Every Woman Should Try This Once

I’m a longtime fan of journalist Danielle Robay’s Question Everything podcast. It used to be called Pretty Smart, a title I loved, but the evolution fits her perfectly. The show now centers on conversations that gently (and sometimes not so gently) challenge the status quo.

At the end of every episode, Danielle asks her female guests rapid-fire questions. If you’ve listened long enough, you can feel it coming: “What is something every woman should try once?”

I’ve imagined myself as her guest more than once, anticipating my answer. I always picture myself talking about shattering limiting beliefs, about helping people see themselves differently.

And then she asks the question.

Here’s my very practical answer: Every woman should try starting a business.

The draft of me from a few years ago would’ve laughed, and probably made a face. Who would voluntarily put themselves through that?

I had all the usual reasons ready.

I’m not smart enough.

I don’t understand money, taxes, or any of that.

Don’t most businesses fail? I’m pretty sure there’s a statistic.

I’m bad at marketing.

Doesn’t it cost a ton of money?

It’s risky.

It’s scary.

It’s just not my personality.

You can probably fill in your own blank: I would never start a business because ___.

But here’s the thing I eventually had to admit: changing jobs wasn’t solving the quiet ache I carried around. What I loved—truly loved—was helping people. That fluttery feeling when someone finally saw a solution to their puzzle? That mattered to me more than titles or stability ever had.

So I tried business. Not because I had a brilliant idea, but because, honestly, I wanted to create additional streams of income that would allow me more flexibility while I searched and searched for the answer to that subtle ache . . .

I started as a medical expert witness. I learned an incredible amount about litigation, medicine, and how systems work. But the nausea I felt wasn’t “new thing” nerves. It was my body telling me this wasn’t aligned.

Then I tried real estate. I bought into the hype, and to be fair, the hype isn’t wrong. Real estate can work. It’s just slow. And hands-on. And absolutely another job.

After six months of running a successful Airbnb (where I HUSTLED to the point my youngest said, "I HATE THAT DUMB RENTAL PROPERTY!"), something clicked.

I wasn’t building the life I wanted, I was constructing a dream house I might never move into. All that energy I spent trying to make money so that I could eventually write? I could’ve been building my writing life all along. I wasn’t avoiding risk, I was avoiding clarity.

Here’s what starting businesses taught me: business isn’t about the business. It’s about who you become when you’re forced to make decisions, take responsibility, tolerate uncertainty, and trust yourself.

Somewhere along the way, I realized the thing I’d been resisting was the thing I actually wanted to claim.

If I wanted to be writer, I wanted to reach people through my writing. So I needed to act like one.

But. BUT . . .

Authors don’t make money! (Is this really about money?)

Self-published authors have to hustle. (Except I know how to HUSTLE, right Jo?)

Am I giving up by not querying agents anymore? (Or am I choosing autonomy?)

I’m not a business person. (Actually, turns out I am.)

So yes. Every woman should try starting a business. Not because she needs one, but because it will show her something about herself she can’t learn any other way.

And sometimes, what it shows you is that the thing you’ve been circling is the thing you’re ready to choose.

Not to hustle.

Not to scale.

Not to make money.

But to see who you become.

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