7 questions to ask yourself when thinking about a career change

Professional woman thinking pink background - changing careers

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7 questions to ask yourself when thinking about a career change

6 min read

Once you’ve set your mind on making a career change, it’s tempting to go full steam ahead, but there are some questions you should ask yourself first.


How times have changed. We’ve gone from our parents staying with the same company for years to it being perfectly acceptable to have at least one career pivot on our CVs. In fact, these days it feels more common to pivot career paths or have a side hustle than not.

Recent statistics show that 23% of people aged 30–34  and 17% of those aged 35–39 are seeking a career change.

And we get it; with all the talk of Sunday scaries, quiet quitting and living our best lives, it can feel as though a career change is a rite of passage these days. Once your head (and heart) have moved on, it can be tricky to claw your motivation for your current role back – but to be sure you’re making the right decision, here are seven questions career coaches and experts advise asking before making the leap.

Do you need a complete career change or just a new job? 

Woman carrying box of belongings - leaving job

Credit: Getty

The first thing to consider is whether you really need a whole new direction or simply a change of scene. Like everything in life, job satisfaction isn’t linear and there are bound to be highs and lows along the way.

“We all outgrow our jobs at some point, usually around the two or three-year mark when we’ve mastered the role and we’re not learning anymore,” explains career coach Alice Stapleton. “However, this doesn’t always mean a whole new career is required, perhaps just a job change.”

People often mistake frustration in their current job for the need for a complete career overhaul, say the experts at Simply Academy. Before quitting, assess whether the problem lies with your role, your employer or the industry itself by asking yourself the following questions:

  • Am I dissatisfied with my current role or do I dislike my industry altogether?
  • Is it about salary, job security or flexibility?
  • Would a promotion or a lateral move within my current field provide the fresh start I need?

“If the thought of a new role or a promotion doing something similar in a similar field still fills you with dread, then a career change might be worth considering,” says Stapleton.

What are the financial implications?

Switching careers can mean taking a financial hit, especially if you need to retrain, start from the bottom or go through a transition period without full-time income. This can significantly impact your day-to-day life, so it’s crucial to determine if this change aligns with your financial reality.

Before making the leap, Simply Academy recommends taking these steps:

  • Calculate a financial buffer. Aim to have at least six months’ worth of expenses saved before transitioning to a new career.
  • Assess your lifestyle. Can you comfortably sustain yourself if your income is reduced for a while?
  • Evaluate long-term earnings potential. If your new career pays less, will it still support your financial goals?

Do you need new qualifications or training?

Some career changes are easier than others. Transitioning from marketing to sales may not require formal retraining, but moving from administration to teaching or customer service to cybersecurity would demand specific qualifications.

Many of the fastest-growing industries – such as financial services, tech and healthcare – require certifications. Consider the following:

  • Part-time study options. Online courses, evening classes and weekend workshops can help you upskill without leaving your current job.
  • Industry certifications. Research what qualifications are necessary to enter your chosen field.
  • Employer-sponsored training. Some companies offer career development programmes that could help fund your transition.

How can you test the waters before committing?

Once you’ve made up your mind that a career switch is the way to go, you’ll need a (preferably non-binding) way of testing the waters. Too often, reality won’t match up to your expectations – and it’s far better to learn this before you’ve ditched your old job and salary.

“If you’re thinking about changing careers and you have some initial ideas into what, get curious about these,” advises Stapleton. “Consider how you can ‘test drive’ your ideas in real life to see if they match up with your expectations, and what you want and need from your career.”

Before handing in your resignation, Simply Academy recommends exploring these ways of gaining hands-on experience without fully committing:

  • Shadowing and networking. Reach out to professionals in your desired field and ask for insights or mentorship.
  • Freelancing or part-time work. Taking on small projects or gigs in your new industry can help you assess if it’s the right fit.
  • Volunteering and internships. These allow you to gain real-world experience before making a full transition.
  • Side hustles. If your new career allows for it, try balancing it alongside your current job before going all-in.

What’s holding you back?

There’s no doubt that changing careers is scary. Being the new girl in a job is bad enough when you’re confident you know what you’re doing, so the fear of failure is real.

“It’s all well and good thinking about changing careers, but consider what’s holding you back – or what will hold you back – from making it happen,” says Stapleton. “Pull together a list of all your fears and doubts in a column of ‘what ifs’ and go through what you will do if they come to pass. Think about how you will cope – there’s always something you can learn and do, whatever the outcome.”

And don’t let that fear of failure hold you back. “So what if you fail? If it doesn’t work out how you’d hoped, what will you do then?” challenges Stapleton. “You’ll cope, adapt and pivot from there, ask for help and support, seek the next opportunity, and so on.”

Consider what’s holding you back

Alice Stapleton

Are you willing to do what it takes? 

You know the drill – you’ve made a decision to overhaul your lifestyle from a sunbed on a relaxing holiday, and when you return to real life, it seems like too much effort. Don’t underestimate the amount of effort required, advises Stapleton.

“Career change can take time, and it requires a lot of thought, hard work, commitment, resilience and determination,” she tells Stylist. “It’s not for the faint-hearted. You need to be prepared (not necessarily ‘ready’, just willing) to move out of your comfort zone and put in the effort to turn your thinking into doing. The short-term pain is definitely worth it for the long-term gain though, that’s for sure.”

Will you be proud of your career when you retire?

There’s nothing like a spot of future thinking to sharpen your focus. What do you see when you’re looking back on your life? Research shows that focusing on future events can help us commit to making them happen and can be a powerful motivator.

“If you’re still on the fence about changing careers, imagine this,” suggests Stapleton. “It’s your retirement party from your current career path. You’re reflecting back over everything you’ve achieved and contributed towards, the impact you’ve had in your career. Are you proud? Was it meaningful? Was it worthwhile? If not, changing career could be worth considering if you want to make your retirement party a memorable one, not one full of regrets.”

Want more advice on making your career work for you? Sign up to Stylist’s How To Work email below. 


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