I've been self-employed since 2010. That's sixteen years of no guaranteed payslip, no HR department to hide behind, and nobody to blame when it all goes pear-shaped but the bloke in the mirror.
I wouldn't change it for the world. Still, I'd be lying if I said I had it figured out from day one. The truth is I've made just about every mistake going, and a few I've apparently had to make twice before they'd stick. So here they are: the ten that taught me the most, in the hope they save you a bruise or two.
1. Underpricing my work
When I started out in 2010 I was knocking out websites for about £200 a pop. Two hundred quid! I genuinely thought I was being clever by tacking on £80 a month for "maintenance". Recurring revenue, look at me, the budding mogul.
The problem is that the maths only works at small scale. Pile up enough £80-a-month clients and you don't get a tidy passive income, you get a small army of people who all, quite reasonably, expect to be looked after. I ended up so swamped by sheer volume that I couldn't give any of them the customer service they deserved. I'd underpriced the work and over-promised the support, which is a properly miserable combination. Charging more would have meant fewer clients, more attention for each, and a version of me that wasn't permanently firefighting.
2. Relying on the wrong people
Here's a hard one: your friends don't always make good members of staff.
When I started my first company I wanted to bring people in to share in the good times, and who better than your mates? It felt brilliant for a while. With hindsight, though, I hired far too quickly, and the place slowly turned into something closer to a social club than a company. Lovely atmosphere; less lovely balance sheet. The hard lesson is that hiring someone you like and hiring someone who's right for the role are two very different decisions, and blurring them does no favours to the business or the friendship.
3. Not budgeting properly
When the first proper cheques started landing, including one from Coutts that I'll never forget (Coutts! me!), I felt like I'd made it. So I did what any sensible young business owner would do: I rushed straight out and spent it.
What I hadn't done was set anything aside for the taxman, or for the boring, inevitable expenses that turn up whether you've budgeted for them or not. A good chunk of that cheque belonged to HMRC. I just hadn't met it yet. Learning to split every payment the moment it arrives, into yours, tax and buffer, was one of the least glamorous and most important habits I ever picked up.
4. Outsourcing my own decisions
This is one I'm still working on. For most of my career I've had a habit of seeking validation, running a decision past this person, getting an opinion from that one, canvassing a little committee before I commit to anything.
A second opinion is healthy. A tenth opinion is just decision fatigue wearing a clever disguise. Somewhere along the way I realised that all that consultation was often a way of dodging the responsibility of simply choosing. And here's the thing: nobody else has the stakes you do. They give their two cents and walk away; you live with the outcome. Usually you know what the right call is and you just want someone to bless it first. Eventually you have to accept that being the boss means being the one who decides, and that your own judgement is the whole reason you're doing this in the first place.
5. Thinking the learning ever stops
Early on I think I assumed that once you'd earned the title, whether consultant, specialist or expert, the hard part was over. It isn't. If you're asking people to part with cold hard cash on the strength of your expertise, you owe them genuine depth, and that depth is built off the clock, on your own time, when nobody's paying you to learn.
And it never lets up. The moment you stop is the moment you start to date. You have to be a self-motivated learner, permanently, which is exhausting to hear and truer than I'd like. The unexpected upside? It's the best cure for imposter syndrome I've found. Once you've actually done the thing, repeatedly, in the real world, with real consequences, you've got something solid to stand on. The fraud feeling fades once you've got the lived experience to fall back on.
6. Paying myself badly in both directions
You'd think paying yourself would be the easy bit. It isn't. Over the years I've managed to get it wrong in both possible directions. Some periods I've drawn too much out and left the business dangerously thin; others I've paid myself so little that I was running on resentment, wondering why I bothered. One route puts the company in jeopardy. The other quietly kills your motivation. Neither one lasts.
What works for me now is a rhythm. Every six months I sit down and do an honest review of both sides, what I actually need personally and what the business can genuinely afford, and I find the balance between them. Pay yourself well, but only ever what the business can stand. You and the business are partners in this.
7. Feeling pressured to expand
There's a particular fantasy that gets every growing business owner sooner or later: the big shiny office, the assistant waiting on your beck and call, the trappings that say I've arrived. I've felt the pull of it more than once. It must be resisted until you are genuinely, boringly, demonstrably ready.
Growth that runs ahead of your cashflow is really just risk with better furniture. Over-extending before you've got money reliably in the bank is one of the surest ways to turn a healthy little business into a stressed and fragile one. Let the numbers tell you when to scale, and keep your ego out of it.
8. Refusing professional advice, even when it was free
Early on I was convinced I didn't need an accountant. My books were simple enough, I reasoned, so why pay someone to do what I could do myself? And technically I could. The trouble was that it was never my priority, so it quietly slid. Returns went in late, or got done in a mad last-minute scramble that cost me a full day of actual work and a chunk of my sanity.
The irony is that the help I was avoiding would have cost me less than the chaos I was creating. Take the professional advice, and especially take it when it's free. A good accountant, a solicitor's free first consultation, an experienced peer: these people see the potholes you're about to drive into. Let them.
9. Painting myself into a corner
If there's one certainty in technology, it's that it changes a lot, and fast. Tie yourself too tightly to one tool, one platform, one way of working, and the ground will eventually move out from under you. I've watched it happen to people, and I've felt the early tremors of it myself.
This is where the constant learning from mistake number five earns its keep. You have to keep one eye on the next couple of years, not only the next invoice, and stay willing to adapt what you offer so you're still relevant when the wind changes. Stay flexible. The aim is to keep yourself loose enough that the future can never quite corner you.
10. Putting health and family last
This is the one I'd most like you to actually listen to, because I learned it the hard way. Through the 2010s my health simply wasn't a priority. I skipped check-ups. I'd knock back painkillers to power through illnesses I should have been resting off. Work came first, always.
Then around 2014 it caught up with me. I was admitted to hospital twice with pneumonia. Things got bad enough that the client I was contracting for at the time literally banned me from the office to force me to look after myself. Let that sink in: I'd outsourced my own basic self-preservation to a contract manager.
Don't do that. Money is just a tool. Ayn Rand put it better than I can:
"Money is only a tool. It will take you wherever you wish, but it will not replace you as the driver."
The actual goal is a healthy, happy life for you and the people you love. Everything else, the rates, the clients, the shiny office, all of it, comes second. It's taken me far too long to be able to say that and mean it.
Bonus. Build a network of equals
I couldn't leave it at ten, because this one underpins all the others. Build a trusted network of equals, and don't let yourself be distracted by people who don't have your best interests at heart. I've lost more time than I'd like to admit getting tangled up in things, whether voluntary commitments, side-quests or the odd shiny distraction, that quietly pulled me away from what mattered.
There's a well-worn line from Jim Rohn that I keep coming back to:
"You are the average of the five people you spend the most time with."
So choose those people deliberately. Surround yourself with quality individuals, the sort who keep your secrets, who want to create value, and who are trying to leave the world a little better than they found it. Their standards become your standards, their ambition rubs off, and on the hard days they're the ones who pull you back up. Guard that circle like it's an asset, because it is.
The thread running through all of them
Read them back and a pattern emerges. Underpricing, paying myself badly, overworking until I landed in hospital, outsourcing my decisions and my self-care: almost every mistake on this list is a version of the same one. I wasn't taking myself as seriously as I took everyone else.
So if there's a single thing to carry away from sixteen years of my fumbling, it's this. Treat yourself with the same seriousness you'd give a valued client. Charge properly. Set boundaries. Protect your time, your health, and your judgement. Be the boss you'd actually want to work for.
I'm still making mistakes, of course, just newer and more interesting ones. That's the job. But these eleven? These ones I've finally put to bed.
Self-employed too? I'd love to hear which of these landed, or which one you'd add as number eleven. Drop me a line.
