The Daily Bet on Yourself

Here is something that only my old friends know about me. When I was 23, I spent a year at a musical theater school in Italy. I learned to tap, do ballet, and took acting classes.

I used to sing. I did musicals in high school, sang throughout college (yes, acapella) but also choirs and solo performances. When I moved to Italy at 22, I continued through private lessons and masterclasses. It was fun, tapped into my creative side, and everyone was quite encouraging. When my contract at my job in Torino ended, I knew that getting a new job would be genuinely hard. I didn't want to go back to the US, so I thought: I'll do this for a year and see.

A lot of people thought I was crazy. I heard family members talking about it years later, asking off-hand  "yeah, what was that about?"

I don't mention it often in my story. Partly because it's a tangent that digresses from my already squiggly career, but also because I'm probably still a little embarrassed.

But I have never regretted it. I learned a lot about myself, including that the inward focus it required just wasn't good for my mental health, and I didn't love it enough to put my energy there.

I'm glad I found this out at 23, instead of spending a decade in an office job wondering what could have been.

At the risk of making this sound like a "How eating a sandwich improved my business" type post, I share this because becoming a solopreneur this time around has had moments that feel a lot like this. 

In leaving my old career, I took a risk and a bet. A risk that this could all be one giant flop and I'd be embarrassed to talk about it. But also a bet on myself. A bet that I was capable and competent enough to figure this all out. That the learnings would build on each other to bring me to something that made sense, aligned with my values, and fulfilled my definition of success.

A few years into it, I'm seeing that the bet isn't a one-time thing. I bet on myself every single day. Years ago, it was every time I fought the urge to job hunt instead of attending a networking event, or today when I'm sending that third follow-up email to someone who had a Clarity Call.

And then there are the days that test it.

Today, a client that had planned to restart our work together got back to me after a few weeks of quiet. When she did respond, I read between the lines: she wasn't coming back. Her business had picked up, she said. Her "AI website builder guy" had done too good of a job helping people find her.

I was thrilled that the strategy we had discussed, adding a blog for SEO, worked. I was less than thrilled that her AI guy got the credit.   

I'm genuinely happy for her. And it still stings a little.

Not because I'm not busy, or because one client changes the picture. But because this is the part of solopreneurship nobody really talks about. The quiet exits. The moments where you sit with it for a minute and wonder what you could have done differently, before you move on. (Usually, the answer is nothing).

Solopreneurship is the ultimate bet on yourself. It requires constant intrinsic motivation, getting comfortable with the unknown, trying and failing and trying again, making decisions when there is no clear right answer.

Betting on yourself doesn't mean the hard moments stop happening. I've had enough of them now to know they pass, and that what you build in the meantime is what matters. But I decide, again, that they're worth it.

I wouldn't want to be anywhere else. And I'll never have to ask "What if?"

What are you betting on right now?