Just TWO DAYS left to get your reset. I know 2026 has gotten off to a rough start for many of us. Join me and thousands of others in resetting this year with our 2026 Daily Stoic Spring Forward Challenge.
Look around. People are rushing everywhere. Rushing through traffic. Rushing to get their kids to bed. Rushing through work to get to the weekend. No time to talk. No time to sit. There is too much to do. There is somewhere to go, the faster the better.
Even in ancient Rome, it was the same. People rushing to get their mail, rushing to the next round of games in the Colosseum, rushing to their next big accomplishment. Or at least that’s what they thought…
Seneca makes the point, however, that what we are really rushing towards—with deliberate speed—is death.
That’s what he means when he says that we get death wrong. Death is not some distant thing in the future, not some one-time thing that looms ahead. Instead, death is something happening to you right now. It’s happening as you read your email, it’s happening as you procrastinate that task on your to-do list, and it’s happening still more as you sit down to that coffee meeting you rushed to, even though you didn’t want to have it in the first place.
You’ll never get to live what has been lived again. So why are you rushing? Why are you thinking about the future at the expense of the present?
Why aren’t you showing up to the right here and now?
There’s still a chance to reset. No season reminds us of the possibility of rebirth, of the possibility for life to start anew, than Spring. It’s the time to reassess, to reset, to refocus. A time to plant the seeds of better habits and routines—so that you can reap more meaningful relationships and success and contentment.
And that’s exactly why we created The Daily Stoic Spring Forward Challenge, updated and refreshed for the unique challenges of 2026. Imagine if you got your year back on course. How much of a difference would that make by the end of the month? By the end of the year? Don’t write off the next nine months because the year got off to a rough start. Reclaim it. It’s yours. Now’s the time to get it back on track.
We start in just TWO DAYS, on March 20th. We’d love to see you in there.
Each morning for 10 days, starting on the first day of Spring (THIS FRIDAY, March 20th), you’ll receive a different Stoic-inspired challenge: an actionable exercise or method that you can put to use in your life right away to rid yourself of the physical and mental clutter holding you back from your goals.
You’ll learn how to tackle:
Digital distractions—inputs that constantly pull us away from what matters
Commitment overload—saying “yes” to everything and spreading ourselves too thin
Making amends—cleaning the slate and mending your important relationships
Mental baggage—unfinished business, unspoken apologies, and unacknowledged truths
Plus, you’ll be invited to attend TWO LIVE Q&A CALLS with Ryan Holiday, where you’ll get a rare opportunity to discuss the challenges and ask him your questions.
In addition, you’ll receive:
10 days of challenges built around the most effective Stoic principles
“I got so much out of the course. I needed the reset. Decluttering areas, knocking inessentials off my calendar and decluttering the mind takes a lot of discipline but is doable with daily practice.” – Lee Ann R.
“This challenge offered me an opportunity to make amends with the negative things that have happened to me in my life. I’ve been able to embrace my situation and found this challenge very therapeutic.” – Yannick
“This was a great opportunity to look inwards. Everyone in the community has been so kind, and helpful.” – Steve
“I’m seeing opportunities to put these challenges into practice everywhere.” – Daniel S.
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The Diet That Is Making You Miserable
A few weeks back, I was down near Phoenix and swung out to talk to the Chicago Cubs and the Arizona Diamondbacks who were in the middle of Spring Training.
These are elite athletes. Preparing for the talk, I was thinking about just how hard it is to do what these professional baseball players do. Hitting a baseball almost defies physics. The amount of time you have between when you decide to swing and when the b
A few weeks back, I was down near Phoenix and swung out to talk to the Chicago Cubs and the Arizona Diamondbacks who were in the middle of Spring Training.
These are elite athletes. Preparing for the talk, I was thinking about just how hard it is to do what these professional baseball players do. Hitting a baseball almost defies physics. The amount of time you have between when you decide to swing and when the ball crosses the plate is almost nothing. It is nearly physically impossible. That’s why so few people can actually do it. And even the people who can do it can only do it maybe three or four out of ten times. It is one of the hardest things in sports.
But it struck me, as I was sitting in the cafeteria after, helping myself to a prepared, perfectly portioned, macro-balanced plate of eggs with turkey bacon and fresh fruit, and chatting with some of the players, that while they spend enormous amounts of time thinking about their diet and nutrition and they have some of the best people in the world helping them optimize what they put in their bodies, they think a lot less about what goes into their brains.
In fact, many of them—like the rest of us—are injecting straight garbage on a daily basis.
We are, after all, flooded with more information than entire civilizations could have produced, let alone imagined.
The key practice in the modern world is not how to consume all of it, but how do we decide what not to consume? How do we stay informed about what’s happening without overwhelming ourselves with distractions? How do we manage our information diet with the same discipline that we would put towards our actual diet? Because just as what we put in our bodies matters, what we put—or fail to put—in our minds matters too.
Presidents of the United States face this problem most acutely. The president famously gets what is known as the Presidential Daily Briefing, typically three pages of top-secret information about international developments and concerns, delivered, as the name implies, daily, with in-person explanations and summaries. The best presidents listen intently, ask questions, and then apply what they’ve learned to their day-to-day decisions.
But we live in a world where the President doesn’t read this carefully curated document assembled by intelligence agencies and experts, and instead prefers to get his news from social media…and not just any social media network but one made up of his biggest, more ideologically zealous fans. If this bubble were not enough, there are also reports that he employs a special assistant whose job it is every day to bring him printed-out positive articles about himself to keep his spirits up.
Elon Musk is another example of how what you consume can warp you. He went from reading rocket manuals and reasoning from first principles to obsessively refreshing his Twitter feed. A man who could pay for a daily briefing rivaling even the most powerful heads of state instead mainlines information from trolls and pundits and conspiracy theorists.
This mirrors the problem we all face. We have access to the kind of information that emperors could have only dreamed of. This is real power, but as always, power corrupts and disorients and distracts. We have more information than emperors could have dreamed of. We are also subjected to moremisinformation than they could have conceived of in their worst nightmare.
Audio. Video. Text. It comes at us at incomprehensible speeds.
It takes discipline and wisdom to manage your information diet properly, to be a discerning and selective conduit for everything that’s coming at you.
Almost certainly, your information diet has too much real-time information in it. The news. The feeds. The notifications. Almost certainly, you would be better off if you read more books. If you focused on information with a longer half-life.
Personally, I prefer a steady diet of books about history and human nature (here’s a list of timely books I put together for 2026). They’re not all fun and sunshine—there’s plenty of darkness, too—but I learn far more from that than from endless scrolling. I’m deliberate about which chats and texts I participate in and who I spend time with. In programming, there’s a saying: “garbage in, garbage out.” I try to let in the opposite of garbage, because that leads to the opposite of garbage out.
“The art of not reading is a very important one,” Schopenhauer said of avoiding popular rubbish. It’s not how much you know, but that you know the right things. It’s not that you read, it’s what and how you read. “Do not be eager to know everything,” Democritus reminded himself in the fifth century BC, “lest you become ignorant of everything.”
Go straight to the source when you can. Check sources always.
Choose quality over quantity.
Find experts you can trust. Verify them first.
Favor information that has staying power over what is “developing” or “just in.” Try to get the big picture. Try to make connections between what’s happening now and what has happened before.
Seek out things that challenge you. Hear what the other side has to say.
Pay attention to where misery, negativity, dysfunction, and chaos sneak into your life. Ask yourself, when was the last time X or Instagram left you feeling informed. Reddit? Cable news in an airport? If it isn’t leaving you calmer or wiser, maybe it’s time to cut it off at the source.
You don’t have to be uninformed—just be intentional about what you consume and who you engage with.
The best hitters in baseball will tell you that what separates the good from the great, at the highest level, is plate discipline. It’s the ability to lay off pitches. To not swing the bat. To be discerning.
That skill applies here too. The feeds. All the hot takes. The notifications. The group chats. The breaking news. Most of it is designed to get a reaction out of you, not to make you wiser or better informed. You need to cultivate the discipline to lay off the junk. To not take in everything thrown on your plate. To discern what’s worth your time and what’s designed to get a rise out of you. To swing only at the right pitches.
Because you are what you eat. And what you read, what you watch, what you let into your information diet.
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3-Item StatusCurrent Location: Milwaukee, WIReading: Catastrophe by Christopher FergusonListening: What Do I Know by Deep Sea DiverIf you have a moment, reply with your own 3-Item Status.New WorkThis week’s Let’s Know Things is about Better BatteriesThis week’s Brain Lenses essay is about the Tocqueville Effect & the pod is about Mental FatigueBreak to MakeI recently updated the operating systems on my iPhone and Macbook Pro, as usual waiting a while because the folks behi
I recently updated the operating systems on my iPhone and Macbook Pro, as usual waiting a while because the folks behind some of the software I use drag their heels on getting confirmed-compatible versions of their offerings out the door. I also try to the avoid the worst of the new-release bugs that hide in every OS upgrade across every possible computing platform, these days.
The new versions of both OSes are pretty terrible. I’m sure this feeling isn’t universal, but the general consensus seems to be that Apple stumbled on this, producing strangely ugly, slow, disarrayed base-layers for their two most important platforms.
Some of the apps I use every day are now borderline unusable, lagging and sputtering under the weight of all the unnecessary decorations and doodads that have been crammed into this “upgrade.” My outdated phone, after years of amiably puttering along like a fresh device, is suddenly acting its age, creaking and sighing every time I ask it to perform even the simple of tasks.
If you couldn’t tell, I’m not happy with all this. And the incessant insistence that I upgrade—please upgrade, don’t you want to upgrade, you must upgrade now—delivered by popups and other dark pattern elements splashed across my screens, only add insult to injury.
They forced this on me, and I’m irritated about it.
That said, in these sorts of moments I try to remind myself that new stuff will almost always be irritating or terrifying at first, at least to some portion of the intended audience. And the older we get, the more likely we are to be thus disarrayed by novelty, because we become more set in our ways, more prone to exploit rather than explore, and more latently skeptical of the unfamiliar (on average, at least).
I also try to remind myself that truly wonderful next-step evolutions seldom arrive fully baked and perfectly conceived. In most cases they’re partway there; an interesting vision bundled up in an annoying, detrimental, maybe even confoundingly bad wrapper. It can take a while for the good to be identified and amplified, and the bad whittled away.
This isn’t just true of tech giants and their products. Every good thing I’ve ever made, all the incredibly valuable, fulfilling, healthful next-steps I’ve ever taken, have been processes, not one-shot pivots. And almost always we have to break things in order to make things: we can patch and suture the old for a long while, iterating on what works. But at some point that awkward collage of ideas will need to be reassessed and, ideally, reborn as something new; a fresh canvas to tweak, refine, and over the course of years revise into its own patchwork masterpiece (which will then be destroyed and replaced).
This isn’t always a fun thought, but it’s this or stagnation.
That’s what I tell myself, anyway, as another app fails to load and another digital tool I rely upon to do my job stutters and shuts itself down, the machines running them collapsing under the weight of un-asked-for tacky UI elements and yet another, buggy software update.
If you want more links to interesting things, consider subscribing to Aspiring Generalist.
We didn’t have too terribly much snow here in Milwaukee—around 6 inches—but it was several feet within the course of just a day or so up north, and the whole state of Wisconsin more or less shut down while the wind blew all that snow around at high speeds (even the Kwik Trip gas stations were closed, which is the local equivalent of the Waffle House Index of determining how bad a disaster is based on how many of these always-open types of businesses are closed).
What Else
After a couple of 70-ish degree (F) days, during which everyone was outside, in shorts, getting sunburned, the state of Wisconsin just basically shut down in the face of an historic blizzard. The weather whiplash is real up here, folks.
In other news, I’m in the process of revising my Truly Simple Tools app portfolio (lots of updates already released) and outlining/planning some new apps I’ve been thinking about for a while, but haven’t had the time to hunker down and tackle.
I’m also about a fifth of the way through a new, major (4th) draft of Methuselahs, which is just such a fun story and I can’t wait to share it with beta readers after this (and then a comparably quick spelling/grammar/etc) draft.
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We all play a part, or I suppose, more accurately, we have the opportunity to play a part. Some take that opportunity, some don’t. This became especially apparent to me last week while Dawn and I were rambling around Ireland for a week. Those that shared a bit of their time, shared a bit of themselves, took it upon themselves to play their part…they made our trip.
Thinking back to the various characters that played their part, that made our trip, makes my heart swell and my eyes we
We all play a part, or I suppose, more accurately, we have the opportunity to play a part. Some take that opportunity, some don’t. This became especially apparent to me last week while Dawn and I were rambling around Ireland for a week. Those that shared a bit of their time, shared a bit of themselves, took it upon themselves to play their part…they made our trip.
Thinking back to the various characters that played their part, that made our trip, makes my heart swell and my eyes well a bit. It also makes me realize that maybe I could do a better job of playing my part here in Rapid City. A better job of openly welcoming and being curious about the lives of those that, of all the places in the world, have chosen to visit the place I get to call home. Once tourist season rolls around, we’ll see if I have that part in me?
It had been 17-years since Dawn and I first visited Ireland, and although I have been fortunate enough to make several visits since then, this was Dawn’s first time back. Of all the places in the world, why Ireland again? If you really want to experience the music you have to go where it began, you have to go where the tunes are played and the songs are sung. Played and sang by those who have never known life without that music in it. That’s one reason, and for me, reason enough.
There’s always a risk going back to a place you have been before. A risk that whatever it was you found there is gone, or that it’s still there, but you are different. Maybe not better, maybe not worse…just different. So it goes. On this trip, when I found myself wishing things to be this way or that, I tried to just be. Not back, not forward, but right where I was, because I will never get to be right there, right then again.
When invited to play a part, play it. It will make all the difference for you and for everyone else sharing that particular scene, that particular time, that particular place. Because, “Quoth the Raven “Nevermore.” Nevermore is much more likely than evermore. While Dawn and I stood atop Mt. Brandon, chilled to the bone, engulfed by a thick shroud of mist and pummeled by a relentless Atlantic gale, a raven reminded me, “Nevermore”, and I couldn’t help but smile and sing.
That’s what you do in Ireland. You smile and you sing.
As we departed Dublin airport, as we climbed and banked towards the west, I watched as the many shades of green passed below. Johnny Cash found inspiration for his song Forty Shades of Green from this same vantage point.
“Again I want to see and do.
The things we’ve done and seen.
Where the breeze is sweet as Shalimar.
And there’s forty shades of green.”
Ireland is a beautiful site from above, but you got to get your feet wet and lean into the wind to really see it, to hear it, and to feel it.
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