I work at one of the biggest companies in the world. I operate like a solopreneur. Those two things are not in conflict.
I'm a Senior Customer Success Manager at Salesforce. I manage a portfolio of enterprise accounts in the Consumer Goods vertical. I work inside a large, structured organization with processes, leadership hierarchies, and all the machinery that comes with scale.
I also take singing gigs on the side. I perform at events, invest real time in developing that part of my life, and think about my work as a performer the same way I think about my work as a CSM: what am I building, who am I building it for, and what does it take to be genuinely good at it?
When I tell people this, the reaction is usually some version of: "Wow, that's a lot — how do you balance it all?" As if the performing is a distraction from the real work, or the day job is what I do until I can do the other thing full-time.
I've come to think that framing misses the point entirely. The question isn't how to balance two separate identities. The question is whether you've decided that you own your career — regardless of where the paychecks come from.
I called it my Grown-Up Gap Year. I didn't plan it that way. That's kind of the point.
I didn't always think this way. For most of my career, being recruited was just part of the background noise — interesting opportunities, good companies, more money. I'd gotten so used to being approached by recruiters that I stopped replying to their outreach if they didn't list a salary above a certain threshold. My skills were in demand. I knew it and acted accordingly.
Then the market shifted. Overnight I went from hot prospect to one of hundreds of people caught in the same wave. The market seemed to be telling me I was worth significantly less than it had told me six months earlier.
I knew better. But I also realized something more uncomfortable: I had been letting the market define my value rather than owning it myself. My confidence had been borrowed from external signals — recruiter calls, competing offers, title progression — rather than built from the inside out. That made me more fragile than my actual skills warranted.
I expected the relief and the freedom that comes with a forced exit. I didn't expect the hurt — the ego-crushing feeling of not leaving on your own terms. And I was wholly unprepared for the roller coaster that followed.
What followed wasn't a job search. It was a portfolio experiment.
I co-founded a generative AI startup. I launched Kinetic Kaleidoscope, a fractional CMO and MarTech consulting practice. I set up outbound sequences and cold called and emailed 354 leads — and got humbled learning that sales enablement and actually selling are quite different things. I attended SXSW for the first time. I set up my performing service and booked multiple gigs. I applied for 100+ positions and in August, I gave up.
That "gave up" was actually the turning point. I stopped trying to replicate the career I'd had and started paying attention to what I'd actually been building — a genuine portfolio of parallel endeavors, each one teaching me something the others couldn't. The consulting work sharpened my strategic thinking. The cold calling gave me sales empathy I'd never had as a buyer. The performing reminded me what it felt like to earn an audience's trust from scratch.
Then I found a Salesforce role that felt like I'd written the job description — and I arrived having earned a mindset, not just survived a gap.
Market timing is real. But it's different from a permanent devaluation of what you know how to do. Conflating the two is one of the most expensive mistakes a talented person can make.
Operating like a solopreneur inside a big company means treating your employer as your most important client — not your entire career.
The solopreneur mindset isn't about going independent. Most people shouldn't. It's about a specific kind of ownership — treating your skills, reputation, and judgment as assets you develop and deploy, rather than inputs you trade for a salary.
At Salesforce, this shows up in how I approach my accounts. I'm not just executing a playbook — I'm building a body of work. The relationships I develop, the frameworks I create, the results I drive: those belong to me as much as they belong to the company. The company gets value from my work. I get value from the experience, the platform, and the caliber of the problems I get to solve.
That's a different relationship with an employer than the old model — where the company was the container your career lived in. In this model, the company is more like your anchor client. Significant. Valued. But one node in a portfolio you own.
We don't have a good "buy and hold" mechanism for being a value investor in our own careers. We should.
We treat skills like current stock prices instead of long-term assets. A bad hiring cycle convinces us our value has structurally declined — when what's actually happened is a pricing dislocation. A temporary gap between what the market is paying right now and what the underlying asset is actually worth.
Value investors don't panic-sell when the market is down. They hold — and sometimes they buy more. The career equivalent is continuing to develop, continuing to build, continuing to show up — even when the external signals aren't reflecting the value you know you bring.
The singing gigs are part of this for me. Not because performing pays at the same level as enterprise SaaS. But because they're a different kind of return. Every time I step on a stage, I'm building something that can't be laid off — presence, discipline, the ability to earn an audience's trust in real time. Those are skills that make me sharper at the day job in ways that are hard to put on a resume but impossible to miss in a room.
The portfolio isn't about diversifying income streams. It's about diversifying the experiences that compound into who you are as a professional.
"Whether your income comes from a W-2 employer or a fee-paying client, you are the common denominator. You are the asset. You are the brand. And that doesn't reset when you change jobs."
You don't have to leave a big company to think like a solopreneur. You just have to decide you own the career, not just the role.
The career infrastructure around us — résumés, job boards, LinkedIn optimization playbooks, performance review cycles — was designed for the old model. It's catching up slowly, and AI is reshaping it in ways we're still figuring out.
But the underlying principle is durable: treat your career like a portfolio, not a paycheck. Invest in it deliberately. Don't let a market cycle convince you your skills depreciated. And don't let a single employer — even a great one — convince you that they're the whole picture.
I work at Salesforce. I also perform. I'm building something in both places, and the combination makes me better at each. That's the portfolio model in practice — not as a career strategy, but as a way of being in your work.
Whether your source of income is an employer or a client, the solopreneur mindset is available to you. The only question is whether you claim it.