To the Person Whose Life Still Works
You can keep doing this forever, and that is the problem
Hi
Some months after my third exit, I sat down to solve the problem.
The problem, as I had defined it, was that I felt flat. The transaction had closed. The number was real. The thing I had spent years building belonged to someone else now, and the feeling that showed up was nothing like the one I had been promised by every version of this story I had ever heard. There was no elation. There was a strange, level quality to the days, as though someone had turned down the contrast on a life that had always been vivid.
So I opened a document and started planning. That is what I do.
I listed possible ventures, sketched the criteria for choosing among them, gave each option a rough weighting, and built something that looked very much like a decision framework. Thirty years of training told me that a flat feeling meant an unclear objective, and an unclear objective is a solvable problem. I had solved harder ones.
I want to be precise about what I was doing, because the error is subtle and it does not look like an error.
I was engaging the feeling the whole time, studying it, journaling about it, discussing it with people I trusted. The error sat elsewhere. I was assuming, without ever putting the assumption into words, that the feeling was a malfunction in an otherwise sound system, and that the person who had built the system was the right person to repair it.
It took me the better part of a year to consider a different reading. What if the flatness was not interference with the signal? What if it was the signal?
That sentence is the whole essay, and I am aware of how easily it becomes a greeting card. So let me spend the rest of this piece making it precise enough to be useful, and honest enough about its limits that you can tell when it does not apply to you.
The reflex that built your life is now running the repair
Watch what accomplished people do when a life stops feeling alive.
Motivation declines, so they rebuild the morning routine. Meaning thins, so they set a larger goal, on the theory that the last one was simply too small. Restlessness grows, so they change the job, the city, the org chart, sometimes the marriage. Uncertainty persists, so they gather more information, which has the additional benefit of feeling like progress while nothing is being decided.
Every one of those responses is a strategy that has already worked, often spectacularly, which is exactly why it gets reached for. A person who has spent decades converting discomfort into an engineering problem has a great deal of evidence that discomfort is an engineering problem.
Notice the assumption riding underneath all of it. Each response assumes that the self doing the assessing, and the values it uses to assess, are entitled to define what counts as a solution. The objective gets swapped out again and again, while the one choosing the objectives never comes up for review.
Some problems are corrections
Depth psychology, the tradition that runs from Jung through Hillman and the analysts who followed them, works from a proposition that sounds modest until you sit with it: a person is never fully transparent to themselves. The part of you that plans and explains and pursues is real, and there is more of you than that. A good deal of what organizes a life sits outside conscious intention.
If that proposition holds, then a difficulty changes status. It might be exactly what it appears to be, a straightforward obstacle to remove. It might also be something more like a correction: a neglected part of the person demanding representation, a capacity that got shelved during the years when it could not pay for itself, a life whose organizing principle has reached the end of what it can produce.
Jung’s word for the forward-looking version of this is teleological, and the word is far older than psychology. It comes from the Greek telos, the end a thing is aimed at, and it carries Aristotle’s oldest question about living things: to explain them fully, you have to ask what they are for and what they are becoming, in addition to what made them. An acorn is explained by soil and rain, and also by the oak it is on its way to becoming.
Jung imported that ancient question into the psyche.
Reading a life teleologically means asking, alongside what caused the present difficulty, what the difficulty may be pressing the person toward. I hold that as a question rather than a doctrine.
I have no way to prove that a psyche has intentions, and I distrust anyone who tells me they do. What I can say is that the question predates psychology by more than two millennia; and questions do not survive that long without paying their way.
But you do not need metaphysics to use the move. You only need to be willing to run one additional question before reaching for the fix:
What would this problem be interrupting, if it turned out to be doing something rather than merely happening to me?
There is a version of this idea currently everywhere, and I want to separate mine from it.
The Stoic formulation …the one that runs through Marcus Aurelius and has been carried to a very large audience by Ryan Holiday, says the obstacle is the way. The very impediment to action advances action.
It is good counsel and I have used it. But let’s look closely at what it preserves: in that reading, the destination stays fixed and the obstacle becomes fuel for reaching it. The obstacle serves the plan.
What I am describing is different because it puts the plan itself in question. Sometimes the difficulty arrives as a challenge to the journey’s authority, and burning it as fuel only postpones the hearing.
Where this reading stops being true
Here is where writing like this usually goes wrong, so I will be direct:
Not every form of suffering is an instruction.
Clinical depression is an illness. It has a physiology, it responds to treatment, and reading it as a summons is both false and dangerous. If your flatness comes with disrupted sleep, changed appetite, a body that will not respond, or thoughts of not being here, that is a medical situation, and it belongs with a clinician.
The same goes for grief in its acute phase, for burnout that has crossed into physical depletion, and for distress that follows real harm. There is nothing developmental about untreated illness.
What I am describing is narrower. It is the specific condition of a person whose life continues to function, who can get up, perform and deliver; and for whom something has nonetheless gone level. The engine runs but the vehicle no longer seems to be going anywhere the driver chose.
Even there, the language should stay provisional, and you will notice this essay leaning on words like may, can, and sometimes. That is deliberate. This is one possibility worth examining before reaching for another solution, never a diagnosis.
Check the instruments
That restraint has a practical edge, and my first career handed it to me.
For the majority of my adult career, my on-the-job training has been in biomedical engineering. I have spent more than fifteen years in the diagnostics industry: the business of designing, building, and validating the machines your lab results come from.
That work installs a reflex that never leaves: before you interpret a signal, verify the instrument’s repeatability and reproducibility (a.k.a. gauge R&R).
To apply this engineering concept in life, we have to simplify it. It essentially alludes to a reading that looks like it means something important but actually simply be drift in the sensor.
So when the flatness in me persisted through the planning and the journaling, my troubleshooting protocol finally reached the layer I had been skipping: the hardware I live in. In plain terms: I went to the lab and had my blood drawn.
A set of comprehensive lab panels to include the full hormone workup: testosterone, cortisol, thyroid, and all the ancillary markers that surround those. This was not the same set of clinical lab tests that your physician might order at an annual physical…it was a much more comprehensive set of panels; all read with a different question in mind.
That question deserves spelling out, because it took me years inside the diagnostics industry to see it clearly. When a physician tells you that your labs are normal, what they mean is that your values fall inside a reference range, and a reference range is a population statistic. That statistic describes where most of a broadly defined healthy population happens to land, the sedentary averaged in with the athletic, the thriving averaged in with the merely upright. ‘Normal’ here answers one question: does anything require medical intervention.
So ‘normal’ says nothing about the question I actually cared about, which was whether a particular system (my body) was tuned for the life its owner intended to run on it. You can sit comfortably inside the margin of normal and be mediocre.
If you expect an optimized life, the hormones that regulate your energy, mood, recovery, and drive deserve better than “within range,” and that is worth an explicit conversation with a physician who understands the difference between treating illness and fine-tuning a system.
Checking matters most in the middle decades, because the biochemistry of the second half of life differs measurably from that of the first. Testosterone declines so gradually from the mid-thirties, roughly one percent a year by the British health service’s estimate, that clinicians resist calling it a male menopause. Average daily cortisol, the stress hormone, tends to rise with age, as well.
For women, the same story compresses into the perimenopausal transition, which a 2023 systematic review in Australasian Psychiatry describes as a distinct window of vulnerability for depression. All of it moves through the same decades that produce most of the reassessment this publication exists to examine.
My own numbers came back the way I suspect many do in this territory: somewhat disrupted, enough to matter, though nowhere near enough to be the whole answer. Nothing in the results called for hormone replacement therapy, so I changed the system’s inputs instead.
I rebuilt my immediate environment and my system’s inputs. I reorganized training around heavy lifting and Zone 2 aerobic work. Sleep went from the first thing I traded away to the one meeting on my calendar that cannot move. And, I added structured breathwork, mostly the breathing practices of pranayama, the Wim Hof Method, and later on Patrick McKeown’s Oxygen Advantage system. This all deserves a fuller treatment on another Sunday.
Sleep deserves its own accounting before I move on, because the baseline out there is bad, and getting worse. By the CDC’s count, more than a third of American adults now run on less than seven hours a night. The evening light of our screens pushes melatonin, the hormone that times the whole system, later than the machinery was built to handle. Circadian disruption is its own subject, as well. This one is large enough that I will give it future essays rather than a paragraph here, as well.
Over the following months the labs moved, and nearly everything downstream of them moved, too. The fog thinned, my conditioning came back and then went past where it had been, in ways I could verify on glaciers, over long miles of trail, and under a loaded barbell.
My wearables data agreed, as well. My Oura ring consistently scored in the high 90s, and even a 99, a personal record. The record matters less than what surrounds it, which is month after month of stable, high-quality sleep where there used to be significant variance.
Here is why I am telling you this, and it is the opposite of a protocol pitch. I am aware of the irony of recommending optimization in an essay about optimization’s limits; the resolution is the layer I’m getting at:
Tuning the machine is maintenance, and the question of where to drive it survives every tune-up.
My experience matched the literature, and I offer it as what it is: a hypothesis from a sample of one, worth sharing because it is testable and because it helped. It has helped everyone I advise, as well.
With the body tuned, the mood lifted and the performance returned. The question the flatness had been carrying was still there, though; sitting exactly where I had left it. The instrument had been adding noise but the signal survived the recalibration.
My advice on this point is simple: run the panel before you run the interpretation. Call it the instrument check. If your results call for treatment, that conversation belongs with your physician, and nothing in this essay overrides it.
But if you tune the body and the question survives the tuning, you have learned the one thing the labs can teach: what remains deserves a different kind of instrument to read it.
Depth psychology built several; and the oldest of them, the patterns it calls archetypes, is where next week’s essay begins.
Seeing it clearly changes almost nothing
This is the part I understand best, because it is the part my earlier training actually prepared me for.
Suppose you accept everything above. Suppose you recognize, clearly and specifically, that the life you built has become too narrow for the person you are becoming. What happens next, in my experience and in the experience of nearly every executive I have worked with, is very close to nothing.
The reason is structural: an identity is maintained by a system, irrespective of what its owner has come to believe.
Consider what actually holds a successful identity in place: income that depends on a particular kind of performance, a reputation that took decades to build and that people now navigate by, colleagues who have organized their own work around your reliability.
Add to this a family whose expectations were formed in the years when you were the one who solved things, routines that have automated the days, sunk costs that make change look like waste. And, least visibly, there is a set of people who benefit from your over-functioning and who will, without any malice, apply steady pressure toward its continuation.
Anyone who has designed a system will recognize what that is. It is a feedback loop with a strong restoring force. Perturb it and it returns to its prior state. Moreover, the return does not require anyone to intend it. Insight is a perturbation, just as much as a weekend of clarity is a perturbation. Both get absorbed.
Which means the useful questions are less inward than they first appear. Who currently benefits from my remaining the competent one? Which rewards still reinforce the identity I say I am ready to loosen? What costs of continuing are delayed far enough that I do not feel them yet? Which relationships would have to renegotiate their terms if I actually changed, and have I told any of them so? Where do the decision rights sit? And what would I monitor, over the next ninety days, to tell development apart from destabilization?
Those questions produce different action than introspection does, because they locate the pattern where it is actually held.
The danger that never forces a decision
Burnout says: I cannot continue doing this. A developmental threshold says something much harder to hear. I can continue doing this indefinitely, and that is precisely the danger.
The first announces itself. It arrives with symptoms, and eventually it forces a decision, which is a kind of mercy. The second issues no ultimatum. Nothing breaks. No emergency arrives to make the choice for you. A person can live inside it for a decade, performing well, admired, entirely functional, and never once be forced to ask whether the life still fits.
That is the condition this publication was built to make harder to overlook.
The practice
One question, and I would sit with it rather than answer it quickly:
Where are you still succeeding at something whose continued success may now be preventing a more important question from arising?
If a specific thing came to mind before you finished reading the sentence, that is worth noticing. Do not act on it this week. Write it down, name one person whose expectations would have to change if you took it seriously, and notice what happens in your body when you imagine telling them.
And if you are willing to write back one line, make it this: what in this essay felt most true, and what felt most incomplete?
Replies reach me directly. I read every one, and they shape what I build here next.
A note about last week: Nims Purja died on Broad Peak with nine of his companions, and I broke the Sunday schedule to write about it. That piece stands outside this sequence: The Grief That Doesn’t Look Like Grief. Today’s essay resumes the schedule.
Next Sunday: the archetypes. The old patterns that organize a life without asking permission, and why understanding yours completely can leave you living it anyway.
Start here
Every essay in this publication builds on the five that launched it. If you are new, they are the place to begin.