8 Powerful Questions to Ask Yourself Before a Career Change

Written By Rachel Elliott

Insights from a Career Change Coach and Former Lawyer Who’s Been There

When I was considering leaving my career as a solicitor, one of my biggest concerns was making the "wrong" decision. I didn’t want to find myself in a new job but feeling exactly the same in a year’s time. I knew it was time for a change, but I also knew I had to be intentional about what I did next.

Now, as a career change coach, I work with people who feel exactly how I felt back then: overwhelmed with ideas, uncertain, and afraid of making a mistake. If that sounds familiar, you’re not alone. The good news is, asking yourself the right questions can bring the clarity and confidence you need to move forward.

In this blog, I’m sharing the questions that helped me - and now help my clients - make meaningful, well-thought-out career transitions.

Why Asking the Right Questions Matters

Before you start applying for new roles or scrolling through job sites, it’s important to pause. A successful career change isn’t just about leaving a job you don’t enjoy. It’s about moving towards something better suited to your values, strengths, personality type and lifestyle.

These questions are designed to help you get clear on what that looks like for you.

1. Why do I want to change careers?

Start with the most important question of all. Are you feeling burnt out? Bored? Undervalued? Frustrated with the culture of your industry? Or are you craving more meaning, creativity, flexibility or autonomy?

Your reasons for wanting to leave will help shape what you want to move towards. Be honest with yourself here. It’s the foundation for the rest of the process.

2. What do I want more of, and less of, in my next role?

Try writing two quick lists:

  • More of: for example, purpose, freedom, variety, collaboration, ownership.

  • Less of: for example, office politics, long hours, micromanagement, meaningless tasks.

This is something I did myself when I was still in law when I worked with a career coach. It helped me realise that I needed more innovation, creativity and complete control over who I worked with and what I did with my days – things I wasn’t going to find in the traditional legal sector no matter how much I liked elements of it.

3. What are my strengths, skills and interests?

A career change doesn’t mean starting from scratch. You’ve already developed a wide range of transferable skills. The key is identifying them and understanding where else they could be used.

Ask yourself:

  • What do people often come to me for?

  • What tasks or projects energise me?

  • What skills come naturally to me?

If you’re unsure, you could try a strengths assessment or work with a career coach to uncover patterns. Think back over your entire life to uncover answers - not just your job.

4. What are my core values, and is my current job aligned with them?

When your work doesn’t reflect what matters most to you, it can feel draining, even if everything else looks fine on the surface.

Example of core values (but there are hundreds of words you could choose from):

  • Freedom vs structure dictated by the business (one isn’t better than the other - just know who you are)

  • Integrity

  • Health

  • Growth

  • Service

  • Curiosity

Try listing your top five values, then ask yourself whether your current role honours them. If not, what kind of role or environment might?

5. What lifestyle do I want my career to support?

Your career affects your whole life, so it's worth asking:

  • What kind of work-life balance do I want?

  • How many hours am I willing or able to work?

  • Do I want to work remotely, in an office, or hybrid?

  • What level of income do I need (and want)?

Getting clear on these lifestyle factors can help you avoid jumping from one unsatisfying job straight into another.

6. What am I willing to invest or sacrifice to make this change?

Changing careers often requires some kind of investment, whether that’s time, money or temporary discomfort.

Ask yourself:

  • Am I open to retraining or studying?

  • Could I manage a short-term pay cut?

  • Am I prepared to start at a different level?

Being realistic about what you're willing to give or risk helps you plan better and avoid being blindsided later on.

7. Who can support me through this process?

You don’t have to go through this alone. Surrounding yourself with the right support can make a huge difference.

This might include:

  • A career change coach

  • Friends, family or mentors

  • People working in your field of interest

  • Online communities or networking groups

Having someone to talk things through with, or hold you accountable, can help you stay motivated and avoid overwhelm.

8. What small steps can I take right now?

You don’t need to have everything figured out before you take action. In fact, small, manageable steps are usually the best way to start.

You could:

  • Research industries or roles you’re curious about

  • Listen to career change podcasts or read relevant books

  • Update your CV or LinkedIn profile

  • Try a short course or workshop on new topics/industries

  • Reach out for an informal chat with someone in a field that interests you

Taking even one small step can shift you from stuck to moving.

Final Thoughts – From Someone Who’s Been There

When I was thinking about leaving law, I didn’t have a perfect plan. What I did have was a growing sense that I couldn’t keep doing what I was doing. It felt scary, but also necessary. What helped me most was taking the time to understand myself better and giving myself permission to explore.

If you’re feeling stuck, I want you to know that clarity doesn’t come all at once – but it does come. By asking yourself these questions, you’re already doing the hard work of moving towards a career that actually fits you.

Need Support From a Career Change Coach?

My team help professionals who feel stuck or unfulfilled take confident steps towards careers that feel more meaningful, energising and aligned. If you’re ready for change but not sure where to start, we’d love to support you.

👉Book a free discovery call I can promise there will be no hard sales. Just a relaxed chat and if we can give you some free tips or advice during the call - we will.


👉If you’re not interested in coaching, The Joy Journal for Career Changes might be a low cost easy way to get exploring what really interests you.

Rachel Elliott