Questions to Ask When Considering a Midlife Career Change

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Last Updated on December 6, 2023 by Erin

Are you unhappy and feeling stuck with your current job? Did you recently discover you were going through a midlife career crisis? Before you walk out on your current job, make sure you read through this list of questions to ask when considering a midlife career change.

questions to ask when considering a midlife career change
Photo by Daria Pimkina on Unsplash

Considering a midlife career change is a significant decision, and asking yourself thought-provoking questions can help you gain clarity and make an informed choice.

If you are new here, welcome to Mom Meets Midlife! I’m a mom of three who experienced an early midlife crisis and decided to make a career transition. As a result, I’m finally at a point where I feel like I’m enjoying my career AND motherhood. I have a renewed sense of purpose in both roles and (for now) things are in balance.

My midlife career change has so far, worked out tremendously, but it may not be for everyone. It’s a major life decision, and one that should not be taken lightly. That being said- if you’re feeling burned out and ready for change, you should absolutely explore those feelings.

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I’ve put together a list of questions you may want to ask yourself as you consider the possibility of a midlife career transition:

1. What Is My Motivation for a Career Change?

Motivation can vary greatly. Reflect on what is driving your desire to change and see if it helps your decision-making process. Consider which of the following (it could be more than one), describes you:


For some individuals, the primary motivation for a career change might be the pursuit of better financial opportunities. Are you trying to aim for a higher salary? Do you need better benefits? Are you feeling unfulfilled or underpaid in your current role?

I didn’t think this was my personal motivation, but after starting my new role I realized my salary felt more like it matched my worth, based on my experience and education. It was an amazing feeling!


Are you feeling like your current job doesn’t bring you a sense of satisfaction? If you are going through a midlife journey, you’ve more than likely been pondering your purpose in life and asking yourself if you’re living out that purpose in the best possible way.

I think most of us would like a career that brings a sense of fulfillment, purpose, and satisfaction. Wouldn’t it be amazing if our work perfectly aligned with our values and passions?


I guarantee whatever you’re doing right now, it’s impacting someone in a positive way. Sometimes it just doesn’t feel that way, though! Maybe you’re feeling called to make a larger, more visible impact on your community or the world at large.

If there is a particular cause that you feel drawn to, maybe you’re wanting to explore the possibility of making it your life’s work!

Work-Life Balance

This was ultimately my biggest motivation for making a career change. For me, “having it all” as a working mom didn’t really turn out the way I hoped it would. I was tired all the time and anything that involved my children during after-work hours, such as extracurriculars or school events, felt like a nuisance. We were eating out and ordering in food all the time because I couldn’t stand the thought of working in the kitchen when I got home. I hated that!

So, if you’re feeling like I was, you’re probably searching for a career change that will allow you more flexibility in scheduling and less stress. Perhaps you’re wanting to consider remote work?

Personal Growth

Maybe you’re feeling stagnant in your job, and there’s no way to continue growing and learning as a professional.

Seeking opportunities for growth, learning, and development can be a strong motivator. Some of you might desire a career change that challenges you and allows you to acquire new skills or earn promotions.

2. What Are My Interests?

Honestly, this question used to stump me. I would nervously giggle and say something like “Ummm…Harry Potter? Reading occasionally? Taking care of my kids?”

When I started experiencing my midlife crisis, it forced me to step back and ask, “Who the heck am I, at my core?”

Introspection Exercise

Take time to introspect and identify activities, subjects, or causes that genuinely excite and engage you. Consider moments in your life when you’ve felt most fulfilled or enthusiastic about something. These could be hobbies, volunteer work, or aspects of your current job that you genuinely enjoy.

Do your interests align with your current career? It doesn’t necessarily have to be super well-defined. For example, if you love throwing parties, does your current job allow you the opportunity to engage in marketing or event planning? If you’re a crafty person, do you get the opportunity to be creative at work?

3. What Are My Skills and Strengths?

You need to really look at your skills and strengths to see if you can leverage them in a new career. I can guarantee you have more skills than you realize. If you are at the stage where you’re ready to start filling out applications and drafting a resume, you need to be able to identify what you bring to the table. Then, when it comes time for an interview, you can confidently show your employer what an asset you will be to them.

Lucky for you, I’ve created a FREE workbook to help you identify your skills, strengths, and values. You also have the opportunity to get feedback from others.

midlife career change self assessment workbook free download

4. Am I Willing to Put in the Work?

Perhaps you’ve identified your dream career, but you don’t have the right training or education. Are you ready to commit your time and money to making it happen?

Make sure you do your research and understand the necessary qualifications or certifications. Are your current qualifications transferrable?

There are multiple ways to gain new skills or qualifications, such as formal education (college degrees, vocational courses), online courses, workshops, boot camps, self-study, or mentorship programs. Which method aligns with your personal preferences, timeframe, and financial situation?

5. What Are My Dealbreakers?

Make sure you understand your non-negotiables before diving into your search for a new career. If you head down an unfamiliar path, make sure the path you’re on aligns with your values.

Here are some potential factors to consider:

  • Does this workplace behave with integrity and use ethical practices?
  • Is inclusion and diversity important to the company?
  • Will this job support my professional development?
  • Is there opportunity for promotion?
  • Do people tend to stay at this job or is it a revolving door of employees?
  • Can I continue my education while working? Will they help me pay?
  • Are there remote work opportunities?
  • Will I have adequate paid time off?
  • Is there is a certain level of autonomy you will have in making decisions?
  • What is the minimum salary I would be willing to accept?
  • What kind of health benefits or retirement plan do I want?
  • Is employee mental health important?
  • Am I ok with a hierarchical structure of leadership?
  • Will I have to complete tasks that I absolutely hate doing?
  • How far am I willing to commute?

It’s essential to prioritize these aspects to find a career that offers fulfillment and satisfaction in the long term. My guess is you don’t want to make a huge midlife career change, only to make another huge midlife career change a decade later.

6. Have I Done Adequate Research?

I heard an interesting discussion on the radio a few weeks ago. The disc jockeys were talking about how there are complaints with every single job. We all think the grass is greener on the other side, but the person in that role might tell you it’s really not all that great. Sometimes we just imagine a job is amazing and fail to consider the potential pitfalls or challenges.

What is the growth potential in the jobs you are considering? What is job satisfaction like? What are the challenges in this field?

Try looking around on online job boards and career websites. Create a profile on Linked In and connect with other professionals so you can engage with them and get insights.

7. What Is My Current Financial Situation?

For the love of all that is holy, do not make a leap of faith into a career change without understanding your finances.

When you change careers, you may experience a transition period with a loss of income. Can you withstand something like that? Will you be able to cover essential expenses without strain?

Even if you are comfortable with your finances, you may need to factor in the cost of education, training, or certifications required for your new career path. Look at your current monthly spending and see if it can handle the extra expense.

Sometimes making a career change means accepting a lower salary. This was the case for me. Ultimately, my husband and I had to evaluate what types of lifestyle changes we would need to make so we wouldn’t feel the burn. You can’t make lifestyle changes, though, without thoroughly understanding what your spending looks like.

If you need help examining your financial situation, I highly recommend writing everything out pencil and paper style OR using a site like Empower. You can connect all your accounts for free and it will show you your net worth, investments, spending, budget, etc., all in one handy dashboard.

8. Am I Willing to Step Outside My Comfort Zone?

Some of us are creatures of habit, and that’s where we thrive. That’s amazing!

Unfortunately, that’s not me, and it’s probably not you if you’re seriously considering a midlife career change. It can be scary to try new things but amazing things happen when we are willing to try.

Be willing to take calculate risks. And even if you aren’t quite there yet, start journaling your thoughts and researching for more information. There’s no harm in that.

Do you think you will be able to adapt to a new work environment? Can you handle working with a whole new team? (I think most likely the answer is yes, but try and picture what that will look and feel like).

How Will This Change Impact Me Long-Term?

It’s really easy to become short-sighted when we’re in a job we don’t love. Consider the current trajectory you are on and how it might change when you take a different path.

Will my financial stability change? Will I have job security? Can I still retire when I want to?

Don’t forget about the people in your life who depend on you. Making a career change might benefit you, but how will it affect others? Will your children still be able to participate in the activities they love? Will you have adequate time at home with family? Will this new job require me to travel a lot?

Will a new job result in a healthier lifestyle and less stress?

Final Thoughts

It can be fun to consider all the dream job possibilities out there (especially when you’re daydreaming at a job you currently hate). Once you’ve considered which jobs might actually be the right ones for you, make sure you’re choosing with discernment.

Don’t up and leave a career just because you’re unhappy. Take the time for self-reflection. Do the research. Ask the questions.

Find a career that aligns with your interests and values. You’ve already spent years of your life in your current career. You’re much wiser and in tune to what matters and speaks to you personally.

Make sure you’re actually in a place to make a transition. Consider your future, your finances, and your family.

I truly hope these questions were helpful to you! Are you in the process of considering a midlife career change? Are you in the process of making the transition now? Have you made the change and lived to tell the tale? Let us know in the comments below! I’d love to hear from you.


Questions to Ask When Considering a Midlife Career Change

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