Learn from my 15 years of mistakes and victories as a self-employed sole trader running creative businesses, and save yourself some headaches.
Creative entrepreneurs, fellow freelancers, copywriters, authors, artists, small business owners and self-employed superheroes… I bet you’re wondering how I’ve bossed 15 years as a self-employed sole trader, running my own businesses while growing a family.
Sometimes, I wonder how I’ve done it too.
May 2023 marked 15 years since I registered self-employed (*waves at HMRC*). I can’t believe it either, but I went freelance at the tender age of 26. It’s been a wild rollercoaster ride filled with glorious victories, cringeworthy blunders, and all kinds of clients. Along the way, I’ve picked up some need-to-know lessons you might find useful in your own business. So, grab a brew and a biscuit (freelancer essentials), and let’s dive into the 15 things I’ve learned during 15 years as my own boss...
Lesson 1: It’s ok to pivot in your self-employed career
As a freelancer, you’re your own boss. Seems pretty obvious, right? But think about it: you can set your own hours, you can work when and where it suits you, you can choose the kind of clients you work with. You also have the freedom to explore new opportunities and reinvent yourself. Don’t be afraid to pivot when the wind catches your sails!
Here’s my pivot story: I started as a freelance writer, working with brands and businesses I’d connected with during my previous work as a magazine writer. But, after a few years, I started to feel disconnected from my projects. When my first child was born, I picked up a new hobby – papercutting – and turned it into a career, taking private commissions, exhibiting my work, and teaching DIY workshops. That pivot lasted nine whole years. After my son was born, I pivoted again. Back to writing – this time focusing on copywriting, which makes my busy brain happy and fits well around my family commitments.
Embrace the flexibility of freelance life. Your career as a creative entrepreneur is an artistic journey, and sometimes you need to take a detour to find your true calling.
Lesson 2: Just do the damn thing
I could talk all day about the opportunities I’ve missed out on because of imposter syndrome, procrastination, and writer’s block:
I could’ve set up so many magazines over the years, but I talked myself out of all of them.
I could have launched writing retreats, or courses on how to self-publish.
I could’ve been among the first papercutting artists in the UK to launch a DIY kit.
But I talked myself out of them. Someone else got there first, or did a “better” job, or had the same idea as me. But I could still do all of those things, because all of them will have my unique approach and my personal touch which appeals to my specific audience. So please, don’t make the same mistake I keep making. Just do the damn thing. There’ll always be someone who loves it, because you’re delivering it.
Procrastination is the enemy of productivity.
Stop talking yourself out of it and get on with it. The first step is always the hardest – so sit down, do five minutes of whatever it is, and just do it. Think of what you (and your future clients) could miss out on if you never get started.
Lesson 3: Get in control of your freelance finances
Ah, money, the eternal dance partner of freelancers. When I first started out, I used my personal bank account to run my business. That led to some fun times sorting out my books and submitting my self assessments! It took me many years to get my head round making money as a freelancer, but I now have four non-negotiables:
Starling Bank (very easy, responsive and transparent business banking).
Intuit QuickBooks Self-Employed (I don’t have a bookkeeper or accountant: this does pretty much everything for me by tracking and categorising transactions and helping me with my self assessment… I also send invoices through it).
Profit First. This is a famous book that a lot of entrepreneurs swear by (you can buy a copy here – it’s an affiliate link). I’ve tweaked the formula to suit me, so every week on Money Management Monday, I put 20% of my earnings into a tax ‘space’ in Starling (so it’s ready for my self assessment tax bill), 20% into a business expenses space, and 5% into a saving space (effectively “Profit First”). The rest is my wage – including my pension contribution, which I set up through Penfold (affiliate link). Penfold is perfect for freelancers as you can put in what you want, when you want.
Charging my worth. This is so important. As a freelance copywriter, I don’t charge per hour. I charge per project. In my calculations, I incorporate my many years of experience, my training and skill, my overheads and expenses, and – perhaps most importantly – the value I provide to customers, and the rate I actually need to earn. You can read some top tips on this from my former copywriting coach Belinda Weaver.
Your takeaway? Learn to manage your finances wisely. And charge what you’re worth: don’t live up to the starving artist cliché like I used to!
Lesson 4: Outsource when you need to
You may be a talented copywriter (c'est moi!) or amazing artist, but that doesn’t mean you have to wear all the hats in your business.
Struggle to sort finances? Hire a great accountant (there are plenty of freelance groups on FB where you can ask for recommendations).
Not great at prettifying stuff? Hire a designer.
Your product photos a bit ropey? Head shots need a refresh? Invest in a photographer.
No great shakes when it comes to being organised? Get a VA to tackle your inbox and schedule your diary.
Hate writing blog copy or social posts? Hire a copywriter (It’s me! Hi!).
Fact: Investing in good services that will support your business will give you time and energy to focus on your zone of genius.
Lesson 5: Build your network
Network, network, network. Not in a stuffy room full of stuffy folk – do it online, do it at events that suit your vibe, do it flexibly, do it in a way that suits you!
Finding that next client can sometimes be a real drag, and freelancing can be a very lonely gig at times.
Over the years, I’ve made some amazing connections through social media, via contacts of contacts, and through sticking my neck out and saying “yeah I can do that job” or “hey, I’m available right now!” Be yourself, be genuinely interested in other people, and put yourself out there in a way that’s comfortable for you. Building a strong network will open doors to exciting collaborations and opportunities.
Also, once you find your tribe you can:
Refer jobs between yourselves (this is a *great* bonus of having a good network. Community over competition, people!)
Talk about your favourite biscuits.
Discuss what you’re having for lunch.
Ask the hive mind to identify what your little darlings smeared on your walls while you were doing a Zoom in the next room (true story).
Lesson 6: Trust your gut
Intuition is rarely wrong. If that client’s initial enquiry gave you red flag vibes, don’t waste your time on them. If the project goes totally against your moral values, walk away from it. If criticism you receive isn’t helpful or constructive, leave it on the table (maybe they’re just having a bad day – after all, you’re the expert in what you do, not them!).
As a creative business owner, you pour your heart and soul into your work. Trust that the universe has your back. Better opportunities, clients and projects are coming your way.
Lesson 7: Find your freelance rhythm
I’m a night owl. Having kids has totally messed up my internal freelance clock, because I need to be up early to do mum stuff. But really I’m at my most productive in the early hours while listening to the Shipping Forecast. Can’t do that anymore! It’s taken a while, but I’ve found my rhythm.
Discover your most productive working style. Are you a night owl or an early bird? Do you work best in complete silence or surrounded by ambient noise? In time, you’ll work out your groove and find the optimal conditions to inspire you and help your productivity.
On that note, if you have periods (nope, I don’t shy away from this stuff), it can be reeeally helpful to track your cycle and figure out when your creativity is on fire and when you need to let your brain and body rest. It’s actual science – this is a helpful intro.
Lesson 8: Protect Your Boundaries
Ooooh the old work/life balance. It’s a juggle, am I right? Launching into freelance life after a corporate career (c’est moi), or switching to self-employed to fit work around your family commitments (if that’s you, you must check out Doing It For the Kids!)... well, it takes some figuring out.
Draw a line between work and personal life:
Set clear boundaries (no I will not reply to your email at 3am, Mr USA client, unless I am up feeding my wombfruit and I cannot sleep. But don’t expect a reply like that every 3am!).
Create a schedule (I use Sunsama – total project management gamechanger).
Stick to it.
Fact: Your mental wellbeing deserves the same attention as your projects.
Lesson 9: Be you
When you’re self-employed and active on social media, it’s very easy to get wrapped up in what everyone else is doing:
She’s landed a bigger client.
His website looks way more professional than mine.
How are they juggling their projects with their family and making it look so damn effortless while I look like a frazzled mess with a laptop bag full of Wotsit crumbs?
Hold up. There’s only one you in the world. You handle your projects, your clients, and your personal life in your own way. If you’re you – in the way you speak to your audience, in the way you schedule your time, in the way you come across on socials – you will find your people, and they’ll love you for you.
I can’t tell you how many freelance working mums I’m friends with because we all share the same juggles, frustrations, client woes, and so on. It’s a lot (and it’s great, because we all refer clients to one another – see lesson 5!).
If you’re a one-person show, don’t pretend to be a big organisation. It’s ok to say “I” and speak in first person, rather than “we” (that’s a big mindset shift for many of my copywriting clients, but it really helps simplify things!).
If you need to take time off from client work or fulfilling orders to care for your unwell pet, support your SEN child, help out your unwell relatives, or just to give your mental health a boost, then do it, and don’t worry about how your clients or audience react. If they see you as human, they’ll relate to you, and appreciate you more for it (and for those who feel you’re oversharing: well, those people are not your people).
People buy from people. So be you.
Lesson 10: Embrace the ups and downs
Being self-employed is like being on a rollercoaster. Ups (first sale), downs (customer complaint), highs (a record income month), lows (red flag client), twisty bits that make you go “aaargh” (a nasty dose of copyright infringement), and amazing moments where you throw your hands in the air and wave them around like you just don’t care… (perhaps an IRL meet-up with fellow freelancers).
Embrace the unpredictability, learn from your mistakes, and celebrate your successes. It’s all part of the wild ride that makes being your own boss so blinkin’ exciting.
Lesson 11: Stay curious and keep learning
Many freelance industries are constantly evolving. From new trends on social media to new selling platforms or AI tools, legal changes and global downturns, there’s always something different to get your head round. Stay curious: read industry blogs, join webinars, take courses, and expand your knowledge. The more you know, the more valuable you become.
Lesson 12: Celebrate milestones
Landed your dream client? Had a mega month of sales? Stood firm with your boundaries? Stepped out of your comfort zone when marketing your business? Launched the thing you’ve been putting off since forever? Celebrate it! Give yourself a high five for all your achievements, big or small.
Quick tip: Create a Google doc or Trello board filled with client feedback, reviews, and testimonials, along with a bunch of other business wins (financials, social media stats, number of lie-ins you’ve enjoyed since you quit your cruddy 9-5)… I look at my doc if I’m on the motivation struggle train, or if I’m doubting my skills.
Double bonus points if you share your wins with your network, so they can celebrate with you too!
Lesson 13: Never stop evolving
Your journey as a business owner is one of perpetual evolution. There’ll always be bumps in the road, new challenges to handle, big moments in life that may force you to take a break from your business, high times and quiet times.
One of my favourite things about being self-employed is the flexibility it gives me… Which also means I’ve learned to flex and change to suit what’s going on in my business and my life.
Embrace change, seize opportunities, and work on your business (researching new markets or tech, updating your website, creating your social media content plan – I can help with the latter two!) if you hit a patch that means you can’t work in it (doing client work/making products/delivering your service).
The path may be winding, but with every step you’re learning and improving.
Lesson 14: When you’re your own boss, mindset is everything
Had someone refer to your ‘little’ business as if it’s a side hustle or silly hobby? Get hacked off when anyone tells you you can’t make money doing what you’re doing? Ever let one negative bit of feedback ruin your entire day/week/month/career?
Stop right there. Mindset is everything as a self-employed person. Shush those negative voices in your head, pull yourself up if you’re having a bad day, and give yourself credit where it’s due: you’re rocking this entrepreneur lark (think of all those folk who are still stuck doing jobs they hate, and how brave you’ve been to take the leap!).
And if you need a little extra support, hit up my mindset coach Janey Holliday for a huge dose of real-life, practical positivity, or get some unmissable money mindset help from the awesome Lauren Malone.
Lesson 15: Only do what feels right for you
It’s your business. You’re self-employed. Ergo, you’ve employed yourself. You’re the best person for the job, and you know your stuff inside out!
Sure, it’s great to take advice, read books, follow inspiring entrepreneurs and network with like-minded folk. But do your thing! After all, it is your business! Only you know what’s best for you, what works and what doesn’t, who your clients and customers are, and what your big hairy audacious goals are. You get to choose. You get to design a life you absolutely love.
All good things must come to an end.
But not my freelance career. No and nope! I’ve worked too hard and come too far to jack it all in (plus I’ve got great things planned).
But I do need to finish this blog. So, to summarise…
Fifteen years as a freelance copywriter (also writer, editor, proofreader, and artist!) have taught me more than I ever thought possible. From pivoting fearlessly to celebrating milestones and everything in between, each lesson has shaped me into the fierce, fabulous freelancer I am today. So, my fellow freelancers, copywriters, makers, creatives, and self-employed superheroes, keep these lessons in mind as you continue on your own incredible journeys. Here’s to many more years of creative triumphs, laughter, and unforgettable adventures!
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