Don't Make a Career Change Unless You've Asked Yourself These 15 Questions First

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Trie Angeleva321
Dream-Job Career Coach
May 22, 2024 at 11:57AM UTC

Sometimes it can be incredibly hard to determine whether or not it’s time to make a change.

And when it comes to careers, there’s a lot on the line. 

Work and changing work are both stressful. Fold in a layer of chaos from the global pandemic, and we’ve got a recipe for mayhem if we are not thoughtful and intentional — or a huge opportunity if we are.

Do you try to make your current job better? Do you look for something new? Do you switch careers? Do you start the side hustle you’ve long dreamt about?

Depending on the job you have and the organization you work for, you have a wide range of options to consider before writing that resignation letter. Leaving your current job could be a really big deal depending on your field, family needs, financial obligations and your ability to transition smoothly to new work. 

It’s not a decision to make lightly, so here are 15 questions to help you determine if staying in your current job or changing jobs or careers is the right path for you now.

1. Is the work you’re doing now going to allow you to make the impact on the world you want?

2. Do you know what else you’d rather do that would address your current areas of dissatisfaction?

3. Do you know what you don’t love in your current career? For example, is it the job, the type of work you perform and skills you use, the people, the company, the field, the money?

4. Are you clear on what your purpose is so your next move aligns well with your long-term goals, values and priorities vs being a quick fix?

5. Is there a job within your current organization that would be a better fit for you or within the same industry?

6. Are you stable enough financially to leave now or do you need to continue in your job while you figure out what’s next?

7. Can you or are you willing to invest time and resources in learning new skills, getting new training or earning new certifications or degrees?

8. Are you operating from a perspective of stress or are you calm and focused so your decision-making will be solid, considered and creative? 

9. Can you envision your ideal workday, including what time you get up, what you wear, what your commute looks like, what skills you use, who you meet with, what you accomplish and what time you get home?

10. Do you know how to find new work and where to begin?

11. Do you know how to tap into the hidden job market and develop an effective job search plan?

12. Do you know how to hone your brand and communicate it powerfully across multiple platforms?

13. Do you have a network to help you identify new opportunities and friends and family who will be supportive as you transition to new work?

14. Is it time to start that small business you’ve always dreamt about, perhaps one that was a hobby or side hustle you dabbled with during the pandemic?

15. Would you know how to leave your current job without burning bridges?

I hope these questions get you started thinking in the right direction. There’s a difference between changing jobs and changing careers, but both require you to take specific steps in a specific order so your approach is strategic and effective.

There are seven steps you need to take in order to find work that is the right fit for your goals, strengths, purpose and intention. If you are considering a change and want to know what these steps are, grab my free resource “Reimagine Monday: Your Exceptional Career Transformation Checklist,” which summarizes the core aspects of all seven steps and provides you with four essential actions to take in each step for maximum career change success.

You want to make a career change with as little stress and as much focus, calm and ease as possible so the decisions you make along the way get you to where you really want to be. Check off each step as you go, and celebrate your success every step of the way. 


This article reflects the views of the author and not necessarily those of Fairygodboss.

Trie Angeleva, M.A., M.A., is a Certified Career Transformation Coach, Career Transitions Coach and Yoga2Life Coach with a Certificate in Executive Leadership from Cornell University. She owns Reimagine Monday and helps professionals learn how to lead themselves and others mindfully, and love the work they do. Connect with her on Instagram.

What’s your no. 1 piece of career change advice? Share your answer in the comments to help other Fairygodboss members!

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