15 questions to ask yourself before a career change

Some common coaching questions to guide you through change

Career coach Karmjit Kaur poses 15 questions to help you decide whether to take the plunge when it comes to a new step in your career.

At the Lowdown, we want to empower you to ask the right career coaching questions when considering a change. Whether you’re thinking about a new job or a complete career shift, a big move deserves proper reflection. Taking time to step back ensures your next move is intentional and aligned with what matters most to you.

Here are 15 questions to ask yourself before making the leap (in no particular order):

What drew me to this career in the first place?
It’s helpful to remind yourself why you’re in your current position. What first attracted you to this role, and what would you like to keep hold of in your next step?

How would I feel looking back at my career?
A common coaching question is: imagine you’re at your retirement party, or looking back at your career in old age. What do you want to be able to say about it? Would you feel proud and fulfilled continuing as you are now? What impact would you like to have made? These reflections can bring clarity on whether your current direction still feels right.

What do I want my life to look like?
It’s easy to think about your job in isolation, but it’s worth zooming out. What does your ideal day or week look like? Do you thrive in teams and in-person environments, or do you prefer flexibility and remote working? Want to explore your own project while maintaining financial stability? A part-time role that fits around your goals might be the right next move.

Is it the job, the people, or the industry?
Sometimes we think we dislike our job when it’s actually the culture, organisation, or even our manager. Take a moment to identify where your dissatisfaction stems from. You might realise you enjoy the work itself but need a better environment, or that you’ve outgrown the industry altogether.

What’s the most important thing to me?
This helps you prioritise. You might want passion to be the most important thing, but right now it might be salary - and that’s OK. Be honest with yourself about your current needs so you’re not left in a role that aligns with your dreams but doesn’t pay the bills.

What impact do I want to make in my career?
We often focus on what we want to do, but why do you want to do it? What change or contribution do you want to make through your work? Thinking about the outcomes that matter to you can point you in the right direction.

What are my values?
Your values are the principles that guide how you want to live and work. Reflecting on them helps you recognise what feels meaningful - and what’s missing - in your current role or industry.

How do I feel starting from scratch?
Will you be the most junior person in the room, and are you ready for that? It’s important to check in with how it might feel to begin again, especially if you’ve built seniority elsewhere. Can you balance humility with confidence in your transferable skills?

If I can’t make a move now, what can I do now?
Career change doesn’t always happen overnight. If you're not in a position to shift immediately, what small steps can you take now to move closer to your goal? That might mean networking, retraining, or exploring new areas of interest gradually.

What level of income will I be happy with?
Changing careers might mean a temporary pay cut. Be realistic: how long could you manage on a lower income, and what adjustments can you make now to prepare? It’s better to face this head-on than to be caught off guard later.

Do I need a Plan B?
Having a backup isn’t admitting failure—it can actually give you more confidence to pursue Plan A. For instance, if you’re trying out a new industry, how might you keep a foot in the door of your current one? If you're aiming to go freelance, is there a part-time role that could support you during the transition?

How do I feel after a break?
Sometimes burnout can look like disinterest and dissatisfaction with your career. If you’ve had time off, how do you feel coming back? If you’re refreshed and re-energised, perhaps you just needed rest. But if certain parts of your job still cause dread, you’ve learned something important about what needs to change.

What did I want to be when I grew up?
Revisiting your childhood dreams can reveal more than just nostalgia. They often reflect your core values and natural interests, before the world told you who you should be. Maybe you wanted to be a teacher, explorer, or artist. What inspired you then, and is there a way to reconnect with that spark?

Who am I doing this for?
Sometimes we stay in jobs because of expectations—family, status, and cultural norms. But whose definition of success are you following? Would you rather impress others or feel more fulfilled yourself? It’s a question worth asking.

What do I need to do first?
Big decisions can feel overwhelming. Instead of jumping to the final step, focus on the first one. Do you need to update your CV? Reach out to someone for advice? Get clear on your minimum salary? Taking one small action can help build momentum.

Bonus question: Are you ready to explore these questions further?
Career change isn’t just a decision—it’s a process. These questions are a great starting point, and if you’d like support navigating your next move, book a 30-minute discovery call with Karmjit.