Two hundred 21st Century Careerists at Escape to the Woods — Escape the City’s annual festival, 4–6 Sept 2015, UK.

How can I build a 21st Century Career?

This is a short guide produced to celebrate World Escape Day on 24th September 2015. These ideas were collected from The Escape Community at our annual festival Escape to the Woods and shaped together online.

We are living through a work revolution…

The way we’re working isn’t working.

  1. On the global scale — big institutions and corporations aren’t adequately addressing our biggest shared challenges,
  2. On the individual scale — these are often frustrating, unfulfilling and painful places to work.

We have very different aspirations to our parents. Whilst we care about security, we also care about social impact, we want to build things, and we want more control over our careers. We believe that “work” can be so much better and we reckon that together we can really shift the culture.

We are lucky — tech is revolutionising what work can look like in the 21st Century. And yet, transition is still hard as hell and many forces align to protect The Established Way Of Doing Things.

We are the revolution.
We reject unfulfilling work.
We reject the suffocating mediocrity of the conventional career path.
We confront the forces that keep us stuck.
We are up for the fight.

We are committed to building careers full of personal meaning.
We are serious about finding ways to fulfil our potential.
And, we believe that if we do this…
Together we’ll make things so much better.

What does The 21st Century Career look like?

Over the past 6 years +230,000 people have joined Escape the City from all over the world and, no matter where we’re based, we all agree: when it comes to most mainstream careers, certain crucial ingredients are missing…

There are 500 of us in The Escape Community (the alumni from our Tribe programmes). We are made up of brave corporate escapees, ambitious career changers and aspiring entrepreneurs. We are united by our desire to support each other in doing work that matters. And this is the advice we’d give to other people seeking to make big, bad, bold career changes…

1. Start taking action before you know exactly what you want to do next.

Experiment bravely (without knowing the outcome)

You cannot think your way to a new career, you can only “do” your way towards it. This is hard. You’re human so you probably don’t like acting before knowing the outcome of your efforts. However, acting (rather than researching or planning) is the most effective way of really learning more about what you might want to do next. Reflect on your interests, follow your curiosity, and scope experiments on the edge of your comfort zone — these will give you the information you need to make more informed decisions about your future.

Just start

There will never be a perfect time. Your mind is clever: it can craft extremely rational excuses for inaction. However, no matter how much is going on in your life, you can always figure out the next tiny but scary step and take it. Resist the urge to think in all-or-nothing terms. Manage your risk by all means and start small — but do start. You can’t predict the serendipitous events that will follow from you taking action and even small-scale commitment is a powerful thing.

Live your values

Your actions express your priorities. Assess how you spend your money, your free time, and where you concentrate your attention and energy. This will tell you lots about what matters to you. If you’re not happy with what this picture currently looks like, what small changes can you make to better live your values? We become what we consistently do.

Start where you are

When we dream of big career changes we often start with a blank sheet of paper, without reminding ourselves that much of what we’ve done is useful. Take your current skills, strengths, passions, interests, experiences, and contacts with you. Start where you are — your current means of earning a living is your beginning point — and work your way to a new place.

Learn (and share)

There are things that would be possible for you to achieve if only you knew more about them. The more you can engage with new people, concepts and skills, the broader the range of potential avenues you can uncover. Get out there and consume information that interests you. But don’t just be a voyeur — learn by interacting, by doing, by getting involved, by teaching. Learn by sharing. Pay attention to what fascinates you — these are the clues for which paths you should investigate further.

Be patient

Career change doesn’t happen overnight. Building a life filled with meaningful work is a process that usually takes years, hard work, resilience, a certain amount of luck, and the help of lots of other people. Having a long-term view will help you keep going on small tasks, experiments and explorations in the short-term. Just remember: the process can’t start until you do… so be patient but do move into action.

Examples from The Escape Community:

Ollie Codrington — @olliecod

In 2010 Ollie Codrington was an in-house lawyer. He now runs two businesses and consults one day a week for a major bank. How did he get to where he is today? He left his job without a plan; his only plan was to be a “Yes Man”. He said yes to every opportunity that came his way: helping other people build their businesses, mentoring entrepreneurs, and taking the occasional corporate gig. This voyage of discovery led him to where he is today. His advice? “Opportunities are everywhere but you’re never going to find them on your lunch break. Action trumps everything.”

Bec Cork — @honey_woods

Bec Cork always knew she wanted to work in nature but without the funds to buy her own land, she thought it would always be a dream. However, she started to run her own events in other woodlands and before she knew it — not only was she running a successful pop-up camping business but had also been given exclusive access to an arboretum to run community events and conservation. Without that first step, she would never have met the people, gained the experience and taken the opportunities that have led to her being fully self-employed in woodlands all year round today. Bec traces the start of her journey to the day a friend sent her the Goethe quote: “Whatever you can do or dream you can, begin it. Boldness has genius, power and magic in it.”

The Sunday Sermon at Escape to the Woods with Eiji Han Shimizu, director of The Happy Movie.

2. Develop a brave mindset to support you through transition and uncertainty.

Don’t avoid risk, avoid regret

When deciding whether to pursue an exciting new path ask yourself this: “If I don’t do this, will I look back in five years and wish I had?” Like anyone else, you want stability in your life, just don’t let your (totally understandable) desire for safety (and your fear of the unknown) win out over your dreams of living a meaningful and impactful life. Try to practise regret-avoidance, not risk-avoidance.

Practise resilience

The more robust you are mentally and physically, the more you’ll be able to overcome the challenges you’ll face and the more you’ll enjoy the process. “The difficulty isn’t that we have negative thoughts. The problem comes when we believe our thoughts are true.” Make sure you look after your health and the world will seem a friendlier, more potential-filled place. Resilience is a habit — find your edge and practise daily.

Define success for yourself

Too many of us wake up one morning realising we are living someone else’s life. Figure out what success means for you at a very specific level, and then bravely protect your definition of success as you build towards your ideal lifestyle. The more you can remind yourself of your core values and why what you are doing matters to you, the stronger your resolve and determination will be along the way.

Embrace imperfection

Your unwillingness to fail, to make mistakes, and to get things wrong (especially in the early days) is one of the main things that will keep you stuck. You need to be prepared to be a beginner again in order to create something exciting and new for yourself. Adopt a growth mindset and enjoy knowing that imperfection is how you grow — experiments are how you learn.

Don’t underestimate yourself

You may not yet be able to achieve what you’re dreaming of achieving, but you are capable of becoming the person who can achieve it. Lack of self-belief is the number one dream killer. Build slowly and manage your risk by all means… but somewhere inside cultivate a stubborn belief that you are capable of achieving these scary things. We know you are. You are.

Examples from The Escape Community:

Sarah Wheeler — Balance Growth Happiness (check out her Facebook group)

Sarah Wheeler used to work as a management consultant and accountant. But she always felt something was missing. After discovering a passion for coaching and positive psychology, she made the decision to leave her secure career in order to build her personal coaching business. Through support from her own coach, a lot of personal development, and community experiences at Escape, she underwent some profound mindset shifts. Having been risk averse — always following the ‘sensible’ path — she realised that the risk of staying in a career that didn’t make her feel fully alive or fulfilled was greater than the risk of forgoing a monthly salary and job security for the uncertainty of self-employment. Taking the leap into running her own business has allowed her the time, space and freedom to fully step into who she is as a coach.

Claudia Rimington — @claudiarimingto

Claudia Rimington worked in marketing but really wanted to start her own business. So she started working evenings and weekends. It was a hard struggle and her first two products (LookFab — personal styling, and LocalPlanet — locally made itineraries for tourists) didn’t take off. Having learnt from her mistakes, she recently left her job to work on her third business. She has created a visual mood board with inspirational quotes to help her stay resilient. She also cleaned out her Facebook newsfeed — going on an information diet, limiting herself to relevant, constructive content. Going into her third product she feels more positive than ever. Her final thought: “I’m not really worried by failure and knock-backs as I know I’ll win some day!”

Keeping warm and plotting brave career changers at Escape to the Woods 2015.

3. Find your Tribe — make friends with other people determined not to settle.

Find people who “get it”

Some of the people closest to you will think you’re mad. They want you to be safe. They want you to stay the same. It is important to surround yourself with people who have similar ambitions, values and levels of excitement. Immerse yourself in the relevant communities. Not as a mercenary, but as a genuine and generous participant. If you get dragged back towards the social pressures of conformity, it is these people who will send a lifeboat.

Give first

It is natural to adopt a customer mindset in our careers (“what can I get from this interaction?”). And yet, the most successful people adopt a supplier mindset (“how can I be genuinely useful here?”). The best way to get what you want is to give first, give generously and give without expectation of return. You’ll get so much back, trust us.

Build a platform

Whatever their subject area, successful people build platforms to showcase their abilities and demonstrate their authenticity, passion and knowledge. This is about building a platform that helps you engage with likeminded people. Your platform might be a blog, a repeating event, a regular newsletter, a podcast, or an online group. Format doesn’t matter, just find somewhere to add value and join in the conversation.

Examples from The Escape Community:

Lorna Morris — @lornamorris

Lorna Morris is a freelance graphic designer who originally escaped the publishing industry. She has spent many years looking for her tribe and discovered it when she joined Escape’s Startup Tribe and joined Tribewanted in Bali. In these communities she says she has found the confidence and support to redefine her design business into becoming more location independent. In the last year she has spent time working remotely in Bali, France, The Netherlands, and California!

Jo Chavasse — @frecklescc

Jo Chavasse joined The Startup Tribe in Sept 2014 and within three months had validated, pivoted and launched her company. One year on, Freckles Childcare is growing from strength to strength. She says that it’s still tough but that she knows that on those days when the inner critic and self-doubt creep in, there is a community behind her who remind her why she’s doing this. Her most valuable piece of advice for anyone who wants to do anything vaguely different with their lives? “Find people like you”.

Sunday accountability sessions at Escape to the Woods 2015

4. Behave in a way that is going to make you stand out — for all the right reasons.

Pursue excellence

Ultimately, the best security is to be absolutely bloody excellent at something. The world doesn’t owe you a living, but if you add enough value you can make it begin to pay attention. In the early days excellence seems like a chicken-and-egg challenge; as you don’t yet know what you want to commit the time and effort to becoming amazing at. In the long-term, however, just remember that excellence is the best insurance policy.

Be remarkable

Be a purple cow (kudos Seth). What makes you different to every other qualified, competent, experienced professional in your current or future field? What makes you remarkable (literally, worth remarking on)? Stop collecting sensible bullet points on your CV and start doing interesting things that will actually make you stand out.

Specialise (eventually) in a clear niche

In what subject area are you going to become an authority? The narrower you can make this, the more possible it will be for you to become the go-to person in your target market / demographic / location. That’s not to say don’t go broad initially (and you don’t have to limit yourself) but the more you can establish an authentic and remarkable reputation in a clear niche, the stronger your position will become over time.

Show, don’t tell

You probably agree that CVs and cover letters are really frustrating formats for trying to stand out. The problem is, they involve telling people what you’ve done, rather than showing them what you’re capable of. What you want is public proof of your abilities, achievements and projects. The trick is to get involved in activities that allow you to demonstrate what you’re capable of, to build trusted relationships and then be able to point other people at real things in the world and say: “see that great thing that happened? I built / shaped / created that.”


Good things come to those who wait, but only what’s left by those who hustle. What is hustling? Hustling is the opposite of waiting to be picked, submitting the 100th application to a crazily popular job ad that you’re not qualified for, standing in line, and hoping for the world to notice you. Hustling is scary, it involves putting yourself out there to find creative ways to build relationships and create exciting opportunities for yourself. Hustling works.

Examples from The Escape Community:

Adele Barlow — @adelebarlow

Adele Barlow was a community member who attended lots of early Escape events in London, building a strong relationship with the founders — Rob and Dom. When they temporarily moved to New York, she volunteered to run the London events alongside her day job. Her competence, passion and positivity meant that she was the only person they contacted when they were hiring their first employee. Over the next 3 years she led the global Escape community, built The Escape School in London, and designed Escape’s core education curriculum. She is now a certified coach trained by the British Psychological Society, has published two career change books, writes for the Huffington Post, and works with Virgin in London. #hustler

Matt Trinetti — @trinetti

Matt Trinetti was an Escape the City subscriber working at IBM in Chicago. His transition started when he negotiated a 7-month sabbatical and booked a one-way ticket to Iceland. He decided to use this time to explore creative projects that he didn’t have the time for in his corporate job. None of this was part of a career change plan, he was simply following his curiosity. On this adventure he met the Escape team and immediately felt a shared sense of purpose. The entrepreneurial projects he built on his personal website ( gave him a glimpse of the type of work that made him come alive and showed the Escape team that he had the skills and passion that they were looking for. He is now a Founding Director and Tribe Leader at The Escape School in London — doing work that he never could have imagined from his cubicle in Chicago had he not started.

Woodland decorations @ Escape to the Woods 2015

A final word…

Escape the City’s motto is “do something different” precisely because if you adopt conventional behaviours you can only hope for conventional outcomes. It is only through doing new things that you can hope to discover new paths. The 21st Century Career isn’t about sacrificing security for meaning — it’s about finding ways to fulfil your potential whilst doing things that matter to you. And the only way to begin doing this is to take a step or two outside your comfort zone.

People often say they feel like fate is rewarding them for making the leap. We think the reality is far more straightforward: they are simply doing the scary work of trying new things. There is no secret toolkit for building The 21st Century Career. However, if you expose yourself to new ideas, experiences, and people, you will build momentum, uncover new paths and succeed in creating new possibilities for yourself. #startsmall (but do start).

Good luck — it’s worth it :)

The Escape Community is a private network for Tribe alumni at Escape the City. We are full of brave corporate escapees, ambitious career changers and aspiring entrepreneurs. Find out more:

If you enjoyed this guide please share it — either click to tweet or “recommend” it on Medium. Let’s spread the love. Thanks!

Further Reading:

Dear Corporates… (our open letter to the corporate world)
Escaping the City: Diagnosing job dissatisfaction (our recent study)
How is the Working World Changing? (a guest post on the Escape Blog)
How can I make a big, brave career change? (by Rob on the Escape Blog)

Current and Future Tribe Leaders @escthecity /
“To be nobody but yourself in a world which is doing its best, night and day, to make you everybody else means to fight the hardest battle which any human being can fight; and never stop fighting.” — e. e. cummings