[This is the talk that I gave at TEDX LSE on Saturday. I was one of 15 speakers. The theme of the conference was ‘Rethink Your Definition’]

I’m going to tell you a story.

It’s a story that explains why I’m standing on this stage in front of you.

It’s a story about fear. About how fear of the unknown can keep us from ever doing anything remarkable with our careers and about how fear of failure can sabotage our attempts once we are out there ‘doing something different’.

The story starts over four years ago. I’m working as a management consultant on the eighth floor of a big corporate building overlooking the river at London Bridge. It’s well paid, everyone I know approves, and unfortunately…. it’s extremely unfulfilling.

The story really starts the day I walk into my annual review meeting and, instead of handing over a polished folder of positive feedback… I hand in my notice in order to do something more independent and exciting with my career.

The story almost ends a year ago when, now running my own business, I have a serious burnout. The irony of feeling that the thing that we built in order to liberate other people from their jobs was now trapping us was not lost on me.

My burnout came in the shape of extreme anxiety. I would wake up every morning feeling like I’d drunk four espressos on an empty stomach. Perfectly normal emails would make me freak out. My accountant made me cry. OK… I know that’s what accountants are for… but you get the picture!

This is a story about fear. It was fear that almost stopped me from making the leap away from the corporate world. And it was fear that got me so overwhelmed last year trying to pull off something remarkable that I completely froze, unable to run my business… self-sabotage in the extreme.

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In this talk I’m going to argue that rather than clinging onto certainty in an ever-changing world, we should embrace uncertainty – for that is where exciting careers lie. Heading into the unknown, comes with a healthy dose of fear. But this should be actively sought, not avoided.


So, there I was, probably like many of you in this room, starting my career working in a big corporate organisation. Crunching spreadsheets and polishing PowerPoint. Conscientious, keen, hard-working, eager to learn, and bored to tears.

The problem?

  • Was this what I had worked all those years for through school and university? I felt like I’d ended up there by accident, the logical progression from a certain type of education and a certain standard of grades. Obviously it made sense: pay off student debt, earn some decent cash, assure a good standard of living, pursue a sensible career… [As an aside: money is always a significant factor in any career decision… we should just be careful not to use it as an excuse as well.]
  • Why didn’t any of the work we were doing seem to matter? I don’t mean matter as in ‘save the world’ matter… I mean matter full stop. There didn’t seem to be any kind of discernible impact on the outside world. It felt like one big inside joke – that I didn’t get – all these people busying themselves with project management, status updates, and career progression… and no one was saying ‘hang on guys, what is all this effort in aid of?’

There were 2 types of people in this world. In camp 1 you had the people who knew why they were there and what they were getting out of the experience. And, in camp 2, you had the people who had ended up there by accident – because it seemed like the logical next thing to do. When I realised I was firmly in camp 2 I knew I had to do something about it.


Fast forward a few years and I’m successfully climbing this corporate ladder. I now know that it’s not for me but I feel stuck…

  • Fear of I’m too inexperienced
  • Fear of I don’t have enough money
  • Fear of certain failure
  • Fear of no transferable skills

Ultimately this all boils down to fear of the unknown. This was fear related to a situation I wasn’t yet in. The result of it? Inaction, procrastination and excuses. The thing is – this fear is relatively easy to ignore. How? Denial and procrastination. You just stay put and ignore the nagging feeling that perhaps you should look a bit closer into the unknown.


February 2009. I’m polishing another PowerPoint presentation in my cubicle. It’s dark outside. It was dark when I arrived and it’ll be dark when I leave.

I’m wondering how on earth I am going to transition my career to do something exciting with my time and energy… when this head pokes its head over the cubicle wall and says: “This is a bit rubbish isn’t it?”

Enter Dom Jackman, slightly more senior to me assigned to buddy me through the ranks. We got on well and ended up confiding in each other how we wished we could do something more exciting (and perhaps entrepreneurial) with our careers.

We ended up brainstorming lots of – frankly awful – business ideas together. Thankfully pursuing none of them, before we realised that the emotion that we were feeling… was the idea that was worth pursuing.

We realised that there were so many people working in big organisations wondering what they were doing with their lives. We reasoned, that if we could build something to help all these people perhaps there would be a business in the idea.

So we started writing an anonymous blog from the safety of our jobs and we saved cash. People seemed to like the idea… and started asking for actual job opportunities. We had the idea of starting a Monday newsletter, sending round 10 opportunities to ‘do something different’ (our strapline).

Week 1 it went to two people. My Mum and Dom’s Mum. Week 2 we sent it round our mates… and within a couple more weeks hundreds of people had signed up – many of whom we didn’t know at all. Fast forward 2 years and over 50,000 people had signed up. We had been written up in all of the main press in the States and the UK.

Hundreds of people had found new jobs through our site – from relatively safe escapes to places like Google and Innocent and JustGiving to crazy transitions to Africa. We even offered a job running the post office in Antarctica for 6 months. My favourite transition was the hedge fund worker Harry who got a job managing a beach lodge in northern Mozambique with an 80 person staff.

Talk about a transition!


It wasn’t just jobs that people were using us for. Business partners were meeting on the site. People were finding whacky expeditions and joining ocean rowing teams as a result of the platform. And one guy even met his girlfriend (now wife) at one of our events!

Yes we’d been pretty poor for two years and no we hadn’t known whether it was going to work. But the ride was such fun and we knew even if it didn’t work out that we would have no regrets leaving our previous careers.

So, there we were, two guys with an idea and a desire to do something outside of the corporate mainstream… running our own business, making a living off it… and slowly we began to realise quite how big it could become.

We were approached to write a book – The Escape Manifesto – being published in a month’s time. We spent 3 months in New York establishing the community out there with our new partner Mikey. It was in New York… that we decided to really go for it.

We knew that big companies around the world were filled with dissatisfied but talented and ambitious workers… and we felt like we could really do something about it.


So here we are… the meat of the story… and this ‘fear of failure’ stuff is getting real.

A year ago, we came back to London and started trying to raise investment to fund our vision. That’s when the trouble really started. We hit the pitching trail, hawking our idea for a forward-looking Linkedin around London VCs.

At the same time I was on point to write the book and of course we had the day-to-day running of our existing operation to worry about. I also took on a few too many personal projects away from our startup.

Slowly but surely the weight of expectation and worry began to get the better of me. After almost three years of unbridled optimism and progress I felt myself begin to push up against some serious negative psychological barriers.

Within a relatively short space of time my worry was so bad that I was beginning to feel really paralysed. Ridiculously, it was first time in my life that I’d had to properly face the prospect of failure.

The anxiety focused on three main things:

  • The book – The Escape Manifesto – a revolutionary handbook for the disillusioned workers of the world.
  • The business plan – We were trying to build a new website based around our forward-looking profiles concept
  • The investment – We were trying to raise at least half a million pounds of investment.

The voice in my head was telling me… you’re not experienced enough, you haven’t got enough time, the book won’t be good, the business plan is crap, we’re not the right people to build this business, etc.

There we are, three weeks short of not being able to pay our team, four weeks till the deadline to submit the book to the publishers. And I’m freaking out. Completely unable to function effectively. Being carried by my two partners.

And that’s where this part of the story ends.

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1. We crave safety

We all strive for certainty in our lives. We fear the unknown. We can’t control the unknown. However, if anything is certain in life it is that nothing is certain. The last 5 years since the great recession started have proved that. Careers that we think are safe are turning out to be anything but.

Faced with the imperative of focusing on our immediate personal challenges, it is very easy to forget that the world is changing – constantly. Clinging on to permanence in a world that is constantly changing is the surest way I can see to make ourselves obsolete.

The traditional career path seems safe because it comes with a monthly salary, graduate training programmes, corporate amex cards and year end reviews. Guess what? As soon as the economy or market changes and it’s no longer ‘safe’ for the big organisation you work for to have you on the payroll… you are not safe.

You may have had the illusion of safety for a while… but the reality (and the past 5 years have proved this) is that none of us are safe. I’d rather control the means of my own income than rely on a massive corporation for my security.

2. We are wired to see threats everywhere

I wouldn’t be the first TED speaker to relate the evolutionary truism that we are wired to fear threats more than we are attracted to opportunities. It makes sense… all the inquisitive, fearless cavemen never made it… the jumpy ones who were afraid of the dark and spent all their time up trees… they’re the ones who survived. They’re the ones we’re descended from!

We are wired to see threats everywhere…

  1. When we consider making a big career change, most of us experience serious fear of the unknown.
  2. And then when we are actually ‘out there’ doing something exciting it is all to easy to suffer from massive fear of failure.

The reason I’ve told this talk in the way I have – telling you how hard it is to leave the established path and how tough it is doing something different – is because I wanted to share how much our minds sabotage us. We catastrophize. We think in terms of failure or success and we don’t realise that most things we’ll do in our lives won’t play out it terms of such stark either/or scenarios.

3. We practice Experiential Avoidance

What this means is that we’re extremely good at avoiding things that make us feel uncomfortable. So much so that our brain actually reinforces avoidance behaviour (even when the thing we’re avoiding is good for us).

You consider doing something that scares you, pitching for investment, quitting your job to start a business, doing a TEDX talk… immediately your stomach tightens, your breath shortens, and you feel scared.

And then, because you listen to the fear and the negative, ‘catastrophising’ voice in your head… you make an excuse… sorry TEDX LSE, my Great Aunt Bettie is having a tea party, I can’t make your talk.

And, in saying no, you immediately feel better, you feel relieved. And guess what your brain does? It rewards you for your avoidance. “Phew, we dodged a bullet there didn’t we?!”

In heeding fear that prevents us from doing things that may benefit from us, we are training ourselves to never, ever, have to face the prospect of failure.

It’s worth repeating that sentence. If you spend your life avoiding the prospect of failure you are also greatly minimising your chances of success (not the labels of success – status/money/power – but actual success: independence, fulfilment and an exciting life).

This is why I had so much trouble last year… because I was putting myself through an imaginary failure before we’d even had the chance to see whether we could succeed or fail in the real world.

Ironically, through heeding the fear you’re making the outcome you’re fearing more likely. Through paralysing myself last year I had effectively failed already. I couldn’t see that at the time.

Rob Archer, from The Career Psychologist, talks about our demons – the critical voices in our heads. He says that we need to scoop them all up, put them in our backpack, and carry them with us as we walk deliberately towards our goal.

4. We should listen more closely to our fear of failure

Based on my experiences last year I’d take that a step further. You mustn’t just carry your demons with you. You must use them to point you in the right direction. A lot of the time we are scared of doing something precisely because it may be worth achieving. Our evolutionary wiring that encourages us to run away from fear doesn’t help us in our careers.

We shouldn’t be looking for safe but boring working environments where we get paid to exist and then one day someone tells us we are no longer needed. We should be looking for opportunities to do something worthwhile and meaningful. We should be striving to do work that matters to us.

Everyone in this room is fortunate enough not to have to worry about their basic necessities on a daily basis. This is a huge privilege. What must we do with this fact? We must accept that ‘doing something different’ comes with a healthy dose of fear… and, rather than backing away from it, we must embrace it as a sure sign that we are heading in the right direction.

In trying to protect you… the voice in your head is encouraging you to play it safe. It is imagining all sorts of horrible worst-case scenarios… usually involving you ruining your career, your life, being a laughing stock, letting people down and ending up living in a box somewhere. Sadly, the voice in your head is also going to lead you to have a boring career if you listen to it.

This is what Shakespeare meant when he said “Present fears are less than horrible imaginings”. We always imagine the worst. When we’re actually in a situation we deal with it – it’s the situations that we’re predicting for ourselves that are really hard to deal with… because they’re invented, they’re imagined! How can we deal with something that exists only in our heads?


So what happened last year?

We kept pushing through a couple of extremely difficult months where I felt like I was permanently wired with worry (and was very thankful for having two extremely grounded and capable business partners).

We ended up turning down an offer from one of London’s top VCs and we crowdfunded £600,000 from 395 of our own members. I also managed to submit the manuscript for the book (only 3 months after the original deadline!).

Today we have over 100,000 members, have launched our education arm – The Escape School, our adventures business (we’re sending 8 people to walk through the Okavango Delta next month) – and we’re proceeding steadily in the direction of our goals.

Am I still scared?

Yes, every day if I think about it.

Am I letting it stop me?

No… I try to use the fear as a radar and go straight for it. If it’s scary it’s usually worth doing. I’d encourage you to do the same… it’s the only way we’ll ever build anything that matters.

Your battle to have a remarkable life isn’t with the outside world, it’s in your head.

Don’t fear failure.

Don’t fear the unknown.

Follow the fear to see if it leads you to something worth doing.

Do fear boredom.

Fear regret.

And then act on it.

Thank you.


Rob Symington (@escroberto) is Escape the City’s co-founder. He lives on a boat, owns a double decker bus called Esmerelda and a motorbike that breaks down a lot. He passionately believes that ‘just because’ things are the way they are is no justification for accepting them. The Escape team are hard at work over on the main site building Escape Profiles that help people make big career changes.

If you want to receive Escape the City blog posts directly into your inbox just click here. We write about leaving big corporates, pursuing alternative careers, building businesses, and going on big adventures. Because life is too short to do work that doesn’t matter to you.


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