I can remember the exact day I decided to become a freelancer.

I was five months pregnant, and working in a stressful senior advertising agency role that I loathed. I knew I couldn’t work there post small human production, but I was too afraid to take the leap.

And then one particularly hideous day my emotions got the better of me and I quit.

Just like that.

What an idiot.

My first day wasn’t a day of celebration. It was a day of gut-churning, butt clenching terror.

I didn’t know any other freelancers, I couldn’t seek advice from The Freelance Jungle (it didn’t exist back then), and it didn’t occur to me to look for a book or course on “Freelancing 101”.

So I just started.

And kept on going.

Recently, my son turned eight, and being the maths genius that I am I realised I’ve been freelancing for eight and a half years.

It made me stop and reflect on some of the big lessons I’ve learned during my clamber up the greasy pole of freelance life.

Lessons that might help those just starting out.

So here are eight (and a half) freelancing lessons I’ve learned so far.

Lesson 1: You don’t need ALL THE THINGS

I started my business with a four-year-old laptop encrusted with cake crumbs. In my first week I acquired an ABN, and had a pal build me a dodgy website on the free WordPress.com platform.

But here are some of the things I didn’t have:

  • Business cards: I finally ordered 100 three months down the track. And I still have 98 of them left.
  • A fancy stand-up desk or ergonomic chair: It was just my sofa and my lap.
  • A drawer full of kikki.K stationery and Typo office frippery: I managed to steal a few pens and Post-it Notes before I left my day job.
  • A library of software and apps: All I had was an old copy of Microsoft office I never updated because I was too tight to pay the upgrade fee.
  • Professional photos: I used a random blurry snap from an office away day.

I didn’t get a business loan, apply for a grant, or borrow money from my mum and dad.

All-up I spent about $2000 on my business in that first year.

Lesson 2: It takes a village

My first year as a freelancer was a lonely one.

With a small human to look after I felt incredibly isolated. I didn’t know any other freelance types, so there was no-one to bounce ideas off or whinge to. (Well, apart from my little human.)

But towards the end of my first year I started going to a shared office space a few days a week. And it was life-changing.

Seeing other freelancers do their thing – like Ryan Linnegar, a photographer who shared the desk next to mine – was utterly inspiring.

I also partnered up with designers and developers to work on projects and share referrals, which helped me grow my business.

And in year three I started some online communities that are still running today.

I really wish I’d found some freelancer buddies sooner. It would have made those early days far less stressful.

Lesson 3: Working with friends sounds great, but often isn’t

In the first year of my business, 80% of my clients were either friends or friends of friends. I did mates rates, contras and whatever else it took to earn a buck.

But as time went on, working with friends started getting tough. It was harder to push back, to be honest, and to say no. And I felt awkward enough having money chats with strangers, let alone my good buddies.

So as time went on and my work flow increased, I began referring my friends to other copywriters. Not only did it spread the good karma, it also meant I could keep business and personal life separate. 

Lesson 4: Find your inner freelance lion

I started my freelance life as a timid beast.

The confidence that bubbled happily in my day job somehow evaporated when I went out on my own. I happily let clients step all over me, pay me late, miss deadlines, and call me at all times of the night and day.

And it made me miserable.

So I decided to make a change. I created processes and templates to deal with tough situations. I set clear boundaries around when and how client could contact me. I pushed back on daft requests, and learned to say “No”.

And my clients loved me for it.

In the freelance dance I believe clients want you to take the lead. By taking control you’re taking away their stress.

Don’t be afraid to be strong.

Lesson 5: One day you won’t recognise your freelance business

The business I started looks nothing like the business I have now. If I met it on the street I’d probably walk right past without even noticing it.

My main focus has become my sideline, and my side ‘hustles’ have become my biggest earners. And I’ve changed my branding, my approach and my services more times than I care to remember.

I’m always thinking about what I enjoy doing, what makes me money, and what people want.

And if a project doesn’t tick all those boxes, I don’t do it. Simple.

Don’t think you need to have it all worked out on day dot. Freelancing is fluid and evolving.

Lesson 6: Realistic expectations are everything

When I started out, my goal was simple: make enough to pay the mortgage and feed myself. I didn’t have any freelance heroes to follow, and so I didn’t compare myself to anyone.

But as time went on, and I became aware of other great people in the industry, it wasn’t long before comparisonitis and imposter syndrome kicked in.

Until I actually spoke to them.

It quickly became clear that all freelancers, no matter how successful they are, have suffered tough times. And the more we can be open about it, the better it will be for everyone. 

Lesson 7: Repeat business is the boom

While many of my clients came via referrals and through my SEO efforts, the truth is I grew my business on repeat clients.

While I like to think of myself as more of a one-night-stand freelancer – get in, delight, get out – the truth is that when I took the time to build long-term relationships it really paid off.

And it’s the little things that made the difference:

  • Allowing for 30 mins of bonus discussion time
  • Giving clients shoutouts on social media
  • Sending little thank you gifts after a job is done
  • Following up with a client six months after a job is done – not for more work, but just to say “How’s it going?”

It’s easy to get captivated by the next sexy client or the next amazing project. But showing some love for your existing clients pays off better in the long run. 

Lesson 8: DIY isn’t always the solution

I’m a huge fan of the Do It Yourself business.

And for years I did everything my business myself. Coding, designing, accounting – you name it.

Why? Because I didn’t have enough money to pay someone else to do it.

It wasn’t until my fourth year that I started branching out into subcontracting. I started slowly – the odd bit of proofing, a random graphic. And while it was an expense, it let me focus on what I do best and actually earn more money.

But knowing how to DIY made me appreciate my suppliers so much more.

Lesson 8.5: Don’t forget why you’re freelancing

You’ve probably watched Simon Sinek “Start with ‘Why?’” video. (If you haven’t, here it is again.)

But despite watching this about 50 times, I still forget my why sometimes.

As 3 o’clock approaches I curse having to do the school run, even though being able to spend time with my small human was a huge part of my freelance ‘Why?’.

I envy smart-looking office people when I visit Sydney, forgetting that I hated having to dress up like a human for work.
I get cabin fever in my home office, forgetting the joy of not having to put up with office politics and the mindless chit-chat.
I freak out about my feast-or-famine income, despite the fact I hated being a wage slave.

But the most obvious lesson I’ve learned since starting out is that I just adore being a freelancer. Yes, it can be tough at times, but I prefer this kind of tough to employee tough.

I have the choice to do whatever I want.
To change direction on a whim.

To try, and to fail.
To work in my undies on a hot day.

Choosing to be a freelancer is a brave thing. And I hope to still be one in eight and a half years from now.

Kate Toon is an SEO copywriter and consultant based just outside of Sydney.

She lives her freelance business life from a hut in the back garden, with her business mentor Pomplemousse – a wise Pomeranian.
You can find her at katetoon.com


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