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Ask Jessica: Should I Change Careers in Midlife?

A woman struggles with career satisfaction, wonders should I change careers in midlife? In spite of a successful career, she questions if this is what she really wants for the next 20 years. Jessica helps her to manage her guilt and then provides a structure for thinking through her options.

Should I change careers in midlife? An African American woman working remotely on a laptop in a modern indoor setting.

Ask Jessica is an advice column for women in midlife. We cover all things related to midlife from changing bodies to career transitions to parenting teens to sandwich generation challenges to shifts in marital or life partnerships and everything in between. My hope is that in sharing these questions and answers I can women as we face the midlife journey together. Got a question or challenge you would like me to address? Fill out this form to submit your issue! Want to see the answers to other questions, check out our archive here.

HEY JESSICA: I have spent years building a solid career that in many ways I am proud of, but now that things are at a pretty stable place, I am looking out at the horizon and thinking, “am I really going to do THIS for another 20 years?!?!” I know I should be grateful for all that I have and proud of all that I have accomplished, but the future just feels so stagnant and uninspiring. Is this a midlife crisis? Should I change careers in midlife? How do I know if I can keep this going or if I am going to need a career change to be truly happy?  ~Is That All There Is?

DEAR IS THAT ALL THERE IS: What you are describing is a super common experience for so many of us in midlife! We started out our careers with great ambitions and plans and over the past 15-20 years we have worked diligently to make our dreams a reality. The good news is, it sounds like in many ways you have done that! Congratulations! The less comfortable news (notice, I didn’t say “bad news”) is that it sounds as if you are questioning whether or not that will be enough for you. You are asking if you take a huge step and change careers in midlife.

As someone who has gone through this process herself, I can tell you that figuring out the answer to that question can be scary and hard, but it can also be incredibly exciting and empowering.

What I have come to believe is that in order to answer the question about whether or not our career path is the one we want to remain on, we first need to take a step back and think more broadly about what we want our life to look like now and into the future. And only after doing that can we determine whether our career fits into that broader vision or whether there is a shift that needs to be made. This can feel like a pretty overwhelming undertaking, so I thought that I would share an exercise that I put together for a workshop I ran last fall that can walk you through the process a bit. Feel free to follow it step by step, or take the pieces that most resonate with you… 

I see doing this work as a multi-step process (that probably takes 30-60 minutes, start to finish). First, we need to ensure that the things that we believe in and value most (what I like to call our core tenets) are in alignment with how we live our lives—which means we need to identify what those core tenets actually are. Second, we need to think about what we want our future to look like, according to those core tenets. Third, we then assess whether our current career path can align with this vision. And finally, we examine what needs to happen to bring all of this together so that we have a future that we are actually looking forward to. Here’s how I like to do this…

For step one, sit down in a quiet place, or at least somewhere where you won’t be interrupted, and do the following:

  • First, take 5 minutes to answer the following prompt: At this stage of your life, what are the things you would never give up?
  • Then, take another 5 minutes to look at that list and see what themes arise and then group those themes into five or so core tenets (values) that you want your life to embody.

For the second step, you are working to visualize what you truly want your future to look like. So, take another 5-10 minutes, again uninterrupted, to write out what you want your life to look like 5 years from now (you can also do this for 10 or even 20 years, but personally I find 5 years to be the most effective for visualizing my own life). Go into as much detail as possible. This can be a really stream-of-consciousness kind of exercise – it doesn’t need to be organized or articulate, it is just a way to let all of those ideas flow out. Some questions you might want to consider are: 

  • Who is living with you (partner, kids, parents, etc.)? 
  • Do you live where you are currently or elsewhere? 
  • Are you still working? If so, how much and are you working for yourself or someone else? 
  • What do your finances look like? 
  • What are your passions? Hobbies? Joys? 
  • Are there challenges you are facing?

Next, it’s time to look at your career within the context of your values (step one) and vision for the future (step two). So, ask yourself the following: In order to fulfill this 5-year visualization, what are priorities for your work? Money? Time? Notoriety? Having a job simply as a way to make a living or furthering a career? Then, look at these priorities in the context of the job you have now. Will your current job be able to fulfill this 5-year visualization and does it help you live up to those core tenets you identified?

Finally, it’s time to assess what needs to happen to bring all of this together so that you have a future that you are actually looking forward to.

If you determined that your current career can in fact line up with your vision for your future, then think in detail about what you need to do with your job, as well as with other parts of your life, to bring this 5-year visualization to fruition. What are the milestones you will need to reach over the course of those 5 years? If, on the other hand, you found that your current career path doesn’t align with your vision, then starting to brainstorm what you might want to be different and what options might very well be in your near future (if you find this is challenging, hit reply and I can give you some prompts to think about).

One final, important note. I know it can feel scary to look this closely at whether or not your life aligns with your core tenets, especially if you find that it doesn’t. But as you look at all of this, I hope that you will also take pride in all you have accomplished. Remember that you couldn’t have gotten to who and where you are without the experiences you have had, and that you still have so much time and adventure ahead of you, no matter whether you stick with the same career or move on to somethin

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