Hannah Clayton: An Unfiltered Guide to Going Freelance: Freedom, Fails, Fears, and Fulfilment

The journey to success isn’t about having everything figured out from the start, it’s about taking bold leaps, embracing the chaos, and learning as you go. This is exactly what Hannah did when she began their freelancing journey. Her story is filled with raw honesty, invaluable lessons, and a reminder that growth comes from action, not perfection... and we love her for it!

So I’ve been freelancing now for just under a year and I get a lot of DMs asking how I started out. And I get it — I used to think there was a glitter-dusted blueprint that made solopreneurship make sense. But turns out there isn’t one. We learn about Pythagoras and Pavlov and the Protestant Reformation in high school. But surviving on your lonesome in the real world? Not so much.

So here it is — my big, sexy, slightly chaotic secret recipe to becoming a freelancer:

I had absolutely no idea what I was doing.

None. Nada. Not a single Scooby dooby Doo (seriously though, biz advice fairy godmother: where were you?)

But I did it anyway.

I pressed “send” on my first-ever project proposal with sh-sh-shaaaaky hands. Sending out my first ever 4-figure quote to a client was nauseating… And they’d pre-agreed the price!

Maybe it’s just one of those things you learn by doing -- like riding a bike, but with more spreadsheets (and existential dread).

Like, we got taught: 

How to find x, but not how to price service offerings.

How to memorise dates, but not how to write a cold pitch email.

Or how to market ourselves when we are the business.

Or how to go from:

• “Ok I’m pretty good at writing” and 

• "I love the thought of storytelling as a career" to 

• “people will pay me for this” → without feeling like an imposter.

  
  

So I’m going to be a sweet little mango and reveal my sticky, juicy lessons with you. Because if starting out as a little indie biz owner on the Isle of Man has taught me anything, it’s these things, here:

1. You don’t have to have it all figured out. You just have to start.

Hard. On. This.

Seriously.

That feeling of “I’m not ready” doesn’t dissipate when you hit defining milestones like onboarding your first client or being recognised as a leader in your space. 

That feeling of “I’m not ready” will always follow you. Like a fly at a picnic. 

That’s why starting is the hardest part. Your first offer might feel clunky. Your first invoice might look cobbled together. Your first social few posts might create tumbleweeds, summoning nothing but crickets.

But none of that matters if you’ve got momentum.

Clarity doesn’t come from planning. It comes from doing.

From launching yourself into the chaos like a human cannonball.

From setting sail with a wobbly compass and a gut feeling.

From learning on the job — one misstep and small win at a time.

So start before you’re ready. 

Start scared. 

Just flippin’ start.

2. Your credentials catch attention. But connection comes from storytelling.

You could have the most impressive qualifications in the world — and hey, I’m not knockin’ ya — that’s great, that’s really really great.

I mean, I’m proud to say I’ve got a shiny stack of GCSEs myself. Including a strong B in French.

BUT here’s the kicker in your two front teeth:

Your clients don’t connect with your grades or your degree or your endless list of accredited course qualifications.

They connect with you.

With the way you talk about your work.

With the experiences that shaped you.

With the story that made this path feel possible in the first place.

Storytelling is the sharpest tool in your toolbox. Use it well, use it often, use it with purpose.

3. Marketing yourself online feels cringe… until it doesn’t.

When you’re first starting out, posting about your work feels a bit like standing on top of the Smelt Monument in Castletown Square — hollering into the wind with burning red cheeks and a shaky voice.

You worry what people will think.

Whether anyone’s even listening.

You dread looking desperate, delusional — a bit too keen.

The thought of someone you know seeing it, scoffing, and muttering, “Who do they think they are?”

That slow, creeping embarrassment of shouting into the void, and hearing nothing back.

But here’s the shift you’ve got to focus on (and it takes a bit of honest, inward-facing work, believe me!): 

Self-promotion isn’t about putting on a performance.

It’s not about showing off or trying to impress or begging for attention.

It’s about positioning yourself as a thought leader in your space. 

It’s about service — offering something valuable, honest, and genuinely helpful — so the right people come to you not just for what you offer, but because they trust your perspective.

That way, by the time they explore your services, they’re already halfway sold — because you’ve shown them who you are.

…And with that approach and lots of consistency, the cringe fades. 

It becomes second nature. A habit. A rhythm.

4. Your dream clients aren’t on the other side of perfection — they’re on the other side of visibility.

Truth bomb in 3…2…1…

Nobody hires you because your Instagram grid is flawless.

They hire you because they saw you.

Because something in your words made them pause.

Because your post landed in their feed at exactly the right time – and it resonated.

Yes, the visuals matter. The words matter. The strategy matters.

But none of it works if you’re hiding behind “almost ready.”

So stop waiting until your brand is “done.” Stop tweaking that caption for the 37th time. 

Publish the post. Send the pitch. Show up - just as you are and with intention.

Because when you’re visible, you’re discoverable. If you don’t put yourself out there, you’re off the map.

6. You didn’t go freelance to burn out. Build something that actually works for you.

Flexibility is one of the few real perks of running your own business.

So if your freelance life feels more draining than a 9-5… something’s off.

Take it from someone who learned this the hard way:

You’re allowed to take rest seriously.

You’re allowed to design your schedule around your energy.

You’re allowed to build a business that doesn’t just make money — but actually makes sense for your life.

You’re allowed to not feel guilty for chilling out.

Slow mornings. Midweek hikes. An afternoon off because the weather is glorious. Three-day weekends when you have plans. Do whatever makes your business (and you) function sustainably.

Burnout isn’t a badge of honour. So aim to keep your workload within the boundaries of that 40-hour work week as much as you can.

Don’t let your business bleed into your weekends, or steal time from the people and things that actually make you happy.

Because if your work takes over your life, what exactly are you building?

7. Money mindset is a beast worth taming.

Here’s a spicy one: 

Undercharging doesn’t make you noble — it makes you exhausted.

You’re allowed to be well paid for your time, your skills, your creativity, your impact, and all the behind the scenes admin for clients that keeps things running smoothly.

Pricing isn't just about numbers. 

It’s about boundaries. 

It’s about energy. 

It’s about respect — for your work and yourself.

So repeat after me:

I’m allowed to be paid fairly for the value I bring.

And anyone who makes you feel otherwise?

They’re not the client for you.

I made this promise to myself:

If I have to explain why a potential client needs me — or justify my pricing line by line — they’re not the right fit.

8. Community > competition. Always.

Especially in small places like our little Isle, community matters more than clout.

Reach out. Collaborate. Celebrate your peers.

Share what you’ve learned. Recommend other freelancers. Uplift each other.

On the Isle of Man especially, we’re lucky to have a strong support network.

We pat each other on the back, pass work along, and fill in the gaps where one person’s strength meets another’s Achilles’ heel.

I got to know pretty quickly: what you give to your community often finds its way back to you.

9. Stay in your lane.

A fitting follow-up to point 8:

Comparison is a creativity killer.

There will always be someone with more followers, more wins, more everything.

But their path isn’t yours.

Their success doesn’t mean you’re behind — it just means they’re on a different road.

So: keep your eyes on your own journey.

Keep at it.

Your timeline doesn’t have to match anyone else’s.

What’s meant for you won’t miss you.

11. Growth is never linear. 

Some seasons will feel like you’re flying.

Others will feel like you’re crawling through fog thick as Manannin’s Cloak atop Snaefell, doubting every decision you’ve ever made. Wondering what fresh, unlabelled flavour of freelancer chaos is this supposed to be.

Neeeeeeewsflash: That’s normal. That’s human.

Growth isn’t a straight line. It’s weird and wobbly and beautiful. And honestly? Some of your biggest breakthroughs will come after your worst weeks.

So give yourself grace. Keep going. You’re doing better than you think.

Final Word

I still don’t have it all figured out. And I don’t think we’re ever meant to.

But I’ve built a business that feels like mine —

one stitched together with joy, freedom, creativity… (and, admittedly, a pinch of chaos).

So if you’re standing on the edge of your own freelance leap…

Jump. Just like I did.

You don’t need permission or perfection.

You’ve got this.You always did.

Hannah is great. And she reminds us that it’s not about waiting for the perfect moment, oh. no... it's about showing up, getting started, and figuring it out along the way. So, whether you’re starting your own venture or leveling up in your career, take Hannah's advice: you don’t need permission or perfection—you’ve got this.

Keep pushing forward, just like Hannah.