A little over three years ago, in the spring of 2023, I left executive leadership. I was about to turn fifty, I had what looked on paper like the ideal job at a foundation, a global remit and a team I admired, and I walked away from it without another job to go to. I did not leave to slow down. I left to work differently, to move across organisations and contexts rather than sit inside one, and to stay closer to the work itself and the decisions behind it. At the centre of that shift was a small advisory business I named after my son Keir, who at ten remains its self-appointed and entirely unaccountable non-executive chair.
I have written more than once about how good the change has been, and it has. But anniversary reflections tend to round the corners off, and enough time has passed now, and enough has happened in it, to be honest about the whole of it rather than only the highlights.
A portfolio career is not one thing. Mine is built around KW Strategy, the advisory work that pays for everything else and now includes two colleagues, Anna and Esha, who took their own risk in joining. Around that sit a small number of non-profit board roles. I am Vice Chair of Play England, and I also sit on the boards of STIR Education, Svitlo Education and Home-Start UK. Alongside those come writing, the occasional judging panel, and the speaking and convening that come with the territory. Described that way it can sound like a tidy diversification of a single asset. In practice it is a set of genuinely different jobs, each with its own rhythm and its own people, held together only by me and by a clear sense of what I will and will not do.
The first thing I learned is that clarity matters more than confidence. I did not begin with a polished plan, and I have come to think anyone who claims they did is rewriting history. What I had instead was a clear sense of the work I wanted to do, the values I was not prepared to compromise, and the lines I would not cross. In rooms where certainty is often performed rather than felt, that clarity has been worth more than any amount of projected self-assurance.
The second lesson is about money, which the gauzier accounts of this life tend to skip. Being calm and direct about fees, early and without apology, saves everyone time and prevents the awkwardness that creeps in when value is left vague. My rates are my rates, because each hour carries more than thirty years of experience, and because other people now depend on me to keep bringing in good paid work. The only unpaid work I take on is the non-profit board roles I have chosen, where I know the contribution is real. Everything else is paid, because a business that quietly subsidises everyone is not sustainable, however generous it feels in the moment.
The third lesson is that a portfolio career will expand to fill every hour you give it. There is no employer to close the laptop for you and no end to the day that someone else defines. The freedom that makes this way of working attractive is the same freedom that, left unmanaged, erases the line between work and the rest of life. Boundaries are not a luxury here. They are what makes the whole arrangement survivable, and I am better at them than I was, though still not as good as I like to tell myself.
There has been another freedom too, and a less obvious one. For most of my career, what I said was heard through the institution I represented and the title I held. Without either, I am taken more simply as myself, and I can move more freely between worlds that do not always talk to one another. Out of that has come a role I never set out to occupy but now value as much as any other: connecting people across sectors and silos, introducing those who ought to know each other and do not, and helping, wherever I can, to make information and knowledge more accessible to more people, rather than leaving it locked inside the few organisations that hold it.
Two of the biggest changes were not really about work at all. Last summer, after almost twelve years living in Singapore and then Denmark, we moved back to London, to the same house in Twickenham we had left behind more than a decade before. Building the work around that life, rather than the life around the work, was one of the reasons I chose this path in the first place, and being closer to family and old friends has mattered more than I expected.
Then, earlier this year, in the same month I turned fifty-three and Keir turned ten, I was diagnosed with bladder cancer. This week I reached a real milestone, the end of the intensive first phase of treatment, six weeks of immunotherapy on top of the two surgeries that came before it. Finishing it is not the same as knowing it has worked, and a biopsy in July will say more, but after the months behind me it is a genuine relief, and I have even started back in the gym.
I have written separately about what living with this has been like, so I will not repeat it here, except to say what it revealed about this way of working. The vulnerability is real and worth naming. There is no sick pay and no employer holding the structure in place when your health gives way, and that is not a small thing.
But I also found that the work itself was steadying. Having something to deliver, something that existed outside the clinical world of scans and waiting rooms, helped more than I would have guessed. The freedom I had built into these years, to choose what to prioritise and to be present for the people who matter, turned out to be exactly the freedom I needed when it counted most. The hardest moment was not the diagnosis or the surgery but sitting down to explain it to Keir, and no structure, professional or otherwise, makes that easier.
There is one thing I would ask anyone reading this to take from it. Bladder cancer is among the most common cancers in the world, and its most common warning sign is blood in the urine. When I first saw mine, I waited five months before doing anything about it, and that is the mistake I would urge you not to make. If you ever see it, even once, see your doctor straight away.
I would not pretend the diagnosis has left my view of any of this unchanged. It has sharpened it. Things that once felt easy to postpone feel more immediate, and time with the people who matter carries a different weight when health can no longer be taken for granted. If anything it has strengthened rather than weakened the case for work built around a life rather than the other way round. The variety is still genuine, the autonomy still real, and moving between philanthropy, education, climate and social impact still keeps the thinking sharper than any single role did. But I notice the ordinary days more than I used to, and I am less inclined to trade them.
Three years on, I would still recommend it, but not in the breezy way these reflections usually end. It asks for discipline, financial nerve and a tolerance for uncertainty that not everyone wants and not every stage of life can absorb, and it offers no institution to catch you when life turns. What it offers instead is the chance to do work you believe in, with people you respect, on terms you have set yourself, and the freedom to put first what actually comes first. After the year I have had, I value that more, not less. The honest advice is not simply to leap. It is to be clear about what you want, direct about what you are worth, disciplined about where the lines fall, and then to leap, with your eyes open.