Double Your Squarespace Business: Do You Actually Have Room To Double? (Part 2)

This is Part 2 of a 3-part Double Your Squarespace Business series.

In Part 1, I talked about two big levers for doubling once you’ve hit a ceiling:

• The fastest path is going where there’s already outsized demand for what you offer.

• The shortest path is getting around people who are already doing business at that level.

Before you go chasing any specific tactic, there’s a quieter question to answer:

Do I actually have room to double?

That breaks down into two checks:

1. External headroom

2. Internal capacity

Everything else sits on top of these.

A quick example

I was talking to a Squarespace designer who'd been hovering around 100–120k for a few years.

Fully booked. Good reputation. Mostly working with local service businesses.

She came to me saying, "I just need more leads."

So we looked.

She'd already worked with most of the higher-end businesses in her immediate area. The rest of her inquiries were from people who wanted "something simple" and balked at anything over 3–4k.

I said, "It looks like you've kind of... maxed out the room you're in."

She went quiet.

"So what, I just leave? I've spent years building my reputation here. Everyone knows me. That's my whole advantage."

I didn't say anything.

Then she said: "But if I'm being honest, I already know who I'd work with if I wasn't stuck here. I've had three referrals this year from people in bigger markets—tech companies, consulting firms. Every one of them was easier, paid better, and I kept thinking 'this is what it should feel like.'"

"So why didn't you chase that?"

Another pause.

"Because it felt like starting over. And I didn't think I could handle more work."

That's when we looked at capacity.

I asked her to walk me through what doubling would actually look like.

She laughed. "If I doubled my revenue like this I'd die. I'm already exhausted. I'd need a copywriter, a developer, a PM… I don't even have a proper onboarding process."

"So you don't just have a headroom problem."

"No," she said. "I have a capacity problem too."

That's the moment. She wasn't stuck because she didn't know what to do. She was stuck because:

1. The market she'd built her reputation in had run out of room

2. The business she'd built couldn't hold what she actually wanted

And she'd been telling herself the problem was leads.

That’s the situation a lot of freelancers are in:

• The market they’re in doesn’t have much clear space left.

• The business they’ve built couldn’t comfortably hold 2x even if the demand showed up tomorrow.

Which brings us back to those two checks.

1. External headroom – is there room to grow where you are?

First, look outside your business.

Ask yourself:

• Is there visible room to grow where I currently am?

• Can I reasonably picture the next 10–20 clients I want?

• Are there enough people with the problem I solve at the level I want to get paid?

If you can’t see that, your first job isn’t to grind harder.

It’s to either:

• find pockets of demand you’ve been ignoring, or

• choose a lane where the headroom is clearer.

That might look like:

• tightening who you speak to (instead of “anyone who needs a site”)

• shifting toward businesses where the stakes are higher and the website actually moves money

• quietly retiring low-leverage offers that keep you busy but don’t move your overall numbers

If there’s no real headroom, no amount of effort will move the ceiling.

You’ll just end up working harder in the same small room.

2. Internal capacity – can you actually hold 2x?

Then flip it inward.

Ask:

• If my revenue doubled, how would that feel in my body – exciting, tense, overwhelming?

• Do I have systems that could actually handle 2x, or does everything fall apart as soon as I picture it?

• What would have to change (offers, scope, boundaries, support) to make 2x feel sustainable?

If the idea of doubling instantly feels like chaos, your nervous system is going to resist it, even while you say you want it.

This isn’t unusual.

It just means some of the “doubling work” lives in:

• simplifying offers

• tightening processes

• deciding what you won’t do at the next level

Otherwise, you’re trying to bolt more revenue onto a structure that can’t support it.

So:

• Headroom tells you whether there’s space to grow where you are.

• Capacity tells you how much growth your current setup can actually hold.

Once you’re honest about both, the picture gets a lot clearer.

Where this leaves you

You don’t need a 20-step plan off the back of this.

You just need to answer one honest question:

Right now, is my main constraint headroom or capacity?

Whichever one it is, make one move in that direction:

• If it’s headroom, lean into a lane with clearer demand and better-fit clients.

• If it’s capacity, clean up one offer, one process, or one boundary so 2x wouldn’t break you.

That’s what Part 3 is about: the difference between doing the work and moving the work, and how that creates the leverage to make doubling real instead of heroic.

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If you want my help working through this in your own business, this is exactly what we do inside the Double Your Squarespace Business cohort. Add your name below if you want first notice when doors open: