Emily Shipp
Dec 21, 2018 · 4 min read

The journey towards finding fulfilling work is often unconventional and nearly always unpredictable.

Whether you’re making a career change or searching for a line of employment that inspires and motivates you, you’ve probably spent a considerable amount of time trying to identify a new path. But there’s one problem. Such a path just doesn't exist.

A path implies a route that has been trodden many times before, but you and your career are unique. No one has made the same decisions as you or had the same experiences, and thus there is no path to follow.

I’ve spent the last year puzzling over the journeys we take to find purposeful work. I’ve been making changes of my own and along the way, I’ve interviewed many others doing the same as me.

One of the things that became clear is that even those with the most outwardly straightforward careers have taken their own convoluted route to get there, often marred with uncertainty, risk and confusion. As Joseph Campbell puts it,

‘You enter the forest at the darkest point where there is no path.’

What this means — and what should reassure you about this — is that if your career path or career change appears unconventional, awkward or difficult, it’s meant to be that way. It always is.

The idea that successful people have straightforward career paths is a myth. That’s just not how it works.

A Classic Tale of Randomness

One of the first people I interviewed this year about purposeful work was a blind adventurer named Miles Hilton-Barber.

Miles Hilton Barber, the blind adventurer who achieved the seemingly impossible.

Outwardly, he is extremely successful; he has set multiple world records as a blind adventurer and has spoken at over 1,000 corporate events as a motivational speaker. But his career path is one of the most impossible imaginable: he set out at age 50 to become a pilot, even though he was blind and no flight schools would admit him.

His career exists only because he believed there was a way to achieve his ambitions, even though almost no one else did and there was definitely no established route for a blind man to become a pilot. He did not foresee a career as a motivational speaker; that was a side-product of his main focus and ambition.

There are others who have been open about taking unconventional routes. Cheryl Sandberg famously borrowed the analogy (from a colleague) of a successful career path being more like a ‘jungle gym’ than a career ladder. She describes an awkward transition from politics to Google, moving to Silicon Valley without work or an obvious route forward.

When I interviewed the British philosopher Roman Krznaric I was surprised — and pleased — to hear him describe his own career history as ‘a classic tale of randomness’.

Learn to Live With Uncertainty

In our interview earlier this year, Sophie Howarth, co-founder of The School of Life told me:

‘I don’t think that the point is to stop wrestling with it and arrive at an answer, I think the challenge is to stay in the uncertainty’.

This is an idea I’ve found hard to live with, until recently. I was waiting for certainty, which of course, stopped me moving forward. I trapped myself in a circle of questioning, waiting for the ‘right answer’.

I’ve finally realised there isn’t one, there are only decisions that feel more or less good.

Follow Your Own Compass

The best thing you can do is to be as honest as possible about what you do and don’t want from your work (hint — it’s always an approximation). Trust your judgment and be ready to experiment with work that feels closest to your intentions.

Don’t begrudge the directions you’ve taken so far, or doubt your decisions. They were made with the best knowledge you had at the time. Even (and especially) if you didn’t like the outcome, it’s never too late to learn from them.

In this sense, the unfolding of your career path is a constant process of exploration, of discovering and of letting go. With each new experience, you refine your understanding of yourself. The point is to stay awake through the process, to notice what happens.

In short, there is no path laid out for you. If you’re following your own direction, the only path is the one you’re walking.

Mind Cafe

Relaxed, inspiring essays about happiness.

Emily Shipp

Written by

Endlessly curious, sponge-like absorber of interesting things. Writing about meaningful work @questionsonpurpose.

Mind Cafe

Mind Cafe

Relaxed, inspiring essays about happiness.

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