What Ten Years in Business Taught Me About Going Bigger (and Choosing Small)

This post was first sent as my newsletter, Entrepreneur Like a Girl, on September 22, 2026: ten years to the day after I registered my business.

Ten years ago today I registered my LLC in the state of North Carolina.

When I think back over the past decade, there are two moments that always come to mind first.

The first one involved champagne.

I’d been teaching myself to code on the side. Dabbling in WordPress. Still applying for jobs on the military base, desperately avoiding the idea of starting my own business… because it was terrifying and I had no idea what I was doing.

And then one afternoon I saw someone in a Facebook group asking if anyone did web development.

I replied. She hired me.

$18/hr.

I drove straight to the store and bought a bottle of champagne. Came home, put it on the counter with two glasses next to it, and waited for Neil to get home so we could open it together.

I celebrated like I’d won the lottery.

It wasn’t about the money (obviously, it was $18/hr). It was that a stranger had said yes to me, based on a skill I’d taught myself in my spare time.

The second moment was eight years later, on a stage in China.

Cartier Women’s Initiative. First place, North America. Me and my company.

Some of you were here for that one.

Let me explain that caption.

That award is, without a doubt, the thing I’m most proud of in ten years of doing this. That hasn’t changed and it won’t.

But something happened in my head afterwards, and it took me a good couple of years to see it.

For some reason, I thought I owed them.

Not explicitly. Nobody at Cartier asked me for anything. But somewhere in there I picked up the idea that if people that serious had backed me, it would be unfair not to keep going bigger. Bigger partnerships. Bigger team. Bigger offers. Bigger everything.

An award is supposed to be a celebration of what you’ve built. I turned mine into a debt.

Here’s the whole decade, so you can see what that stage was sitting on top of.

Watch the hiring.

2016: registered the LLC. Applied for jobs anyway.
2017: figured out how to run a business(ish). Hired my first coach. Turned $18/hr into my own web design agency.
2018: launched GeekPack from an RV.
2019: agency clients by day, GeekPack by night.
2020: COVID hit, the business boomed. Hired.
2021: still booming. Hired more.
2022: a local accelerator program, a Udemy partnership, a $250K grant. Hired more.
2023: more grants. Hired again.
2024: awards. Travel every single month. Cartier.
2025: corporate partnerships, Verizon, our own app in the App Store.
2026: all in on in-person events. Sponsors. St. Louis.

It reads like a highlight reel and I promise you it was one. I don’t regret a single year of it.

But look at where the hiring starts.

2020. Four years before that stage.

The award didn’t start the pattern. It just made the pattern impossible to question.

I’d been choosing “bigger” for four years already. After China, bigger stopped being a choice and started being something I owed somebody.

And I want to show you one week from the middle of that list, a full year before the award, because it explains more than any of these lines do.

September 2023. Durango.

I flew my whole team in for our first-ever retreat. Seven of us. One came from Switzerland. One from the UK. One from Australia. Some of them had never met each other in person.

We spent that week talking about how big this thing was going to get. How many of us there’d be in two years. What we’d build. Someone sketched a version of the org chart and I remember looking at it and feeling like the luckiest person alive.

And on one of those afternoons, I sat down with my ops manager in a separate room and told her we were running out of cash, and walked her through exactly what we needed to do to make payroll without gutting our reserves.

Then I walked back in and kept planning.

Both of those things happened. A few hours apart.

That’s the entire decade in one sentence.

And that was 2023. Before the stage in China. The crack was already there. I just spent the next year getting an award that made it much, much harder to say so out loud.

2024 looked spectacular from the outside. Awards. Stages. Travel every single month. I had breakfast with Richard Branson on Necker Island, which is still a sentence I can’t say with a straight face.

And the P&L barely moved. The reserves were draining fast… so fast that I was too embarrassed to look at the bank account. I could feel things breaking underneath and I kept telling myself it was fine, we’ll push through, what’s the next big thing.

2025 was the panic year. Revenue up and down. AI changing everything. Me questioning all of it.

So I decided to go bigger. Bigger than I’d ever gone.

Last September, another team retreat, and we went all-in on in-person events for 2026. Locations, dates, sponsors, all of it. And we pulled it off. St. Louis this past April was phenomenal and I will be proud of it forever.

It also cost more than it made. And I kept digging faster than I could climb.

Every single move was “bigger.” Until it wasn’t.

Here’s the part that took me two years to see.

Every one of those bigger decisions was a decision I already knew how to make.

Hire someone. Add a tier. Say yes to the partnership. Book the venue. Build the bigger version of the thing.

I was good at those. They felt like progress, they looked like progress, and they paid out the same afternoon.

The smaller decision was the one I didn’t know how to make. The one where you look at something you built and say this isn’t working, out loud, in front of people who watched you win an award for it.

So I kept picking the one I was good at.

Bigger wasn’t the brave choice. Bigger was the comfortable choice.

Which is really uncomfortable to type, because it’s the exact thing I say to you on a regular basis. Your competence isn’t always the solution. Sometimes it’s the hiding place.

I just didn’t think it applied to me at 9 employees.

So. Where I actually am. September 2026.

The team is small on purpose now. One core offer. And a very clear picture of exactly who I’m talking to.

(ps: if you’re currently agonising over whether to niche down… here’s your sign.)

I want to be careful here, because this is the bit where I’m supposed to tell you it all worked out.

It hasn’t yet. I’m about five months into rebuilding and it is slow. St. Louis cost me money I haven’t made back. The simpler version takes longer to build than the complicated one did, which nobody warns you about.

But I can see it compounding. Five months of unglamorous work that nobody clapped for, and I can finally see the evidence of it stacking up. That’s not the same as done. It’s just the first time in about three years that the direction has been obvious.

And somewhere in the middle of all that, I fell back in love with my business.

I did not expect that one.

Small isn’t a retreat. It’s a choice made with complete information.

Because I don’t think I could enjoy this version if I hadn’t had the other one first.

I know what a big team feels like, and I loved it. I know what a huge revenue month feels like (loved that too, obviously). I know what it’s like on the big stages, in the rooms with all the right people.

I’ve had the big version, fully, and I found out exactly what it costs. In cash, in energy, in three-in-the-morning payroll maths.

Here’s the thing I keep coming back to, ten years in.

Every year on that list is a year you might be sitting in right now.

Starting the thing, even though it’s terrifying.

Referrals dried up, and for the first time in years you have to go out and actually find clients.

Twenty years of expertise, six months self-employed, and absolutely no pipeline.

Working endless hours while the bank account refuses to reflect any of it.

Looking at something you built and knowing it isn’t serving you anymore.

Simplifying, and terrified it looks like giving up.

And then there’s the other list. Not where you are, but what you’ve been told you’re supposed to be doing.

That you need to be better at social media, because that’s what everyone keeps telling you.

That niching down means turning people away.

That a real business needs a membership and a high-ticket offer and a low-ticket offer and a workshop and a YouTube channel.

I’ve done all of those. Every version. Some were exactly right at the time and a good number of them absolutely were not, and I could not have told you which was which while I was doing it.

It also took me the full ten years to notice that the name of my newsletter was the answer the whole time.

Entrepreneur Like a Girl.

It’s been sitting at the top of my readers’ inboxes for a couple of years now without me fully knowing what I meant by it.

Here’s what I mean.

It means being bold and completely terrified in the same week. Sometimes the same hour. Sometimes the same room.

It means making the big decision and the bad decision, occasionally the same one, and finding out which it was about eight months later.

It means the unglamorous version, done when nobody’s watching, with nothing to post about it.

It means getting it wrong (publicly, expensively) and being kind to yourself about it anyway. That one took me the whole decade and I’m still not good at it.

It means accepting the highs and the lows and knowing there will be plenty more of both.

I have entrepreneur-ed like a girl for ten years. Badly sometimes. Brilliantly sometimes. Always, always my own way.

And I’m going to keep doing exactly that.

Which brings me to the only thing I want from you today.

Tell me where you are. Join my newsletter, Entrepreneur Like a Girl, and hit reply to the first one.

Doesn’t have to be fancy. One line is completely fine.

“Just got my first client.”
“Referrals dried up.”
“Too many offers, no clarity.”
“Everything looks fine and it isn’t.”
“Simplifying and freaking out about it.”

And I’ll tell you what I’d have told myself at that exact point.

Not advice from a stage. Just the thing I wish someone had said to me while I was standing where you’re standing.

Join the newsletter →

Cheers to the next decade… with all my geeky, ten-years-in love,

Julia

P.S. Ever since that bottle on the counter, every time something good happens in this business, we mark it with champagne. I’m not naturally good at celebrating myself, and I think most of us are famously bad at it, so a bottle of fizz became my way of forcing the issue. Maybe that’s part of entrepreneur-ing like a girl too. Finding a way to pause, take note, and celebrate like you won the f-ing lottery.

P.P.S. One thing on that list hasn’t changed once. The coach I hired back in 2017, when I was still working out what a business even was, is still my coach. Next year we’ll hit ten years together. Every single other thing I built, I built bigger and then took apart again. Her I just kept. Clearly I don’t love change.