The last big job is different, mostly because you finally understand what it costs.
“I’ve got one last big gig in me,” they’ll say, usually followed by something along the lines of, “and I want to make this one count.” Not necessarily in the old sense of making it count, either. They’ve done the big titles and the remuneration and the teams and the airports and the years spent building things, fixing things, growing things. There is still ambition there, but they now want both their work and their life to mean something more.
They want to contribute, but they are increasingly conscious of what that contribution will cost them in time. They don’t want to wake up two years into another enormous role and realise that they accepted it mostly because somebody important asked them to.
I think this is one of the more interesting career transitions because, for perhaps the first time, the usual career questions stop being particularly useful. Is this a bigger role? Is the company growing? What does it pay? Where could it lead? These are questions designed for a career that is still accumulating. When you are contemplating the final decade or so of your working life, I wonder whether the more useful question is not what you want to achieve at all, but who you want to be while you are achieving it. What kind of person do you want to be on an ordinary Monday morning? What do you want occupying your mind when you’re walking the dog or having dinner with your family? What kinds of problems are you still willing to lose sleep over? Because accepting a job is, of course, accepting all of these things as well. We tend to think we are choosing the work when, in fact, we are choosing a way of spending a fairly substantial chunk of what remains of our life.
There is something to be said for not knowing what comes next for a while. This is deeply uncomfortable for successful people. Most have spent decades being very good at knowing where they are going and, when one thing finishes, immediately begin applying all that competence to solving the next thing. The calls are made, recruiters contacted, LinkedIn updated, coffees arranged. The empty space is treated as a problem to be fixed. However, could there be value in deliberately resisting this and creating what we call a “messy middle”; a period in which you remove enough of the usual scaffolding of your professional identity that you can see what remains without it.
One client of ours had just left a CFO role at a Fortune 500 company when he was out for dinner with his wife and got talking to the woman pouring their wine. He asked how she knew so much about it. She told him she’d grown up on a vineyard in Italy. That night, with no plan beyond wanting to feel free for a while, he booked a flight to Italy. He ended up working unpaid on a vineyard, pruning vines during the day and sleeping in a tiny cabin at night. Quite a departure from running the finances of a Fortune 500 company.
Paul, a former global Managing Director, took a more local route. After leaving corporate life, he walked down to his local food bank and volunteered to help. They put him on potato peeling duty. He spent weeks doing it until, as he tells it, he got fired for being a terrible potato peeler. So he found another way to help. He used the skills he’d spent his career building to raise $1 million for a new kitchen. There is something wonderfully levelling about this image to me. After years of being the person people come to for decisions, strategy and direction, you are handed a pile of potatoes and a peeler and that is, for now, the entire assignment. I suspect experiences like these work precisely because they interrupt the constant reinforcement of who we think we are. Nobody in the vineyard particularly cares about your former title. The potatoes certainly don’t.
A sabbatical doesn’t have to involve Tuscany or root vegetables, obviously. It might be travelling alone for a few weeks, volunteering somewhere in your own community, learning something you are spectacularly bad at, walking a long distance, or simply resisting the urge to immediately replace the structure you’ve just left. The point is less what you do and more what happens when you create enough distance from the noise to notice what you miss, what you don’t miss at all, and what starts to feel important when nobody is asking you for a five-year plan. We are very good at filling space before it has had a chance to tell us anything.
The same applies, I think, to our networks. By this stage of a career most executives have accumulated an extraordinary number of people: former colleagues, bosses, clients, board members, friends from three companies ago, the person they worked with intensely for four years and then somehow haven’t spoken to since 2017. We call this a “network”, which makes this rather wonderful collection of human beings sound like infrastructure. Marc Miller and Susan Lahey, in Repurpose Your Career, use the word “tribe” instead, and I think that gets closer to what is useful at this stage. Not 500 LinkedIn connections to announce your availability to, but a smaller collection of people who know you, remember different iterations of you, and might help you see possibilities you can’t yet see yourself. Reconnecting doesn’t need to begin with I’m looking for my next opportunity. It can simply begin with I realised we’ve lost touch and I’d love to know how you are. There is something rather nice about allowing the relationship to become human again before asking it to become useful.
Board work can offer another version of this. I speak with many executives who see paid board seats as part of the final phase of their career, and there is good reason for that. But I wouldn’t necessarily begin by chasing the paid seat. Find a not-for-profit organisation whose work matters to you and offer the thing you now have in abundance: experience. You get to learn governance and become a better board director, certainly, which may well help with paid opportunities later. But you also get to experience what it feels like to deploy 30 years of accumulated judgement somewhere because you care about the outcome rather than because it advances you.
Perhaps this is the broader shift underneath all of it. For much of a career we are necessarily concerned with accumulation: more responsibility, more experience, more money, more influence, more proof that we can do increasingly difficult things. There is nothing particularly wrong with this; it is how careers are built. But eventually there comes a point where you have accumulated enough evidence. You know you can do difficult things. You know you can lead. You know you can get another impressive job.
What becomes interesting then is what you want to do with everything you’ve accumulated.
And, perhaps more importantly, how much of your remaining time you want to give to it.
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