Time for a career change? Twenty questions you need to ask yourself ahead of 2020.


What are your new year’s resolutions for 2020? Perhaps to lose weight, or to start exercising more? Or maybe it is to give up something detrimental to your health (alcohol / meat / smoking / Hinge)?

If you are anything like a lot of people, the chances are that ‘career change’ will feature on that list.

January is the prime time for a career change.

Many of us will have thrown everything into this last working year: tempted by the promise of pay rises and bonuses and career development, we have got up early, come home late, gone the extra mile, pushed past our limits and done a damn good job of doing our job.

We are wrapping things up for Christmas, leaving next week with a clear inbox, feeling exhausted but triumphant.

We are looking forward to relaxing over Christmas and celebrating the New Year, temporarily forgetting about work. But the thing is – when January hits (and it soon will) and the glitter of the festive season has faded – we will find ourselves oscillating between mild dread and fear at the prospect of returning to work.

Whilst this isn’t a good thing, it is – I assure you – totally normal. After a bit of time off work and everyone being in a good mood for most of December, January is bound to feel a little bit flat and anxiety inducing.

What if what you are feeling is something more than that?

If you are feeling less than in love with the idea of another year where you are, then it’s good timing. This Christmas break is the perfect time to re-examine, to take a long, hard look at not just our daily routine with work, but our longer term goals, and general levels of fulfilment and whether a career change is on the cards for 2020.

So: in cases where you think you might want to make a career change, the first thing to ascertain isn’t actually “what do I want to do?” but it’s “am I ready to move on from my current role and organisation?”

Changing employer can feel very scary. Work represents economic security, income and safety. It’s a known entity, even if imperfect, like a threadbare but comfortable jumper. If you have been working for the same employer for a long time, the thought of taking the plunge into anything new can be terrifying.

However, I see it every day: subconscious fear of the unknown can play a deep part in keeping great people in substandard roles, keeping them a bit miserable, and ensuring that they are not fulfilling their potential on a daily basis.

It’s tough to realise, but true.

If you work full time, you’re spending significantly more time at work than you are at home. This means that what you do and who you surround yourself with in the workplace really does matter – because the reality is that it’s an enormous part of your life.

It is absolutely possible to have a hand in designing your daily routine, but in order to do that we first need to understand precisely what it is you actually want – and what you don’t want.

The best way to do this is to pick up a pen and paper, ask yourself the following questions and write down the answers.

Answer each one honestly – please be true to yourself. It might feel difficult, but the results will absolutely give you the basis of your career roadmap – so it’s very much worth it.

You don’t have to tackle this in one go: even if you answer two or three a day, it’ll help you build a clear picture in order for you to move forward.

Twenty questions you need to ask yourself ahead of 2020:

Do you ever look forward to going to work in the morning?

Does your job challenge you?

Which part of your day do you enjoy the most?

Do you feel at ease with your colleagues?

Do you feel supported by your boss?

Is your workload fair and manageable?

Does management or HR help set you clear goals to work towards?

Do you ever feel fearful or worried at work?

Do you feel proud when you tell other people what you do for a living?

Do you know what your company’s vision is?

Does your working environment work for you?

Do you feel that your company’s culture is aligned with your outlook?

Are you able to see the part you play in achieving wider company goals?

How often do you receive praise at work?

Do you feel that you are being financially rewarded appropriately for your time and effort?

Do you see your long term earning potential being fulfilled in this role?

If there were one element you could change about your role itself, what would it be?

When you first took this job, how long did you think you’d stay in it? And how long has it been?

Imagine you are told you are being made redundant. What’s the first emotion you feel? (hint – you’d be surprised how often this is relief, and this is very telling!)

If you could keep just one thing from this role when you move on, what would it be?


How was that? Despite the amount of time we spend at work on a daily basis, the chances are that you probably haven’t asked yourself many of these questions in a while – if at all, ever!

So, don’t be worried if answering some of these questions triggered a few interesting emotional responses.

Take some time to read your answers through slowly. There might well be a few things that surprise you here. It’s all incredibly valuable information, because what you are looking at now is your own personal blueprint for career fulfillment.

What should I do next?

Try to remember that it’s important to draw a distinction between job and employer.

Aligning yourself with your career goals and becoming conscious of changes you want to make in your working life don’t have to mean changing company.

Often, I see people who stay much longer than they should in unfulfilling jobs because they like the company they work in, have tight bonds with their colleagues and don’t want to leave an environment that works really well for them.

Talk to your line manager first

In those cases, as a recruiter, I’d always suggest going to speak to your line manager first and foremost and explaining precisely what it is you want. Good managers will bend over backwards to keep good people – but you can’t expect your manager to know by osmosis what it is you want.

Share your career goals and aspirations with them, keep them in the loop and open up to them (you might find it helpful to read our post on Appraisals: How to get what you want). You never know, your goals might be aligned – often, job specs are designed by HR rather than the people actually working the roles, and you might find that the bit of your boss’ job you are dying to do, they are desperate to hand over to someone!

You will never know – unless you ask.

Once you have a clear plan and have your line manager on board, it’s then usually HR you need to be going to have a chat to. Request a meeting in writing and give some context before the meeting so that your HR representative can come prepared. Do bring your line manager with you to the meeting for added clout if you like – this can work wonders.

Be prepared to compromise.

Emma Reynolds, 29, was working in operations for a financial marketing firm in London but felt unfulfilled. After doing a similar exercise with me last year, she realised that a career in social media management was what she wanted to do.

Emma expressed this goal to her line manager, who was supportive of her ambition but expressed his concern at Emma’s lack of direct experience in this area.

“It actually worked out really well” Emma explains.

“Given that I had only looked after the company’s social media on an ad hoc basis he was worried that I didn’t have the experience yet to step up into the role full time. He suggested to HR that the company pay for me to go on a digital marketing training course, which they followed through with last summer.

“Since then I’ve taken on much more responsibility in this area, I’m better qualified, I’ve got a pay rise, I feel valued. I feel like I’ve fallen back in love with my job.”

What if a career change is right for me?

If you decide that a career change is right for you, take your time.

Have a look on jobs boards in your industry and notice what employers are looking for. Go and speak to a good recruiter about what’s out there, and what you need to do to be approached for the sort of opportunity you want. And when it does come to interview time – make sure you are prepared by reading our post on ‘Common Interview Mistakes’. 

Finally, remember that work doesn’t have to be a depressing reality, or just something you struggle through in order to pay the bills.

It’s absolutely possible to gain a huge amount of satisfaction from what you do for a living: and it all starts with understanding exactly what it is you want.

About the Author

Jessica Marchant is Founding Partner at Sidekicks, the leading London operations search firm.

She is a Corporate Director of the The Recruitment & Employment Confederation, the professional body for the recruitment industry.

She is the Founder of Work To Recover – the mental health support nonprofit dedicated to facilitating people back into meaningful, fulfilling employment, and the author of job seeking manual ‘How To Get A Job’.