How to make your career a voyage of self-discovery

In preparing for this blog, I reflected on the number of times in my career that I asked myself the question: “What should I do next?”

For most of us, the answer to the question is never that close to the surface, be it a promotion you’re not sure you want, that random introduction to a new opportunity by the ever-opportunistic recruitment consultant or the role you’ve enjoyed for years that no longer feels that comfortable — or maybe feels too comfortable?

Our motivation changes at different times in our life.

Sometimes the career decision is forced on us, quickly.

Other times it can be a nudge from a partner.

Or from the bank.

A few years ago I was introduced to the writer David Whyte — through his poetry initially, a piece called Self Portrait.

Since then I have enjoyed his many discussions with Rick Rubin on creativity, philosophy and writing on Rubin’s podcast.

Whyte is a very versatile thinker and writer.

In 2001, Whyte published a book that reframes the whole premise of career thinking.

Crossing the Unknown Sea: Work as a Pilgrimage of Identity, makes a disarmingly simple premise — work isn’t just something we do to fund a life — it’s one of the primary places where a life gets made.

It’s worth reading again.

Work is where life gets made, not just a means to an end — a framework for identity formation, in real time, with real stakes.

Which goes much further than that old idiom “Find a job you love and you’ll never have to work a day in your life.”

The wrong question

Whyte, who I have claimed as Irish, even though he is Yorkshire-born, spent years consulting inside Fortune 500 companies and had a startling observation.

Over time, humans have quietly agreed that meaning belongs to religion, to hobbies, to the weekends.

Work on the other hand is neutral — a transactional part of life that we either endure or optimise.

“Maturity and energy in our work,” he writes, “is not granted freely to human beings but must be adventured and discovered, cultivated and earned.”

That’s not about being more productive.

It’s a claim that work is earned identity — something we grow into through risk, not something we’re handed once we pick the right job title.

According to Whyte, “What should I do next?” is undoubtedly the wrong question to ask of ourselves.

It assumes we already know who we are and just need a role to match, when in many cases it’s the role of our parents, grandparents, friends of family or the end product of pedestrian careers advice — of which I know only too well.

Whyte’s book suggests the opposite order: the role, the risk, the crossing — that’s how the person finds out who they are.

Identity isn’t the input to a career choice. It’s the output of one.

When I read that — it was an epiphany on a grand scale.

Work as pilgrimage, not path

The title does a lot of work.

A path is planned — you can see the end from the start, and the job is to walk it efficiently.

A pilgrimage is different.

You go because something in you needs the going, and the person who arrives is not the person who left.

Whyte’s metaphor is a sea crossing: setting out into water you can’t fully chart, trusting a process you can’t fully control.

That’s a hard sell to someone who wants a five-year plan.

But it’s often the more honest description of what a real career transition feels like from the inside — less like following a map, more like committing to a direction and finding out, through the actual sailing, what you’re made of.

As a coach, it has changed how I think and how I question.

Instead of interrogating the destination (“where do you want to be in five years?”), you start interrogating the willingness (and ability) to cross (“what’s the unknown water you’ve been avoiding, and what has avoiding it cost you?”).

The conversation is the method

Whyte describes a fulfilling working life as “a never-ending courageous conversation with ourselves, those with whom we work, and those whom we serve.”

Conversation, not strategy.

Not a five-year plan executed in isolation, but an ongoing exchange — with your own doubts, with colleagues, with the people your work actually serves — that gradually reveals what you’re for.

Growth isn’t a solo cognitive exercise. It happens in the friction of real exchange.

If you are someone who wants to change, the problem is rarely a knowledge gap. It’s usually a conversation that you have been avoiding — with a boss, with a former version of yourself, with an ambition you’ve quietly downgraded because it felt safer.

Whyte argues that the crossing doesn’t happen until that conversation does.

Inheritance: none of us start from zero

It’s important to understand that career conversations are usually not bound exclusively by free will — ancestry, inheritance and legacy are all hugely influential.

We’re all carrying inherited scripts about what “acceptable” ambition looks like, what work is “for,” who in our family got to want things and who didn’t. And with that, it is always important to ask where this notion of a career originated.

Where too the boundaries and barriers for ambition?

9–5, Monday to Friday. EastEnders on a Tuesday, fish and chips on Friday, pints on Saturday, Donegal for the fortnight.

Rinse and repeat until death.

Whyte also allows us to reframe the idea of burnout too — not as a signal of failure or poor resilience but as a sign that something inside you has just gone to sleep and is demanding to be woken, not medicated into compliance.

How many of us have reached for the app that will track all of the symptoms — I did last month — sleep, diet, steps — as if it will in some way make it all ok?

Maybe the question should be “What is this burnout trying to end, and what is it trying to start?”

Maybe we should resist the urge to fix and instead listen more closely to the signal?

The question underneath all of it

According to Whyte, we’re not remembered at the end of our lives for our accomplishments.

We’re remembered for what we loved, and for who loved us.

This is not to diminish work, but rather to suggest that work be shaped by that reckoning now, rather than deferred to some post-retirement chapter that may never arrive.

To be ever influenced by poetry when it comes to career guidance is mind-boggling — Whyte has been doing just that with Fortune 500 companies.

He’s as much a philosopher as he is a writer, and he certainly is a dab hand at asking questions.

Some of his reframes are worth considering:
– Instead of “What’s your five-year plan?” try “What’s the unknown water you’ve been circling instead of crossing?”
– Instead of “What are your strengths?” try “What conversation have you been avoiding that would tell you what you’re actually for?
– Instead of “How do we fix your burnout?” try “What is your exhaustion trying to wake up in you?”
– Instead of “What job do you want?” try “Who is this work quietly asking you to become — and is that someone you want to be?”

The harder the question, the more useful the answer?

None of these have tidy answers and that’s the point.

Whyte’s whole argument is that the discomfort of not knowing yet is not a problem to be solved before the real work starts — it is the real work.

A career, seen this way, isn’t a series of decisions optimised for outcome. It’s a pilgrimage of identity, and the point was never simply to arrive but to make the journey more meaningful.

If you fancy getting into the weeds, get in touch.

Thanks for reading.