Theme 11: Intelligent Transition

Manage your way through career change logistics.

“All courses of action are risky, so prudence is not in avoiding danger, but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not the strength to suffer.”

Niccolò Machiavelli

Why is this theme important?

Transitions take time and personal finance is just that: personal. Treat your escape like a startup, understand your own appetite for risk, and plot your escape intelligently, but not at the expense of never starting and never actually escaping.

Core Ideas

Accept that personal finances are personal.

We’re not going to skirt the issue: transitioning is hard and concerns about your finances, relationships and security are real. This will likely be a large and persistent headache in your escape.

Some of your concerns are real. Some also may be perceived blockers and may be less real or not actually as daunting as they appear. We’ll be confronting these. Unfortunately there is no ‘one size fits all’ (we’d share it if we had it), but there are methods and strategies that can help you transition more intelligently.

Paul Graham, founder of the Y Combinator tech accelerator programme wrote an excellent essay called ‘How to Do What You Love.’ In it, he talks about the “Two Routes” we have on the path to pursuing work we love:

“One has to make a living, and it’s hard to get paid for doing work you love. There are two routes to that destination:

The organic route: as you become more eminent, gradually to increase the parts of your job that you like at the expense of those you don’t.

The two-job route: to work at things you don’t like to get money to work on things you do.”

Which route should you take? He goes on:

“That depends on how sure you are of what you want to do, how good you are at taking orders, how much risk you can stand, and the odds that anyone will pay (in your lifetime) for what you want to do. If you’re sure of the general area you want to work in and it’s something people are likely to pay you for, then you should probably take the organic route. But if you don’t know what you want to work on, or don’t like to take orders, you may want to take the two-job route, if you can stand the risk.”

All of this depends on your own personality and your own appetite to risk. Ideally you will have learned enough in the earlier themes about yourself to understand your tolerance to risk, your values, and the things that matter to you. Remember these and hold them tightly. No two paths are alike and you must act for yourself.

Understand that transitions take time.

The story of Matt Lane starting his company BeerBods is the epitome of an intelligent escape. Matt had a mortgage, was married, and had new child. He couldn’t afford to leave his job, but he was deeply driven to work on something he really loved. And that love was beer.

Here’s BeerBods’ timeline to date:

  • SPRING 2011: Matt starts holding beer tastings in a shed.
  • SUMMER 2012: Matt puts up a one page website (£0) explaining his idea for a beer club and subscription service. If 20 people sign up in the first week he will turn it into a business. Over 250 people sign up in the first 24 hours.
  • AUTUMN 2012: BeerBods does not have a business plan and Matt still has a full time job. Using measly savings, some credit cards and many favors, Matt launches a BeerBods website.
  • AUTUMN 2013: BeerBods hits 1,000 subscribers. BeerBods is voted “one of the 100 most innovative, disruptive and resourceful small businesses” in the UK. Featured in the Guardian and Financial Times. Matt is still running BeerBods in his spare time.
  • SPRING 2014: Matt decides to crowdfund to grow the business and raises £150,000 from 101 investors in 36 hours.
  • SUMMER 2015: BeerBods now brews its own beer for subscribers, has a YouTube show about beer, and hosts meetups. Business is good.

Matt’s story prompts two lessons. The first: great escapes take time. The distance between the spark of his idea (starting meetups around good beer) and operating a real business was more than four years.

The second lesson is that Matt did not leap all at once. He slowly and deliberately transitioned, launching little projects and testing mini assumptions along the way. In fact, if you look at Matt’s LinkedIn page, he still works for The Midcounties Cooperative as a Director.

Treat your escape like a startup.

Every business has revenues and costs, assets and liabilities. Every startup has to get their revenues above their costs before they run out of time (and money). Your escape and your personal finances are no different (whether or not you’re building a business).

You have revenue streams (your salary and any other incomings). You also have costs (your rent, your living expenses, etc). If your revenues are above your costs – you’re in the black. You can (and should) try to move both numbers. Decrease your spending. Try to increase your income. Ideally both.

Start-ups have a certain amount of time to find a scalable business model before they go bust. You are a person in search of a scalable new career. You have a certain amount of time to figure out your “business model” before you go bust (i.e. before you have to go back to your old job or find a new job).

Try adopting startup-esque principles:

1. Keep your costs as low as possible whilst you’re finding the way that works. Question everything you spend your money on and be prepared to ratchet things back.

2. Get someone to pay you for something (anything) whilst you free up time to figure things out.

3. Know what your monthly burn-rate is (therefore know how many “months-till-death” you have).

4. Place small bets and test towards the way that works (rather than guessing or planning your way through uncertainty).

Become an expert in something new.

D.H. Lawrence said that travel is the only thing you spend money on that makes you richer, and we agree. But we’d also extend that to include applied education – education not merely as an academic exercise, but learning something new to help build yourself up as an expert in a new field.

The democratization of the Internet has gifted us the ability to learn anything we care to learn. You have the same information available to you (for the most part) as a child in the Philippines or the CEO of Amazon does. The playing field has been leveled in terms of access to information. Use this to fuel your own education and build you up as an asset.

If there is something you want to learn or a skill you want to develop, set yourself on the track to begin to learn it. In the process, you can become an expert in it. Here’s how:

1. Study the topic religiously. Follow the top 3 blogs on the blogs/bloggers on the topic. Read the top 3 bestselling books on it. Attend 3 meetups in your local area or have conversations online. Immerse yourself in it all. Don’t spend too much time here because simultaneously you must…

2. Begin (and complete) a project. While you’re studying religiously, start a project to get your hands dirty and immediately begin applying what you’re learning. This is not an academic exercise. You must engage with it to learn it.

3. Share what you’ve done (and help others). What did you learn from your experience? What was the outcome of your project? Good, bad, or ugly, share with the world what you’ve learned. Write an article about it. Host a meetup and talk about it. Help advise someone who’s working on a similar project.

Congratulations! You are now an expert in something. You probably know more than 99% of the population on your particular topic. Could this be a new income stream in your escape? Could this open new doors? Could you form new friendships and create new opportunities for yourself? Possibly and probably. This is a new asset and tool for yourself. Try to use it.

Remember that reality is negotiable.

Author and entrepreneur Tim Ferriss has a saying we love: “Reality is negotiable.”

In terms of your escape and your perceived constraints – what constraints are you adopting? Can they be questioned? Even if your company doesn’t have a formal sabbatical policy. Even if no one has ever negotiated Fridays to work from home. Even if you don’t think anyone would pay you a day rate for your skills. Are these false constraints?

Many people in our past Escape Tribe have asked for things and have been surprised when they received them. You never know until you ask. So ask we must. When you’re courageously honest with yourself and the people you work with, freely communicate your own dreams and ambitions, and confidently ask for the things you would like, support can come from the most unlikely places.

Our perceived reality is just that: perceived. Question your constraints and think of creative ways to circumvent your reality. Your escape depends on you thinking creatively, challenging the status quo, and trying things no one you know has done before.

Your Objectives
  • Understand the ingredients of a good plan and the pitfalls of trying to plan everything.
  • Plan for difficult conversations and potential negotiations with your employer.
  • Assess your relationship with money and audit your personal finances.
  • Make a realistic, viable yet brave plan for your transition – based on your decision criteria.
Useful Resources

Oops, if you’re landing on here and can’t see anything that’s because we’re just updating this page.

Please check back shortly.

Share This