How can I make a big, brave career change?

These are the ideas that I want to share with every person who comes to us, wondering why they feel so unfulfilled in their jobs and what they can do about it. These are the ideas that I’d invite every person who attends an event with us to read beforehand – so that they have a frame of reference and some starting ideas to test with their fellow attendees in a safe environment.

These ideas come with a double caveat:

1. You can learn new concepts and theories and accept them to be intellectually sound but you will only really know them to be true when you experience them yourself. This requires accepting new ideas as simply new ideas and taking small steps to test them in the real world.

2. There is no such thing as objective truth – certainly not in the context of what works for a career change – there is simply what works for you. We are all so unique in terms of our aspirations and values and personal situations. Believing there is “one way” will hold you back.

If I were a doctor prescribing a cure for an unfulfilling career, this would be my prescription. The prescription would start with some tough love…


1. Accept the fact that “The Secret Toolkit” doesn’t exist.

We’ve all been there. I’ve lost count of a number of times I’ve read a blog post or bought an online PDF that claims to be able to teach me “how to make my business a success” or “how to live without fear” or “how to find my passion”. It is too easy to believe that anyone whose life you admire or envy has a secret that you haven’t and, once you find it, you’ll also painlessly and seamlessly be able to change your own life and build the career or the business that you want for yourself.

Have you ever said this to yourself?

“I know what I want to do, I just don’t know how to do it.”

This is an extremely dangerous thought because it keeps you stuck waiting for the perfect moment when you will know exactly “how” to do it. The only secret you need to know is that successful people who you admire have spent the time that you spend thinking or worrying or dreaming about your plans actually doing theirs (whilst yes, facing all the same difficulties as you and no, not knowing “how” to do it when they started).

The reality is that anyone whose success you aspire to has built their life by consistently operating in the face of uncertainty, discomfort and fear – and that’s what you’ll need to do too.

2. Be prepared to feel uncomfortable.

This second point has taken me a long time to understand and even longer to get used to (I’m still not there).

Everything you want is on the other side of some kind of discomfort.

It is worth reading that line again.

Everything you want is on the other side of some kind of discomfort.

You are hard-wired to avoid pain. It is deep in your psyche. Pain = bad, pleasure = good. It’s no surprise either; it is evolutionarily extremely smart. The problem is that while your instincts are useful for keeping you safe in the jungle, they are rubbish when career fulfilment is at stake.

In our “getting unstuck” workshops we talk about a psychological term called Experiential Avoidance. The idea is simple; when we are faced with something that scares us we typically move away from it. Our brain congratulates us on avoiding danger and rewards us with relief (reinforcing the behaviour for the next time). If we do this enough (which most of us do) we will train ourselves to avoid fear on all levels. This process is subconscious in most of us.

It’s a given that whatever potential career path you could pursue is far less certain than the one you are on. All your instincts are telling you to stick with what you know because the unknown is scary. This is what Shakespeare meant when he wrote “Present fears / Are less than horrible imaginings” – you don’t know what is going to happen and you expect the worst.

How much do you want to do something different with your life?

If you aren’t prepared to feel uncomfortable then you are probably not going to manage to Escape the City. I don’t write this in some kind of gung-ho “No Fear” way. I simply mean that stepping off the travelator and making exponential step-changes in your career and your life is going to be scary.

Incremental change, linear change – that’s fine and you can probably manage that without being too uncomfortable – you apply for one job from your current job, you get the job, and you make the move across, etc. You don’t need Escape the City for that kind of change. That’s just career progression.

However, if you are aspiring to something more… if you are aspiring to impact, autonomy, creativity, connection, independence, and meaning… the chances are that you’re going to need to create that kind of opportunity for yourself (it’s not sitting around on job boards waiting for you).

If you accept that uncertainty and fear and discomfort and the unknown are core to the journey then you can grit your teeth and use the fear as a radar.

Ask yourself this: “Am I scared about this new thing because it is a genuine risk / really dangerous or am I scared about it because it could be great (i.e. I’m just worried, uncertain, scared)?” Manage the risks, avoid the dangers but don’t let the worries stop you from taking the first small steps in new directions.

3. Avoid thinking in black and white.

As you read the paragraphs above you may have had all sorts of thoughts flash through your mind:

“What about the mortgage?”

“But I have financial commitments, I can’t risk a change!”

“This is all very well but I don’t know what I want to do.”

“I can’t afford to take risks.” 

Humans dichotomise. We think in binary: “Happy / Sad”, “Rich / Poor”, “Job / No Job”, “Success / Failure”. When we think of something like escaping the city or making a big career change or starting a business or going on a big adventure, we miss the nuances and think in terms of stark opposites.

To make this more tangible let me offer two examples of people who rejected stark contrasting options and found the way that worked for them:

Matt Trinetti…

Matt works with us at The Escape School. Previously he trained as an engineer and was a consultant at IBM in Chicago. He had the nagging voice in his head telling him that he should be doing something different with his time. He couldn’t stop thinking about going on a big adventure but he didn’t want to let people down. He felt like he would be stupid to turn his back on what was ‘a really great career’.

Matt Trinetti

Matt stopped thinking in terms of job/no job contrasts and simply asked for a sabbatical. IBM ended up giving him 7 months off, with his job guaranteed at the end of it. Matt used this time to build a website, start a blog, meander around Europe, start a self-publishing company, and grow and explore in ways that he hadn’t previously done in his life. Unsurprisingly he lasted two weeks back in his old job at the end of this incredible experience and is now walking purposefully in the direction of an as-yet-still-unknown future.

Matt Lane…

Matt wanted to start a business around his passion: beer. He couldn’t afford to go without a salary (mortgage to pay and, further down the line, a baby on the way) so he devised a phased approach to starting BeerBods. In the beginning, whilst testing his idea (building a simple landing page, sending craft ale subscriptions to people, storing beer in his shed) he simply ran his business on evenings and weekends.

Matt Lane

As more customers began signing up Matt negotiated a part-time agreement with his work. He worked 4 days a week, then 3, and then 2. Eventually, he resigned but made sure he could do the odd consulting gig for his old employer to keep the money coming in. He had a line in the sand which was his target for resigning, I think it was 500 paying customers. This is another great example of the power of rejecting black-and-white thinking in pursuit of a way that will work for you.

What if escaping the city was a process that has already started in your head way and could go on for another three years before you even handed in your resignation?

What if, rather than a Jerry Maguire moment of glory, escaping the city was simply a philosophy that you applied to the rest of your life – a way to navigate the many circumstances and opportunities you are going to create and come across over the coming years? A promise to yourself not to settle?

4. Stop waiting for the eureka moment.

Have you ever said one of these to yourself?

  • “If only I knew what I was passionate about I would go and do it.”
  • “I don’t know what I’m meant to do with my life – what is my one thing?”
  • “I just don’t have any good ideas, if I did I’d be happy to start something.”
  • “I don’t want to change until I know it is right – I want it to be perfect.” 

Here are some things we believe in opposition to those statements:

You: “If only I knew what I was passionate about I would do it.”
Us: “Passions are grown not discovered. Start doing.”

You are not going to suddenly “just know” what you are meant to do with your life in a searing moment of clarity on your commute to your job. You cannot think or analyse your way to a passion. Passions are grown through inquisitively pursuing interests, getting good at things, and making yourself useful to the world.

Through the hard work of doing different things you will find yourself drawn towards certain activities and, if you are self-aware and keep acting with purpose, you can become passionate about new things.

You: “I don’t know what I’m meant to do with my life.”
Us: “There is no “one thing” for each of us. Start doing.” 

In the same way, as there isn’t just one potential partner for each of us, there is no such thing as your one calling. You could certainly turn an activity into your calling by following your interests, doing it enough, eventually mastering it and dedicating your life to it so that it becomes your “thing”.

However, the belief that you have a single path is extremely dangerous because it will stop you taking even the first step in a new direction if you have even the slightest doubt that it might be the wrong direction.

If callings are grown through taking actions (not discovered) and if you aren’t taking any new actions because you’re waiting till you “just know” – then you will never create a new life for yourself.

You: “I don’t have any good ideas if I did I’d start something.”
Us: “Explore other people’s ideas and other people. Start doing.”

You may not currently be having any good ideas but that doesn’t mean that you’re not capable of having good ideas. Your job might be taking up all of your time, energy and creativity. You may be discounting new ideas before they can really fully form. You may simply be stuck in a rut.

All of this might be true but you are still capable of having good ideas.

If you aren’t having any good ideas why don’t you start by allowing yourself to have hundreds of bad ideas? Write them all down. The ability to have ideas is like exercising a muscle. Slowly you’ll get better at it and the ideas themselves will get better.

Good ideas aren’t formed in a vacuum. The information and people we surround ourselves with influence us massively. Who are you surrounding yourself with? Outside of work – what events or meetups or communities are you a part of? What conversations are you having? What information are you consuming?

Change up your routine to expose yourself to new stimuli and exercise your idea muscle by having lots of bad ideas – you’ll be amazed what comes up.

5. Start (small if you need but do start).

You don’t need to know what you are going to end up doing at the end of this process of transition in order to start. If you don’t know what you want to do with your life and your career, the best way to figure it out is to start trying new things. Take the pressure off: don’t even think about quitting your job or making any kind of decision that feels risky, just start doing.

(Beware that it is really easy to feel like you’re being constructive and proactive around your career change or startup idea when you’re actually just spinning your wheels.)

I would challenge you that the following behaviours do not qualify as properly starting – as they either involve stuff that is happening in your head, stuff that gives permission to someone else over your fate, or stuff that doesn’t really involve you interacting with the world in some way.

What doesn’t count as “starting”?

  • Browsing job boards does not count.
  • Writing 100-page business plans does not count.
  • Googling for career inspiration does not count.
  • Keeping a Pinterest page of inspiring quotes does not count.
  • Reading self-help books does not count.

It is only when you interact with the world that you have the chance to create new possibilities for yourself. Here are some ideas, all of which you can do without resigning or risking your financial security…

  • Shadow someone – Ask a friend or a contact for a half-day following them around their place of work to see a new walk of life
  • Ask for a sabbatical – What’s the worst that can happen? They can only say no. If they say yes you’re on a new path.
  • Ask for a change of role – What’s the worst that can happen? They can only say no. If they say yes you’re on a new path.
  • Organise a meetup – Go on www.meetup.com and create a group around any topic that you’re interested in.
  • Attend a group – If you don’t start a meetup group, join one, and actually go to a meetup and ask strangers about their lives.
  • Create space – Take a day off work and explore your town or city, watch how other people are leading their lives and filling their days.
  • Start a blog – Write 5 articles about things that you passionately care about and send them to everyone you know.
  • Ask for help – reach out to someone who you admire and articulate the beginnings of your plans to them, see if they can help you.
  • Do free work – So you want to work for a cool organisation? Offer to do them a fixed piece of work for free, send them 5 project ideas.
  • Start a book club – Find 4 like-minded souls who also want to change their lives and meet monthly to discuss life/business books
  • Try new things – They don’t have to be anything to do with your career or work, just go and do something new in your time off.
  • Give a talk ­– Find a topic that you know enough about and care enough about to give a talk on it, and talk in front of ten people.
  • Create a product –In the time in between work and sleep create a product or a service and try to sell it to one person for real money.
  • Volunteer – Find a group whose work you admire and give them three hours of your time a week. See what you learn by committing. 
  • Reach out Don’t be afraid to connect directly with those at organisations you admire – even if they aren’t publicising new job roles: reach out to them to see how you can help (see ‘do free work’ above!)

If there is a secret it is this…

Doing something different with your life and career is hard. Accept that discomfort is the journey.

Know that action is the antidote to not knowing what you want to do with your life. Remember that we learn by doing (which means you’ll never be truly ready until you start). Remind yourself that you can do all of this without taking big risks. Accept that this is a process and that the fun is in the journey, not the destination.

Start saving an escape fund today – even if you don’t know what it is for, money gives you time and options. Take care of yourself – it is impossible to feel resilient or confident or strong if you are physically, mentally or emotionally exhausted. Be patient – this doesn’t happen overnight. Hustle – behave differently to the competition in everything you do.

Finally, police your own cynicism. Building a life on your own terms is hard enough and plenty of cynicism will come at you from other peoples’ fears and desires and expectations for you. Don’t add your own cynicism to the challenge. There are lots of real obstacles between you and your ideal life; you don’t want to add to the challenge by handicapping yourself with negative thoughts of your own.

Make no mistakes; this is a fight. It’s a fight to the death. Either the City wins and you live a life you didn’t actively choose for yourself while the “what if’s” stack up in the corner or you fight tooth and nail to spend your precious time on this earth doing things that matter to you and to the world.

It will not be easy but it will – however it turns out – be worth it.


If you’re ready to take the leap and make a change, check out the opportunities currently live on our site, here.

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