How to Back Yourself in Business Before You Feel Ready
- Ben Hickman
- Mar 17
- 3 min read
Reflective Rebels Podcast Season 2 Episode 3 - Cat Park
How to Back Yourself in Business Before You Feel Ready
Most business owners know the feeling. You've got an idea, a gut feeling, a thing you keep almost doing. And then the thinking starts. What if it doesn't work? What if I'm not ready? What if I wait until I've got a proper plan?
Backing yourself in business is one of those things that sounds simple until you're actually standing at the crossroads.
Cat Park has been at that crossroads more times than most. And her answer has almost always been the same: why not?
What does backing yourself actually look like?
Cat's story is full of moments where the sensible thing and the brave thing were nowhere near each other, and she chose brave every time. Not because she had a safety net, but because her default answer to uncertainty has always been to just go for it and figure the rest out as she goes.
She bought her first house at 18. Walked out of a flooded home at 21 carrying her ferret in a Topshop shoebox and came out of it thinking, right, what's next? Moved to London on two weeks' notice with no job lined up. Quit retail to learn plastering on a whim. Talked her way into a job at a Sky music channel and told her friend on day one she'd be managing it within six months. She did.
None of it came from conventional confidence or a carefully laid plan. It came from something simpler and harder to hold onto as you get older: the belief that if it doesn't work, you change it.
Why backing yourself gets harder as you get older
Cat is by her own admission the biggest overthinker, and she'll be the first to tell you that the fearlessness she had in her twenties isn't quite what it was. The older you get, the more you question things. The finances, the what ifs, the is this actually sensible. She notices it in herself and names it honestly in this conversation.
But she keeps making the brave call anyway. Not because she's solved the overthinking, but because she knows what the alternative feels like. Stuck. Anxious. Waiting for a moment that never quite arrives.
If you've been telling yourself you'll do it properly when you've got a plan, and the plan never quite comes together, Cat's story has something useful in it for you.
How to know when to let go of your business
Backing yourself isn't just about the bold starts. Sometimes it's about knowing when to walk away from something you've built from nothing.
After twelve years building Ten Letter PR into a genuine name in the UK music industry, working with artists you'd recognise and getting commissioned by major labels to do the grassroots work they couldn't, Cat walked away. Not because it had failed. Because it had served its purpose and she knew it.
She'd been through a serious personal crisis in January 2020 that put her in hospital and left her with brain damage, losing her sense of taste and smell. Then COVID hit. She describes that period simply as survival mode. When she came out the other side she was waking up anxious about opening her emails. That was the line she wouldn't cross.
Handing Ten Letter over to Nina, who'd been with her for years, was one of the hardest things she'd done. Not because it wasn't the right call, but because letting go of something that's been your identity and your income for over a decade is its own kind of grief. The courage that builds things, it turns out, is the same courage that releases them.
The why not instinct is a muscle
Cat was raised by a mother who modelled it. She grew up with enough independence to trust it. And she's spent her whole adult life exercising it. It gets harder as the stakes get higher and the responsibilities pile up. But it doesn't have to disappear.
The question isn't whether you'll ever feel ready. You probably won't. The question is whether you're going to go for it anyway.
Listen to the full conversation
Cat Park joins Ben Hickman on the Reflective Rebels podcast in Season 2 Episode 3. The full conversation is on Spotify, Apple Podcasts and YouTube now.
If this has got you thinking about your own next move, Ben works with business owners who are ready to stop waiting and actually do something about it. Find out more here.



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