v12 Make Your Career Yours

Jing Chen

30 Apr 2025 — 8 min read

Have you ever felt caught between two voices in your head — especially when thinking about your career?

One telling you to stay safe, stick to what you know.
The other whispering you're meant for something more — even if you don't feel ready yet.

If you're standing at a career crossroads — wondering whether you're qualified enough, ready enough, allowed to want more — you're not alone. I've been there too.

Recently, I had two conversations with friends facing big career decisions. They weren’t sure if they were "ready" to move — or if they should stay where it felt safe. Sharing my story helped them see new possibilities for themselves. It made me realize: If those conversations could help two people, maybe they could help more.

Over the past decade, I've built a career not by following a neat ladder — but by taking smart, imperfect bets:

Moving from data analytics into product management.
Shifting from manufacturing to tech startups.
Becoming a Chief of Staff without ever holding that title before.

At every step, there were people who doubted me — and people who believed in me. The nos stung. But they cleared the path for the yeses that changed my life.

You don't have to live inside the boxes others build for you.
You get to make your career — and your life — your own.

Let me show you what I mean. You're more ready than you think. And to back it up? We’re bringing in a little math. (Because if the numbers say so, who are we to argue? 😉)

The Galton Board: Normal Distribution

Random Bounces, Predictable Outcomes

Imagine a Galton Board — one of those machines where a ball drops from the top, bouncing randomly left or right on pegs before landing at the bottom. Each bounce feels chaotic. But when you drop enough balls, they form a predictable bell curve — a normal distribution — where most outcomes cluster around the center.

Most risks you take in your career aren't catastrophic. They’re just small bounces that still land you somewhere good. You don’t have to be perfect at every step. You just have to keep bouncing, learning, adjusting.

The Venture Portfolio: Power Law Distribution

A Few Big Bets Change Everything

In venture capital, investors don't expect every startup to succeed. In fact, they expect most to fail or return very little. But a few — maybe 1 or 2 out of 20 — return 10x, 100x, even 1000x the investment.

That’s a power law distribution — where a tiny percentage of outcomes drive the majority of the results.

You don't need every move to be brilliant. You need a few bold bets that create breakout opportunities. When you realize this, everything changes: You stop trying to be perfect. You start thinking bigger — and braver.

Seven Lessons That Helped Me Build a Career Outside the Box

1. Most Risks Aren't Catastrophic (The Galton Board Truth)

When I moved from digital marketing into managing a $20M+ physical product line, it felt like standing at the edge of a cliff.

Some days, I felt like an absolute idiot — terrified of messing up a launch or losing retail placements. Other days, I felt like I could conquer the world.

It was a year-long roller coaster. But here’s the truth: most risks aren’t catastrophic. They're messy. They're uncomfortable. And they almost always lead somewhere better. I didn’t just survive that leap —I launched new products, secured top retailers, and built confidence I still use today.

Later, when I chose a risky startup over a safe CPG offer, every friend I trusted told me to stay safe. They meant well. But at the end of the day, only I knew what would light me up.

You can listen to advice.
But you have to bet on yourself.

Recently, when a friend wondered if she should plan her whole career around a baby 18 months away, I told her:

You don’t need to freeze your life today for what might happen tomorrow. Choose what excites you now. The future will adjust.

🎯 If you're asking:
"What if I make the wrong choice?"
Remember: most bounces land somewhere good. Pick what lights you up today.

2. Network Compounding: Maximize the Factors You Can Control

In the Galton Board, balls bounce randomly — but in real life, outcomes aren't purely random. There are forces — relationships, reputation, skills, and timing — that tilt the board in your favor.

I realized over time that career success isn’t just about showing up — it's about stacking the odds:

Building relationships before you "need" them.
Becoming known for trust, competence, and generosity.

That’s how one of my early friendships — with someone I respected deeply — eventually became a powerful reference point to my Chief of Staff opportunity.

🎯 If you're asking:
"How can I increase my chances of getting noticed or considered?"
Focus on tilting the board: build trust, be known for excellence, and help others long before you ask for anything.

3. Manufacture Good Luck: Make Your Skills Impossible to Ignore

Luck favors the visible — and the bold.

As a student, I didn’t just send resumes. I built my own personal website, showcasing real case studies. That website helped me land a prestigious summer internship — out of hundreds of applicants — and later, a role leading a national retail channel for a major brand.

Similarly, when I started my first corporate role, I didn’t wait for someone to "promote" me. I shared dashboards, presented insights, and made my work seen.

Recently, I gave similar advice to a friend:
Don't just apply for jobs online. Build a product, a case study, or a real project. Show people what you can do — not just what you say you can do.

🎯 If you're asking:
"How can I stand out when I'm applying for roles?"
Create luck by creating proof — visible, undeniable evidence of your value.

4. Direction > Speed: Choose Growth, Even If It's Messy

After my daughter was born, I pivoted into the startup world — seeking faster growth, bigger challenges, and deeper learning. It wasn't a smooth path:

I got laid off while pregnant with my second child due to company run-way.
I navigated career uncertainty while balancing newborn life (twice).

But despite the risks and challenges, the career acceleration, learning, and resilience I gained far outweighed the "safe" corporate ladder I might have otherwise climbed.

And as someone who's experienced postpartum life twice, I told my friend — who is thinking about family planning:

Returning to a job that excites you matters.
Because motherhood brings huge physical and emotional changes.
Doing work you don't love only makes the hard seasons harder.

🎯 If you're asking:
"Should I take the safe job now because of future plans?"
Prioritize joy and growth today. The future will thank you for it.

5. Play Impatiently with Actions, Patiently with Results

Early in my career, I didn’t have the luxury to pick the "perfect" roles. Visa sponsorships and job market realities meant I took what was available: data analyst or product/channel manager for power tool and accessories.

Not glamorous. Not even my biggest strength. But I squeezed every ounce of learning out of those roles:

How to interpret Data
How to tell a story with Data
How to manage profit and loss
How to work cross-functionally
How to sell and negotiate with external partners

Today, those skills are part of why I thrive as a startup operator. They built a foundation that "sexy" roles alone couldn't have provided.

🎯 If you're asking:
"Am I wasting time in a job that doesn't feel aligned?"
You're not. Skills are compounding under the surface — if you show up with urgency and intention.

6. Optimize for Extremes: Be Too Good — or Too Unique — to Ignore

I wasn't the most traditional marketing student — not a native speaker, no deep local market intuition. But I leaned into my passion for graphic design, becoming the go-to person for powerful visual storytelling.

Later, I carved a niche by blending eCommerce and Omni-Channel expertise — long before it was trendy.

Today, my combination — Fortune 500 P&L experience, Startup operations leadership, Chief of Staff exposure — makes me rare, not average.

Recently, I told a friend with a background in both graphic design and product management:

Your difference is your strength.
You aren't "behind" — you're a category of one.

🎯 If you're asking:
"How can I stand out in a competitive job market?"
Lean into your edges. Own the weird, powerful combinations that make you irreplaceable.

7. Refuse to Live in a Box Others Build for You

At every stage of my career, there were boxes waiting for me. Some built by circumstances:
"You're an international student — stay safe in data roles."
"You started in Fortune 500 — why leave it?"

Others built by well-meaning people:
"You're a mom now — why risk starting over in Startups?"

And honestly? I didn’t always have the perfect title. I didn’t always have the textbook experience. On paper, I hadn’t "technically" done the job before.

Some people didn’t believe in me — and told me no. And yes, sometimes the nos stung. But here’s the gift: If not for those nos, I would never have found the people who said yes. The ones who saw potential, not just credentials. The ones who gave me chances to grow into something bigger than my resume.

When those opportunities came, I treated them with enormous gratitude — and repaid that trust with outstanding performance.

Because I knew:

The nos didn’t define me.
The yeses didn’t complete me.
I defined my own story — one brave move at a time.

Not every leap made perfect sense. Not every move felt easy. But every time I stepped outside someone else’s limits, I found a wider, wilder, more honest version of who I could become.

🎯 If you're asking yourself:
"Can I really pivot if I don't have the perfect resume?"

The answer is: Yes. There will always be people who say no. But there will also be people who say yes — and sometimes, their belief will open doors you didn’t even know you could knock on.