This month marks two years since I left my post at the Mozilla Foundation and became an independent consultant as founder of Dynamic Skillset Ltd.

Now then, I’m aware that in sitting down to write this post, there’s is an expectation for me to follow certain conventions. One example is that last sentence: I’ve just used the phrase ‘sitting down’ when I’m actually standing at my standing desk.

Tired phrases and worn out cliches aren’t what I’m about. They’re of no use. I don’t deal in dead metaphors, but in lived experience. As a result, and having never been a fan of convention, I’m going to attempt to turn the usual tropes upside down. Here goes…

1. “I should have made the leap years ago”

Well, no actually. I remember being promoted straight into senior management straight from being a classroom teacher. It was an extraordinarily steep learning curve and, coming at a time when we had a young son and I was writing my doctoral thesis, I wasn’t ready for it.

This time, I was ready for it, having worked at two organisations that gave me progressively more responsibility for managing my own time. Had I not spent two years working on projects at Jisc, and then three years working remotely for Mozilla, it would indeed have been a ‘leap’ instead of a fairly smooth transition.

2. “It’s been a rollercoaster ride”

Yes and no. Mostly, it’s been about finding a sustainable rhythm that allows me to do work I enjoy with people that I like.

I can remember meeting a freelancer at a Nesta event just after I’d become a consultant. That old cynic’s words of encouragement? “Welcome to being skint”. In actual fact, it hasn’t been like that. There’s certainly been months where I’ve earned more and months where I’ve earned less, but I try not to measure my life solely on profit.

Instead, I measure it at how successful I’m being in removing from my life what the Ancient Greeks termed ‘akrasia‘. My aim is to live, as much as is in my power, a simple, upright, and moral existence. To do that, I have to be in control – of myself and my working conditions.

3. “It’s been really hard work”

Hang on, walking up a mountain in a blizzard is ‘hard work’. While I certainly haven’t slacked off, I wouldn’t say I worked any harder than I did while employed. I definitely work differently, and more flexibly, though. I’d already cut out my commute, but not having to attend meetings unless I really want to is pretty awesome. I’ve definitely applied Derek Sivers’ philosophy in that respect.

About six months in, I increased my day rate and went down to working four days per week. After all, I’m the boss, right? So now, most Fridays you’ll find me reading the things that I never used to get around to reading or, better yet, clocking up the Quality Mountain Days as part of my training for the Mountain Leader award.

4. “I’m happier than I’ve ever been”

I think a certain utilitarian philosopher said it best:

I have learned to seek my happiness by limiting my desires, rather than in attempting to satisfy them.

(John Stuart Mill)

Yes, we still have all of the creature comforts, but my attitude towards them has changed. I’ve stepped off the hedonic treadmill. When you’ve got more time on your own, and time to think, you realise that you’re not in competition with anyone.

That being said, the time alone also means you have to exercise greater self-care. That’s physical – making time to walk, swim, and go to the gym – but also mental. In fact, learning to live comfortably within your means (and your own skin) is an incredibly difficult thing when you don’t have as many things to distract you.

Am I ‘happier’ than I was when I was employed? Well, that’s an emotion that comes and goes. Do I feel like I’m more in control of my life? Yes. Do I feel like I’m flourishing more as a human being? Definitely. Happiness can be synthesised. Flourishing can’t.

5. “I couldn’t have done it without X”

In these kinds of posts or speeches, the individual thanks their family (usually) and their friends and colleagues (sometimes) in a quasi-apologetic way. Doing so in this way puts the focus back on the individual themselves, as they thank others for ‘putting up’ with them, or for looking after things (children, pets, other organisations) while they pursued their dream.

On the contrary, this has been a collaborative endeavour from the start. My wife gave up one of her positions in a Ofsted ‘Outstanding’ school to help me with admin and logistics. She’s supported me in very practical ways, suggesting things I never would have thought about, and developing a real head for business.

In addition, and I’ll perhaps expand upon this when we reach our one year anniversary next month, setting up We Are Open Co-op with friends and ex-colleagues has been a revelation. The work we do together is often different from the work I do by myself with my own clients. Both are enjoyable. What the co-op brings, however, is camaraderie and collegiality.

So thank you, Hannah, Bryan, Laura, and John. Not for supporting me on some ‘crazy dream’, but for the everyday comments, advice, and guidance that you give me to help things tick along.

Final thoughts

I still get several people per year emailing me to ask whether I think they should pursue a PhD. It’s always a difficult one to answer. Likewise, I know there’ll be a lot of people reading this post thinking that they quite like the idea of being self-employed. So, given I don’t know your situation, I’m going to point you in the direction of Epictetus for some advice:

In every act observe the things which come first, and those which follow it; and so proceed to the act… A man wishes to conquer at the Olympic games. I also wish indeed, for it is a fine thing. But observe both the things which come first, and the things which follow; and then begin the act. You must do everything according to rule, eat according to strict orders, abstain from delicacies, exercise yourself as you are bid at appointed times, in heat, in cold, you must not drink cold water, nor wine as you choose; in a word, you must deliver yourself up to the exercise master as you do to the physician, and then proceed to the contest. And sometimes you will strain the hand, put the ankle out of joint, swallow much dust, sometimes be flogged, and after all this be defeated. When you have considered all this, if you still choose, go to the contest: if you do not, you will behave like children, who at one time play at wrestlers, another time as flute players, again as gladiators, then as trumpeters, then as tragic actors: so you also will be at one time an athlete, at another a gladiator, then a rhetorician, then a philosopher, but with your whole soul you will be nothing at all; but like an ape you imitate everything that you see, and one thing after another pleases you. For you have not undertaken anything with consideration, nor have you surveyed it well; but carelessly and with cold desire.”

(Epictetus, Enchiridion, XXIX)

Given that Epictetus was writing 1,900 years ago, I’m going to add ten very practical points to the above. Some of this is advice I was given to me before I started out, and some I’ve learned along the way:

  1. Get an accountant — preferably via a recommendation.
  2. Use online bookkeeping software — the same one as your accountant!
  3. Backchannel like crazy — reach out to people who may be able to help you, call in favours.
  4. Sort out your first six months — get contracts in place, verbal agreements don’t pay your mortgage.
  5. Create productive routines — as any creative person will tell you, it’s extremely difficult working in an environment without any constraints!
  6. Update people often — create something (newsletter, podcast, etc.) that makes it easy for those interested in your work to keep tabs on you and remind them that you’re available for hire.
  7. Build a realistic pricing model — otherwise you’re just licking your finger and putting it in the air.
  8. Share your work — it’s the best form of marketing.
  9. Meet with people often — both online and in-person, to build solidarity and to stave off loneliness.
  10. Book your own professional development — think of conferences and events you can go to, podcasts you can listen to, and books you can read to develop your practice.

I could go on, but for the sake of brevity I will stop there. Questions? I’ll happily answer them!