posts/entire websites that can help you launch a blog; and launch a blog that gets a lot of attention and success early on; and then use that success to turn it into a blog that not only helps people see you as an expert but also makes you a lot of money. I can’t write a blog post like that. Some of my friends can! I have friends who are really smart and know everything it takes to build a successful blog with a huge mailing list that proves you are an expert and can make you a lot of money. But I can’t.

Instead, I can write a blog post that tells you I launched an anonymous blog on October 1, 2010 to document my debt repayment journey. I can tell you I deleted the first version of that blog in early 2011, then restarted it when I was completely maxed out. I can tell you I connected with a few people and companies I loved on Twitter, and ultimately got my first two freelance writing jobs from doing so. I can tell you I wrote my blog anonymously for close to two years before I grew tired of lying to my family and friends about my “double life”. And I can tell you that, shortly after that, I got a full-time job offer from a company in Toronto.

Of course, a lot has changed since then. I moved to Toronto in 2012, then moved back to BC in 2013 and continued to work remotely for that same company. I built more relationships and got more freelance writing work, and then I quit my job in 2015 and have been self-employed ever since. Working for myself was never part of the plan. I always thought I was going to climb a corporate ladder, then maybe jump off one ladder and onto another. I never thought I would be my own boss, and I especially never thought that this blog would make being my own boss a possibility. It wasn’t part of the plan.

For the past seven years, I’ve shared all of this + the ups and downs of my life here with you. I didn’t start this blog to get attention from the press or reach any level of success, or to grow a huge audience or make a lot of money. I started it to document my debt repayment journey. The success that has come from it has been a result of consistent writing, plus a lot of careful considerations, and the intentional decision to forego all the usual advice and do things my way. It’s also a result of putting people (YOU) over profit. It’s been slow and steady, but I’ve stuck to my gut and built something that feels GOOD.


That’s the best blogging advice I can give: do what feels good.
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But for those of you who have asked for more of a step-by-step solution for growing a blog, here is the list of rules I’ve created for myself.

1. Reply to Comments

Those of you who have been reading (and commenting) for a while know this to be true. It’s the first blogging rule I made for myself: if someone takes the time to comment, I will take the time to reply. It’s not only a sign of respect, it also helps us have actual conversations (vs. one-sided responses) and has, in turn, created a real community here. As the years have gone on, I’ve changed it slightly so I usually only reply to comments that come in within the first 2-3 days of a post going live. But this same rule applies to email, too. Depending on how flooded my inbox gets, it might take a couple days or even a couple weeks to reply to them all (and it took even longer after the girls died). But I read everything and I do reply.

1b. To go along with the first rule, I’ve also always monitored comments and sent trolls to spam. It’s fine if someone has a different opinion from me or disagrees with something I say, and I’ll publish anything that’s constructive, or challenges me to think or even change my mind. But I won’t let trolls come in and dominate the conversation, and I especially won’t let people be mean to other people. If you don’t like me, save yourself the energy and just don’t read what I write, because I won’t publish your comment. This is a safe space for people to open up and have conversations, and I won’t let anyone come in and take that from us.

1c. I’ve also always been the one who responds to comments and emails personally. I know bloggers and business owners who hire virtual assistants to do this work, but that has always felt disingenuous to me and is something I can’t do. People write to you because they want you to read their words and they think you will be the one who replies. Even if it means there is a delay, it has to come from me.

2. Support Other Bloggers

A couple weeks ago, Stephanie asked if I could recommend ways for writers to “get their blogs out there”. My first response to this question is always the same: support other bloggers. And don’t just visit their sites and write short comments like “this was a great post” or “I do the same thing”. Write a comment because you care about this blogger and you want to see them succeed. Write a comment because you read someone else’s comment and you want to help them succeed. Write a comment because you want to be part of a community. And then share the post with everyone who follows you online, because you want to help this person’s message be heard.

When I first started blogging, I engaged with a lot of bloggers who were also documenting their own debt repayment stories. We cheered each other on, celebrated our successes, and helped each other with any challenges we had. It was not a strategy to get more readers or rack up pageviews. We were a community within the personal finance community, and I don’t know what they thought of me but I needed them. No one in my real life knew what my financial situation was, except for my blogging friends. I was more honest with them than I was with my own family. So, I always treated them like friends because that’s exactly what they were (and are).

When I finished paying off my debt, I gave a huge amount of credit to my fellow bloggers because I truly felt that I couldn’t have done it so quickly without their support—and I’ve always wanted to give that same support back to others. For years, that support took shape in the form of comments I would leave on people’s posts. I would comment because I read a post and thought OMG I NEEDED TO READ THIS and it felt really good to connect with like-minded people. And I would comment to thank someone for sharing their story, or for being honest and vulnerable, or for writing something that made me feel a little less alone in this world.

Again, as the years have gone on, I’ve had less time to comment on posts but I’ve found other ways to support bloggers. For starters, I help curate all the personal finance content you read on Rockstar Finance, which means I skim hundreds of blog posts each week and share my favourites with Jay. I used to share a lot of posts on Twitter, but now I compile a list of the ones I love and put them into my newsletter. And when something really touches me, I email the blogger personally. So no, I don’t comment as much anymore, but I still find ways to say OMG I NEEDED TO READ THIS and THANK YOU and then share it with my readers.

3. Write What Feels Natural (Not What Will “Perform” Well)

One thing I see over and over again in emails from people who are considering starting blogs is that they get overwhelmed by all the steps it will take to build something “the right way”. They think they need to have the perfect name and the perfect look and a bunch of perfect blog posts, before they can go live. Trust me when I say that it doesn’t need to be perfect. For over a year, the majority of my posts were just weekly spending reports!

On top of feeling like things need to be perfect, there are also a lot of formulas out there for what could make a blog post rank high in Google or get more shares or even go viral. Here’s the only personal lesson I can share about that. Whenever I have tried to write a post that was more formulaic, I hated the process and hated what I was writing and usually deleted it. Whenever I write something that’s on my mind, the writing flows naturally and it gets a great response. These posts are honest and personal, and typically only take a couple hours to write. The result: they get more comments and emails, and support from friends around the world. Who the heck cares about ranking high in Google? I could never ask for more than that. <3

Oh, and my advice for anyone who is thinking of starting a blog: write a handful of blog posts first. Write them on your computer or in a Google doc or by hand or whatever you like. Just write the first few posts that come to mind and see if you actually enjoy the process. At the end of the day, if you want to maintain a blog, you just have to enjoy writing stuff and putting it out into the world. If you like those first few posts, come up with some ideas for your next ones and then start getting the technical stuff setup. But always start with the writing. Everything else will come together, after that.

4. Don’t Worry About the Numbers

There are a lot of numbers you could consider, as a blogger: your pageviews, your unique visitors, the number of comments you get on posts, the number of times your posts get shared, the number of people on your mailing list, all the followers you have on social media, and so on. And there are a lot of ways you can boost each of those numbers. But, to go along with the idea that you don’t need to force yourself to write content that will “perform” well, you also don’t need to do other things strictly so it will boost your numbers. You can, if you want to. But you don’t need to—and here’s why I don’t.

I didn’t start my blog with the intention that I would ever make money from it. And, unless you’re trying to make a lot of money from ads or affiliate links on your site, these numbers are just a vanity metric. Nobody cares if you have 1,000 followers on Twitter or 10,000, except for you. It doesn’t mean anything. And for that reason, I won’t play games online that do things to dramatically increase the number of readers or followers I have. Continuing with the example of Twitter and even Instagram, some bloggers follow tons of accounts in the hopes that many of those accounts will follow them back. I’m not kidding. This is a thing. It is a vanity metric, and it is also a false way of determining someone’s potential “reach”. (That’s a note to companies who pay “influencers”.)

Instead of worrying about increasing your numbers, focus on engaging with the readers and followers you have right now. This goes back to my first rule: reply to comments and emails. Also reply to people on social media. There are people right here and now who are interested in what you are saying. Say hi to them! Answer their questions. Help them in any way you can. They are human beings, not numbers. And if you become focused on getting the next 100 or 1,000 or 10,000 followers, you will look past the ones you already have—and those are the ones who matter most. So don’t worry about the numbers, and instead put your energy into fostering relationships with the people who are here and now.

For bloggers who are curious how this rule affects your numbers, I opened up my Google Analytics, mailing list, social media accounts, etc. and looked at how it affects mine. As far as blog traffic goes, I’m on track to have the same number of pageviews I’ve had for the past two years (so now three years in a row). I finished 2016 with about 20,000 followers across Facebook, Twitter and Instagram, and currently have about 25,000 (+5,000 in 9.5 months). And I went from having 6,300 people on my mailing list at the end of 2016 to 9,600 right now (+3,300 in 9.5 months). With so many people out there writing about how you can grow a blog quickly, these aren’t exactly numbers to write home about.

You know what two numbers I find interesting, though? My bounce rate was just 7.09% in 2016, and the open rate on my mailing list is 50.92% so far in 2017. People are engaged. And the community we’ve built together here means more than any number could.

5. Put People Over Profit*

I’m adding an asterisk to this point because I need to start by saying that this all depends on the reason you are launching your blog in the first place. If your goal is to make money, great! You probably don’t need to read this point. But if money isn’t your goal, that’s ok too. That also doesn’t mean you’ll never make a dime from your blog; it just gives you more control over how you want to earn that money one day. Here’s my story.

At some point, every blogger starts receiving emails from random companies all over the world who ask if you accept sponsored content (they will pay you to write a post about their product) or paid links (they will pay you to add links to random words in old blog posts). There is a lot of money to be made in this world. I have friends who make anywhere from $1,000 to $5,000/month in sponsored content alone. Add banner ads or sidebar ads to that and they are laughing—at me. I say “at me” because I have turned every single one of these offers down and earned exactly $0 from advertising on my blog. In fact, I even have a line on my contact form that tells people I don’t reply to these offers. I delete the emails.

There are so many reasons I don’t advertise on my blog, and they all come back to putting myself in the shoes of a reader. I hate going to sites and being bombarded with ads, so I don’t want anyone to have that experience when visiting mine. That’s also the same reason I’ve never added (and will never add) a pop-up to my site. Seeing those on other sites almost always makes me click “X” in my browser and then never visit them again. I don’t care about having a bigger mailing list. I care about my readers and the experience they have on my site—the experience that helps us build and foster a community. And let’s also remember that I am in the space of telling people to STOP BUYING THINGS THEY DON’T NEED. Can you imagine if I placed a banner ad at the top of that message?

At the end of the day, I won’t advertise on my blog because it just doesn’t feel good to me. I know this rule has probably cost me tens of thousands of dollars. My old boss once told me I could earn a minimum of $3,000/month from banner ads alone based on my traffic. But I don’t care and I won’t change my stance on this. It doesn’t feel good to me, and I’ve always told myself I could earn extra money in other ways—ways that do feel good to me. For years, that took shape in the form of freelance writing and even a few public speaking events. Yes, that means I actually had to work for the money (vs. earn passive income from my blog) but those opportunities came from having my blog and they felt good. Looking back, I can see they also helped me get my name out there in ways that posting sponsored content never could.

That’s not to say I’ve never made money from my blog. Going back to the first paragraph in this point, it just gave me more control over how I wanted to earn the money. In 2015, I decided the one way I would be comfortable making money from my blog would be by creating a useful tool and selling it. Since April 2015, I have profited exactly $26,807.34 from something I made for you: Mindful Budgeting. The print templates that I originally charged $20 for but are now free, and the physical 2016 and 2017 planners. I made those for you, and built a community around it for you, and have earned an average of $893.58/month for doing so (minus the 5% of sales I give to charity). It’s a tool that I know has helped people, and I made it myself vs. had a company pay me to tell you about it. That feels good to me. It’s not a product everyone needs and I’ll likely never earn a full-time income from it, but that’s ok. It feels good to me.

6. Always Be Gracious + Grateful

This last rule is one that is mixed into all the others. The kind way of saying it is: you should always be gracious with people + grateful for the opportunities that come your way. The simple but more brash way of saying it is: don’t be a jerk. One of the most interesting things I have observed as some blogs have grown is that egos grow right alongside them. I will never understand this. Of course, I think we are allowed to be proud of our work, and be proud of the blogs and businesses we’ve built. But at the end of the day, we aren’t saving lives. We are just people—humans who are trying to make it in this world, just like everyone else. And if we aren’t kind to the people around us, why would anyone want to read what we have to say or even work with us?

It starts by being gracious with your readers. If no one read your blog, you wouldn’t be where you are. Then, be grateful for every opportunity that comes your way—even the ones you don’t take. Whenever someone in the media contacts me for an interview, I genuinely still think to myself: really? Me? That’s so cool!!! The same goes for freelance writing and public speaking opportunities. And you can’t even imagine how literally every step of the book publishing process has made me feel. I’m constantly pinching myself asking if this is real life.

This all goes back to the golden rule you’re taught as a kid: treat others how you want to be treated. I don’t think the world owes me anything. And I don’t do things because I’m looking for something in return. In fact, I think blogging with zero expectations of what kind of response you’ll get from others is what helps you stay humble and so appreciative of whatever does come your way. As for me, I’m just over here documenting my life and all the experiments I’ve done in the past seven years, and feeling extremely grateful for everyone who has been interested enough to read, say hi and share it with others.

Before I wrap up this post, I want to add that I didn’t write this list of rules before I started my blog. It is something that has slowly developed over time, as every new interaction, opportunity and period of growth has occurred. And it took this shape because I always had my readers in mind. Some of these rules were made only after playing around with certain things the “experts” say we should do and quickly realizing it didn’t feel good to me. So yes, I have experimented with their ideas, and I think it’s perfectly ok for people to follow all of the advice and/or do things in whatever way feels good to them. It just doesn’t feel good to me.

I always knew there had to be another way, and there is—it’s called “your way” and you make all the rules. Mine will result in slower growth and will probably make you less money. But it puts people first and helps you stay humble and grateful for whatever comes from it. And in my experience, looking back now, I know that some really amazing things can come from it.

Do you have any other questions about blogging that I didn’t answer here? I’m happy to answer them (or share links to sites that can)!

  • βœ‡Cait Flanders
  • Why I Set Travel Intentions vs. Make Travel Plans
    My first trip to New York City was a blur. It was December 2012 and I had recently decided to give up on the idea that sobriety was right for me. Sobriety was not right for me. I wanted to drink. We spent our nights bar hopping and, I, getting blackout drunk, and we spent our days rushing all over the city with a hangover. Repeat, repeat, repeat, for three days. We saw a lot of sights (you can see the pictures: Day 1, Day 2, Day 3 Part 1 and Part 2) and did a lot of drinking. Bu
     

Why I Set Travel Intentions vs. Make Travel Plans

14 November 2017 at 20:00

Why I Set Travel Intentions vs. Make Travel Plans

My first trip to New York City was a blur. It was December 2012 and I had recently decided to give up on the idea that sobriety was right for me. Sobriety was not right for me. I wanted to drink. We spent our nights bar hopping and, I, getting blackout drunk, and we spent our days rushing all over the city with a hangover. Repeat, repeat, repeat, for three days. We saw a lot of sights (you can see the pictures: Day 1, Day 2, Day 3 Part 1 and Part 2) and did a lot of drinking. But without those pictures and the few drunk moments that still make me feel icky, I would tell you the one memory that stands out the most from that trip is how much my feet hurt.

It might seem like I travel a lot, but the truth is I feel like a bit of a late bloomer. While many of my friends went to Europe and Southeast Asia after high school and college, I didn’t go anywhere except for a trip to Vegas in my mid-20s and that trip to NYC when I was 27. I suppose there was also one trip to Toronto in my mid-20s, and partway through we took the train to Montreal and then visited friends at the Royal Military College in Kingston. But again, I was blackout drunk for most of that trip. (I don’t even remember what RMC looked like.) And again, one of the memories that stands out from all of those trips is how much my feet hurt.

I used to do the same thing Holly did in many of her early trips: tried to see as much as I could. The first trip to NYC is a perfect example. I listed all of the things I wanted to do and see, figured out which neighbourhoods they were in, and then mapped out our days in a way that we might actually be able to cross most things off the list. And we did! The pictures prove we did and saw all of the things. But the pictures don’t show how much my feet hurt at night, how I had to soak them in hot water before going to bed, and how much I cringed at the thought of having to put my shoes back on the next day. I didn’t want to walk another step.

That wasn’t what I wanted to remember from my trips. I wanted to remember the conversations we shared over coffee and meals; the taste of those coffee and meals; and the names of the cafes and restaurants I loved so much that I would hope to visit again. I wanted to remember how good it felt to get to know a city so well in just a few days that I could find my way around without directions; and how cool it felt to be able to give someone else directions, when they asked. I wanted to remember what the sky looked like when the sun went down over each landscape. I wanted to remember being there—really being there.

Fortunately, it only took a few trips for me to learn this lesson—and to learn how nice it could be to travel at a slower pace. I have the memories of my sore feet to thank for that, but I can also thank my blogging friends. It wasn’t until I started travelling to their hometowns to visit them that I realized I didn’t have to rush around to see everything each city had to offer. All I wanted to do was spend time with them. That’s why I was there. And whenever I travel somewhere now, I ask myself that same question: why am I going here? The answer helps me set an intention for the trip, rather than make a strict plan.

When I used to make travel plans, I felt busy and anxious. I also never felt like I got enough time anywhere I went—probably because I didn’t. I was so focused on getting from Point A to Point B that I didn’t soak in the journey it took to get there. I couldn’t remember the streets I had walked or neighbourhoods I was in, and I definitely didn’t remember the conversations we had. I just knew I had a couple hours to spend in every point I’d marked on the map, so I squeezed in as much as I could at each stop and then moved onto the next one. This always ended with me going home (to my hotel or a friend’s place) feeling like I’d run a marathon. (And did I mention the sore feet?)

The first time I decided to set an intention vs. make any formal plans for a trip was when I went to Denver in October 2014. My intention was to finally meet my internet BFF Clare, and to soak up any time I could spend with her. You’ll read a bit more about that in the book, but that was my only goal for the trip—which made everything else that happened feel like huge bonuses. Would I like to go to Red Rocks with another friend? Yes! Go on a spontaneous hike? Yes, please! Have lunch in a part of the city I’d never thought of going to? Yes, again! Because I didn’t have a calendar full of events, I was able to say yes to whatever came my way, and it felt good.

Not only did it feel good to be spontaneous, it feel good to let go of any expectations I had about what that trip might look like. And if I were to give anyone travel advice now, it would always be that: don’t expect anything. Just be open and be happy with whatever happens. That doesn’t mean you shouldn’t plan ANYTHING. I actually love the questions Holly included at the bottom of her post, and think of many of those myself. There’s usually 1-2 attractions I’d like to see, some friends I want to spend time with, etc. So I make sure I do those things. But I also leave a lot of room open in my calendar, so I’m not rushing from one to the other.

The result is always a trip I actually remember every detail of. I remember the conversations we shared over coffee and meals; the taste of those coffee and meals; and the names of the cafes and restaurants I loved so much that I hope to visit again. I remember how good it felt to get to know a city so well in just a few days that I could find my way around without directions; and how cool it felt to be able to give someone else directions, when they asked. I remember what the sky looked like when the sun went down over the landscape. I remember being there—really being there.

And that’s true of every trip I’ve been on since October 2014. I set an intention, leave my calendar fairly open, and am open to every opportunity that comes my way. And I come home remembering every detail and feeling totally content with how it went. Nothing is a blur. In fact, I can probably describe how I experienced a city through all five senses: what it looked like, how it smelled, what the food/drinks tasted like, what the sounds were and how it felt to be there. I might not “do it all” or “see everything” but that’s ok. I remember what I did do. Nothing is a blur. And the bonus: my feet never hurt.

The reason I’m sharing this story now is because I am in the middle of a month full of travel—and even though I’m moving at somewhat of a quick pace (four cities in one month), I’m trying to take it slow, set an intention for each trip and enjoy my time in each place. Here’s what it looks like:

Experiment #9: Slow Travel

  • spend a week in NYC (Nov 3-10)
  • spend a week in Toronto (Nov 11-18)
  • spend a week at home (Nov 1-2, 19-23)
  • spend a week or so in Victoria (Nov 24-Dec 3?)
  • enjoy downtime in every city :)

I’m happy to report there was a lot of downtime in NYC. I didn’t see many sights, other than what anyone sees when they walk around the East Village and Midtown and Central Park. But I went to one play (Tiny Beautiful Things – if you’re in NYC, please check it out). I also spent quality time with my friend Shannon, shared a few delicious coffees and meals with friends, and even met up with a friend from Vancouver who also happened to be there at the same time. And I narrated my audiobook. (!!!) That’s why I was there, and it was an incredible experience I’m so grateful to have had. Everything else was a bonus.

Looking ahead to next year, people keep asking why I want to go to the UK and what I plan on doing when I get there. Truthfully, I have no plans. I just want to go. I want to book a one-way ticket and have enough money that I can afford to stay for as many weeks or months as I want to. I just want to go. That is the intention. And by going with no expectations or plans, there is no real chance of being disappointed. Everything will be a bonus. :)

  • βœ‡Cait Flanders
  • My Top 10 Favourite Posts
    Hi friends! It’s been almost a full year since I stopped blogging. In that time, I’ve thought a lot about what I want to do with the archives—and, ultimately (after asking myself what 34-year-old Cait wants), I’ve decided to delete them. Last week, I went through 350+ posts, copied the content, and started hitting delete. (Fun fact: I published more than 260,000 words on this blog! And wrote tens of thousands more that I never shared. It’s safe to say I found my
     

My Top 10 Favourite Posts

19 August 2019 at 11:00
My Top 10 Favourite Blog Posts

Hi friends! It’s been almost a full year since I stopped blogging. In that time, I’ve thought a lot about what I want to do with the archives—and, ultimately (after asking myself what 34-year-old Cait wants), I’ve decided to delete them.

Last week, I went through 350+ posts, copied the content, and started hitting delete. (Fun fact: I published more than 260,000 words on this blog! And wrote tens of thousands more that I never shared. It’s safe to say I found my voice here.) Throughout the process, I noticed there were a few I wasn’t ready to let go of: the posts that were the most enjoyable to write, or the most honest to share, or that show who I am today. In old school-Rockstar Finance style, I picked out my favourite quote from each one and will leave them here for now. Enjoy <3

First, Let’s Talk About Money

Choose Your Own Financial Adventure – “Whatever you do, don’t do nothing. Be an active participant in your life—financial or otherwise—and choose the adventure you’d want to write home about.”

You Weren’t Born to Pay Off Debt and Die – “You might get 85 years on this planet. Don’t spend 65 paying off a lifestyle you can’t afford.”

On Being a Mindful Consumer

What Consumes Your Mind Controls Your Life (and Finances) – “The social media accounts you follow can take a serious toll on your finances.”

What It’s Like to Shop After Not Shopping for Two Years – “If I could sum up what the shopping ban did for my actual shopping habits, I would say that’s it: it taught me how to take the emotion out of it, so shopping is strictly a transaction now (as it should be).”

The Personal Stuff

I Got Sober at 27 (and I Didn’t Quit to Save Money) – “My Internet BFF Clare said it best: Not drinking is serious business. … But I can confidently say that I know I’ll be sober forever—because I need to be, in order to live my happiest, healthiest life.”

The Best Gift My Emergency Fund Has Ever Given Me – “My emergency fund gave me the best gift of all: the ability to invest in my mental health. It gave me the freedom to scale back on work. It gave me more time and energy to focus on myself. And it put my life back into my own hands.”

Why Spending Time Outdoors Matters to Me – “I love the outdoors because it’s the one place where I can truly be myself. My beautiful, messy, happy, sad, sober, uncoordinated and hilarious self.” (Featuring an #atwildwoman by my friend Amanda!)

What My Dogs Taught Me About Slow Living – “While I’ve been trying to figure out what slow living looks like, the girls have been exemplifying it their whole lives. And while they have needed me this month, Molly and Lexie have taught me lessons I will carry with me for a lifetime.”

And Finally, the Work :)

How I Slowly Grew My Blog My Own Way – “I always knew there had to be another way, and there is—it’s called “your way” and you make all the rules. Mine will result in slower growth and will probably make you less money. But it puts people first and helps you stay humble and grateful for whatever comes from it. And in my experience, looking back now, I know that some really amazing things can come from it.”

Why I’m Retiring from Personal Blogging – “I don’t want to be an expert. I just want to be a human.”

The post My Top 10 Favourite Posts first appeared on Cait Flanders.

  • βœ‡Spencer H Fry
  • What to expect when your team grows from 10 to 20 people
    I've been a guest on a few podcasts recently and one of the things that keeps coming up are the changes a company goes through when growing from 10 to 20 people — which is exactly what happened at Podia during 2019 (well, 9 to 19 people to be exact 😉 ). I’d like to share a few of the things that happened during this time and what you can expect if you’re experiencing similar growth. You're going to need to give things up Throughout my career as an entrepreneur, I've
     

What to expect when your team grows from 10 to 20 people

16 December 2019 at 15:03

I've been a guest on a few podcasts recently and one of the things that keeps coming up are the changes a company goes through when growing from 10 to 20 people — which is exactly what happened at Podia during 2019 (well, 9 to 19 people to be exact 😉 ).

I’d like to share a few of the things that happened during this time and what you can expect if you’re experiencing similar growth.

You're going to need to give things up

Throughout my career as an entrepreneur, I've gotten my hands dirty in every area of the business: product, marketing, support, community, success, and so on, but at 19 people, I just haven't had the time to be everywhere at all times.

I have to pick and choose what I do and what I don't do. I've chosen to continue to lead product, but I've given up almost all of my responsibilities in regard to marketing and support.

Part of that change is due to the fact that we've hired great people to fill those roles, including a Chief Marketing Officer who runs our 7-person marketing team and a Lead Support person who runs our 4-person support team.

At our size, it just makes sense for me to give up control over things that I can't spend a lot of time on — such as marketing and support — and give those responsibilities to people who are focused on doing them and doing them well.

Management is a necessity

When we were under 9 people, we skated by for quite some time with no real managers. In fact for a long time, it was just me running all departments, but as we began to grow, that broke down quickly.

Our individual departments got bigger. There were questions that needed answers more quickly. New hiring responsibilities. Individuals on a team needed a leader to help guide them. Strategy needed to be set for each department.

We needed to organize. We needed a leader to run the various departments. Things were breaking down without them. Who is responsible? Who owns the success here? Who owns the failure?

At 9 people, everyone could manage themselves and their own projects without stepping on anyone's toes, but as the product got bigger and as we got more customers, we needed to better coordinate across the company and the various departments.

We now have three managers (marketing, support, and development) who each run their own teams and their own 1:1s and are responsible for their “area” of the company.

We've always been an extremely productive company, but adding a management layer has allowed us to continue to be extremely productive as we've grown. A lot of companies get bogged down as they grow, but we haven't.

Company policies are a necessity

We've gone from informal, never written down HR policies to a dozen thoughtfully crafted, Podia-specific policies we now post in our new company wiki.

This lets everyone in the company be on the same page about how we do things from compensation philosophy to what kind of side projects are acceptable.

Policies written too early often won't match the vibe of the company you're trying to build, so waiting until things "break" is a great forcing function to know what's important and what isn't. I'm really happy we waited until we passed ten people before writing all of these down, but I'm glad we didn't wait any longer than that.

Knowledge sharing is harder

With more people working at Podia, it's harder to keep everyone up-to-date with everything that's going on.

We continue to have our Monday meeting that gives almost everyone a chance to talk about what they're working on for the week, but it's definitely more difficult for everyone to have a deep understanding of all that's happening. It's even difficult for me at times as the CEO.

It's also more difficult for individual departments as they grow. We now have 6 product developers — if you include our CTO — and they're often working on different projects. It's common that all product developers won't know every part of our codebase as well as they might have when our team was only two or three people.

Continuing to learn and grow is key

As a founder — and as a company — you need to continue to learn and grow every day. The skills you had at ten people are not going to be the same skills you need at twenty people.

You'll need to learn, listen, read, and adapt to the new situations that are thrown your way or else you're going to be behind.

I've been thankful to have a CEO coach this year who has helped me talk through lots of different situations we've had as a company throughout the past nine months, but if you can't afford a CEO coach, find CEOs who are at your stage or one or two stages above you and talk to them about how they got to where they are and what advice they can give you as a founder.

Learning shouldn't stop when you graduate (or don't graduate) college. You need to continue to exercise your brain and take in as much information as you can as your company continues to grow.

More people challenges

As you grow from 9 to 19 people as we did, you'll find that there are new people challenges. I think it's mostly because there are just more people on the team with different personalities, needs, and wants, but it's also because there's a new guard vs. an old guard mentality that you need to work through.

The early folks will always be the early folks, and you need to make sure you're integrating the new people as best you can.

Along with that, more people = more room for things to go wrong. You have to keep track of everyone's likes, dislikes, how they prefer to communicate, what's the best tone to take with them, and many other things.

People will continue to be the hardest part of the job for any CEO, but it definitely only gets harder as you grow.

That's why having great managers is so key when you grow. See above.

Plan, plan, plan

Lastly, with a growing team, it’s important to keep everyone on the same page, which can be accomplished by being really thorough with your company's plans. Whether that's the broader company strategy, the product strategy, the marketing strategy, or whatever, it's important to lay things out in a clear and concise way so that everyone understands what's happening.

While you could get away with not writing down a lot things when you were small, you need a "source of truth" for everyone to be able to refer to as you grow. You won't be able to have individual conversations with everyone as you grow, so having a really well-thought-out plan can do the talking for you.

  • βœ‡Anthony's Notes
  • allow the time that it takes
    There is this constant pressure in life to change how things are so that they’ll be how they can be. Looking back on the last decade of my life, I wouldn’t say I exactly had a plan, but I never went long without a side project or some adventure. I’m not sure if the drive to always have a side-hustle came from my discontent with how things are and a desire to build a different existence, or simply my broad diversity of interests.Either way, I’ve never felt content just do
     

allow the time that it takes

14 February 2017 at 06:13

There is this constant pressure in life to change how things are so that they’ll be how they can be. Looking back on the last decade of my life, I wouldn’t say I exactly had a plan, but I never went long without a side project or some adventure. I’m not sure if the drive to always have a side-hustle came from my discontent with how things are and a desire to build a different existence, or simply my broad diversity of interests.

Either way, I’ve never felt content just doing one thing. Mastery really was never a consideration for me, at least until recently–I have always been incredibly engaged until the moment the learning curve starts to taper. Once I have a foundational understanding of something, I’m pretty much ready to move on.

These days I find myself thinking more about how a two-pronged needle doesn’t pass through fabric. One hundred shallow wells will produce no water, yet a single deep one is much more likely.

Removing distractions and focusing on our goals is a beautiful thing and it allows us to make some serious progress towards the life we want. But that isn’t to say that it should be rushed–allow the time that it takes. Most things in life could be considered a practice, a daily one at that, one that we simply get better at slowly as time goes on. This is what most paths to mastery look like, slow, steady, intentional practice and honing of craft.

These things don’t have to be rushed, we don’t have to scramble to get to a place where we aren’t already. Perhaps much of contentment comes from appreciating and simply existing where we are while honing our practice for continual improvement. Finding that balance between pushing forward and sitting still.

Somewhere in there, lies the secret to happiness and contentment, that balance between personal growth and achievement, and seeking bliss within our current beings. So instead of rushing forward, perhaps we may allow the time that it takes and enjoy the journey along the way.

  • βœ‡Anthony's Notes
  • Looking Beyond The Surface of Entrepreneurship
    I remember when I decided that I wanted to be an entrepreneur–it was the day I realized that no job I could ever get would keep me engaged in a meaningful way. Unless, I suppose, I was able to work at a company that offered unlimited flexibility and creative control.In my early 20’s it always happened around my six month mark, when I’d start to feel the boredom strike. If the job was simple enough and I couldn’t find any particular ways to improve the processes involved,
     

Looking Beyond The Surface of Entrepreneurship

4 July 2017 at 06:29

I remember when I decided that I wanted to be an entrepreneur–it was the day I realized that no job I could ever get would keep me engaged in a meaningful way. Unless, I suppose, I was able to work at a company that offered unlimited flexibility and creative control.

In my early 20’s it always happened around my six month mark, when I’d start to feel the boredom strike. If the job was simple enough and I couldn’t find any particular ways to improve the processes involved, it felt very empty to me. In my younger days, that meant disengaging with the job and eventually, just not doing the job very well.

Starting a business changed all of that–all of a sudden there was no end in sight, no limit on the processes that I had to master. The work was never done and there was always some aspect of learning curve to tackle. It opened up an entirely new world of what work could look like for me.

Up until that point, I had learned that the way I did things, often quite differently, was completely wrong. School taught me this–I found myself only ever wanting to fit in, to look the same as the people around me, and just do what I was told. Because I wanted to fit in, I’d just sort of follow along with the way my teachers told me to think, accepting that it was the right way to do things.

You may be familiar with the below cartoon–in this case, I felt like the elephant.

College helped further affirm that I wasn’t very good at climbing trees. I remember sitting in lecture halls during my freshman year wondering how any of it was going to work–things just weren’t clicking for me.

Entrepreneurship is a mold-breaking opportunity–it widened the playing field to where I saw that the tree I was continually asked to climb was just one small part of life as a whole. It was just one test of a particular type of intelligence, one that largely reflected learning how to follow directions really well.

In business, you have to do the opposite.

If you do the exact same thing as everyone else in your field, you have no competitive advantage. When it comes to marketing a business, blending in is the absolute last thing you want to do. In almost every area of life oddities are rewarded–they’re what makes us stand out from the rest and allows us to be chosen over others.

Those oddities may provide a strategic advantage over our peers, even though it may be initially perceived as a flaw.

The Struggles Are Amplified

The hardest thing about being an entrepreneur is that the things you struggle with are amplified. If you thrive within a structured environment, you’ll be required to create your own that meets your needs. There is no longer anyone to tell you that you’ve done a good job for the day, you can head home content with your work complete. There’s no one to decide how productive you are, no quarterly review to determine your eligibility for a raise.

There is only your effort, your goals, and your definition of what a successful day looks like. How much is enough? When can we be done for the day? If you struggle with figuring these things out in a day job, taking the leap will blow these struggles wide open.

If You Want Something Different

If the structure that society has set up for gainful employment isn’t working for you, if you want something different, you should build something. Something you care about, something you’d like to see in the world if it doesn’t yet exist. If the “correct” way to do something isn’t the way you’d do it, but you got the answer wrong on the test anyway, try making your own test instead.

You don’t have to quit or take the salto mortale right away, but start building something and see where it goes. It takes a very long time to undo the damage done to our psyches throughout our lifetime. I’m only just beginning to learn that I can challenge authority when I don’t believe something is right. Just because someone says that’s the way it is, doesn’t mean that’s actually the case.

Do what feels good, do what feels right.

❌