Small by design.

Jennifer and I are spending this winter in California, and we're enjoying our new little town, Healdsburg. This is prime wine country, a landscape that suits us well, and we're not doing Dry January.

So last Sunday, we walked into a tiny Champagne bar late in the afternoon. It's appropriately named, The Healdsburg Bubble Bar, and it has about 12 seats. The place is a hidden gem with cozy decor and Parisian vibes.

You won't find beer or cocktails on the menu. And they don't cook anything. Sparkling wine and champagne are the only things they serve, and that's what this place is all about.

As we sat down, a friendly woman emerged from behind the bar and greeted us with such enthusiasm that we suspected she must be the owner. We watched her move around the room, pouring champagne and chatting with customers about wine, dogs, traveling, and all kinds of other things. And it wasn't long before we were chatting with her, too.

Her name is Sarah, and we confirmed that she is, in fact, the owner. Sarah's energy perfectly matches her menu. Bubbly. She's the kind of person who makes you want to stay longer than you planned. You can tell she loves this.

Sarah told us she spent 25 years working in the wine industry. She's an award-winning winemaker who ended up overseeing more responsibilities as her career grew. Somewhere along the way, she got tired of staring at spreadsheets. And when Covid came along, she found herself gravitating toward sparkling wines, inspired by Pops, a champagne bar she loves in Chicago. She started wondering why her wine-loving town, the one she'd grown up in, didn't have a bar dedicated entirely to sparkling wine.

So, at age 57, she opened one herself.

Sarah had the resume to do something much bigger. Decades of experience, deep industry knowledge, and serious connections in wine country. She could have opened a winery or launched a full-service wine bar or restaurant with investors and employees and all the complexity that comes with that kind of operation.

But she opened a bubbles-only bar with limited seating, no hot food, and she doesn't take reservations. She told us she has no employees, and she's running this small operation all by herself.

I asked her if she ever thought about going bigger, and she laughed. "I spent 25 years going bigger. I know exactly what that costs."

What bigger almost cost me

I know what it costs, too. Or at least, I almost found out.

When I left my corporate job, I was pulled toward scale. I'd spent years as a Chief Revenue Officer, and I believed my next thing should at least match that level. Going smaller felt like moving backward, so I looked for opportunities to "go big, or go home."

Eventually, I went pretty far down the rabbit hole with another entrepreneur, and our idea was to go all-in on a SaaS idea. Our business plan was legitimately good, and we'd both be playing to our strengths. I had the marketing and sales chops, and he brought a strong operational background to the table.

We'd spent months on that business idea when I called him to back out.

I thought about the team we planned to build, the office space we'd need, the infrastructure, and the stress that would surely come with building the business we imagined. And it just hit me all at once.

I was setting myself up for days that would look and feel a lot like the career I'd just left behind. And that vision crystallized my decision to scrap the idea.

I'm still not sure I made the right call. For all I know, that business could be doing eight figures in ARR by now. I'll never know where that path might have taken me. I can only speak for the path I took instead.

My office is a bedroom in our house, but I spend most days writing from my kitchen island. No employees. No team meetings. No business partner to negotiate with, and no investors to answer to. The only person who influences whether or not I can book a vacation is our petsitter.

Some days this feels like total freedom, and I just pinch myself. And other days, I wonder if I just got scared.

The question I keep asking myself

There's a version of going small that's a conscious choice. You know what kind of business you want to build, you know what it costs, and you create something that fits.

And there's a version where staying small is just letting fear win.

I think about "more" and "scale" pretty often. I do wonder what it would be like to be featured in the big magazines and to be in rooms where teams are raising rounds of funding. Every time I see a friend raising a Series A or hitting some massive revenue milestone, there's a little voice that says, "You could have done that."

But then I imagine what my life would probably look like today if I'd built that almost-business.

I'd be in meetings all day and managing people again. I'd be checking Slack after dinner and feeling guilty about taking time off on a weekday to take my dog to the vet. I'd be putting out technology fires from vacations like I did back in my startup days.

I'd have traded my relaxed lifestyle, my flexible hours, and my ability to spend the winter in California for equity in something that might not even work.

The money might have been better. The press and headlines surely would have. But I'm quite certain my life wouldn't be.

What Sarah actually figured out

When I got around to asking Sarah about her days off, she told us Sunday nights are her Friday nights. (It was a Sunday.) She said she spends her days off cooking, visiting the coast, and painting.

An award-winning winemaker with 25 years of experience spends her Mondays and Tuesdays painting.

That's not something you get to do if you run a 50-seat restaurant with a staff, a reservations system, and a chef. Or when you're managing inventory, HR issues, and investor expectations.

Hobbies like painting and cooking (and having the time to do them) are usually the first things you sacrifice when you build the bigger version.

Sarah didn't go small because she couldn't go big. She went small because she'd already seen what big costs. She spent 25 years watching herself and other people pay that price. And when it was her turn to build something, she made a different choice.

Not because she was scared. Because she's confident about what she wants.

The bottom line

We had a lot of fun watching Sarah work the room, operating her business. She had a big smile on her face as she poured glasses of bubbly, encouraged us to do a blind tasting, and waved more people in from the sidewalk.

She decided to use her expertise and experience to build the smallest possible version of something she loves.

Most people will spend their whole careers chasing scale they never needed. They'll drive themselves into the ground trying to find more clients, more revenue, more of everything. And somewhere in the middle of all that chasing, they forget why they started doing it all in the first place.

Scale is the default. Enough is a decision.

I'm still figuring out what "enough" looks like for me. I feel like I'm getting closer all the time. And sitting in that tiny Champagne bar, watching Sarah do exactly what she wants to be doing, I got a glimpse of what it might feel like to stop wondering.

So here's my question: What would your version of the Bubble Bar look like?

If you stripped away everything you think you're supposed to build and just focused on the part you actually love, what would be left?

Reply and tell me. While we can't reply to everyone, Jennifer and I read every single response.

That's all for this week.

See you next Saturday.