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How to find the courage to make a big leap in life

There’s a reason why people talk their whole lives about starting a business, writing a book, opening up a hostel, or moving to Kenya and never do it. Leaping away from what’s safe and predictable is scary. Really scary.

However, sometimes you get to a point where it’s easiest to do the difficult thing, rather than not do it and live with unanswered questions of “what if?“, regret, or envy.

What do you keep thinking about doing, but put off because of fear?

When I was living in Switzerland, I kept thinking about how much I wanted to write a book about my time by the mountains. It was like the idea wanted to be listened to and made real. 

I knew that by ignoring this idea for a book, I’d lose something of myself. I’d end up questioning my identity as a writer, creative person, and someone who gets things done. 

I knew writing and sharing the book was the far easier option, even if it meant triggering constant imposter syndrome and feelings that I was creating a whole lot of crap.

So I decided to just do it. I wrote and published Mountain Song, and it’s now one of the things I’m most proud of. It’s not 100% perfect (the text of the hardcover is way smaller than I thought it would be), but it’s done. That’s what matters most.

When people say that you’re lucky, sometimes they’re right. But other times they actually mean that you’re brave.

You took a risk, and it worked out. You got to somewhere they’d love to be but are terrified of taking a step towards. Even if you screwed up a hundred times before you reached it. But you were brave enough to try, and that’s honestly more than most people will do.

When I quit my job in 2018, I never really thought about starting a business. It felt like something that other people did when they were older and more experienced, even though I’d always loved creating things and doing things my way.

I’m also a terrible employee with anarchist instincts, and in my full-time roles I kept secret lists of what I’d do differently in my utopian business.

The day I handed in my notice, I had €6,000 saved and thought I’d have to leave to go back to England soon. I’d had interviews with other companies, but no concrete offers. With my rent, I had enough to get me through one to two months before I’d need to give my landlady notice.

I had a hundred worries about what was coming next, but I knew I had to leave that job. And somehow, it worked out.

A friend of a friend asked if I could do some freelance work, my previous boss did the same, and a few projects immediately lined up for my first day of freedom (which also happened to be my twenty-fifth birthday). 

These projects felt like miracles, but looking back, I’d opened up space for them to fall into. I’d worked hard in my office job, built a network of people who liked my work, and was surrounded by a small network of people who knew what I was good at (often more so than I did.)

I was mostly still working in tech and my projects weren’t perfect, but they had given me time, flexibility, and options to do things my way. That meant more than any pay rise in my previous job, or an offer from the huge tech companies I used to want to work for.

Know the worst case scenario

Stability is incredibly hard to walk away from. Having a clear, growing feeling that you need to take a leap makes it easier, or at least more urgent.

If you’re in a good or decent financial position, taking a sabbatical or going part-time become great options, both to figure out who you are and to explore different ways you could work. 

I didn’t have much financial security back then, but I did know my worst-case scenario if everything failed. I’d mapped it out on paper one day, sitting on my balcony overlooking the Grimselpass in Switzerland’s Berner Overland. 

Scenario 1: quit my job, don’t find anything else, and run out of money. 

Ok, so then I’d move back in with my Dad and apply for jobs from the UK. Maybe I could pick up my old part-time jobs in the village bookshop and cafe and figure out other options at the same time. 

Scenario 2: quit my job, think up a better way of working, and earn enough money. 

Then I could hopefully enjoy lots of hikes and stay in my house by the mountains for another year before Iain finishes his PhD.

If that scenario worked out, amazing. But if it didn’t, I’d deal with it. I didn’t know much about where I was going, but I knew one thing and it was incredibly freeing: that failure wouldn’t be disastrous. For me, at that moment, it made sense to take the leap.

Decide whether to take a big leap

The only real way to decide to take a big leap – and find the courage to do it – is to familiarise yourself with the worst-case scenario. Only then can you decide if it makes sense.

That means trying on that situation, walking around with it for a while, and understanding what it would really look like.

If I had a mortgage and a kid, I wouldn’t be so quick to hand in my notice, at least not without first looking more at other income options. But I had some sort of safety net.

Decide whether to take a big leap

(To help with this, here’s a free link to the Big Leaps Worksheet I share in Life Studio. Check out the course if you want a drawing board to engineer the next chapter of your life and channel your energy to what matters most to you. Here’s how I use it in my own life.)

A few years after I became self-employed, I took another leap: away from the security and predictability of my tech consulting work and towards the unknown but potentially much more fulfilling allure of more creative work.

I’m still figuring things out, but it’s been a much safer leap than my previous one. It’s not an all-or-nothing thing, I have more savings, and I’m married (largely thanks to Brexit and visa requirements, but also love.)

That said, unpredictability still fills me with dread. It always will. But without facing it, I’d never work out what’s on the other side of my fear.

Each time I took a big leap, things were safer than I thought. Things are often so much safer than we think.

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