Is It Brave or Reckless? How to Know When You’re Ready to Go Freelance

If you’re waiting to feel 100% ready before going freelance, I have a bit of tough love for you: you might be waiting forever.

When you’ve spent years climbing the finance ladder — proving your worth, leading teams, solving big commercial problems — the idea of walking away from that security feels…bold, at best.

But is it brave? Or is it reckless?

The truth is: it’s not either/or.

Most Portfolio FDs I know didn’t feel ready when they took the leap. They felt scared. Unsure. Even guilty. But they also knew, deep down, that they wanted more control, more variety, more freedom.

And that they were tired of being exhausted, over-delivering in a business that no longer lit them up.

Five signs you might be more ready than you think:

1. You’re already the go-to problem solver.
   People trust you to bring clarity. You don’t just report the numbers — you help shape the decisions. That’s what business owners are crying out for.
2. You’re not frustrated with finance — you’re frustrated with the noise.
   It’s not the work you want to leave. It’s the endless meetings, politics, and change resistance.
3. You think like a business owner.
   You’ve caught yourself saying, “If this were my business…” — and meaning it. That mindset is gold to a business owner.
4. Sunday night dread has nothing to do with spreadsheets.
   It’s about the lack of autonomy. The inflexible hours. The way your life fits around work, not the other way around.
5. You know your value — but you don’t know how to sell it.
   Totally normal. Most FDs have never had to “market” themselves. But these are skills you can absolutely learn.

So what’s really holding you back?

For most people, it’s not a lack of experience. It’s fear of:

• Not finding clients
• Inconsistent income
• Putting themselves out there
• Looking like they’ve “failed” if it doesn’t work

That’s exactly why I created PowerUP — to support FDs through this transition with structure, guidance and a community of people who get it.

We cover everything from: 

✅ Setting up your business
✅ Building a credible brand
✅ Finding (and winning) clients
✅ Pricing and packaging your services
✅ And staying accountable to your version of success

And here’s the exciting bit…

In May 2025, we’re running PowerUP as a live cohort — the first in over a year.

• Live sessions
• Built-in accountability
• A proper community of like-minded professionals
• All for the same price as the self-led version (£1995+VAT) — before the price rises (to £2495+VAT for the next cohort)

If you’ve been thinking about making this move for a while…now’s the time to back yourself.

Because maybe the question isn’t:
Am I ready?
Maybe it’s:
What’s my next step?

Want to know more about PowerUP?
Take a look here or apply now.

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