Your 20s aren’t just for building a résumé; they’re for stress-testing your risk tolerance — choosing, and living with choices without a safety net.
Each of my pursuits across VC, entrepreneurship, real estate, and more began with a decision that seemed risk-prone from the outside.
Some weren’t “well-timed.” Some weren’t “financially optimal.” Most weren’t recommended.
But they’ve taught me things no job description can teach — about clarity, consequence, identity, and values. Here’s how the biggest risks I ever took are shaping not just my career, but my mindset about work, ownership, and who I’d like to become.
1. Joining a Startup on the Side after the Founder Cold-Messaged Me
Risk: No pay. No job description. No guarantees.
Why I did it: I liked the vision — and my intuition.
What I learned: True upside starts where clarity stops.
A founder DM’d me out of the blue. No open role. Just an idea, early traction, and a lot of conviction. I said yes.
I helped build core ops and product in AI-fintech — not because I had a map, but because I was learning faster than any classroom ever could. I didn’t realize it then, but that one yes created a chain reaction that paved the way to everything that followed: my experience advising VCs, my obsession with product-market fit, and the trust to bet on other unscalable things (including myself).
Lesson: When you’re doing early-stage work, you aren’t joining an organization. You’re joining a bunch of open-ended problems — and choosing to claim them.
2. Starting My MBA Right After Undergrad
Risk: Going back to school while still trying to figure out my direction.
Why I did it: I didn’t want to wait to know just to “look more experienced.”
What it taught me: Learning is leverage when you’re still setting the context.
Most of them instructed me to hold on and apply later. But I was already deep in startup life, advising founders, and making difficult choices — and I wanted to learn while they were still fresh experiences.
My MBA provides me with the language for what I see every day: unit economics, go-to-market strategy, incentive structures. It’s not learning — it’s translation. Every week, I convert theory into actual work. And that in-bucket application is the ROI.
Lesson: Timing is less critical than momentum. If you’re learning rapidly, close the feedback loop sooner.
3. Building a Fashion-Tech Business From Scratch
Risk: Building a business in a highly competitive, capital-intensive industry.
Why I did it: I had to produce something that felt authentic.
What it taught me: Taking chances with creativity is real risk — and sometimes the most characteristic kind.
Fashion was present in my life forever. But I didn’t just want to create clothes — I wanted to design smarter experiences around how people interact with style, identity, and technology.
So I built it myself. While consulting. While modeling. While in school.
There’s no cookbook. No success warranty. But this is the most authentic work I’ve ever done — and it’s honed how I make decisions, tell stories, and think about consumer psychology.
Lesson: The startup that is a reflection of you will push you harder — and teach you the most.
4. Managing a Rental Property At 24
Risk: Having money invested in property while bulldozing everything else.
Why I did it: I wanted to learn about what “ownership” is.
What it taught me: There is no passive income. But active accountability changes the attitude.
The money worked — barely. But aside from that, I wanted to learn operational thinking from the other side. Managing a property was instructing me in contracts, negotiating, fixing things, being hospitable, and thinking ahead all packaged in one sale.
What surprised me most? How much real estate is about trust, not excel spreadsheets. Each tenant interaction is a micro-leadership moment.
Lesson: Owning stuff — not just equity, but responsibility — teaches you in decisions that snowball over time.
5. Pledging Multiple Roles at Once
Risk: Attempting too much and doing each well.
Why I did it: I perceived the connections others wouldn’t.
What it taught me: Range is worth it — if it’s intentional.
I’ve heard it a thousand times: “Focus on one thing.”
But I believe context-switching is a competitive advantage if you use each role to learn from others.
Modeling taught me how to manage energy and perception — which I use when pitching or presenting.
VC taught me how to think in systems — which allows me to create scalable product logic.
The startup keeps me reality-checked on execution — which keeps my MBA studies reality-checked.
Operating a rental had conditioned me to think in cash flow, not upside.
Lesson: When you live in the middle ground, your real work is integration — not optimization.
What These Bets Have In Common
Looking back, each of these risks had one common thread:
They were self-initiated. Nobody told me to do them. I had to choose to do them.
They weren’t “safe.” There were no guaranteed returns — only expansion.
They each demanded a different form of leadership. Sometimes soft skills, sometimes strategic vision, sometimes emotional toughness.
And every time, the result wasn’t just outward momentum — it was inward alignment.
If You’re in Your 20s, Here’s What I’d Say
Your biggest asset isn’t your network or your degree or your job title.
It’s that you can still figure out what you’re really capable of — before you’re instructed on what works.
The danger is not failure.
The danger is waiting for someone to say that it’s okay to try.
So build your own bet. Even if it’s imperfect.
Choose the path with the better story.
And pay attention to not just what you’re doing — but who you’re becoming along the way.