Okay, Not That: Dialing Back on the Solopreneur Life
When I was 17 years old, I spent the summer before college working a nine-to-five office job in a publishing house in Manhattan, earning money for tuition.
It had seemed like a glamorous field, but in reality I spent most of my days typing (extremely poorly, having taken AP Physics instead of keyboard class in High School) and staring alternately at the blank wall in front of my desk and the clock to the left of me.
The minutes til lunch, and til 5, ticked by. Slooooowly.
That summer I made myself a vow: I would never, never work a job like that again. No rigid nine-to-five for me. I wanted every day to be different, to be an adventure.
And I have pretty much kept that vow for my entire working life. Sure, I’ve had jobs - but never quite like that one.
It has a price. Everything does.
Most recently, that vow has taken the form or running my own businesses. For years, I’ve worn the title of "solopreneur" like a badge of honor. Freedom to create my own schedule, to say yes to only the projects I loved, to “be my own boss.”
So empowering, right? And for a long time, it was.
But somewhere along the way, the freedom that once felt exhilarating has started to feel, well, lonely.
Sometimes There Are Too Many Things to Juggle
So after years of hustling as a speaker, author, and voice talent—answering to nobody but myself (well, actually, to clients)—I’m feeling like “freedom” comes with its own set of handcuffs.
So I’m saying yes to a job again. Okay, it’s not nine-to-five, but it is five days a week. I’m getting me some golden handcuffs. I’m dialing back on the solopreneur life.
I’m not giving up on a dream. I’m simply choosing a different one. Priorities are shifting.
Don’t get me wrong - I am so glad to have been in this life. No week has been just like the week before. Every theatre show eventually closes. Every conference comes to an end. Always new creative challenges, changes to be made, schedules to piece together like a mosaic.
But lately - it hasn’t felt like fun anymore. If you’ve ever chased a big dream, you know it’s not always the straight, shiny road we imagine at the start.
“I’m not giving up on a dream. I’m simply choosing a different one. Priorities are shifting.”
Lately, I”m realizing that while I’m free to work in my pajamas (seriously who ever really does that?) I am also free to sit alone at my desk or in my recording booth day after day. I miss the belonging—the kind you can only find in a space where you’re part of something bigger than yourself.
Belonging—being part of a team, showing up to brainstorm sessions where ideas fly, and knowing that someone else will be worrying about the spreadsheets (because they actually like detail).
Enter radio- again. Though Theatre was my first love, Radio became another one later in life, when I was raising my kids.
Radio is where I found a way to do a fresh show every day, have a predictable schedule for my family, reach thousands of people with my words every day, and combine my own creativity with the mission of the station.
Ever since I left commercial radio almost two decades ago, I’ve loved the freedom of re-inventing myself. I’ve written a couple of books, spoken on keynote stages, travelled internationally, narrated audiobooks, worked in theatre and in a couple of films. I’ve raised my family and paid my bills doing it, thank you very much.
I also satisfied my itch for broadcast by being the steady reliable fill-in announcer at a local radio station. Fill-ins can always say no. So- always one foot in the door, one foot out.
Now, I feel a different need - the need to belong somewhere. Both feet in.
And I am learning to listen to my heart.
…and listen to your heart.
What if freedom isn’t all it’s cracked up to be? What if real freedom comes from knowing when to step off a path that no longer serves you?
I have the chance now to be a full employee at this radio station. Yep, five days a week. Gulp.
I wrestled with this decision in my head, but my heart felt excited about it.
The solopreneur life isn’t just a career choice; it can feel like part of your identity. Admitting that it’s no longer working for me feels a bit like failure. But here’s the thing: changing course doesn’t mean you’ve failed. It means you’ve grown.
And, as I recently heard on an episode of Somebody, Somewhere (yes, I binge-watched it in 3 ways while my husband was out of town), “Change can bring miraculous growth.”
(They were talking about crop rotation, but you get the idea.)
“Changing course doesn’t mean you’ve failed. It means you’ve grown.”
This isn’t about choosing between two extremes; it’s about recognizing when the road you’re on is no longer the right one. Sometimes, the bravest thing you can do is turn around and head back toward what feels right—even if it wasn’t part of the original plan.
So, I’m trading the title of “my own boss” for something better: team member, collaborator, someone who shows up to the same place every day and knows they belong. I’m heading back to radio, a world that feels like home.
Am I giving up freedom? Maybe. But I’m gaining so much more: boundaries that protect my evenings and weekends, colleagues who celebrate wins and share struggles, and the satisfaction of knowing I’m part of a mission bigger than just my own.
And honestly? A paycheck that doesn’t hinge on me pitching “just one more client” sounds pretty sweet too.
I’ll still do voiceover and theatre work. I’ll still be a speaker and keep writing when I feel like it - but I won’t feel like I always have to be hustling so I can feel like a success.
This isn’t the end of my creative journey; it’s a pivot. And maybe that’s the real lesson: freedom isn’t about doing it all yourself. Sometimes, it’s about knowing when to let go of what’s not working and embrace what makes your heart feel right.
If you’ve been wondering whether to make a similar shift, I’ll leave you with this: It’s okay to change your mind. It’s okay to want something different. And it’s okay to prioritize belonging over the illusion of freedom. Sometimes, going back is the best way forward.
