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15 Thought-Provoking Questions For A Career Change At Midlife

career change questions

Are you feeling burned out trying to make a job switch while working 40 hours a week? This is a paradox I faced myself. I was burning out and feeling stressed. I knew I was having a midlife career crisis, wanted to change my job, and trying to search for answers stressed me out even more! Feeling a little overwhelmed by all this, I wanted to get a quick fix. I was desperate to get out of a career rut and wanted to take the next step.

I was tempted to find a similar position somewhere else. I thought it’ll be quick and I could discover a new career path.

But then I asked myself – Is that really what I need? A quick fix?


For a successful career transition, I had to -

- Push myself out of my comfort zone - Shift into a growth mindset - I CAN change! - Find a mentor or a coach, or better still - BOTH Are you in a similar situation?

Have you asked yourself how you can have a career change at midlife?

Which Career Change Questions Have You Asked Yourself Today?

Here are some thought-provoking questions that helped me make a career change in my 40’s.

15 Thought-Provoking Questions For Career Change At Midlife (30's, 40's)

career change questions

1. How Happy Am I At My Job?

Always listen to your heart. It knows you well.

2. Why Do I Want A Change?

Simon Sinek would agree. Start with why.

3. What Does A Career Change Plan Look Like?

You don't need pages of planning. Do you have a back-of-napkin version to start with?

4. Do I Have The Support I Need?

You're not in it alone. Family. Friends. Coaches. Mentors. Make them part of your story.

5. What Transferable Skills Do I Have?

You're not starting anew. You're changing. What are you taking with you?

6. Can I Afford A Career Change?

The all-important money question. Do you have enough to handle a few bad days, weeks, or even months?

7. What Are The Issues That Make Me Want To Change Careers?

What are you struggling with in your current job? Think about what you would love to do in your new job?

8. Will I Have Work-Life Balance In My New Job?

If you miss spending quality time with family in your current job, maybe it’s time to find a more flexible work arrangement.

9. Do I Have The Skills, Interests, And Motivation To Pursue A Career Change?

You want to change careers, but do you have what it takes?

10. What Do I Want Out Of My New Job?

Learning, Growth, Adventure? Make a list.

11. What Challenges Will I Face During Career Transition?

Maybe you don’t have enough work experience, have fear of uncertainty, lack of direction, or feeling under-confident to make a major career change. Remember, you don’t have to do this alone. Talk to someone.

12. Is Quitting My Job The Only Way Out?

If you are feeling unhappy at your job, can this be fixed? Are you facing a short-term or a long-term problem? Ask yourself if quitting is the only way out.

13. What Makes Me Stand Out From The Crowd?

Check if you need to upskill or complete certifications to find a new job. Think about how you can uniquely position yourself in an interview. Do anything that’ll help you gain confidence for a new start.

14. How Am I Going To Handle Stress?

Are you going to say “I can’t do anything about this”, or going to take control of your situation?

15. Am I Too Afraid To Change Careers?

Steven Levitt of Freakonomics fame suggests that we would all be better off if we did more quitting. Levitt says - “A good rule of thumb in decision making is, whenever you cannot decide what you should do, choose the action that represents a change, rather than continuing the status quo.”

Think You’re Too Old For A Career Change?

Changing your career at any age can be a bit of a nightmare. Moving from a zone of comfort into an unknown area can be pretty scary.

But there’s one piece of advice that has got me results -

Enough thinking! Start doing!

When I first heard that statement, I stopped in my tracks. Start doing? How do I start doing when I don’t know what to do? I don’t even know where I am going. How on earth do I start?

But I thought about it some more and realized that it was the best piece of advice EVER.

Unless I start, how will I know what I DON’T KNOW?

I can keep second-guessing myself, or I can take those first few steps and figure out the rest of the plan.

Fight your fears and move forward.

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