My Startup of One. 18 lessons from 18 years working for myself.

My Startup of One. 18 lessons from 18 years working for myself.

In the picture on the left, I’m standing on Greek Street, Soho. I’m at the start of my new independent life, having left the security of an organisation after seven years. I think I look a bit worried. On the photo on the right, taken last year, I’m standing on the same stretch of Greek Street. I’m pleased to say I look much happier, after having worked 18 years for myself.

If I’m honest, it’s been no mean feat. But here I am at the end of 2017, about to launch into another new year of fresh challenges. And it’s great to be able to look back on those 18 years and feel proud that I’m still here.

It’s strange now to think that in 2000 we didn’t have WiFi, we didn’t have coworking spaces and there was no such thing as the Gig Economy. It wasn’t so common to work as a freelancer. Today many people choose to work for themselves. As we’re nearly putting another year to bed, I’m looking back over what’s been good, what’s been hard and what I’ve needed to keep me going on my journey. Here I share some of the things I’ve learnt along the way:

  1. It’s an adventure. You know what to expect with an adventure, right? It’s fun, but it’s also scary. Full of ups and downs. That’s been my story. Working for yourself might sound like the ‘easy’ option. All that flexibility and freedom. But it’s been harder than any experience I ever had working for an organisation. You have to expect the troughs as well as the highs, just keep the faith, keep learning and hang out with good people who can give you some advice (see “2").

  2. Two heads are better than one. Okay so you need to be self-sufficient, you need to be able to win the business, do the business and admin the business. But sometimes — or more likely often — two heads are better than one. You need a collaborator, a supporter, a sounding board. My secret weapon these last few years? My wife. She’s become my business partner. A sounding board. An editor. A critical eye. I keep being me, and I don’t always accept the advice, but it’s good to stress test my ideas and plans with someone who really understands me.

  3. It’s okay pursuing multiple paths, but get focused. I’ve always been driven by curiosity, by seeing where the water flows and acting on opportunities. That means I’ve embraced lots of different types of projects and taken a lot of different paths. In the early days I started a little content agency, Ignission. Then there was a creative agency OHM London. I wrote books and for newspapers, I took on marketing projects and advised creative businesses. The plurality and experimentation has been part of the adventure. I knew I could do all those things, so I did them. I spent a good chunk of my time experimenting, and in doing so I’ve been able to understand what I like doing and where I can bring the best value. Now, I can really focus on helping businesses, organisations and individuals on their journeys (and bring all I’ve learned into the process).

  4. Collaborate, but choose your partner-mates carefully. In all these years I’ve only had one relationship with a collaborator that went badly wrong. A guy approached me about us writing a book together. I got us the book deal, went to the U.S. for a week, started writing the book. And then he vanished. I never saw or heard from him again. That was painful. But looking back, I would have never have guessed. He seemed ‘legit’. I’m sure he was. Now I can be more pragmatic about it. Perhaps he was just bad at communicating. At the time, I was mad and upset — a week of my life away from my family that I’ll never get back. It gave me a valuable lesson: pick your projects and those you work with very carefully.

  5. Be part of a community. Working for yourself can be hard and it can be lonely. So you need a space or a group that you can hang out with. It doesn’t have to be a full time residency at a coworking space, it might be a monthly Meetup group or a hot-desking arrangement somewhere. It feels good to be part of something.

  6. Tools matter. You need to be organised. You need spreadsheets for expenses and revenues. You need templates for invoicing. You need apps like TeuxDeux and Google Drive to stay on top of everything. But mindset and discipline beat sexy software. I just rely on some Excel spreadsheets to manage everything, I don’t have any bookkeeping software. And that works just fine. It’s boring, but make sure you stay on top of admin and invoicing.

  7. The worst thing? Debt chasing. If you’re a startup-of-one it can be hard if you’re the one winning the business, schmoozing the client but also chasing late payment of invoices. That isn’t fun. The energy expended on getting invoices paid on time is my biggest stress point.

  8. Don’t work from home (at least, don’t only work from home). If you care about your mental health, if you want to be productive — please, get out of your house! Coffee shops, co-working spaces, hotel lobbies — whatever floats your boat. I do my best work all over the place. Sometimes I need a train ride somewhere, or some time out in a different city altogether. It gives you space and time to physically and metaphorically get away, and get some perspective on what you’ve got going on (and it helps planning for the future).

  9. Set out your metrics for success. A friend of mine who recently went freelance as an independent consultant laid out his business model to me. How he would have failed (his words) if his day rate went below a certain level, how he would have failed if he didn’t bill a certain number of days a month. That’s not my philosophy. Working like this is a way of life, not a business model. Sure, of course, revenues matter. But I choose another metric of success: whether I am happy, fired-up and making an impact (that’s why I still track my Good Times, it’s the best measure of success for me).

  10. Get a reputation for one thing. This has been hard for me. Ask ten different people I’ve worked with over the last ten years, and you’ll get ten different answers of what they think I do. It’s a symptom of having pursued those multiple paths I talked about earlier. Now I’m consolidating all my years of experience and am carving out a more single-minded and purposeful path as a storyteller, coach and consultant. But throughout, I’ve had a reputation for being ‘a safe pair of hands’ — reliable and helpful — two traits that go a long way when working for yourself.

  11. Look after yourself. Woah, looking back one thing I haven’t been good at is looking after myself. I’ve worked too hard, I haven’t given myself enough down time. My health suffered. I learned the hard way. Now my priorities are different. It’s so important to prioritise what you need over everything else, because if you’re not functioning properly you’re no good to anyone else, and certainly won’t be able to do your best work.

  12. Find a guide. Sometimes you need someone who’s ahead of you on the journey to show you the way. That’s why I wrote my first book ‘Leap!’ — to help others on their self-employed journey. Today, I help people on their career journeys as a coach and mentor. I’ve checked in with coaches and mentors from time to time. The key is to finding someone who’s right for you. Take time to find someone who can be that guide, someone you feel you can build a good relationship with and trust.

  13. Stretch yourself. I’m proud to say I have never stood still, I have constantly pushed myself out of that comfort zone. Trying new things, seeking to up my game, constantly learning. Don’t stand still. Often the only way to prove you can do something (that you might not have done before) is to do it. It’s hard to throw yourself off the cliff sometimes, but you have to have faith that you’ll fly.

  14. Don’t follow the £. That sounds silly advice, doesn’t it? Surely that’s precisely what you should do to earn a living working for yourself? Follow opportunities — yes. But, if you choose an assignment or project or client because you’re seduced by the money, that’s where it can all go wrong. There’s been a correlation between high-billing projects and projects that killed me creatively, where I hated them so much, I desperately wanted them to end. It’s not always worth it.

  15. Be brave. No sick leave, no-one to hold the fort when you’re feeling ill or not rocking it one day. The uncertainty of where the next project is coming from. It’s hard. You have to dig deep, put on your armour or grow a thicker skin and get out there. Cultivate resilience — it’s partly about keeping going when things get tough, partly about having a level of self-belief that you can do it and partly having supportive partners or people around who have faith in you and can give you words of wisdom to keep you strong.

  16. Stick to who you are. My self-employed life improved hugely — and my health and happiness and confidence along with it — when I stopped trying to be something or someone else, and stuck — like a magnet — to who I really am. That’s powerful. Knowing what you stand for, what makes you tick and using that as a compass to navigate your paths and choices. Along the way, you might make choices that you look back and regret, but through trial and error you will find your way to where you should be. Give yourself some credit — trust yourself.

  17. Give yourself a pat on the back (cos no-one else will…!). That thank you email from the boss. When your CEO sends you a bunch of flowers. The sticky note on your desk with a ‘well done’. You won’t get any of that! So take the time to celebrate your achievements, pat yourself on the back. Hey, even allow yourself to re-tweet a few successes from time to time ;)

  18. Set yourself free. Yes, there’s ‘free’ in freelance, and that doesn’t mean working for love not money. Enjoy the freedom of the path you’ve chosen. When you have the flexibility, take your work to the park. Go and sit in an art gallery. Go for a lunchtime swim. Celebrate the freedom of working for yourself…

What I wished I’d known earlier in my career. Build a single Lego tower, not multiple ones.

What I wished I’d known earlier in my career. Build a single Lego tower, not multiple ones.

Getting teams out of their bubble: my workshops at the BBC.

Getting teams out of their bubble: my workshops at the BBC.