It’s not that I’m anti-social. It’s not that I don’t play well with others.

It’s just that when something is important — I simply prefer to do it myself.

👉 “Solo” doesn’t have to mean “alone” — but it does mean “in control”.

👉 If you’re a solopreneur, or thinking of becoming one, go read this report right now.

And now — the story behind why this advice matters. 👇

I can’t f*cking spell.

For someone who writes about business and entrepreneurship, you’d think I’d be able to spell “entrepreneurship” in my sleep.

Nope. I always mix up the “u” and the “e” in the second half of the word. Luckily, modern technology saves me:

But here’s the problem with spell check — it only works on words it recognizes. And this issue of Drunk Business Advice isn’t about entrepreneurship.  

It’s about solopreneurship. 👇

Even though Merriam-Webster officially added “solopreneurship” to the dictionary in 2020, most spell checks still don’t recognize the word. I didn’t have “being professionally and emotionally invalidated by spell check” on my 2026 bingo card, but here we are. 

Ladies and gentlemen, if you haven’t guessed yet — I am a proud solopreneur.

Why have I chosen the solopreneurship path at this stage in my career? Two big reasons:

(Ok… “never” is a strong word, and life is long, but I’m pretty darn committed to this right now.)

I’m now on my third solo business, and I’m beginning to recognize the pattern that keeps attracting me back to this lifestyle:

👉 If I’m not in control, I’m miserable.

And no amount of money or stability can ease the stomach ache I feel when things go poorly due to factors I could have influenced — if only I had control. When I screw something up myself, I can live with those mistakes, because I learn from them. They help me grow and improve.

But to watch a project fumble… knowing I could have saved it if only my hands weren’t tied behind my back… that’s just pain for the sake of pain.

A shrink would probably tell me that I need to work on my control issues. That I need to learn how to trust people. That all this hoo-ha is negatively impacting my relationships. 

After all, no one ever says “control freak” like it’s a good thing. Folks don’t aspire to be control freaks. Parents don’t raise their kids to be control freaks. And no one wants to marry a control freak.

But here’s the thing—

A lifetime of evidence suggests that I’m happier in my relationships, and happier in my work life, when I’m flying my business solo. And since solopreneurship is a valid career choice, why not lean into my strengths?

The origins of the word “solopreneur” date back to the early 90s, and although there’s no official coiner credit, many look to Terri Lonier as the flame which ignited the solopreneur movement.

In 1993, she published the book Working Solo, which was the first ever practical guide to solopreneurship.

And earlier this week, I hopped on a call with her. 👇

But here’s the nutty part: I didn’t have the slightest inkling of her background prior to this call. 

I wasn’t doing research on solopreneurship for Drunk Business Advice (even though I’ve been planning this article for weeks). I wasn’t looking to rub shoulders with the badass who blazed the path for folks like me to run solo businesses.

We just wanted to talk about books.

Terri and I are both working on historical fiction novels set against the backdrop of the industrial revolution — so we decided to get together to nerd-out on history and fiction writing.

Business talk was not on the agenda.

But as we were easing into the conversation, I asked Terri how she got into writing, and she humbly told me about her first book… ya know… the one that shaped the entire solopreneur industry.

I had no clue I was speaking with a damn LEGEND. And this leads me to the most important lesson of solopreneurship:

You don’t have to be alone.

Solopreneurs might be “control freaks”, but we’re also humans who thrive on the creative juice that can only be squeezed by other humans.

We join communities and masterminds (which is precisely how I met Terri). We go to events. We learn about each other’s stories and outside interests. We’re less protective of our social bandwidth because we’re not bogged down by the barrage of conversation that comes with managing a team.

And I would argue this enables us to have stronger, more diverse, and more supportive professional relationships. We might be solo, but we’re far from alone.

So if you’re currently running a solo business, hit reply to this email and tell me about it. Let’s be solo — together. ♥️

If you’ve read up to this point, you might be thinking “Omg this sounds like me, I’m going to quit my job (or dump my team) and go solo!” —  But hold up a minute.

This. Shit. Is. Not. Easy.

For instance, in 2025, my business’s revenue plummeted nearly 80% compared to 2024. There are two big reasons for this:

When YOU are your business, it’s a high-risk game. 

Get sick? No one is going to cover for you. So it's imperative to build a model that accounts for this possibility, unless you’re genuinely cool with that risk, which most of us aren’t.

While there’s a stupid amount of money in client work, the health issues I had last year were a wake-up call in this regard — so I embarked on a gambit to mitigate that risk in the future. Which means my income is peanuts right now.

And this is just one of many uncomfortable considerations:

Solopreneurship is not for everyone, and if you’re listening to advice from some bro on LinkedIn boasting about how he built a 7-figure solo business in three months, you’re already starting on the back foot.

One of the best breakdowns I’ve ever seen on this topic comes from my friend Adriana Tica, (who also writes a killer newsletter called Strategic AF).

She put together the State of Solopreneurship, a zero-bias report about how soloprenuers actually make their money. She interviewed over 150 of ‘em. Then she analyzed the shit out of what she learned, and crafted a practical guide to what it takes to be a successful solopreneur in 2026.

And since she’s a doll, she’s agreed to share it with Drunk Business Advice readers for free. You can grab it here.

Y’all — let’s all commit to making solopreneurship a little less lonely. I invite you to reply to this email with whatever is on your mind. It will give me the energy I need to make it through another week, and hopefully you’ll feel the same! ♥️

Cheers! 🍻

-Kristin

P.S. — Terri is (bravely) writing her novel in public! Go check out her Substack. Our conversation inspired me to carve out more time to work on mine, which has already been in progress for 8 years. Hopefully I’ll have something exciting to share with you on that front soon!