How to Pick a Career (Under Duress)

I’m sure this next statement will come across as dramatic, but I genuinely mean it: Tim Urban is one of the most influential writers I’ve ever followed. Which, to me, is remarkable for a simple reason—he uses stick figures and plain English to explain ideas most people overcomplicate.

One of his most enduring pieces for me is “"How to Pick a Career (That Actually Fits You).” I first read it in 2019, cover to cover, probably five times. Each pass revealed more nuance—a testament to how well it’s written. At the time, I used Tim’s framework to narrow my next career branch toward a clear north star: partnering with business owners and operating at the intersection of finance and entrepreneurship. I believed that this path could satisfy mission alignment, compensation, value creation, and value capture, the four tenants often described as “Ikigai”.

Tim’s framework worked. It helped me refine an internal compass I could continually recalibrate. With it, I set my sights on an MBA, specifically to pivot back into finance through investment banking. Three years later, in 2022, I graduated from UCLA Anderson and landed at Moelis, a firm known for excellence and interest-aligned work across Tech, Media, and Consumer. By any reasonable measure, Tim’s framework was doing exactly what it promised.

Then the conditions changed.

In November 2024, my brother Aaron and I sold the blockchain-turned-ticketing company we had founded in 2021. We had built a platform that gave creators—musicians, sports teams, business influencers—direct ownership and connection to their audiences. We found paying customers and ultimately partnered with a company that wanted to scale the technology further. On paper, this was mission success.

But success, I learned, doesn’t always feel the way you expect.

Overnight, you can lose a surprising amount of intangible value: identity, purpose, daily contribution. You also lose tangible things—income, benefits, a place to show up and be useful. This story is common among founders, whether they exit successfully or shut a company down, and for better or for worse (especially the latter) I’d lived enough versions of it to know the pattern.

The nine months that followed felt like starting from scratch. I needed to reassess what motivated me, where my energy actually came from, what skills I had that still mattered, and where real opportunities existed—whether as a founder again or as a W2 employee. Naturally, I returned to Tim’s framework.

But this time, it didn’t land.

I wasn’t a stable employee looking out at the horizon anymore. I was technically unemployed, and had no network having just moved to Nashville to be closer to family, and—crucially—I was no longer in my twenties. Pride, maybe naturally, crept in. I was far less willing to take a step “backward” in title or responsibility. Surely my résumé, my education, the logos I’d worked at, the company I’d built and sold—all of that should count for something.

Reality disagreed.

For every attractive role, there were thousands of applicants, many with a decade of specialization in a single function. Turns out, Google doesn’t want a finance-turned-founder-turned-generalist for an enterprise sales role; they want someone who’s spent ten years doing exactly that job. And frankly, that makes sense. I don’t blame them!

Looking back, I’m grateful for that period—not in a sentimental way, but because it revealed a lesson I hadn’t fully appreciated before. Here’s the punchline:

Whole-body orientation is a prerequisite to meaningful career decision-making.

Before my MBA in 2019, I took this for granted. But when your nervous system is dysregulated, even the best career advice falls flat. This is where most life-design frameworks quietly fail—not because they’re wrong, but because they start too late in the process.

That insight only fully clicked once I found myself working alongside cutting-edge science at iXpressGenes. Despite my last formal encounter with science being high school chemistry, Aaron and I became involved through advising work and was drawn to the mission: producing objective, preventative signals of inflammation-driven disease. What struck me most was how modern science often validates what humans have known intuitively for millennia. Common sense your grandmother lives by—rest, rhythm, rituals, regulation—now explained through biomarkers and neural pathways.

One such truth is simple but profound: when your brain is in fight-or-flight, you are making decisions from a different version of yourself. A version optimized for survival, not long-term coherence. Career decisions made in that state may be rational, but they often aren’t aligned.

That realization is what compelled me to write this.

We’re standing at the edge of a massive wave of white-collar displacement. Elon Musk—love him or hate him—has described AI as a “supersonic tsunami” for education and skill development. By sheer coincidence, I experienced a version of what tens of millions in the U.S., and hundreds of millions globally, will face over the next decade. That’s why I wrote this, and who I wrote it for.

I’m not worried about recent graduates. They’re digitally native, lightly encumbered with financial burdens, and physiologically adaptable (their brains are still plastic!). The group I’m deeply concerned about is the 30–60-year-old white collar worker: someone at peak earning years, with a mortgage, tuition bills, healthcare obligations. Upskilling gets harder with age (something about a old dogs and new tricks). Replacing a six-figure income under pressure is brutally difficult. You can do everything “right” and still find yourself exposed. This piece is for you.

After my own reorientation, I realized there was a formula that worked—but only when applied in the right order. I call the process Restoring Your Agency, guided by a simple mantra: Control the Controllables.

Here’s the sequence that mattered:

Phase 0: Physiological Baseline
Before agency can be restored, the system must feel safe enough to act. Non-negotiables:

No goals. No tracking. No identity claims. Just stability.

Phase 1: Social Re-entry
Only after regulation do:

Phase 2: Useful Action
Then:

Phase 3: Meaning and Structure
Only here do strengths, enjoyment, structural opportunity, and future orientation become honest rather than defensive. This is where Tim Urban’s framework—and others like it—can actually work.

Most career advice starts at Phase 3. I’m arguing that Phase 0 is the necessary foundation most (unknowingly) skip. Agency restoration is a descent before it’s an ascent. Down into body, basics, rhythm, repetition. Only then back up into choice, narrative, skill, and future.

If there’s one thing I hope you take from this, it’s this: you are not late, broken, or behind. You are navigating a structural shift no résumé could have prevented. The task isn’t to immediately reinvent yourself or outrun the future. It’s simpler—and maybe harder. Re-establish rhythm. Re-enter the social field without shame. Do something small and useful. Let competence return before demanding clarity.

Agency isn’t reclaimed through insight alone. It’s rebuilt through repetition.

Control the controllables. Get your feet back on level ground. From there, the path won’t reveal itself all at once—but it will open, one faithful step at a time.

RC