The Case for Career Breaks

How do you frame freedom for yourself?

A friend of mine has a successful corporate career but wants to be a dog trainer. Another wants to be a botanist. Another dreams of owning fast food franchises and optimising the processes that run them.

Other people might want the Tim Ferris and Joe Rogan type of freedom, where they get to nerd out on their obsessions with millions of fans. Others might want the Paul Graham type of freedom: create iconic companies. Quit at the top. Prioritise family and spend your days reading and writing. Some may want the Brunello Cucinelli type of freedom - a couple of hours of exercise each day, a walk to work, a siesta after lunch, and evenings spent surrounded by books, or at the local café discussing philosophy, politics, economics, and religion.

Everyone has their own idea of freedom. Ask them about it and they'll tell you. How do you frame freedom for yourself?

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Work and careers fascinate me. Mainly because I think great work stems from finding what you're obsessed with, but also because I've seen firsthand how a job you don't enjoy makes every aspect of your life significantly worse.

The truth is we work more than we do anything else—more than we eat, sleep, or see our families and friends. How we spend those hours matters.

I've been fortunate to experience the satisfaction and personal growth that work can give you. My first job was delivering robotics education to children living in informal settlements, my second job was as a software engineer building intelligent systems for global water utilities, and my current role is as an early-stage startup delivering super-cheap, super-fast fibre internet to informal settlements in emerging markets.

My career up until this point has been maximised for impact. Each role has significantly impacted the lives of the people we build for. It's also been a solid career strategy. Each role has come with increased scope, responsibility and financial reward.

If I wasn’t trying to maximise impact, it’s a reasonable assumption that I’d instead be optimising around personal lifestyle preferences. I might want total freedom to choose how I make my living. Or extreme flexibility in my schedule, including the ability to stop working altogether for long periods of time at short notice. Or I might want to work on a certain kind of problem with certain kinds of people.

When I talk to people about their careers and ambitions, the conversation usually leads to freedom and trying to achieve it. There's always some idea of freedom that they're working towards.

We spend an awful lot of time pursuing freedom and it seems wasteful to go through all the work of getting it only to realise that it isn't what you actually want. How can you test it along the way? How can you taste freedom before ordering the whole dish?

I like the idea of a career break. Taking time away from your work to consider what you truly want to work on, to trial the life you're building towards. I've come to think of these as mini-retirements littered throughout your career and I suspect it's an exercise that can yield a whole lot of clarity and energy.

It’s not taking 6 months off to do nothing. It's taking a break to learn and explore the things you say you want to but never find the time for. It's 6 months to be a dog trainer. 6 months to take botany classes. 6 months to taste the freedom you crave and decide whether it's worth pursuing.

I can’t wrap my head around the idea of having just one career for my entire life. Our interests and abilities change as we grow and develop. The things I liked and was good at when I was 18 are vastly different to my strengths and interests now. Our goals and desires change over time. It doesn't make sense to commit to a career for 40+ years based on a decision you made as a naive teenager.

These breaks are an antidote to that kind of thinking. They’re periods of reflection and introspection. An opportunity to think long-term. An opportunity to live the life you think you want.

Whatever idea of freedom you’re pursuing, consider a career break when you’re 10% of the way there. Don't go 100% of the way and realise you're at the wrong destination.