the $350,000 mistake i almost made / #15
on ambition, approval, and opting out
I was committed before I was certain.
A meticulous error log, tracking every mistake. 90% of my social outings, rejected for months. Dozens of coffee chats instead, with students and alumni. Thousands of dollars spent on admission prep.
All in pursuit of something I felt I needed.
I just didn't know it wasn't what I actually wanted.
See, I approach big decisions the same way I approach design: research, plan, execute.
In the product management process, it’s that ambiguous early part of understanding your problem space, before jumping to solutions.
But somehow, with this decision, I'd skipped that step entirely. I'd assumed the question was: “How do I get an MBA?”
I even booked a Tokyo trip as a reward (or consolation, depending on the results) for completing the GMAT — this wasn't just an idea; I was doing it.
For the GMAT, the critical reasoning part came easily to me. My struggles with mathematics have been chronicled over my schooling years, so—
90th percentile — and I was proud. A little inflation to the ego, even. I thought: Maybe I'm built for this, after all.
But here's what I didn't want to admit: somewhere in the middle of all that planning, I'd lost sight of the user requirements. In this case, the user was me.
People asked, "Why an MBA?"
I had polished answers, shaped to sound like the essays I’d paid to get help with, or design roadmap presentations I gave at work:
“I want to bridge the gap between design and business.”
“I'm ready to lead at a more strategic level.”
“This is the credential that will unlock the next stage of my career.”
All technically true.
But beneath it all was a quieter assumption I’d never questioned: “I’m investing in myself, so it must be the right move.”
It’s a seductive logic. Plus, no one questions it. Who could argue with ambition?
As the most senior person from the design team in the room, I still had the least influence. My job title didn’t reflect the work I was doing.
I could guide the team to push the pixels, shape the design vision, and handle exec conversations — but I still wasn’t the one setting the strategic direction.
The ceiling was real, and an MBA looked like a crowbar.
Mentors agreed: designers like me were rare in those rooms, but “rare” didn’t equal “respected”. The MBA was supposed to be the proof: that I could speak their language, make their trade-offs, earn the seat.
So I did what always made sense to me: built more systems. Notion pages for each program type — full-time, part-time, executive — pros and cons laid out. Spreadsheets tracking calls, notes, takeaways.
I was climbing the ladder before I thought to check if it was leaning against the right wall.
At the time, it didn't feel like a decision to make. Just logistics to sort out.
Weeks after, the corporate machine reminded me of its indifference.
Layoffs hit. People I'd mentored, fought for, and believed in were suddenly gone. People who'd mentored me — gone, too.
That night, I updated my MBA spreadsheets — adding another column for layoff implications?. My stomach was feeling uncomfortable — not from the late dinner because of a 9pm call, but from something I can’t name yet.
The question I’d been dodging slowly surfaces, over meandering days and weeks of worrying.
What am I trying to fix here?
And I realized: the system itself was the problem, not my position in it.
I had a qualifying score. I had the plan. But I didn't have a why strong enough to justify two years and $350,000 to climb higher, in a machine that had just proven its fragility.
I’d built a perfect system.
It just wasn’t for a life I actually wanted.
So, here’s what I know now:
I thought I needed a crowbar to break into the room. Turns out, I just needed to stop trying to force the wrong door open. Or maybe even the wrong house?
The most dangerous goals are the ones that seem obvious — because they bypass your skepticism.
It’s easier to say “I’m getting an MBA” than “I’m walking away to figure out what matters”.
The former gets applause. The latter gets awkward expressions and unsure responses.
That social validation makes it dangerously easy to say yes to a path without asking: Is this even mine?
Now when I find myself spinning up plans — I try to pause and ask:
What problem am I actually trying to solve? And is it the right one?
Spoiler: This all happened in December of 2023, and I didn't go through with getting an MBA. (Obviously.)
I’m also not gonna lie: I still think about it sometimes, even now.
I don't regret taking the GMAT, and spending all that money on admissions prep. I don’t think it was wasted effort, and I’m proud of following through, and of what I'm capable of (especially in quant!).
But pride isn’t the same as clarity, and clarity doesn’t hand you blueprints — just a sketch of what no longer fits.
What I wanted was the freedom to design my own learning, on my own terms. Agency.
But what does agency look like in practice?
It looks like choosing my own constraints instead of accepting someone else's.
It's running experiments without waiting for approval.
It's building my own curriculum from books, online rabbit holes, random conversations, and whatever else sparks something.
No degree. No alumni network. No pre-mapped milestones.
Just me, learning out loud — writing, building, testing, rethinking everything I thought I knew about designing a meaningful life.
All the strategy and systems stuff that drew me to the MBA in the first place? I’m still doing it.
Just not in the $350k version they sell — and I’m glad I caught it before it became a mistake I’d have to justify for years 😅
Other things
This week’s experiment: Naps! Unfortunately, it’s not really working out the way I wanted it to: I get in the 20 minute nap in the afternoon, and can’t sleep until 11:30pm — with my usual bedtime at 10pm.
That said, maybe it is a hugely successful outcome if I ever needed to lengthen my day in the future.Also got a spiffy new domain for this newsletter: bydesign.is! Read aloud, it feels like an open question: exactly the way the writing is intended to be.
Until next time,
Jalyn