Before we begin…Solo(ish) is back.

I’ve missed writing about the realities of working for yourself. The wins, the struggles, and everything in between. There are conversations here that don’t quite fit anywhere else in my advisory practice.

If you’re building a business on your own, I hope you’ll find ideas, encouragement, and the occasional reminder that you’re not the only one figuring it out.

So, let’s pick up where we left off…

Right after college, I freelanced for several agencies.

Invoices instead of paychecks. That was the only real difference. I still showed up every morning. I still solved someone else’s problems in someone else’s office.

That wasn’t entrepreneurship. It just looked like it.

In 2015, after almost a decade back in-house, I went out on my own again. For real this time (1999 was the first time). More experience. More perspective. A much clearer picture of what it would actually take.

What I didn’t expect was how often I’d think back to a lunch in 1999 with my cousin Steve, an attorney who built his own practice from nothing. He told me that running your own business feels like there’s a sinkhole behind you. Always expanding. No matter how fast you run, you’re managing the gap between where you are and where the ground gives way.

Here’s the thing.

That gap doesn’t close. It just changes shape depending on when you’re standing in it. At 29, on my first jump into self-employment, the risk felt manageable. If it didn’t work out, I could always get another job. There was time to recover.

The fear was real, but so was the freedom. Later, standing in that same gap again (at 45) after being pushed rather than jumping, the fear looked different, but the tradeoff underneath it didn’t.

Whether you jump or get pushed, there will be moments of doubt. You’ll question your decision. You’ll stare at the ceiling, wondering if you’ve made a mistake. But somewhere in that mix of fear and freedom is the spark that keeps you moving.

That’s the trade-off nobody tells you about going in. You don’t get the freedom without the expanding responsibilities.

The people who keep going aren’t the ones who stopped doubting. They’re the ones who kept moving anyway.

Working for yourself doesn’t mean you work alone.

Andy

P.S. Have a question or topic you’d like me to tackle in a future edition of Solo(ish)? Leave a comment or send me a DM. I’d love to hear your ideas.

If you’re interested…

→ Continue reading. I’ve written more about deciding whether to go out on your own:

• The Best Self-Employment Advice I Ever Received: https://www.brenits.com/the-best-self-employment-advice-i-ever-received/

• The Scariest Thing I’ve Ever Done? Going Solo: https://www.brenits.com/going-solo-the-scariest-thing-ive-ever-done/

→ Never miss an issue. Tap the 🔔 at the top of my LinkedIn profile to be notified whenever I publish a new edition.

→ Book an IdeaStorm. Whether you’re deciding what’s next or simply feeling stuck, an outside perspective can help. Book a Focused Clarity Session. https://www.brenits.com/ideastorm-focused-clarity-session/