5 Tough Truths About Your Career Change (From Unlikely Experts)

Image of woman holding a glass ball at sunset

Newly Updated

A dog psychologist, a radio host, and a painter... These people aren’t (technically) qualified to give you guidance on your career change. But they’re also not scared to tell you the truth. If what you’re doing isn’t working, try these five provocative lessons, collated by Natasha, to bring new ideas and energy to your shift.

You know a lot about the world of work.

You've spent years getting to know the ins and outs of it: climbing the career ladder, applying for jobs, landing clients, developing your CV, going to interviews… all the rest.

However stuck and confused you might feel in your career change right now, we can safely say it's not because you're not well-versed in how to navigate a career.

So what's the problem?

How is it possible that an intelligent, ambitious, capable person like you, with a good grasp on the world of work, is feeling so utterly crippled in finding and moving into a career that doesn't make you want to poke yourself in the eye?

Maybe it's because traditional careers advice is designed to help you travel upward, not sideways. Perhaps it's because your careers counsellor at school (and your parents, and most people who feel qualified to guide you in your first steps on the career ladder), trained you more thoroughly in concepts like security and speed than they did in heartfelt work and navigating mistakes.

But there's no time for finger-pointing when there's work to be done.

So, if the people, institutions and systems who are designed to help you aren't able to, it might be time to seek inspiration elsewhere: in places entirely removed from the world of work as we know it.

In the musings of a dog psychologist, for example, a radio host, and a painter who's paralysed from the neck down...

1. "We are not blinded, but we have blinders"

Alexandra Horowitz teaches psychology, canine cognition, and creative non-fiction writing at Barnard College, Columbia University.

In 2013 she published On Looking, Eleven Walks With Expert Eyes, the story of her inquiry into what opens up when you bring fresh perspectives to a familiar walk around the block.

Horowitz was amazed by how much of her everyday world had become hidden under a creeping blanket of familiarity. The day-to-day reality of her life had made the world and all its possibilities increasingly invisible to her:

"I find myself at once alarmed, delighted, and humbled at the limitations of my ordinary looking. My consolation is that this deficiency of mine is quite human. We see, but we do not see: we use our eyes, but our gaze is glancing, frivolously considering its object. We see the signs, but not their meanings. We are not blinded, but we have blinders."

There's no escaping it: your world (and your ideas, your perspectives, your opportunities, your abilities, and even your imagination) is only as big as your experience. Even the things you can imagine are only ever combinations and variations of things you already know.

And there may be possibilities for your future career, right in front of your face, that you're blind to.

So if you're struggling to come up with ideas, techniques, possibilities and options, it's worth considering: what are you unable to see?

And if there are options and ideas and possibilities out there, and the only problem is that they're hidden from your view, what could you do to shed a light on them?

For Horowitz, all it took was a new companion for her walk around the block. She took eleven walks, each time with a new expert in a different field: an artist, an architect, a doctor… and she discovered a whole new set of conversations and possibilities in every fresh perspective:

"A man's onion-chopping cadence sounded like it might be a ping-pong game, and Kalman's face brightened at the possibility. A connection between ping-pong and onion-chopping was thereby forged in my brain."

Now, ping-pong and onion-chopping are unlikely to be the keys to your career change. But I bet you've never thought of those two things in connection before.

And I wonder what might open up in your search for fulfilling work, if only you began to systematically discover new ideas and new connections in your day-to-day life?

Jamie took part in our Career Change Launch Pad and discovered that just one new experience could have a huge impact on what the world of work looked like to him:

"What made a huge impact was placing myself in opportunity's way and taking myself to different environments.

"For example, I attended an evening where a well-known adventurer was the guest speaker. He talked about how even the smallest escapes can refresh our spirits.

"Listening to this talk was my first step away from my normal life. It was huge for me. It was the first time I felt I could actually do something different, and this made me think long and hard about the idea of using adventure as a tool for personal development."

This lead to Jamie starting the process of setting up a business combining short adventure breaks with coaching and personal development – something it's unlikely he'd have hit upon by staying in his usual rhythms as an accountant.

What could you do to see the world through fresh eyes?

Where could you go to get a new perspective on what's available to you?

  • Follow Jamie's lead, and go to a talk, a workshop, or a seminar on a topic that interests you – but, crucially, one that you've never explored.
  • Try a class in something new – something you've never tried before.
  • Make some new friends – people who do fascinating work, or people who have a different perspective on life than you've ever encountered. If you're currently unhappy in an artistic job, go to a meetup for economists. Fed up with being stuck in an office all day? Find a friend-of-a-friend who goes rock climbing every weekend.
  • Or maybe, like Horowitz, you could look at what you've already got in your life through fresh eyes. Take a different route home from work each day for a week. Look for ways in which other people make careers from your existing hobbies.

Get out of your rut. Connect onions with ping-pong. Give your blinders a wiggle.

2. "It is not your business to determine how good it is"

Carl Van Vechten [Public domain], via Wikimedia Commons

In 1943, dancer and choreographer Agnes de Mille choreographed the musical Oklahoma!

She had produced a number of pieces of work in the years beforehand, all of which she felt were superior to the choreography in Oklahoma!, but none of which had achieved the success of this multi-award-winning musical.

She was confused. How was it possible that the world saw such greatness in a work that she felt was only mediocre?

She took her confusion and frustration to Martha Graham, perhaps the most influential dance choreographer of the 20th century.

Here's what Graham had to say:

"It is not your business to determine how good it is, nor how valuable, nor how it compares with other expressions. It is your business to keep it yours clearly and directly, to keep the channel open. You do not even have to believe in yourself or your work. You have to keep yourself open and aware to the urges that motivate you. Keep the channel open… no artist is pleased."

When I was changing career, I came up against smaller versions of de Mille's frustrations myself.

I was convinced that there was no point in trying to become a coach. I was only 25 years old – who would take me, and my work, seriously?

Every time I put pen to paper to draft an article for Careershifters, I was convinced that I was about to set myself up for huge public humiliation. I didn't have the experience. I wasn't a good enough writer.

Mike, a participant in our Career Change Launch Pad, experienced something similar when he followed a hunch and designed a short course on entrepreneurship.

"I've been worrying: what's good about me? What do I know that's unique and that people would want? I don't know anything unique – or so I tell myself. But giving up on needing to find a unique-ness, and just getting on and doing something, that's the only way anything's going to happen. I'm constantly fighting myself, but actually, when I give up fighting and just go with what I've got, it feels great. And, perhaps more importantly, it works."

Mike's course was picked up by a university, and the test versions he's run with practice groups have been a great success.

What Agnes de Mille, Mike, and myself all learned is that we're not very good judges of ourselves, our work, and our contribution to the world.

And, as Graham explained to de Mille in the 1940s, it's not your job to judge the quality of your work. It's not your job to decide if you're good enough to even apply for that job you're excited about.

For those of you waiting for some self-belief and confidence to appear from the ether, stop.

You don't get to say if you're worthy of a career you love – certainly not before you've even tried.

Your job is simply to show up. Do the work. Share what you have to share, right now, from where you are.

You will be rejected from some opportunities you apply for. You will be told you're not experienced enough, or your portfolio isn't up to scratch, or what you're offering isn't worth the price you're asking.

And that's fine. You can learn from the experiences, tweak your techniques. And you can rest easy in the knowledge that if they don't think you’re a good fit right now, they're probably right. They're most likely doing you a favour. On to the next.

As long as you're showing up, doing the work, producing what you have to offer, you're doing your job. Something will click.

Be aware, also, that this predisposition to judge yourself, to question your skills, and to dismiss ideas… it's killing every last drop of opportunity you have. It's keeping you exactly where you are.

  • Look at all the ideas you've dismissed in the past, because you think you know how they'll turn out, and find a way to test them, rather than simply dismissing them because you think you already know how they'll turn out. Here's a great technique for testing ideas that we use at Careershifters all the time.
  • Start doing what you want to be doing, even in a small way, right now. Don't wait for the opportunity to show up and then get caught with your pants down.
  • Dreaming of opening a bakery? Start baking a new 'product' every week, and share it with friends and family. Love the thought of getting into interior design? Offer your services to that friend who's just moved house. Do it for free if you have to. But do the work.

Do what you love. Show up. Stop wasting time getting all judgy with yourself and what you have to offer. It's not your job.

It's not your business to determine how good it is.

3. "Nothing any good isn't hard"

By The World's Work (The World's Work (June 1921), p. 192) [Public domain], via Wikimedia Commons

In 1936, F. Scott Fitzgerald wrote a letter to his daughter, who had recently enrolled in high school. She was discouraged by a low mark on a story she'd written, and he responded to her with an attempt to prepare her for "the sort of things it took me years to learn."

Fitzgerald wrote:

"Nobody ever became a writer just by wanting to be one…. Nothing any good isn't hard."

The career-change corner of the internet, of magazines, of the media, is full of the shining faces of people who have made it to the other side.

It's wrapped in delicious-sounding things like "passionate" and "happy" and "finally feel like myself". Coaches and writers and career-change experts have wonderfully positive "You can do it!" attitudes, which are inspiring and uplifting… at least for the length of time you're on their websites.

But the reality of a career change isn't just one big leap into a lifetime of happy Mondays. It's more like a series of frustrating Wednesdays, and paralysed Thursdays, and procrastinating Saturdays. It's hours of nervous attempts, and weeks of dealing with failure, and, if you're lucky, throughout it all, a guiding glimmer of hope.

In The Consolations of Philosophy, Alain de Botton talks about Nietzsche's examination of this uncomfortable marriage between human struggle and everything worthwhile:

"The most fulfilling human projects appeared inseparable from a degree of torment, the sources of our greatest joys lying awkwardly close to those of our greatest pains…

"Why? Because no one is able to produce a great work of art without experience, nor achieve a worldly position immediately, nor be a great lover at the first attempt; and in the interval between initial failure and subsequent success, in the gap between who we wish one day to be and who we are at present, must come pain, anxiety, envy and humiliation.

"We suffer because we cannot spontaneously master the ingredients of fulfilment."

Your career change is going to take time. It's going to take some tentative, hopeful attempts at pinning down ideas, and finding out they're not right. It's going to take some reaching out for help and getting nothing back. It's going to push you right up, face to face, against your own fears of being not-good-enough or not-smart-enough or not-rich-enough, over and over again.

And if you're going to make it out the other side, and join the ranks of happy faces, you're going to have to embrace that tough reality.

Not just accept, it, embrace it.

 About three weeks into taking part in our Career Change Launch Pad, Kelly sent me an e-mail:

"I can't believe what's happening in my life at the moment! I've spent the last week considering dropping out of the course – it's been so hard for me to try the things you're asking us to do. But I thought that's probably why I haven't made any progress in my career change over the past couple of years, because I've been shying away from anything that feels too challenging.

"So I bit the bullet and I did what you said, and I just got back from a coffee with a woman who does EXACTLY what I want to do… and she mentioned she wants to keep in touch because she's going to be hiring next month! I guess if I want things to change, I'm just going to have to deal with the fact that some of it's going to be unpleasant some of the time… Doing something different is always going to be uncomfortable to begin with, right?"

Kelly had been so good at avoiding the tough parts of career change, she'd managed to simultaneously dodge any progress whatsoever. But as soon as she gathered her courage and broke through the resistance, even in a small way, she started seeing results.

Where are you avoiding the struggles, and therefore missing out on the rewards?

Where are you encountering the "pain, anxiety, and humiliation" that de Botton referenced, and immediately giving up?

Where could you embrace the torment, safe in the knowledge that struggle is usually a sign of progress?

  • There's something you've been avoiding doing in your career change. Do it, tomorrow. (And then come back here and let me know in the comments!)
  • Share what you're struggling with. Kelly (from the example above) found huge relief, support and inspiration by talking about her challenges with her fellow Career Change Launch Pad participants. Find a trusted friend or family member to help you tackle the tough stuff. It might be hard, but you don't have to do it alone.
  • Whatever progress you do make, whatever you manage to achieve or push through or discover, acknowledge yourself. Give yourself some credit. Not everyone's willing to do what it takes to achieve something meaningful. You're in the game. And that's really something worth celebrating.

Nothing any good isn't hard.

4. "Inspiration is for amateurs"

By Metropolitan Transportation Authority of the State of New York (86thStreet: Chuck Close, Subway Portraits) [CC BY 2.0 (https://creativecommons.org/licenses/by/2.0)], via Wikimedia Commons

On 7th December, 1988, painter and photographer Chuck Close suffered a spinal artery collapse and seizure which left him paralysed from the neck down. After months of physical therapy, he regained slight movement in his arms and began to paint again, with a brush strapped to his wrist.

In 2003, he gave a candid interview to artist Joe Fig, where he spoke about the value of a work ethic, and a process, over inspiration:

"The advice I like to give young artists, or really anybody who'll listen to me, is not to wait around for inspiration. Inspiration is for amateurs; the rest of us just show up and get to work.

"All the best ideas come out of the process; they come out of the work itself. Things occur to you. If you're sitting around trying to dream up a great idea, you can sit there a long time before anything happens.

"But if you just get to work, something will occur to you and something else will occur to you and something else that you reject will push you in another direction. Inspiration is absolutely unnecessary and somehow deceptive. You feel like you need this great idea before you can get down to work, and I find that's almost never the case."

Most people love the thought of being a rockstar. But they don't love the idea of playing guitar for four hours per day to get there. Multi-millionaire? Yes! But bootstrapping and risking everything for six years, learning how to run a business? Not so much. Mindful, meditating yoga guru? They'd love to be one of those! But sitting still every single day? Cultivating a daily yoga practice? That doesn't appeal.

And that's why more people aren't rockstars. That's why not everyone is a spiritual leader.

It's one thing to want the outcome – it's quite another to want the process.

And with career change, you're also usually grappling with the challenge of not really knowing what you want your outcome to be.

You want to be in a career you love. But you don't really know what that career would be, and the process of getting there (wherever 'there' is) looks boring and unpleasant.

How can you take action on your career change when you don't know for sure what you want?

How can you get started when you don't know which direction to head in?

Start by doing things you enjoy. Start hanging out with people that excite and inspire you. Immerse yourself in all the things that pique your interest – and if you're already doing them, look for ways to ramp those things up to a new level.

These small, individual, seemingly unrelated actions will become your process.

One action will spark an idea for another action.

You'll go to a class and meet someone with a great piece of advice. Or you'll attend a talk and see a leaflet for another talk, where you'll get chatting to someone who'll tell you about something you never knew people got paid for. You'll try something else and realise it's the polar opposite of what you thought it was, and sigh with relief that you'll never fall into the trap of applying for a job in that field.

Louise took part in our Career Change Launch Pad. A couple of months ago we had a chat about getting into action, and how even small forays into faint possibilities opened up doors she never knew were there.

In her words: "I found that as I pursued little ideas, they turned into bigger ideas."

Louise had a feeling that mentoring and supporting people was an area worth exploring. So she took a few small steps to get into the process of exploring it. She chatted to a couple of people she knew who had experience of coaching. She researched it at home. And then, safe in the knowledge that she was still interested, she took a slightly bigger step:

"I found a short coaching course over a long weekend that would give an opportunity to practise coaching and be around other like-minded people who might (and did) turn out to be part of my tribe. The course was exciting, and lots of fun, and I got the practical experiences I wanted.

"It was surprisingly easy to make the decision to continue training – so easy it didn't even feel like a decision – and I've done more and more coaching-related things, like writing my first piece of marketing copy. From that small inkling of an idea, I now have my first clients!"

It's a shift in perspective – from chasing an outcome to immersing yourself in a process.

It's not about making a giant leap from one thing to another.

It's an unfolding, a revealing, a chipping away, an opening up.

It's about relaxing into rhythms that nourish and inspire you, and trusting – yes, there's a bit of blind faith in here too – that those rhythms will carry you to their inevitable destination.

  • In the simplest terms, without diving into the finances and the who-will-employ-me and the where-are-the-job-ads of it all, what would you love to wake up and do every day? Start doing it, every day, even if only in the smallest possible way.
  • Challenge yourself not to think about the end-point of your career change for a whole week. Instead, just focus on enjoying the process of figuring it out. This is your chance to poke into lots of different things that interest you; research topics that fascinate you; reach out and connect with people that inspire you. What if there was no 'end point' to your shift at all? How would you approach your career change if it were a never-ending process?
  • Make a list of all the industries, jobs, careers and ideas you have for your future work. Then for each one, find someone who does something connected with it. Invite them for coffee, request a 15-minute phone call, drop them an e-mail. Find out about their 'process'. What do they do all day? What's the daily reality of their work? What's great about it? What's not so great? Get your head out of goal-mode, and focus on processes.

Get with the process.

Inspiration is for amateurs.

5. "Imagine Immensities"

By Chase Jarvis [CC BY-SA 4.0 (https://creativecommons.org/licenses/by-sa/4.0)], from Wikimedia Commons

Debbie Millman is a writer, educator, artist, and host of the 'Design Matters' podcast.

In 2009, she published her book Look Both Ways, which featured an essay entitled Fail Safe. In it, she writes:

"Do what you love. And don't stop until you get what you love. Work as hard as you can. Imagine immensities. Don't compromise and don't waste time. In order to strive for a remarkable life, you have to decide that you want one. Start now. Not twenty years from now. Not thirty years. Not two weeks from now. Now."

Life owes you nothing.

It will not rearrange itself for you.

It will not adjust your circumstances at any point soon, suddenly making your career change path clear, and open, and time-rich.

You must demand what you want from it.

A career change is, by its very nature, a significant disturbance. It's a rearranging, a realigning, a major adjustment.

And when your life is chugging along in an organised manner, ticking smoothly along its rails, and you decide to change tracks…

You're summoning a derailment.

And derailment requires upheaval.

It's uncomfortable, to begin with. That's why there seem to be so many reasons why you can't make a shift.

Making a shift might require going to a lecture, to a class, to a networking event, and that might require changing your schedule. It might require making requests of people that you wouldn't normally make. It might require spending money on a coach or a course. It might require difficult conversations with your family. It might require putting yourself out there to the world in a way you've never done before. It might require vulnerability, or an extra level of strength.

Those are all excellent reasons to stay right where you are, reading articles like this one, doing what you're doing, behaving how you've always behaved. It would be very reasonable to decide to simply stay on the tracks.

But if you're hearing a call for something more, reasonable isn't going to help you answer it.

If you're one of those ambitious, committed people for whom a life of mediocrity and second-best isn't enough, reasonable isn't going to fulfil your dreams.

Reasonable settles. Reasonable gives in.

If you're committed to making this year the year you finally start feeling motivated, inspired, and fulfilled by what you're doing, it's time to get a little unreasonable.

Yes, you might have to change your schedule. Yes, you might have to spend some money. Yes, you might have to get some new friends, have tricky conversations with your family, and push the boundaries of your comfort zone.

And in the context of living a life you love, that's probably not too much to ask.

Which of these pieces of advice resonates with you most? And what could you do this week to put it into practice? 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.