How can I make progress on my escape plan this weekend?

By this age, they were meant to be doing something cooler. Ken and Ryan were old enough to have friends who were buying houses and raising babies, but young enough to feel like their seemingly adult lives didn’t quite belong to them. Fed up one day with sheer boredom, the two friends decided to go away for a weekend, to get some headspace on where to point their careers.

Ken left the weekend energised and ended up changing careers within the year. Ryan felt the trip was a waste of time and remains both in a job he hates as well as in firm denial. What was the difference? During my time at Escape the City, I often asked myself this question as I watched various members start to hatch an escape plan, and this is what I found to work best.

Ken and Ryan had different careers but the same problem – life felt like this:

The two friends set off for a countryside weekend hoping that they would return with more career clarity. Only Ken found it, because he worked on his career change instead of in it. He treated himself like the CEO of his own life and saw the away weekend as a strategy retreat. He didn’t focus on where he was going to end up, he focused on finding people who could help him figure out that destination. Also, he focused on a longer-term plan of attack.

Work on your career plan, not in it.

Ken understood this:

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He knew that life doesn’t shift in the space of one weekend but that he could use the uninterrupted alone time to formulate an approach for his Escape process. The plan for his weekend was to make a plan.

He wasn’t the first or last person to go through career change. So the first thing he did was to read through Working Identity by Herminia Ibarra, which talks about how ‘we cannot regenerate ourselves in isolation’. Typically career change takes two to three years, it is not a linear process, and it is rarely driven by a clear objective.

Ibarra talks about crafting experiments (trying out new activities and professional roles on a small scale before making a major commitment to a different path), shifting connections (developing contacts, role models and new reference groups who can open doors to new worlds) and making sense (finding or creating catalysts and triggers for change and using them as occasions to rework our story). Ken familiarised himself with the typical trajectory of a career-changer and identified the phase that he was currently in.

He also read through The Escape Manifesto, highlighting the lines that resonated most with him, like this one:

“As you’ll see, there’s no such thing as a fool-proof plan that will carry you through your escape (such a thing is impossible). What you need is the belief that you can start making career decisions based on the key principles that are important to you. The tactics could change but as long as you stay true to the core ingredients you should be able to weather the inevitable ups and downs, uncertainties and triumphs.”

Meanwhile, his friend Ryan skipped the books and launched straight into thinking about potential next careers. Should he start a social enterprise? Volunteer in Africa? Maybe he should do his pilot’s license. He’d always fancied running his own business someday. But what would be a good business idea?

Ryan found himself with a list of different opportunities he could possibly pursue but soon enough he’d talked himself out of all of them. The more he thought about other paths, the more he recognised he was lucky to have what he already had. If he couldn’t figure out what came next, maybe he should stop complaining.

Ken gave himself permission to discover while Ryan put pressure on himself to ‘know’ the answer. Ken set up an exploration process while Ryan leapt straight into trying to guess the ending. Ken worked on his plan, while Ryan worked in it.

Avoid the temptation to jump into making a plan and instead realise that the plan for the weekend is to make a plan for the rest of the year. Give your plan context by doing your research.

Action plan (Ken style) – Part 1:

  • Read Working Identity (or at least the summary).
  • Read the Escape Manifesto.
  • Later, talk to a friend and tell them the gist of the book. When you have to explain to someone else what you’ve learned, the information sinks in better.

Find your Tribe.

Ken found that when he tried broaching the topic of career change with his friends, they laughed him off. Instead of letting this deter him, he spent time researching a more structured getaway and booked himself a space on Escape to the Woods (new dates coming soon). Similar retreats also include Tribewanted.

Ken also spent the second part of his day making a spreadsheet and going through LinkedIn stalking all of his professional connections and making a list of companies, jobs, and roles that resonated with him. He then crafted an email to send out that explained what questions he was looking to answer and seeing whether they had events or contacts they could recommend to him.

Later on, when Ken attended Escape to the Woods, he found a group of peers that made him feel like he wasn’t crazy for quitting his job. They ‘normalised’ his dreams and reinforced what he was already thinking. In Working Identity, Ibarra talks about the importance of finding new communities of people that you get along with most comfortably and enjoyably, as they can often give you clues on what you should be exploring.

Ryan, on the other hand, figured that he could lean on friends and family. But what he found was that everyone gave him the advice that they’d want to hear. Still, he wasn’t interested in going on a retreat. He could sort this out on his own.

Peer support is necessary in your escape. You can find it through Tribes, or you can find it through creating a tribe of your own. But spend the second chunk of your weekend making it your goal to find a group of people that you will be able to bounce ideas off.

Action plan (Ken style) – Part 2:

  • Make a spreadsheet of potential groups you could join, people you could contact, and interests you want to explore with them.
  • Find an Escape buddy – someone else who also wants to make a change who can bounce ideas off you; or a coach.
  • Use Meetup.com to browse interest groups you could join and sign up for an event that will introduce to an entirely new and different group of people.

Longer-term plan of attack.

Now that Ken had a broader overview of how career change worked and who might help him get there, he started planning the next six months with his diary, booking time in his calendar for researching new careers, meeting new people, and doing side projects that would help him learn more about various areas.

Ken would adjust his career strategy based on the conditions around him, but he knew that his decisions were only as good as the data he was using to make them. The data included talking to people in the new field, learning the new area, and experimenting there.

Ken had decided that he was interested in psychology and made time to research the different courses available to him. He ended up doing a psychology Masters and then realised that it was too academic. He switched to a CBT short course and also did some coaching of his own. He did contracting work to pay the bills and then balanced exploring psychology on the side. But he couldn’t have ‘decided’ this when he left law – it was a process.

Ryan didn’t bother calendarising. Instead, he decided that he was interested in tech startups and so attended a few General Assembly events. He had a few conversations with a couple of developers but ideas never really went anywhere. Unlike Ken, he didn’t really invest any time into his career change, and so eventually he just fell back into old patterns.

“The things that matter most should never be at the mercy of the things that matter least,” said Goethe. The important part of this phase is deciding what you are going to say no to, so that you know what you can say yes to.

Action plan (Ken style) – Part 3:

  • Picture your ideal self in a year’s time. What do you notice? What have they done to get where they are? What can you say no to over the next six months that would give you the time to explore new activities?
  • Book out time in your diary for this career change – meeting new people, reading relevant materials, side projects in the new space.
  • Create a system for this time, to track it – use Google Docs or an Excel spreadsheet to track your progress.

Bonus resources:

If you can afford it, it’s great to get away from your screen and into the natural environment – more suggestions here.

Also, I found myself constantly recommending the following resources to Escape members:

  1. Goodbye Career, Hello Success.
  2. Learned Optimism.
  3. Getting Unstuck.

Ken treated his Escape plan strategically instead of getting caught up in the details. He invested time in finding his tribe. He made a six-month plan and adjusted his approach accordingly.

Mainly, he treated the weekend as simply the start, whereas Ryan subconsciously set himself up to fail, by thinking: “If I don’t ‘figure out’ my escape plan this weekend, then I’ll never figure it out.”

Escape is a process. Members who successfully made the change took it slow and steady, created space to take action, and treated the process as a journey of self-discovery. They treated the weekend as a space to create a new exploration framework, instead of putting pressure on themselves to ‘know’ the answers. They focused on sharpening their compass instead of trying to build themselves a map. This made all the difference.


Doing something different with your life and career is hard… but you don’t have to do it alone. If you need help with your Escape and if you are ready to re-take control over your life, join our Tribe.

“No one can tell you what to do with your life and there is no “one-size-fits-all” escape that will lead you to happiness. What does work, however, is exposure to new ideas, likeminded people and a safe environment for you to figure out what it is you really want.”

– Rob Symington, Escape the City co-founder.

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