“It’s Going To Be Messy, And It’s OK If It Hurts” – 7 Hard-hitting Career Change Lessons From Society’s Great Minds

Image of hourglass amongst pebbles

Feel like you're the only one struggling to work out what you want to do with your life? The questions you're grappling with have a long lineage, explored by great thinkers and creatives for thousands of years. Here, Natasha shares a collection of their tough-love truths that you can use, today, to help you move forward in your shift.

“There is an ugliness in being paid for work one does not like.” – Anaïs Nin

You're frustrated with feeling out of place every working day.

You're ashamed of knowing you're way off-course, but not knowing what to do about it.

You're amazed at how helplessly you're watching yourself shrivel and morph into a smaller, meeker, angrier version of who you used to know yourself to be.

And you're not alone.

The questions of who we are at work, what we choose to do with our days, how we navigate change and what it means for our lives – it's a subject that hundreds of thousands of career changers just like you are wrestling with every day.

“When we consider that each of us has only one life to live, isn't it rather tragic to find men and women, with brains capable of comprehending the stars and the planets, talking about the weather; men and women, with hands capable of creating works of art, using those hands only for routine tasks; men and women, capable of independent thought, using their minds as a bowling-alley for popular ideas; men and women, capable of greatness, wallowing in mediocrity; men and women, capable of self-expression, slowly dying a mental death while they babble the confused monotone of the mob?” – Neil Gaiman (writer)

And they're questions that some of the greatest minds in the world have attempted to grapple with, too.

While, perhaps, there is no single Holy Grail of an answer to what it means to live well, and to find your way to your own expression in the world, there are thoughts and ideas and words that can bring some solace and insight to an often lonely and confusing process.

And, I hope, in the following seven lessons from artists, composers, scientists and philosophers on what it takes to find and move into work you love, you may find some insight to apply to your own journey.

Because (in the same way as you can't get the toothpaste back in the tube), once the question of what your life is for presents itself to you, it requires you to go in search of the answer.

Or, in the words of poet Nayyirah Waheed:

you can not
what you want to say (who you really are).
what you should say (who you pretend to be).
your mouth was not designed to eat itself.

— split

1. 'Finding yourself' isn't first

“On the road that I'm on I must continue; if I do nothing, if I don't study, if I don't keep on trying, then I'm lost, then woe betide me. That's how I see this, to keep on, keep on, that's what's needed.

“But what's your ultimate goal, you'll say.

“The goal will become clearer, will take shape slowly and surely, as the croquis becomes a sketch and the sketch a painting, as one works more seriously, as one digs deeper into the originally vague idea, the first fugitive, passing thought, unless it becomes firm.”
– Vincent Van Gogh (artist)

Rife in society is a potent and dangerous myth: that in order to begin, you must first know where you will end.

That to live a life of purpose, you must first find it and identify what your ultimate purpose is – and only then may you begin living it.

How long have you been vacillating over your career change? How many weeks, months, years have passed while you wait for your purpose, your passion, to reveal itself so you can finally act?

As Van Gogh (and Picasso, who said: “to know what you're going to draw, you have to begin drawing”) offered, you can wait forever for the end goal to reveal itself. Or you can begin anyway – begin somewhere – and trust that the act of moving will get you closer to the end goal than staying still.

“How often I found where I should be going only by setting out for somewhere else.” – Richard Buckminster Fuller (architect, systems theorist, author, designer, inventor and futurist)

2. Ears, not shoehorns

“One of the interesting things about success is that we think we know what it means. A lot of the time our ideas about what it would mean to live successfully are not our own. They're sucked in from other people. And we also suck in messages from everything from the television to advertising to marketing, etcetera.

“These are hugely powerful forces that define what we want and how we view ourselves.

“What I want to argue for is not that we should give up on our ideas of success, but that we should make sure that they are our own. We should focus in on our ideas and make sure that we own them, that we're truly the authors of our own ambitions.

“Because it's bad enough not getting what you want, but it's even worse to have an idea of what it is you want and find out at the end of the journey that it isn't, in fact, what you wanted all along.”
– Alain de Botton (philosopher and author)

What's the difference between who you are and who you want to be?

What's the difference between what you want to believe and what you do?

And what's the difference between what you think you should love, desire, and be fulfilled by, and what actually makes you feel satiated and alive?

When I listen to people who are thinking of making a shift into more fulfilling work, the things you most often start talking about are external.

  • What transferable skills do you have, and where can you apply them? Who will accept you, based on what you've already done?

  • You're an introvert – isn't it better to be an extrovert if you want to change career? Should you maybe take a charisma course for when you have to go to networking events?

  • Of course you've always loved working with animals, but that's not exactly a proper job, is it?

  • You've spent years climbing the career ladder – won't starting again mean you've failed? Surely 'success' means being at the top?

  • How much of a pay drop will you have to take?

  • What's a good career idea and what's just a hobby?

The paths and rules that we live by are some of the most powerful in society – so powerful, in fact, that they're almost entirely invisible.

What work should look like, what you should be, how you should act, what you should want, where you should aim for.

And those almost-invisible rules can make it incredibly hard even for you to make out the distinction between what you think you should want and what you actually do.

So out comes the shoehorn.

  • Yes, I do hate being indoors, but maybe if I just put up with working in an office, I'll still have a proper job.

  • I'm supposed to want to do something worthwhile, aren't I? It's awful that I'm not actually that bothered about politics… but maybe I'll just work for this charity and after a while I'll get what it's all about.

  • Of course I don't want to stay in this sector. But if I start in a new industry I'll have to start from the bottom, and everything I've done before will have been a waste.

  • International travel sounds flashy, doesn't it? Everyone's always talking about how great it is to get to travel for work. Really, I just want a short commute so I can spend more time in my garden, but that's not very exciting, is it? Maybe I need to broaden my mind… I can probably manage a couple of trips overseas per month.

You end up constructing a life that looks 'good' from the outside, but feels inauthentic and awkward on the inside.

Learning to notice, and then listen to, and then act on, the truth of who you are, is an unfamiliar practice for most of us.

But it's the first step to finding a 'fit'.

“Before you tell your life what you intend to do with it, listen for what it intends to do with you. Before you tell your life what truths and values you have decided to live up to, let your life tell you what truths you embody, what values you represent…

“If the self seeks not pathology but wholeness, as I believe it does, then the wilful pursuit of vocation is an act of violence toward ourselves – violence in the name of a vision that, however lofty, is forced on the self from without rather than grown from within.

“True self, when violated, will always resist us, sometimes at great cost, holding our lives in check until we honour its truth. Vocation does not come from wilfulness. It comes from listening.

“I must listen to my life and try to understand what it is truly about – quite apart from what I would like it to be about – or my life will never represent anything real in the world, no matter how earnest my intentions.”
– Parker Palmer (writer, speaker and activist)

3. Play the 'ecstatic creative game'

“There is nothing in a caterpillar that tells you it's going to be a butterfly.” – Richard Buckminster Fuller (architect, systems theorist, author, designer, inventor and futurist)

When I was starting out on my career change, I would study my CV like it was a crystal ball. Where was the clue in those carefully formatted bullet points?

If I leaned back and squinted, would the answer appear?

I made lists of pros and cons.

Lists of strengths and weaknesses.

Likes and dislikes, budgets and SMART goals, awards, hobbies, personality types.

But when everything I was doing was stuff I didn't want to do any more, what good was that doing me?

You can't drive with your hands on the rear-view mirror.

Who you have been up to this point might carry some clues to where you're headed, but if you want to create something new, something exciting, something that takes you into the realm of the things you don't even know that you don't know… where you've been and what you already know won't get you far.

So how do you make forward progress? How do you work out what you want to do without examining who you are right now?

You play.

You explore and engage with the world without an attachment to the outcome – because you don't yet know what the outcome will be. You follow the Little Yeses, and you do more of the things that feel good, and you tug on the ends of them to see where they lead.

You turn ideas upside down to see what they look like from a different angle. You find playmates to explore with – because they know places to play you've never heard of before.

You allow silliness and pleasure and joy to drive you forward, to break through the futile rigidity and awkwardness of trying to apply logic to the ineffable.

You allow joy to be your guide, feeling for the buzz and the activities that elicit that sheer physical pleasure of being alive in the world.

And ultimately, you trust.

You trust that by following your curiosity, getting your hands dirty, and allowing, rather than pushing, the way forward will be revealed.

It sounds foolish and illogical and unlikely… but if nothing else, it's worth a try, no?

Because what you've been doing so far hasn't reaped the rewards you're looking for.

“When it comes to the operas that I am composing with writers like Mohammed Hanif and David Ignatius, we tinker away, we joyfully preoccupy ourselves, we allow the text and the thrust of the drama to prey on our minds, possess, and haunt us. We play the ecstatic creative game. And we do all this until a structure emerges, like a piercing beacon of light, so clearly that we simply know how to proceed. The story has revealed to us how it needs to be told.

“Just as a cellist, no matter how professionally advanced, will always 'play' the cello rather than 'work' the cello, a great diplomat, poet, philosopher, mathematician, astronomer, or architect will always find the heartfelt game in their respective craft that illuminates the grand gesture.”
– Mohammed Fairouz (composer)

4. September is coming

“Do you mind even a little that you are still addicted to people-pleasing, and are still putting everyone else's needs and laundry and career ahead of your creative, spiritual life? Giving all your life force away, to 'help' and impress? Well, your help is not helpful, and falls short.

“Is it okay with you that you blow off your writing, or whatever your creative / spiritual calling, because your priority is to go to the gym or do yoga five days a week? Would you give us one of those days back, to play or study poetry? To have an awakening? Have you asked yourself lately, 'How alive am I willing to be?' It's all going very quickly. It's mid-May, for God's sake. Who knew. I thought it was late February.

“Oh my God, what if you wake up some day, and you're 65, or 75, and you never got your memoir or novel written; or you didn't go swimming in warm pools and oceans all those years because your thighs were jiggly and you had a nice big comfortable tummy; or you were just so strung out on perfectionism and people-pleasing that you forgot to have a big juicy creative life, of imagination and radical silliness and staring off into space like when you were a kid? It's going to break your heart. Don't let this happen. Shoot the moon.”
– Ann Lammott, (writer)

The question of priorities comes up a lot in career change.

Actually, that’s not strictly true.

The question of time comes up a lot in career change, and the question of energy, which are questions of priorities in disguise.

If finding fulfilling work is truly something that matters to you – if it's something you're committed to – it has to start coming first.

Or if not first, because your children or your mortgage will always come first, then at least way up above the other things that swallow your time and drain you of energy and won't, ultimately, dictate the way you look back at your life from your deathbed.

A big, bold, daring dream like moving into work that lights you on fire… it doesn't happen on its own. It won't politely get on with itself while you go to the gym and re-tile your bathroom and wash the car.

Time is passing.

And it will continue to pass no matter what you do with it.

Maybe you're waiting until you're 'ready', whatever 'ready' might look like.

Maybe you're putting off exploring that business idea you daydream about constantly until next week, and then next week, and then next week, because the oven needs a clean, and your partner really does prefer it when you cook in the evenings, and there's just so much laundry… and your dreams can wait.

Maybe you're avoiding speaking to people in an industry that interests you, because you're not entirely sure if it's right for you, and the kids will start school in September, and then you'll have more headspace to focus.

September is coming, either way. Would you rather be starting from nothing, then, when all this headspace arrives, or already ten steps ahead of where you are now?

This is your life. Your happiness. Your health. Your dreams and commitments and wishes and values and hopes.

Stop pretending they don't matter.

Make time for them.

“I worried a lot. Will the garden grow, will the rivers
flow in the right direction, will the earth turn
as it was taught, and if not how shall
I correct it?
Was I right, was I wrong, will I be forgiven,
can I do better? Will I ever be able to sing, even the sparrows
can do it and I am, well,
hopeless. Is my eyesight fading or am I just imagining it,
am I going to get rheumatism,
lockjaw, dementia? Finally I saw that worrying had come to nothing.
And gave it up. And took my old body
and went out into the morning,
and sang”

– Mary Oliver (poet)

5. You may never find 'forever'

“I feel I change my mind all the time. And I sort of feel that's your responsibility as a person, as a human being — to constantly be updating your positions on as many things as possible. And if you don't contradict yourself on a regular basis, then you're not thinking.” – Malcolm Gladwell

Perhaps you're a little ashamed of where you've found yourself in your career.

A little embarrassed, maybe, that you seem to have got such an important choice so wrong.

Surely by now you should know what you want to be when you grow up?

The idea of 'career' has a socially constructed kind of Platonic Ideal to it: one career that makes your heart sing for the rest of your life. A calling, an obsession, a life's work. Something you were born for.

You've seen people who are wholeheartedly passionate about something – who dedicate their whole lives to it – why can't you find yours?

Maybe you can't find yours because you don't have one.

Maybe you can't find yours because the people who have one single, clear 'calling' are actually the exceptions, not the rule.

You are a very different person today than you were at 6 years old, at 16, at 21.

You are a different person today than you were yesterday, this morning, five minutes ago.

Your self is evolving and learning and growing and shifting with each passing moment. So to expect that one focus and pursuit will fulfil that unfolding heart for the rest of your life is, like everything that is excessively romanticised, misleading and unfair.

When a child outgrows a shoe, we don't get angry with the child.

We don't get angry with the shoe.

We just go find some new shoes.

See if you can shift your view of a career from The Destination to The Adventure.

What if the rest of your life were a dance between who you are becoming and how that can be expressed in the world?

“Work is a constant conversation. It is the back-and-forth between what I think is me and what I think is not me; it is the edge between what the world needs of me and what I need of the world. Like the person to whom I am committed in a relationship, it is constantly changing and surprising me by its demands and needs but also by where it leads me, how much it teaches me, and especially, by how much tact, patience and maturity it demands of me.” – David Whyte (writer)

6. Know that you won't know until you get there

Certainty is seductive.

Wait – just wait – until you're sure of what you want to do.

Don't make any rash decisions – don't risk what you already have, no matter how miserable it makes you.

Because what if you get it wrong?

What if you take the wrong forest path in this grown-up version of the fairytales of your youth, and then you can't go back?

There you stand, on the edge of a transformation, utterly paralysed by the unknown.

How do you make a choice when you don't know what's on the other side?

But how can you ever know what's on the other side until you get there?

Philosopher L.A. Paul illustrates this paradox with a challenging and playful thought experiment, The Vampire Problem:

If you were given the opportunity to become a vampire, painlessly and without inflicting pain on others, gaining incredible superpowers in exchange for relinquishing your human existence, with all your friends and loved ones having made the transformation and loving it… would you do it?

Paul writes:

“The trouble is, in this situation, how could you possibly make an informed choice? For, after all, you cannot know what it is like to be a vampire until you are one. And if you can't know what it's like to be a vampire without becoming one, you can't compare the character of the lived experience of what it is like to be you, right now, a mere human, to the character of the lived experience of what it would be like to be a vampire. This means that, if you want to make this choice by considering what you want your lived experience to be like in the future, you can't do it rationally. At least, you can't do it by weighing the competing options concerning what it would be like and choosing on this basis. And it seems awfully suspect to rely solely on the testimony of your vampire friends to make your choice, because, after all, they aren't human any more, so their preferences are the ones vampires have, not the ones humans have.”

It turns out that becoming a vampire is much like making a career change; there's only so much you can do to rationally assess what life will be like once you've done it.

Yes, you can speak to people who are already in the career you're considering, to gather information from them – but since they're already in that line of work and don't know what it's like to be you, the information you glean from them is biased.

And yes, you can find ways to try out the work you're considering, to feel what it's like to do the work, but a day or a week of experimenting and work-shadowing is a day or a week – not a year or a lifetime.

And career is about so much more than who you do every day – it's a part of our identity. How can you feel a whole identity until it becomes your own?

You can't.

“In many ways, large and small, as we live our lives, we find ourselves confronted with a brute fact about how little we can know about our futures, just when it is most important to us that we do know. For many big life choices, we only learn what we need to know after we've done it, and we change ourselves in the process of doing it. I'd argue that, in the end, the best response to this situation is to choose based on whether we want to discover who we'll become.” – L.A. Paul (philosopher)

7. It's going to be messy, and it's OK if it hurts

“Poets have never used the word balance, for good reason. First of all, it is too obvious and therefore untrustworthy; it is also a deadly boring concept and seems to speak as much to being stuck and immovable, as much as to harmony.

“There is also the sense of unbalancing that must take place in order to push a person into a new and larger set of circumstances.”
– David Whyte (writer)

In a search for fulfilling work (as in all matters of the heart), you have to be ready for the ride.

Because if a safe and quiet life were the most important thing to you, you wouldn't be on this journey in the first place.

You'd settle back into your uncomfortable hole, waving away the sparks of light and energy and joy: "No no, no thank you. Nothing thrilling for me, thanks, that's fine, I'll just stay in here with the devil I know.”

And maybe you've been doing that for a while – venturing out a little way, feeling yourself tip off-centre, and scurrying back to safety, afraid of what that slightly out-of-control sensation might mean.

Slightly out-of-control is where growth and discovery live.

Just beyond your comfort zone is where new ideas are waiting.

The sensible, the familiar, and the orderly are sensible and familiar and orderly because they've been a part of your life for long enough to feel that way – but if you want to discover something new, expand into something you don't yet have access to, you need to be willing to let go.

You need to know that growth always looks like chaos in the beginning.

And you need to allow yourself to trip and stumble and make mistakes, and go to places you've never been before, and try things you've never tried before, and ache and stretch and embarrass yourself and fall in love and get your heart broken and drop things.

Give yourself permission to get things wrong for a while.

Embrace the highs and the lows.

Make friends with the feeling of falling.

“You have had many and great sadnesses, which passed. And you say that even this passing was hard for you and put you out of sorts. But, please, consider whether these great sadnesses have not rather gone right through the center of yourself? Whether much in you has not altered, whether you have not somewhere, at some point of your being, undergone a change while you were sad?… Were it possible for us to see further than our knowledge reaches, and yet a little way beyond the outworks of our divining, perhaps we would endure our sadnesses with greater confidence than our joys. For they are the moments when something new has entered into us, something unknown; our feelings grow mute in shy perplexity, everything in us withdraws, a stillness comes, and the new, which no one knows, stands in the midst of it and is silent.” – Rainer Maria Rilke, Letters to a Young Poet

Which of these lessons lands most strongly with you? Let me know in the comments below.

Natasha Stanley's picture

Natasha Stanley is head coach, writer, and experience designer for Careershifters. When she's not working, you'll find her listening to neuroscience podcasts, learning pottery, and dreaming up her next adventure.