Questions to Evaluate Your Career Field

We’re digging into job dissatisfaction today. Here’s what I see repeatedly in my practice: Clients are unhappy – and they’ve lost perspective. Is it time for an entirely new career? A pivot to a new industry, or job function within their same industry? Or do they just need to find a different employer?

For reference, I talked about this topic back in episode #61, and I’m bringing that content into 2026.

Let’s start at the beginning – dissatisfaction.

Step 1: Analyze WHAT you are dissatisfied ABOUT. How big of an impediment is that thing to your job satisfaction – and can you change it? I recommend journaling.

Here’s what I mean: If what you are dissatisfied with is that the company has had 3 rounds of layoffs with more rumored to come – You’re probably dissatisfied with your company more so than your job.

Your options, then: Have a discussion with your boss about how to avoid being laid off in future rounds – can you take on additional responsibilities? Move to another, more secure, area of the organization? You also, reasonably, may choose the option of beginning to look for the same (or higher) role in another organization that appears to be more financially secure.

Another scenario: If you are dissatisfied with your boss because she has thrown you under the bus 4 times in the past six months, you may very well be dissatisfied with your job because of your boss.

Your options: move to another area of the organization with a different boss or look elsewhere for a new job.

A third scenario: You’ve been in the same career field for X# of years and find the work no longer energizes you. You find yourself researching other careers or self-employment whenever you have a free moment. 

This scenario is a good one for a career coach’s help, so that you make an informed decision. Knowing you want to change career fields is very different from knowing what you want to change TO.

A final scenario, although there are virtually limitless possibilities: You are struggling to work collaboratively with a coworker – let’s call him Jeff. He takes credit for your efforts, doesn’t loop you in on meetings or important decisions, and takes advantage of every opportunity to “tattle” on you to the boss.

While you have all of the options available to you above, what can you do to change your mindset about Jeff? You can’t change Jeff, but you can change your experience of Jeff – and that can make all the difference.

Analyze your current situation.

Here are some great questions to ask yourself – I recommend journaling your answers, which should provide a lot of insight into your current situation (our brains tend to either catastrophize or sugar-coat; writing everything down tends to give you more factual information). 

Take your time. Put it down and come back to it later.

You might want to have someone else look at your answers and provide feedback. A significant other or close colleague who knows you well and might pick up on blind spots or biases.

About Your Current Job

1.   What do I love about my current job, and why do I love it?

2.   What percentage of my work week is spent doing (or being around) the things I listed in #1?

3.   What Motivated Skills do I possess that aren’t being used in my current job? (Motivated Skills are those that you are very good at AND enjoy using very much – I recommend using AI to provide you with a list of potential skills)

4.   On a scale of 1-5 with 1=not at all possible and 5=totally possible, what is the opportunity for me to use the Motivated Skills I listed in #3 in my current job? (Score each Motivated Skill separately and explain your rating for each.)

5.   If I were to reconfigure my current job, what 2-3 changes would I make? (Could be job duties, work environment, management style, etc.)

6.   One year from now, here is what I would like my work life to look like (describe in as much detail as possible):

7.   On a scale of 1-5 with 1=no similarity whatsoever and 5=completely similar, how well does my current job fit with my description in #6?

About Your Career Field

1.   Career field I am in, and reason I chose that field:

2.   On a scale of 1-5 with 1=doesn’t fit at all and 5=perfect fit, how well does my current job fit into my career field?

3.   What would the next logical step be in my current career field?

4.   On a scale of 1-5 with 1=not at all exciting and 5=complete excitement, how thrilled am I with the prospect of that next logical step?

5.   Do I fantasize about a different career field? If so, please describe.

6.   What perceived barriers do I think there are in pursuing that different career field? How difficult do those perceived barriers seem to be to overcome?

7.   On a scale of 1-5 with 1=not at all interested at this time and 5=exceptionally interested at this time, how interested am I in pursuing that career field?

What should you do with this self-knowledge? Your answers to question #7 in each section really give you the information you need.

--If you scored less than 3 on question #7 in the first section (On a scale of 1-5 with 1=no similarity whatsoever and 5=completely similar, how well does my current job fit with my description in #6?), then I recommend you think about a job search. By scoring that question low, you have essentially said that your current job bears little resemblance to your ideal job.

What’s important is to decide what you want to do about your dissatisfaction and then make a plan to do it. Meet with a professional such as myself if possible to help you map out a plan. DON’T just wallow in the knowledge that you hate your job.

--If you scored MORE than a 3 on question #7 in the second section (On a scale of 1-5 with 1=not at all interested at this time and 5=exceptionally interested at this time, how interested am I in pursuing that career field?), then I recommend you think about a career shift. By scoring that question high, you have shown a great deal of interest in a new career field.

It’s quite possible that you will score low in the first section, and show a great deal of dissatisfaction with your current career field, but not have an idea of a different career field you would be interested in. If that is the case, I recommend working with a qualified career coach such as myself to flesh that out.

The other important difference in working with a career coach is the accountability – you are much more likely to take action when you know an unbiased professional is holding you accountable AND calling you out, with compassion, on your excuses. 

Additional Thoughts

To close: It can be hard to look at your dissatisfaction objectively to determine what steps you might want to take. The combination of journaling, self-assessment, and possibly working with a career coach can help you make the right decision for yourself.

And finally: knowing you are on the path you’ve chosen for yourself – having your own back about your decision – will help you when the going gets rough.

If you decide to look elsewhere – it may mean the difference between a successful job search and giving up.

If you decide to stay – it may mean the difference between changing your mindset so that you have a more positive work experience and continuing to grouse about what’s wrong.

If you decide to change career fields – it may mean the difference between persevering in a more difficult job search and giving up after a few “no’s” or closed doors.