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Home / People / Into The Unknown: Winging Toward A New Career

Into The Unknown: Winging Toward A New Career

September 12, 2025 · Leave a Comment

At a family dinner recently, my mother-in-law stated that her service as a teacher brought her so much joy that she would choose it again if given the chance. Lucky woman. 

I have met other people for whom that is true. Their jobs bring them meaning and are a key aspect of how they define themselves. I know others whose work leaves them utterly depleted. Most people I know, however, fall solidly in the middle. There are good days and bad days, and they are grateful to have a job and accompanying paycheck.

This is a topic of fascination for me, in no small part because my job over the last year has been to help middle- and high school students set career and education goals for their lives after graduation. You may not be aware that most students are asked to choose a career pathway in eighth or ninth grade these days. It’s a valuable exercise in many ways — helping young people to consider their likes/dislikes, skills, and interests so that they can find meaningful work later. But my, oh my — the choices! It’s daunting. I feel a certain kinship with these students, because I’m attempting the same thing at a very different stage of life. 

In the Paradox of Choice, Barry Schwartz writes, “Learning to choose is hard. Learning to choose well is harder. And learning to choose well in a world of unlimited possibilities is harder still, perhaps too hard.” 

So true. Also, not true. None of us truly has unlimited possibilities, and I recognize how fortunate I am to have the luxury of changing course so often. I chose English as my major in college because I love to read and write, and I became a certified teacher because my lifelong-educator parents basically made me do so. I have found meaningful work as a classroom teacher, an advocate, a trainer, a facilitator, and an advisor in one form or another — in classrooms, courtrooms, and hospitals — for more than 30 years. It’s been terrific, and…

I don’t want to do it anymore. 

It’s tough to write that sentence, and it’s hard to be kind to myself in this situation. What kind of person gives up on such impactful work, especially without a clear plan for the next step? How can I be considering departure from yet another role dedicated to helping others? Selfishness? Just who do I think I am? (Oh, how I love to play this rotten record in my mind!) Like so many other people, I spend my days encouraging people toward a positive self-regard and then do not give myself the same grace.

In January 2025, I decided to cut that out. No more negative self-talk. Only the search for my next adventure! I started as I do with the kids: a list of my likes and dislikes, my current skillset, and what I’d like to learn. I added my list of values and must-haves, as well as what I no longer want. 

Then, I wadded that paper up and threw it away. I have made that darn list in one form or another every time I look for change. It always leads me to basically the same job. I’m trying to create change here!

My next steps included:

  • Requesting that my current job be moved to part-time so that I could take time to explore while still making some money (fortunate, I know)
  • Contacting people who work in roles that appeal to me and asking to pick their brains about their work
  • Volunteering in a variety of roles so I could get a feel for the work
  • Signing up for classes and community events where I could learn more
  • Thinking hard about my hobbies and free-time choices — could they become paid work?

As I write this, I’m about five months into the exploration and have decided to fully step away from my current position sometime this month. I have had four job interviews, each for work that is quite different from anything I’ve had before and each of which I would be proud to do. I don’t know if I will be offered one of these positions, or if I will find something else entirely. 

The exercise has been meaningful. I’ve been able to more clearly define the parts of my work life that mean the most to me. I’m ready to step away from other parts that have run their course. I have a lot of heart and spirit to give to my work in ways that benefit my family, my community, and myself. I’ve learned a lot about myself over the last few months, and I look forward to seeing where I land. 

By Megan S. Willman

P.S. You may also get inspired by reading this article: Retirement Goals.

Filed Under: Featured, Meaningful Work, Money and Finances, Passions, People, Positive Mental Thinking, Volunteering

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