I quit my corporate job to become a professional juggler (Part 1)

That's the story I tell myself when I wake up every morning. It's not entirely true, but it captures the essence of my journey into the world of portfolio careers.

Ana Calin

Sep 28, 2024

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"I Quit My Executive Role After 15 Years... to Become an Artist."

Sounds crazy, right? It’s the classic midlife crisis move: abandon the corporate ladder for something *wild* and unpredictable. But here's the twist—it worked, and it transformed my life in ways I never saw coming.

For over 15 years, I was living the executive dream. Jet-setting across continents, managing high-stakes projects, and enjoying the perks of financial security. But deep down? I was *bored out of my mind*. Corporate life looked glossy on the outside, but inside, I was craving something more. I was done with climbing a ladder that just led to more stress and fewer meaningful moments.

So, one day, I did the unthinkable. I quit my cushy executive role. No backup plan, no “exit strategy”—just a raw desire to do something that felt *real*. Art was calling to me, and I jumped headfirst into it, despite having zero formal training. Trust me, people thought I’d lost it.

The Crazy Part? It Worked.

Fast forward five years, and here’s where I’m at now:

1. Featured in 107 Top Media in 3 Years:

I’ve been in Forbes, Inc., CEO Weekly, you name it. Not because I’m some marketing wizard, but because I have a story people actually care about.

That’s what they don’t tell you in those ‘build your brand’ courses—people connect with authenticity, not the polished version of you.

2. Forbes Marketing Council Group Leader:

Yep, I’m now leading a group of top marketing professionals. The funny thing? I didn’t get there by “networking the right way.” I got there by being unapologetically *me* and saying things nobody else was willing to say.

3. $1 Million in Brand Deals:

This one baffles me. I thought I left the corporate world behind, but now brands are knocking on *my* door. Not because I have the perfect pitch deck, but because I tell real stories that align with their values.

Authenticity sells, folks.

Diversified Portfolio:

My income streams are all over the place—media features, online courses, speaking gigs, investments, board advising, newsletters, even art sales. It’s chaotic, but it works, and it lets me chase my passions without being tied down.

What I’ve Really Learned (It’s Not All Fluffy Advice)

Here’s the part where I get real. It wasn’t all sunshine and rainbows, and the lessons I learned aren’t the ones you'll find in a self-help book.

1. Your Past Is Your Secret Weapon, Not a Curse:

I used to think my corporate background was baggage I needed to shed. Wrong. It’s the very thing that gave me an edge. My corporate experience taught me about branding, marketing, and managing high-pressure situations. Don’t *erase* your past—use it to bulldoze a path forward.

2. Personal Branding? It’s Overrated Unless You’re Real.

Everyone’s saying, “Build your brand!” But here’s the deal: It’s not about curating a perfect image. It’s about being *real*—sharing your highs *and* lows. People can sniff out BS a mile away. Show up as you are, flaws and all. That’s what draws people in.

3. Diversifying Income Streams Is Non-Negotiable:

Look, relying on one income stream is risky. That 9-to-5 can vanish tomorrow. I’ve got seven different ways I make money now, and not one of them is stable on its own. But together? They’re solid. It’s the financial version of *don't put all your eggs in one basket*—except it’s true.

4. Networking Is Bull If You’re Faking It:

“Join a mastermind group,” they said. “Connect with influencers.”

No.

Be intentional. Surround yourself with people who *actually* inspire you and challenge your thinking.

Forget schmoozing your way up; find people who add *real* value to your life.

5. Curiosity Is Your Best Weapon:

Don’t be a know-it-all. Stay curious. Trends change, and industries evolve. Keep learning, keep experimenting. That’s how you stay ahead—not by becoming a carbon copy of what’s already out there.

6. Celebrate the Small Wins—But Don’t Brag:

People love to post their highlight reel online. I get it; I’ve done it too. But learn to celebrate *quietly*. It’s for *you*, not for validation. The real flex is doing the work, not broadcasting it.

7. Trust the Messy Process:

The path to building a portfolio career isn’t a straight line. It’s a zigzag, a mess. It’s full of failures, awkward pivots, and some “what the hell am I doing?” moments. Embrace that. It’s where the growth happens.

8. Have Fun—Seriously:

Why do we make work such a grind?

Building a portfolio career is supposed to be liberating.

If it feels like just another corporate job, you’re doing it wrong.

Let it be fun. Explore. Experiment. Fail spectacularly. It’s your ride, enjoy it.

Ready to Break Free?

The portfolio career model isn’t a trend; it’s now.

And it’s not for everyone—it’s for the bold, the curious, the ones tired of coloring inside the lines. So, are you ready to redefine what a career can look like?

P.S. What’s the one thing holding you back from a portfolio career? Drop a comment. Let’s talk about the real stuff.

I quit my corporate job to become a professional juggler (Part 1)

That's the story I tell myself when I wake up every morning. It's not entirely true, but it captures the essence of my journey into the world of portfolio careers.

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