Three things we should never do at the same time

Where we live, who we are with and what we do are three big parts of anyone’s life. We should change them one at time. Or not?

A few years ago, when I was still CEO of Makers, I met with my then-chair, Claudia Harris, for breakfast at Granger in Clerkenwell, a fancy London café.

That day, we closed a funding round that we had worked hard on, and the cash hit the bank as we made our orders.

We had every reason to celebrate with a couple more million in the bank to fuel our growth. However, I had a different topic to discuss.

“Claudia, one day, we’ll need to hire a new CEO to replace me”, I said.

Instead of feeling relieved that we closed the funding round, I felt I ran out of options. My marriage had collapsed. My number two in the business was about to leave. The business was struggling. I was seeing a psychiatrist that afternoon to talk about my mental health. I wasn’t feeling ok.

I was happy to keep running the business for however long it would take, so it wasn’t a resignation. However, I knew that the business deserved a better leader. Just as importantly, I knew that something in my life had to change.

Popular wisdom says that out of three things — where we live, what we do and who we are with — we should only change one at a time. My problem was that each of them felt intractable on their own.

First, I couldn’t see how to replace myself with a great new CEO. I had a perfect candidate in mind — a successful, intelligent, accomplished businesswoman who at the time was a CEO of another business (I’m talking about Claudia Harris, my then-chair, of course) — but what were the chances she’d agree to be the CEO of a startup? Plus, I wanted to step down to build a coaching practice, but I didn’t know how to make a transition. I felt stuck.

Second, there was someone I fancied, but we were colleagues. If there’s one thing a chief executive should not do is to ask their colleague out. It’s not a good idea!

Third, I was thinking about leaving London for a while, to live closer to nature and work remotely, but how to do it if I’ve got a startup in London with two offices?

My moment of truth that year was a commitment to a wholesale change of my life circumstances without knowing how the chips would fall and trusting that I have what it takes to navigate the challenges.

This trust that I would find a way forward allowed me to aim higher than I would have otherwise and take risks that I wouldn’t have taken otherwise.

I hired Claudia, my then-chair and my dream CEO candidate, to replace me. She’s been running the business better than I ever could since then, taking it to new heights.

I asked my colleague Egle out, something a CEO should never do. I’m glad I did. Now, a few years later, we’re preparing to get married. It’s the best relationship I ever had.

Third, we moved to Portugal during the pandemic without much of a plan, trusting that we’ll figure it out and we did. Living near the ocean beats living near a Tube station.

Looking back, I’m very happy with how everything worked out. My biggest lesson was that by raising the stakes and trying to do three difficult things at the same time was exactly what allowed me to find a way forward.

On their own, each looked intractable. What I didn’t realise was that they looked hard in isolation. Attempting to solve all of them together was precisely what allowed me to see the possibilities that I couldn’t see when I looked at them individually.

That’s the biggest lesson that I took from that year.

What changes are you holding back from, fearing their complexity?