when is a good time to leave my job

When Is a Good Time to Leave My Job?

The lazy answer is that there is never a good time to leave your job. This is the answer that the “just do it” brigade will give you (trust me, I know, I’m often part of it). The trouble with truisms is that they’re usually true. But the problem with this answer is that it suggests that if there is never a good time to leave your job, then there must never a bad time to make the leap either.

Of course there ARE bad times to leave your job…

1. You don’t want to leave your job just before you’re going to receive a bonus or raise that could give you more runway for your escape.

2. You don’t want to leave your job just because you hate it – without a viable transition plan in place for what you are going to do next.

3. You don’t want to leave your job for another job without knowing whether your new environment will be any better than your current one.

Etc, etc, etc.

But the problem with these statements is that there is always a flipside

See 1) above

The more you earn, potentially the more you are stuck in an environment that doesn’t fulfil you. The notorious golden handcuffs. Waiting till you’ve saved just another XX,000 doesn’t necessarily make leaving your job any easier. Our expenses tend to rise with our income which can trap us further.

See 2) above

Sometimes it is impossible to see, feel or think clearly when we’re working long, stressful hours in an environment that is having a negative impact on us. Yes ideally you’d leave with a foolproof, risk-free plan – straight to running a sustainable startup or a new job on a great salary – but sometimes you need those empty spaces in between to reconnect with yourself and figure out your next move.

See 3) above

Loss aversion is a powerful force (the idea that you’re so committed to your current path in terms of career advancement, skills or salary that you can’t risk changing). The “better the devil you know” mentality can be just as risky as staying put. Fast-forward 10 years and the inevitable highs and lows of your life and career – do you think you will look back on today and wish you’d just gone for it?

All of this is kind of theoretical without examples…

This is just one perspective, but it’s a useful one in the context of the title of this essay…

I was recently talking to the CEO of a fast-growing, VC-funded tech startup. They’ve got a team of 15 and will soon be expanding to 30 people. The founder came from the corporate world and transitioned across relatively early in his career. He was a high-achiever in that world and now he’s kicking ass in this new world.

He has been using Escape the City to recruit for his team (with some success). He recently gave me some interesting feedback about some of the applications he has been receiving. It’s slightly counter-intuitive. Essentially he said that although he has interviewed some really strong people, a frequent warning sign for him is someone who has stayed in their sector for a few more years than he would expect.

He justified this on a few fronts…

1) If candidates are as interested in tech and startups as they profess then he wants to know why have they taken so long to make a move. He argues that the people he is looking for already have half a foot in this world. They are too impatient to wait.

2) Each year they stay in their corporate jobs is another year that their skillset is getting less relevant to digital and startups and more calcified in corporate ways of working. He reckons the basic transferable skills from corporate to startup are acquired in the first 2 years or so.

3) Finally, peoples’ corporate salary expectations rise yearly (as they do in any sector of course) which makes transitions-away-from-big-corporate harder by the year. Startups don’t want MBAs and consultants used to theory and big budgets, they want scrappy doers.

This goes against the prevailing wisdom that you “should do at least 2 years in any job before making a change” (most Mums’ favourite advice). This makes sense in as much as you don’t want to seem like someone who can’t get their teeth into anything. You need to demonstrate that you can ship on projects, deliver to a high standard, and build strong working relationships with people.

However, what if you know that you don’t want a long-term career on your current trajectory? In this scenario, every extra year you spend without changing you are is another year that you’re not building a reputation, a skillset and a career for yourself in the area that you do want to commit to.

If, like us when we escaped consulting to start Escape the City, you look up the ladder and don’t see anyone you want to be like in 10 years time, perhaps you should think about cutting your losses sooner?

For sure save as much as you can, wring every last bit of valuable experience out of the job, and make sure you behave professionally throughout your exit period – but, ultimately – if you know you want to be in a different area, don’t saddle your CV with too much of what you don’t want.

Sometimes it requires a leap

Understandably there is fear of the unknown.

It is irresponsible to advocate taking a blind leap. Escape the City is all about responsible, viable transitions. It’s not about opting out – it’s about dreaming big, ambitious plans for ourselves – and then doing.

The problem is (because you’re human like the rest of us) you can’t see how things are going to turn out and you expect the worst. And, because there’s rarely a good time (and certainly never a perfect time) to leave your job, it’s much easier not to…

“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).”- See a talk I did for TEDX LSE: Rethink Fear In Your Career

You’re right to manage your risk but you’re equally right to take a calculated leap…

“Until one is committed, there is hesitancy, the chance to draw back. Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves too. All sorts of things occur to help one that would never otherwise have occurred…”

[See the full version of one of my very favourite quotes: http://blog.escapethecity.org/2010/12/21/committed/]

So where does that leave us?

Our motto is ‘do something different’ precisely because if you adopt conventional behaviours you can only hope for conventional outcomes. Think differently about your life and your career. Once you reframe the way you feel about some of this stuff you’ll find it much easier to make changes that you’ve previously been really blocked on.

We believe that the answer is to be found in learning, experimenting and networking. 

Exposing yourself to new ideas, new experiences and new people is the best way of opening yourself up to new possibilities. Escapees 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. It is only through doing new things that you can hope to discover new paths.

Have a great Easter break.


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Rob is Escape the City's Co-Founder. He used to be a management consultant at Ernst & Young. When him and his co-founder, Dom, wanted to change jobs they looked for a service to help them find exciting new career opportunities. There wasn't one... So they built their own. Escape the City is a global community of +140,000 talented professionals seeking exciting new opportunities. It's about entrepreneurial work, exciting brands, and social impact. It's about building businesses, changing jobs, and going on big adventures.

RobWhen Is a Good Time to Leave My Job?
  • Rikki-Lee

    I really enjoyed reading this and feel a lot resonates with me particularly point “see 2)above”. I’m someone who’s not scared to leave my corporate job (counting down the remaining four days), not fussed about having more than enough money to get by for now, and genuinely think I am interested in and would be good at working in a startup environment. A couple of questions I have in regards to the example; how do you make yourself stand out on paper to even get to the interview stage with a startup company when your experience might make you seem unsuitable? I feel like maybe the focus for employment techniques in the future should be less based on your past experience and more about what you can do for and will bring to a company and how that ties in with your personal goals and aspirations. As, if you are going to benefit intrinsically from employment then surely it will make you more motivated in the work you do for others. Everyone can learn new ways of thinking and doing and so many of us are keen to continue learning and picking up new skill sets. I think that if someone is moving out of a corporate environment these factors might be motivators (they are for me), and why should we be judged (or thrown back) when we’re trying to break free of the rigidity of the corporate mould.

    • Rob Symington

      Hey Rikki-Lee,

      Thanks for a great comment.

      I don’t necessarily think that it’s right for people from the corporate world to be judged for their experiences but I’m also awake to the real-world blockers that count against someone who has spent (for example)5 years in finance versus someone who has spent (for example) 5 years doing digital marketing in startups – when it comes to getting a job in a startup.

      Some ideas that might be useful for helping you to stand out:

      1. Read as much as you can about how startups work. What is the history of startup culture? Who are the thought leaders? What is the lingo? As with every industry there are norms and techniques and conventions – you need to credibly speak the language even if you have never worked directly in startups.

      2. Attend events and meetups in the areas you want to get into. Build an authentic network, hang out with people in the areas you are interested in. Follow people in this space on Twitter – understand the trends, the successes, the failures.

      3. Work in startups before you get a job in startups. Have you got space in your week to do 3-4 hours of free work for a startup? Volunteer at an event? Write a report? Conduct some user research? Many small companies will be up for you gaining experience in exchange for some of your existing skills / time. Note – this is not to say you should quit your job and do unpaid internships – what you’re getting here is an inside look at startups before making the transition.

      4. Start something yourself. Many people I know who work in startups have also started their own side projects. Again, you don’t have to quit your job to start something modest that a) gives you the chance to learn new skills and b) demonstrates that you are serious about this area of the job market.

      5. Think like a founder. A job in a startup isn’t just a 9-to-5 job… entrepreneurs want self-motivated, self-managing people who will use their initiative and get stuff done across a wide range of areas. If you can demonstrate you know what it takes to start something you’ll be so much more attractive to a startup employer than someone who has spent their past 5 years in a corporate and not spent at least some of their free time starting things.

      6. Educate yourself. The past three years has seen a huge proliferation of informal education in and around digital and entrepreneurship. Schools like General Assembly, Decoded, Steer, etc will teach you many of the hard skills that you will need in the new world you want to work in. They will also serve to demonstrate your commitment to the companies you want to work in. You will be a less risky candidate than someone from the corporate world who hasn’t invested this time and money in themselves (again, you can do all this without quitting your job). Of course there’s also the Startup MBA and all of The Escape School courses – http://school.escapethecity.org/

      7. Write. Keep a blog about what you’re learning. This will serve as a tracker for the evolution of your understanding about startups and will also prove your interest to the startups you want to work in. Check out what Sharon Sandman has done – http://blog.sharonsandman.com/ – for 26 weeks!

      8. Stop behaving like everyone else. Speculative cover letters and applications are a waste of time. You are in a big pool full of people with potentially better or more relevant experience than you. You need to fight smart and hunt for opportunities where you are in a pool of one (you!) even if that means “applying” for jobs where there aren’t actually jobs being advertised. I’ve lost count of the amount of times people have landed amazing jobs where there wasn’t actually a job being advertised for. It’s about making yourself known, making yourself useful, and proving yourself to be a low-risk candidate (or lower risk than your CV might make you seem).

      All of the above can (and probably should) be done without leaving your job.

      I think you recently read The Escape Manifesto? There is lots of advice in there about how great jobs aren’t found on job boards – they’re the result of authentically doing three things: Learning, Experimenting, and Networking.

      Learn about the areas you want to get into (study the sector), conduct small experiments and tests (start your own thing, do work experience – both without quitting your job) and network (hang out with people who are in the areas you want to get into, be genuine, be helpful).

      Hope that’s helpful.


    • Escape the City

      Also wanted to share Adele’s most recent essay: http://school.escapethecity.org/essays/get-a-job-at-a-startup/

      Some great ideas in there!

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