Optimize from Altitude
Clarifying a Friendly Misunderstanding with Don Watkins and Chris Williamson
A few months ago, I came across Don Watkins’ provocatively titled video, “Optimization Is for Losers.” Not long after, I saw a similarly charged title from Chris Williamson: “Trying to Optimise Your Life Is Killing You.”
Both got my back up.
I’m an advocate for optimism. And to me, optimism means the rational pursuit of better outcomes—of living well on purpose. So when I hear “optimization” treated like a pathology, I don’t just disagree—I feel compelled to respond.
Because I don’t just believe optimization is compatible with joy, spontaneity, and sanity.
I believe it’s what makes them possible.
Like them, I want a life full of freedom, spontaneity, and deep engagement.
Don, for instance, describes a values-oriented approach to living—focusing on what needs to get done, what aligns with desire, and what he has energy for. In doing so, he’s actually shaping his life to support the experience he says he wants.
Whether or not he calls it this, he’s optimizing for life. The clarity with which he filters his actions through values and energy isn’t a rejection of optimization—it’s an implicit endorsement of the very approach I’m defending.
He jokes about maximizing "whim worship," and while he distances himself from hedonism, the core desire is clear: to live in a way that feels light, authentic, and free.
Chris similarly warns against hyper-mechanical living and the trap of excessive self-tracking.
I understand and share these instincts. But here's the crucial difference: I believe the only way to live that kind of life consistently is to optimize for it.
That is: you must optimize your environment, your systems, your energy, and your focus around your actual values. Otherwise, the freedom you crave will remain elusive.
What Are We Optimizing For?
This is the central question that gets glossed over. Both Don and Chris seem to conceive of optimization as an impossible state of flawlessness to be achieved by nitpicking at the margins. From this view, anyone who attempts to optimize is embarking on a kind of Mission: Impossible—constantly tweaking, never arriving, and inevitably burning out. They rightly critique this mode of living as inefficient, stressful, even self-defeating. But what they’re criticizing isn’t optimization at all—it’s a suboptimal parody of it. In doing so, they mistake the disease for the cure.
Properly conceived, optimization isn’t about maximizing everything all the time—it’s about defining a clear, meaningful goal (your own flourishing), and deliberately organizing your life to serve it. We don’t optimize from the weeds—we do it from altitude. From the level of values, where we can see the whole terrain. That’s how we make wise trade-offs, prioritize cleanly, and keep the system in motion without getting lost in the mechanics.
It includes sorting priorities, deploying your time, energy, money, and attention strategically, and building systems that sustain progress. It means designing your days in a way that includes space for flexibility, spontaneity, even idleness. It is precisely this thoughtful planning, this structured freedom, that makes it possible to live with what I’ve called a “strolling” rhythm: relaxed effort against welcome resistance, growth without grind.
Perhaps a better term is cruising.
Like a well-planned road trip, you press the accelerator with purpose, then ease off and coast when you can. You push harder when the moment calls for it, but never lose control.
Optimization, rightly understood, is what allows you to glide through life with focus, energy, and joy.
The Soundboard Analogy: Tuning Life’s Dials
Another way to understand this is through what I’ve called the soundboard analogy. Imagine each area of life—health, work, relationships, recreation—as a dial on a soundboard. Optimization doesn’t mean cranking every dial to 10 (or 11!). That would be noise, chaos. It means adjusting each thoughtfully, knowing that focus in one area requires letting others hum steadily in the background. You prioritize growth where it’s needed, hold others steady, and then rebalance. Over time, the whole mix gets better—your systems improve, and the baseline quality of life rises. Over time, your cruising speed increases—even as the effort feels the same.
That’s what growth through optimization looks like: calibrated, integrated, rising.
In this sense, optimization is not just compatible with flourishing—it is its method. Optimization means deliberately identifying what matters, and systematizing your life to maximize your ability to attain it.
Selfishness, Misunderstood
This misunderstanding mirrors the popular confusion about selfishness.
Most of the versions people reject are actually forms of self-destruction—hedonism, narcissism, sadism, the victimization of others in pursuit of power, or even nihilism dressed up as indulgence.
These are distortions, not examples, of what selfishness actually means.
Self-destruction is not selfish.
True selfishness means identifying and pursuing what genuinely supports your life.
The same applies here: true optimization isn't dehumanizing—it's humanizing. It's how you deliberately pursue the kind of life you want.
Optimization ≠ Perfectionism
Don and Chris both push back against a version of optimization that’s really just perfectionism in disguise. But perfectionism is something else entirely. It demands flawlessness. It paralyzes. It fears error.
Chris, in particular, makes this conflation explicit in his video. He argues that striving to optimize inevitably leads to burnout, anxiety, and an endless chase for self-betterment. But that’s a framing error. By treating optimization as a kind of neurotic idealism, he ends up rejecting the very method that makes sane, strategic living possible.
It also explains why he proposes “deliberate de-optimization” as the remedy. But what he’s reacting to isn’t real optimization—it’s a stereotype: the obsessive spreadsheet-wielder, tracking inputs and outputs without joy, context, or connection. That person exists—but they are not our model. They are what happens when optimization is divorced from values.
Real optimization is practical. It’s human.
It begins with reality and asks: What’s the best move I can make?
It grows. It learns. It adjusts.
As I put it in Perfectionism Is Anti-Optimism:
“Perfectionism demands flawlessness, and therefore immobilizes. It halts effort, hides joy, and often winds up in self-loathing or collapse. Optimization, by contrast, is driven by possibility. It says, ‘Given what is—what can I do?’ It engages. It experiments. It moves.”"
The Freedom of Systems
In Delimit to Be Free, I use the image of a fenced-in schoolyard: when children have no boundaries, they huddle in the center, unsure. But once a fence is built, they run to the edges. Structure expands their confidence.
The same is true of adult life. Structure doesn’t restrict your freedom; it enables it. When you know your priorities, when your environment is set up to support them, when you've pre-decided the basics, you're liberated to act, to create, to play. You can stroll through life, because you're not constantly chasing or reacting.
Don may say he doesn’t optimize—but by his own description, he wants to be extremely rational at the level of values. That’s the giveaway. If your values are clear and you're living in harmony with them, you're already optimizing—even if you resist the label.
Don't Abandon the Tool—Refine the Concept
I don’t reject the criticisms Don and Chris make. I share their distaste for mechanical living, for shallow hacks, for soul-less self-quantification.
But the answer isn’t to abandon the idea of optimization. It’s to refine it.
Because I am an advocate of optimism. And to me, optimism means acting on the conviction that good outcomes are possible—and pursuing them intentionally. That’s what optimization is.
So when people I admire take aim at the concept—whether directly or in passing—I feel the need to step in. Because words matter. And if we let “optimization” be misdefined as joyless rigidity, we risk discarding one of the most powerful tools for human flourishing.
What It Really Means to Optimize
Optimization, rightly understood, is not the enemy of joy. It's how you build a life where joy has room to show up.
True optimization is not mechanical.
It is not about cold efficiency or sterile output. It is about living as a full human being—engaged, value-driven, and alive.
The alternative is not freedom, but drift: a life of reaction, disarray, and missed opportunity.
Optimization, when grounded in values, is what lets you live deliberately while life feels almost automatic.
This is the joyful, flowing state we all crave—and one we each deserve.
Optimization is for winners. Trying to optimize your life isn’t killing you—it’s how you live fully, freely, and joyfully.
(—Optimization isn’t the enemy. Confusion is. If this post brought clarity—stick around.)