You Can't Schedule A Surprise
If trying to outsmart our fears is what gets us to a mid-life crisis, it's not going to be the strategy that will take us through it.
Mid-life crisis is something that comes up at times in my conversations with my psychoanalyst. It would be strange — and wrong — if it didn’t. Strange, because I’m, well, at mid-life, when such things tend to happen. Wrong, because it’s profoundly normal.
It’s called a crisis because it can feel like a crisis, but we don’t call, say, teething a “teeth crisis”. Maybe we can say it’s a stage in our psychological development.
It can be tempting to try to outsmart the mid-life crisis. After all, with so many books written about it and so many people having gone through it, surely we just need to find the right map that will allow us to avoid all the problems and have a mid-life celebration instead?
Yet, somewhat paradoxically, this very attempt to avoid trouble is what sometimes make it worse. The way forward is through it, not around it.
You can build a small library of books covering mid-life crisis from various perspectives: psychological, spiritual, cultural, and countless more. In my work with CEOs in transition, the topic of a mid-life crisis tends to come up in two guises:
I worked hard but failed to achieve what I wanted. Now what?
I achieved what I wanted, but didn’t get what I was looking for. Now what?
The reason these questions tend to feel very serious is because they’re inviting us to confront some of our biggest fears. Maybe one way to describe what happens before the mid-life crisis is to say that we’re attempting to either ignore our fears or outrun them. Entrepreneurs tend to do this by building things, hoping that money, fame, legacy, or some other achievement will alleviate the existential anxiety we all feel.
The irony of the situation, which is lost on most people in the midst of such a crisis, is that we habitually try to outsmart the situation by doing more of what know well. More achievement, more building, more progress. Yet, that’s precisely what contributed to the crisis. The invitation is to learn to relate to life in a radically different way.
A founder once told me: “I wish some crisis happened that would jolt me out of this and force me rebuild everything.” I hear the sentiment. And it’s true that sometimes a real crisis — an illness, an accident, a death of a loved one — shocks us enough that everything changes. But it doesn’t have to be so painful.
The answer to a mid-life crisis is to let go, of course, but of what? And how? The problem is that no one can really tell us. The entire point is finding it out for ourselves and letting ourselves be transformed by the process.
Trying to script and outsmart this process would be like trying to schedule a surprise for yourself for this weekend, describing in detail what the surprise should be to make sure it’s the way you like it. It wouldn’t be much of a surprise then, would it?
What does all of this have with CEO succession in startups? Well, stepping down as CEO and doing something else can look like an incredibly convenient answer to the questions that come up at this time.
Yet, it could be a mistake. There are plenty of reasons to replace yourself as a CEO, but it’s important to recognise if the questions that life wants us to answer are fundamentally different in nature.
As it’s always the case with fear — and a mid-life crisis is very much about fear — the way to approach it is by facing it. Slowly, if necessary. With respect, if possible. But pretending the fear is not here and hoping it will go away is never a good approach.
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P.P.S. And if you missed the last episode, we had an amazing conversation with Graham Hobson, founder of Photobox (£400m exit!), who spoke about his choice not to continue as a CEO.
