Unhandled Exception Error

Optimization failure ahead.

Written by Courtland, edited by Paige. Note: this post is long, and the email may cut off. We recommend reading in the app.

It’s not about the running.

Today’s a tempo day, and yesterday almost broke me. This should feel like punishment. But somehow, my legs are turning over, and I'm not just getting it done—I'm objectively feeling great. I can't exactly say how I got out here in the early dark, but the music syncs with stride in a way that flattens hills, inflates lungs, and makes me certain that headphones are a performance-enhancing drug.

It doesn’t happen often. But every now and then, things click. The machine hums—not because I let go, but because something I built holds. And every time it does, I wonder: is this the payoff? Is this what I’m chasing?

One of the things I’ve been trying to get right for the better part of a decade is "The Morning." It started in earnest when the office stopped being a daily expectation. Around 2017, structure became my responsibility in a way it hadn't been before, and changes were in order. I’ve always been an early riser. Initially, this was part of my “I don’t need sleep” fiction, but since delusion is weaker than biology, I eventually started going to bed and realized the mornings—not the nights—were what I truly wanted. Morning feels like wealth: quiet, cool, and dark. Unspent time.

And if it's precious, it must be used optimally. Maybe even maximally.

Fast forward years, and my daughter arrived—scowling, skeptical, and thoroughly unimpressed with the world—and suddenly all the potential slack in my imagined mornings went taut. There was still time, but none at all to spare.

So I engineered it: wake up—no alarm, get dressed, hit bricks. Run, then yoga. Shower—end cold. Meditate, journal, hydrate: feel superior. Breakfast was half-heartedly penciled in, but I've been failing that test since undergrad, and I don't believe in miracles.

In the right order, they were supposed to compound. In theory, if I could reduce transitions and calibrate the flow, I could put energy in once and collect on that energy forever.

In practice, every touch, every change created friction somewhere else. It took three weeks to drag reveille from 5:30 a.m. to 5 a.m. consistently—and even then I wasn’t really “awake.” For every minute earlier I rose, I was a minute slower to get moving. For every silky transition from sheets to shoes to shalabhasana, there was a 20-minute grey-out in a shower that should’ve ended icy 21 minutes ago.

But that tempo day was the morning everything lined up. Clothes stashed by the door meant no creaky-stairs detours, so the earbuds went in early and the music swelled into a soundtrack. Suddenly, soreness dissolved and sleep inertia reversed—I was the main character. It’s immature, but tempo days feel like performance, not training, and when I ask and the body answers, it all feels inevitable. I won the run, yoga felt like the podium, and the cold shower refreshed rather than punished. In flow—on rails—I lowered myself to meditate.

Then my daughter cried—early wake-up, of course. Mentally, I was instantly up and moving; physically, I barely caught myself, eyes pinched shut, frozen in indecision. Obviously parenting first... But she's clearly fine. My inhale collapsed. I braced. Tension feathered through my neck and hands, and for the first time since starting meditation, I could account for every second.

I bolted to settle her like a horse out of the gate—reflexive, story-driven, very “mindful”—then plodded through the rest like I’d forgotten to finish the lap. Technically, I’d executed the routine, but I wasn’t holding anything I’d built. I was just… spent. Like I’d passed through the morning rather than lived it.

Huh. Well, that’s unacceptable. The point of a system is that simple completion delivers value. Ugly or pretty, if the bear is still in the carnival machine claw by the time the claw gets to the chute, then I get the. damned. bear.

That’s what makes even complicated systems worth it. I don’t identify variables for fun. But if I’m clearheaded—if I take time to surface the moving parts, build around them, control for noise—then minor fluctuations don’t matter. A missed assumption reveals itself; you recalibrate. The whole point is to make it safe to throw effort at the thing and get something back.

To complete the steps and get nothing?
That’s a violation of contract.
Like a ball rolling uphill.

Perhaps some of this is noteworthy in the specifics, but in general, it’s an old story. There’s a culture behind it. And while I’m uncomfortable with determinism—pretty sure this was just me, trying to brute-force better living through scheduling—the similarities across our 70-million-strong millennial cohort are hard to ignore.

I think our origin story for this goes something like: fed an undifferentiated glut of stuff by a capitalist machine tuned for attention capture, we work indefatigably to avoid post-decision dissonance on a second to second basis; we strive for The Best.¹ There’s always a best—taco, shoe, playlist—and there’s always a tool to chase it. So we do.

We optimize because we believe it will save us. Or at least spare us the regret of having chosen poorly. Not me, of course—I was just trying to live a ‘90s movie montage. But one notices the pattern.

In fact, the wrinkle in the narrative, for me, probably looks pretty thin from the outside. Outcomes and externalities don’t care. But for the record: whether delusion or fact, I don’t optimize out of avoidance. It’s not about fear, or conformity. It’s about excellence.

I did it because it felt like the most ambitious use of a limited resource. There were gaps; I could close them. So why wouldn’t I?

Every system is an opportunity to learn, a potential area of expansion, and—fundamentally—a bet on myself. If you want something, build the machine that makes getting it inevitable. It’s not anxiety. It’s conviction.

Decades in, I flatter myself: I’ve made something of it. Refined it—optimized it? Certainly personalized it. I option, select, and combine by reflex. High art in process.

But it’s just a damn breakfast taco. Any more headspace than “two, please” is certifiable.

The problem is, optimization isn’t a tool I use—it’s a home I live in, and occasionally take a vacation from. Still, my running shoes probably are better for me than yours are for you. I’m clearly sick. But my strain of the illness has been, and will continue to be, demonstrably useful.

And that’s the trap.

So when the energy feels justifiable, the outcomes are visible, and you chronically undervalue your own time—but you set modest goals (local presence, morning clarity, personal satisfaction)—the logic holds. You account for the 45 minutes outside, the 20 to 40 minutes of meditation, a reasonable fitness benchmark. Nothing kicks back. Everything delivers.

So how do you know it doesn’t work?

You don’t—until it doesn’t. Until you hit something you didn’t model for, didn’t control. And then all bets are off. Which, to state the obvious, is disorienting. Because if this doesn’t work… what does?

I didn’t find a bug; that wouldn’t be a problem. I overfit the model—tight tolerances, brittle logic. The system broke because you don’t bend your kid to your will. Which means there are things that don’t bend. Which means optimization isn’t safe. You can’t just “optimize better” and expect to escape the problem.

A hybrid approach is needed. Maybe a new model entirely.

Because the thing is, my generation doesn’t want good. We want exceptional—dominant across all criteria. That sort of works when you’re the kid in the Volvo, ferried from piano to soccer to tutoring. But if you’re still trying to dominate every axis by the time you’re the one driving the Volvo, you’re cooked. Domination isn’t presence. Control isn’t peace. And “intentional” is just a hashtag if you’re still keeping score.

So we learned our lesson. Identified the problem. Adapted accordingly.
Just kidding.

We changed nothing. We kept the system and mass-produced the part we couldn’t make room for.

Perfect lighting. Outfit sponsored. Green juice on deck. Vibes dialed. It looks expensive and smells cheap—but I get it. We industrialized intentionality.

System became ritual. Ritual became content. Content became performance. And now we act like systems failed us. They didn’t. We just stopped aiming them.

Optimization—real optimization—isn’t a list. It’s not aesthetic. It’s the internal search for meaning, followed by the external search for alignment. Then friction. Then iteration. And repeat.

It’s slow. It’s personal. It doesn’t scale.

So no, I’m not done with systems. They’re still the best leverage I know. But I’ve stepped away for now. And that means doing less of the things that aren’t actually optional—which is hard, and deeply uncomfortable.

Still, once you see that the old way can leave out what matters—even when it works—
you start to think: maybe don’t level up yet. Maybe build something new first.

And that’s worth a little discomfort.

1. For more reading, see: Barry Schwartz’s book The Paradox of Choice, or How Modern Life is Screwing Up Millennials.