Midlife Career Change Quiz: 10 Questions to Ask Yourself

Written by Jacqueline B

Have you come to the realization that you are unhappy, unfulfilled, or just plain bored with you career? Or perhaps you are looking to change out of necessity? Either way, you aren’t the only one.

While change is typically for the better, there are still a lot of aspects to consider before jumping into that change.

To help you make this decision, we’ve outlined 10 questions to ask yourself before considering a midlife career change. These questions will help you understand why you want to make this change and whether or not this change is the appropriate choice for you or not.

  1. Why Am I Unhappy With My Current Career?

If you do not know why you are unhappy at your current career, it will be difficult to understand what new direction you take.

Take time to reflect on your job and your situation and really figure out what it is that is causing you to feel unhappy with where you are.

Are you stuck in a position with no opportunity for advancement? Are you struggling to connect with or feel comfortable with the people you are surrounded by in the workplace? Is it the actual work required of you that you do not enjoy? Perhaps you are not earning the pay you think you deserve?

Maybe it is something else in your life making you unhappy and it is carrying over into your work life, causing you to associate the unhappiness with your job.

Understanding the root of your discontent is the first step in figuring out if a career change is the answer, or if you can simply fix the problem you are facing at your present job.

  1. Is This Unhappiness Temporary/Can It Be Fixed?

Once you’ve determined why you are unhappy with your current job, you will be able to tell whether or not a less drastic solution is possible.

If your unhappiness stems from something unrelated to your career, then changing careers will not necessarily lift this feeling; you will simply continue to feel unhappy even at your new job.

If it is something associated with your work that is leading you to feel this way, then take a deeper look into it; determine whether or not it is a situation that can be addressed and remedied, or if it is something fixed and incapable of changing.

  1. What Will This New Career Offer That My Current One Does Not?

The main reason you are thinking of a career change is because you feel you can gain something from your potential new career that your current one does not offer.

Is it higher pay? A better work-life balance? Work that makes you feel accomplished? Fulfilling something you are passionate about? More stability? Better location? Work you can be proud of?

Think about the answers you gave.

Do you believe these aspects are worth the risk of changing careers? Are they worth the time, effort a career change demands and the obstacles you will undoubtedly face in doing so?

  1. Is This New Career Something I Am Passionate About?

While there are multiple reasons someone may leave their current career, such as out of necessity (for financial reasons, health reasons, etc.) or boredom, it is important to enter into a new career for the right reasons.

If you choose your new career based solely on materialistic or logistical reasons, you may find yourself quickly regretting your decision and wanting yet another change.

Many people underestimate the importance of doing something you are passionate about. It is easy to fall into a monotonous routine, simply going through the motions because you think it is what you need to do. This can cause a strain on you both physically and emotionally. Enjoying the work you do not only impacts your job, but many other aspects of your life.

  1. Do I Have the Skills Necessary to Succeed In This New Career?

Don’t go into a career change blindly.

Do you have the proper qualifications for the job you want? Will you need to do additional training, or even return to post-secondary for a new degree? Do you have experience in the field? Do you possess the skills required to complete the job on par with or better than your competition? Do you have a network of individuals to help you succeed in this new field?

Entering into a new profession, especially later in life, can bring unique obstacles with it. Your best chances at success are to ensure you are prepared and equipped with the tools and skills required to no only do the job well, but to do so at a competitive level.

  1. Does This New Career Offer Long-Term Opportunities?

Before jumping head first into a new career, think about the long-term opportunities (or consequences).

Does this new career afford you the opportunity for advancement or personal growth? Will it provide you with the chance to relocate or work remotely if you wish to move or travel? Does it offer retirement plans, benefits, etc.? Is the option you are considering rewarding enough for you, or will you be left desiring more still?

Most importantly, is this new career something you think you will still be happy doing twenty years from now? If you feel it is something you may tire or bore of quickly, then sorry to say, but it may not be the best option for you.

Changing careers is a big move, and while some jobs may seem worth it for the moment, you want to choose something that will remain worth it in the long run.

  1. Am I In A Place, Financially, To Handle A Career Change?

Not only is a career change a big move, but it can also be an expensive one.

First of all, you will most likely be starting out at a lower pay grade than what you are making at your current job. Starting work in a new field typically involves starting at the beginning, meaning it will take months or even years to work your way back up to a pay equal to what you currently earn.

Second, you may not find work immediately after leaving your current job, meaning you will be without income for an unknown period of time. Unless, of course, you remain at your current job until you have new work lined up.

Be sure to take into consideration all of your current financial responsibilities, i.e.: mortgage, bill payments, vehicle costs, your children’s’ school or extra curricular activity costs, etc. If you do not have another income in your family that can cover these costs, or enough money set aside to do so, until you are earning enough at your new job to cover them, perhaps it is not the right time for a career change.

  1. Are My Career Change Plans Realistic?

We all have things we are passionate about or interested in, but that does not mean they are feasible as career options.

For example, you may love woodworking, but starting your own woodworking company may not be feasible if you have no knowledge on how to run a business, no clientele built up, and have a lot of financial responsibilities. Starting your own business is expensive; it takes time to build rapport, and therefore income; and, if it is something unique, it may not have the potential to grow as large as you hope, want, or need, in order to make a successful living off of it.

Take a step back and really think about whether or not the career you have in mind is realistic, or if it is better left as a hobby.

  1. Do I Have The Support of My Family and Friends?

Having the support of your family and friends can be important for two different reasons.

First, while you may be contemplating a career change for very valid reasons, you need to remember that you are not the only one affected by something so big. If you have a spouse and/or children, they will be the most directly affected by this move.

Before making any rash decisions, ask them how they feel about it, and make sure the decision you make won’t have any negative impacts on them (Ie: you taking time away from spending with them to spend on your new job or your new, lower income putting a strain on them, financially).

The second reason their support is important is because it will make going through a large change easier on you. Changing careers later in life can be stressful, intimidating, tiring, and just flat out difficult. Having a strong support system behind you can alleviate a lot of the negative aspects, especially the emotionally draining ones, which come with something like changing careers.

  1. Am I Committed?

The last, and one of the most important, questions to ask yourself is whether or not you are fully committed to the change you are about to make.

Once you quit your current job there is, more often than not, no going back. This means that if your new career choice is not what you expected, you do not enjoy it, or it doesn’t pan out for one reason or another, you will be back to square one.

Are you committed enough to the prospective job that you are willing to take risks such as that one? Even more so, are you committed enough to the new job that if it proves to be more difficult than you anticipated you will continue to work through it?

If you couldn’t answer yes to both of those questions without a doubt, it may not be a good idea to take such a large risk on something you are not 100% certain on.

Is It Time To Make The Change?

If, after going through these questions and reflecting on your answers, you still feel the career change is what is best for you, then it might just be time to start your new adventure.

Taking such a big jump at this stage in life can be nerve-racking, but if it is towards something that will bring you more joy and help you feel fulfilled, then any risks you take can surely be worth the rewards.

Do your research, plan things through, think logically and rationally, and work your butt off, and you are well on your way to beginning a successful new career.


  1. https://medium.com/career-relaunch/jumping-ship-why-so-many-mid-lifers-change-careers-f4e619f298e9
  2. https://www.careergeekblog.com/2017/02/27/hot-new-jobs-career-changers/
  3. https://www.inc.com/jayson-demers/are-you-unhappy-at-work-here-s-why-and-what-to-do-about-it.html


About the author

Jacqueline B

Our favorite Canadian Jacqueline is a graduate of the University of Alberta. She freelances for variety of online publications, and we're thrilled to to have her as part of the Career Geek team.