On the day I retired I got two cards. One from my Mum and one from myself. Inside the one from myself I wrote “Was that it?”. When I told my therapist she gave me a bollocking and told me not to be so negative. She said most people would envy my career and to buy another card and put something positive in it. That’s not easy if you’re a moaning old git who is clinically self critical.
My career started and ended in the same place: Bankside House, Leadenhall Street in the City where I walked through the door in the photo below in January 1975 as a trainee reinsurance broker. Forty seven years later, that building is now a restaurant and I walked out of exactly the same door having just ended my business career over dinner with colleagues on my last day of actual work. (That’s me below, leaving my career behind me).

What happened in between? I answered that question a couple of years ago when I decided to plot a timeline analysis of “What did you do with your life?”. This is the title of a talk given by the legendary Harvard Business School professor, Clay Christensen. I met him in Oxford at a lecture and college dinner. He was instantly recognisable as he was so tall. He was also a genuine, good bloke. His talk was a warning about chasing too hard doing things and behaving in ways you might regret later in life. Had I done that? I opened a spreadsheet. TBH I wasn’t that interested in the exercise at first. My objective was to do something else rather than go to the pub. I was 64 and in my flat in the Barbican where I lived two nights a week during the days I spent in London. In column A I put the years going down the page. I started with 1961 when I was five and took it down to 2019. Column B was age, column C occupation. D happy or unhappy, E annual earnings or losses for the year, F Type of employer, G Sector, blah blah Once I filled it in I did my analysis. The results were shocking.
- 18 years in full time education since the age of 5.
- 24 years in start-ups of which 13 years paid no income of which 10 involved pouring my savings into ships that seemed determined to sink.
- 25 jobs, average duration 2.5 years, longest 5 years, shortest 6 months. (Never been fired though).
- Happy and unhappy years evened out at 50/50
- ROI / Income – Millions have washed through my hands. There were some big paydays and one huge loss that more or less wiped them all out. At retirement my net worth is >£1m and <£5m. (Sorry to be cagey, I dunno, I can’t be sure and I don’t care but if you want a hard data benchmark my salary when I retired was £280k, which is well into the top 1% but way less than the £1m paid to waster partners in Big 4 firms). You might think “that’s not much, you would have been better off as an accountant or big company exec”. My reply to that is that my DNA would not have allowed me to be either, and, as I started out with nothing and grew up never expecting to live in a detached house I am not complaining. I live in a big farmhouse in North Devon, I have my classic Porsche and Land Rover in the stables, five acres of paddocks, loads of toys, my children had a good education and along the way I’ve had millions of pounds worth of experiences of both types (good and bad). I rolled the dice. I played the Great Game. I ended up better off than most who follow an entrepreneurial career. Win.
Looking at the data made me feel … tired. Had I really done that? There were surprises. Such a long time spent in education. So many adult years not earning or even worse, not earning and also risking every penny in new businesses. And, so many jobs and companies. Unlike many of my peers I followed a course that will become normal for millennials. I did a lot of different things marketing, sales, development, project management, general management, country manager, board director, CEO. I talk about this to my dentist, who is only slightly younger than me, and far superior academically. He has spent his whole life looking down people’s mouths, smelling what they had for dinner and seeing what’s left of it stuck in their teeth. I couldn’t have done one thing for a whole career for one employer. But choosing a lifetime profession was what many people did when I was young. At thirty I chucked in a really good job with 3M, having risen quickly to a senior position. People thought I was mad. But I wanted to run my own business. Twelve months later, having thrown in every penny I owned, we were on the edge of disaster with one month’s money left to pay the wages and then bankruptcy, losing my house etc to follow. Somehow, only six months later we had wiped out our debts and started paying ourselves. Imagine the buzz. It’s like crack. You can never get enough of it.
Close friends who have known me since university haven’t got a clue what I do. My own son once made the mistake of asking. We were in the car and he was talking to his friend. They had both made a good decision to drop out of rubbish university degrees. He asked me “Dad, what is it you do?”. Shocked at his ignorance of how his lifestyle was funded I said “You’ve got an iPhone, look me up on LinkedIn”. Though I quickly relented and said I had done lots of things but don’t worry, you don’t need a plan. I heard Sir Ken Robinson make this same point to US HR execs in a lecture in Cirprianis on Wall St. Sir Ken made Ted. This link is to his famous Ted Talk, the most watched of all time.
He said it would be impossible to plan an entrepreneurial career. It is in large part opportunistic. You need to take advantage of qualities they can’t teach you at school. You need an appetite for risk, confidence, determination, resilience, a willingness to turn your hand to whatever needs to be done and a lot of other things it is hard to describe on a CV. I told them they would make it ok if they worked hard, took pride in their performance, did what they said they would do, turned up on time, helped colleagues, embraced problems – you know all that Boy Scout stuff from Kipling’s “If”. Do all that and opportunities find you and another thing, you grow a confidence that opportunities will always find you, so you are never trapped. It’s more important than grades in A levels and degrees. As a business leader there are so few people who you can trust to be reliable and “do what it takes”. At 20 they were too young to listen. At 30 my son has now seen it and believes it.
About 12 months after we set up a tech spinout owned and funded by Unilever, Graeme Pitkethly (Unilever’s CFO) asked me to describe what it was like being an entrepreneur in a global firm. At 64 this was not an opportunity to show off to a top exec to further my career, which was largely behind me. I saw it as a chance to tell it like it is. I didn’t do a PowerPoint or a report. I printed off a Mindmap on one sheet of A3 and we sat side by side, chatting over the good and bad of trying to be a speedboat dragging a supertanker. Here it is.

Sorry, I had to blur the words. It’s confidential! I can clearly remember Graeme was enthusiastic. Like all execs in global firms he was frustrated by the time it takes for the company to innovate and the reluctance of long serving careerists to take risks, and the delays of rules and bureaucracy. I explained how we got around a lot of that by operating outside normal processes by breaking rules and asking for forgiveness not permission etc I said this created powerful internal enemies who didn’t want us to succeed, and when we launched, they did what they could to bury us. I don’t think that was paranoia. That’s how it would be in any big organisation. It was exactly like that when we set up a business wargaming spinout from KCL War Studies. The fact that I had two top professors on the board of directors; Mike Clarke (head of RUSI) and Sir Lawrence Freeman seemed to make it worse. Big organisations are highly political and rivals expend vast energy on internal competition. I retired a few years later. I claim my eclectic career makes me the first retired Millennial. Lots of jobs, lots of employers, permanently in education and reskilling, no occupational pension. I cleared the path. The end of career report? My honest appraisal, the truthful one that went in my replacement retirement card is embarrassing to quote. It’s hard for someone who grew up in a self deprecating traditional English culture, to accept praise, especially from yourself but I promised to be honest, so here it is.
“My career was a total blast. The experiences, the achievements, the failures, the highs and lows, the fantastic people I have worked with (that is genuinely the best thing), the places I’ve been, the people I’ve met and the reward and recognition have all been beyond, far beyond most people’s experience. I won’t play down my own role in it. Under the rules of honesty, I must treat myself as I would anyone else who presented the data to me. On that basis I have to give myself a hearty “Well done” and a firm pat on the nut. For sure, there was unfinished business and I never had that big cup final win (that I nearly killed myself trying to achieve), but there were many great victories. I know how difficult it all was. Not many people could have done it. You made me proud”.
Wishing all the best to “my fellow millennials”, the real ones who are living the Future of Work. Go for it dudes.

