Thinking Of Leaving Your Job Or Changing Careers? Ask Yourself These Questions First
By: Laura Lewis
Tags: Startup, Career Change, Career Development, Career Advice

Thinking Of Leaving Your Job Or Changing Careers? Ask Yourself These Questions First

Some practical exercises from someone who’s been there and has all the t-shirts

Photo by Jeshoots on Unsplash

Is it time to leave your job?

There’s plenty of great advice out there about how to find a new job, how to graciously leave your current one, and how to try and improve your situation at a job you’re not currently enjoying. For the record, the latter should always be your first port of call — there’s almost always something you can do to try and improve your job, and it’s worth exhausting these options before looking for something new. This post is instead about the process of actually making the decision that you want to find a new job or career.

Why I feel qualified to talk about career changes

I consider myself a bit of the expert in the area, having worked in academia, then the public sector, then a couple of startups and now at Amazon.

I started off my career as an archaeologist, in the extremely niche area of the application of statistics and data science to the archaeology of human evolution (admittedly not the most widely applicable of subjects!). I then decided to leave academia for the civil service, and worked there for a couple of years — first as a statistician in the NHS, then as a policy advisor on venture capital in the Treasury.

After being exposed to the wonderful world of startups I decided to swap the civil service for somewhere a bit more fast-paced, and joined a proptech startup. I started as a pricing analyst and worked my way up to the head of the analysis team and the product manager in charge of all our data products. I then realised that what I really wanted to be was a data scientist. I quit my job to do a data science bootcamp, then joined the transport startup Citymapper as a data scientist. I then realised the best thing I could do for my career was to go somewhere bigger and surround myself with other data scientists, which is one of many reasons I’m now working as a data scientist at Amazon.

I’ve written more in-depth about the reasoning behind some of these career changes in another post. In this post, I hope to offer up some explicitly practical advice on questions to ask yourself and exercises you can do to help you decide what your next step should be once you start feeling that itch to move on.

Follow your dream? But how do you know what your dream is?

At school, you’re told that the hard thing in life that it is important to do is to go after your dreams. But the thing is, a lot of the time figuring out what your dream actually is is the hard part. Once you know what you’re aiming for, figuring out how to get there is the (relatively) easy part. Just point yourself in that direction, and make sure each step you take is related to that aim in some way. Importantly —and I cannot stress this enough — it’s absolutely fine and normal if the thing you’re aiming for changes, as long as you know what it is at that moment in time.

So how do you figure out what your dream actually is? Below I’m going to set out some practical suggestions and exercises that you can do. The first section focuses on high-level career changes, figuring out whether what you’re itching for is a career change, and if so what that change might look like. The second section focuses more specifically on changing jobs, how to figure out if now is the right time, and how to go about doing it.

Changing careers

Firstly, and most importantly, it is totally ok to change careers at any point during your working life. Your working life is long, and your career is an iterative process. Life expectancy is increasing. Retirement age is increasing. If you’re going to be working for 50 years, you owe yourself a career that you genuinely enjoy — and you’ve got plenty of time to get there. Here are some exercises I’ve found useful in figuring out my slightly meandering, but ultimately very happy, career path.

Figure out what interests you by analysing your habits

When you suddenly find yourself with a spare hour, or evening, or day, what do you do with it? What do you wish you could do with it? When you go to your favourite news site, which section do you go to? For me, I used to nab my then-partner’s copy of the Economist when he was done reading it, but because it was already part-way through the week I never quite had time to read all of it and so I had to choose my sections. I asked myself this exact question of the Economist, and realised I always went to the tech and business sections first. This might seem pretty standard, but coming from a family of pretty much entirely public sector workers, it was genuinely a bit of a surprise to me that I was interested in the private sector and the goings-on of various companies.

Look around at the people in your organisation who are one or two careers steps ahead of you. Look at the person or people who are at the pinnacle of your chosen career path. Ask yourself this question: do I envy them?

I realise this may sound like a bit of a strange (and not entirely pleasant) question. But this is the question that provided the final Aha! moment for me in deciding to leave academia. Academia is a very wide triangle shape, with lots of PhDs and post-docs at the bottom, and very few tenured professor positions at the top. This is particularly the case in smaller subjects like archaeology, where you basically have to wait for one of the half dozen or so professors in your specific field around the world to decide to retire. Or, as with my old professor at Cambridge, literally refuse to retire and force the university to hire an extra professor.

I looked around at the burnt-out post-docs one step above me. I looked at the teaching fellows one step above them, living off decades of one or two year teaching contracts strung together, which could require them to move to any corner of the world without them getting to choose where. I looked at the tenured professors; kings and queens of their own ivory tower empires, but having to devote their entire lives to a small area of a small field in an under-appreciated and under-funded discipline. And I realised that I didn’t envy any of them.

So who do you envy?

When you read about people out there in the world doing awesome things, what counts as awesome to you? Sometimes it’s really easy to overlook this question, because it’s very easy to fall into the trap of assuming that everyone thinks the same things are awesome. For example, I assumed that everyone thinks big tech is cool and awesome, so obviously everyone else must also want to work in tech so basically it must be impossible for me to find a job. But actually plenty of people want to work in banks, or hospitals, or consultancies, or a million other places. So if you genuinely envy people whose job it is to sit in a room full of coders thinking up new kinds of machine learning infrastructure (other options are available…), this is a useful thing to know about yourself.

Changing jobs

So, perhaps you’ve decided that a career change is on the cards, or even that you want to stick with the kind of job you already have but in a new organisation. In doing so, you’ve learnt something about yourself and what you want out of your career, and that’s great! However, before writing out that resignation email or putting an ominous-sounding meeting in your line manager’s calendar, I’d highly recommend working through some of the practical exercises below.

I’ve found these exercises really helpful over the years. Sometimes these have even helped me realise that, actually, a new job might not be the solution I think it is, and that spending time trying to improve my current job is the right answer. No job is perfect, and you’re responsible for your own happiness, so if a job isn’t working for you your first step should always be to try and take control of the situation and see what you yourself can do to improve it. This isn’t always possible, for example when a toxic work culture is stopping you from being able to do your best work. But it’s worth trying first, so that if you do decide it’s time for you to move on, at least you know you gave it your best.

It is very easy to keep kicking the can down the road: “well, the last few months have sucked, but I’ll just give it a bit longer and maybe it will pick up”. If you’re at the point where you’re just crossing your fingers and hoping it will pick up, I can pretty much guarantee it won’t.

So here’s my advice:

Be specific

There are a thousand different ways to dislike your job. When you’re thinking of leaving because you’re not enjoying your job any more, write down all the things that are currently causing you to hate your job. Put this list away and don’t look at it for a set period of time — I’d suggest two or three weeks. Do what you can in the meantime to try and improve your situation. There are plenty of other great blogs and articles full of suggestions, like finding opportunities to teach others, volunteering for a new project, learning a new skill, volunteering for a new project, etc. Then look at the list again. Has anything changed? Are the same things still annoying you? Try repeating the exercise again. If after a couple of tries at this nothing is getting better, this is a pretty good sign that it might be time to look for other opportunities.

Talk to your manager

This isn’t easy, and will probably be fairly awkward. But a good manager is there to support their staff and help them do their best work, so it’s quite literally part of their job to make sure you’re enjoying your job enough to be able to deliver your best. When I was a manager, I would always ask my direct reports in my one-on-ones whether there was anything they weren’t enjoying about their jobs, and what I could do to help. Not all managers will be pro-active about this, which is why it’s also your job to bring this kind of thing to them. They might be able to help, for example by giving you new work or projects, or moving you to a different part of the company.

When I was thinking of leaving the civil service for startups, I talked to my manager before I’d even started interviewing elsewhere, to see whether there was any possibility of me getting the things I felt like I was missing (more fast-paced work, more responsibility, the opportunity to experiment and iterate quickly on new projects and products) out of the job I was in. We worked on some ideas together, and although none of them worked out and I did eventually leave, it did teach me that good managers can be open to considerable changes to your current role in order to keep you in the organisation.

Give yourself deadlines

This can be even less easy — and something I’ve certainly failed to do in the past. It is very easy to keep kicking the can down the road: “well, the last few months have sucked, but I’ll just give it a bit longer and maybe it will pick up”. If you’re at the point where you’re just crossing your fingers and hoping it will pick up, I can pretty much guarantee it won’t. If you’re not giving yourself a deadline at which point you will re-evaluate your situation, you’re at serious risk of getting stuck in a job you hate.

Set yourself a date — or a series of dates — and an action to take at that date if things haven’t improved. For example, maybe in one month, if things haven’t improved, you could make sure your CV is up to date and change your LinkedIn job-seeking preferences to let recruiters know you’re open to opportunities. These are small, easy, relatively un-scary but practical and positive steps that you can take. If things haven’t improved a week or two after that, maybe start signing up for job alerts from LinkedIn or other job-searching sites.

Your next step might be to get in touch with some recruiters or start going to networking events. By this point, either you’ll be feeling much more positive about your future because you are taking positive steps in the right direction, or you’ll have realised this is all a horrible mistake and actually maybe you’d rather stay at your current job after all. Either way, you’re taking active steps to improve your situation.

Try to keep yourself sane by finding the good in each week

No job is 100% awful all the time. You took the job for some reason or other, right? So at some point there were good things about it. This is actually a tip that came from my partner, and kept me sane while I was deciding what my next step was going to be.

At the end of each week, write down — or, better yet, get someone to ask you — three things that you enjoyed that happened at work this week. They can be small things, like someone actually remembering to thank you for getting something to them on time, or someone in a meeting calling someone else out for interrupting you. But you have to think of three things, and they have to be actually about your job — finding a great new katsu curry place near work does not count (I know this because I asked).

Try to find the good in each week. If you’ve already made up your mind to leave, this will help keep you sane while you look for something better. And if you’re still undecided, the positivity that comes from this small exercise might just help you to turn the situation around, and learn to enjoy your job again.