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At 55, I’m Stepping Into a Midlife Gap Year — and Feeling Proud

In early June, five days after my 55th birthday and following a recent promotion, I gave notice that I was leaving my well-paid, tech marketing job to take a midlife gap year and figure out my next career move. Not long after that, links to articles, such as this one from the Washington Post, and to podcasts like Ezra Klein’s, started rolling in from friends affirming, “You’re certainly on to something!” 

It was the “Welcome to the YOLO Economy” article that first tipped me off that I was now living my best New York Times trend piece life. Then I realized that all these stories about people chucking unsatisfying jobs, in what’s also being called “The Great Resignation,” included not one white collar, mid-lifer like me. In true Gen-X fashion, I was at once cynically bitter and ultimately relieved by this omission.

Like so many entering The Great Resignation, the pandemic lockdown afforded me time and resources to work through my quit-this-job-and-pivot plan. But it was something I heard on the LinkedIn-produced “Hello Monday with Jessi Hempel” podcast that really resonated: “It feels to a lot of us like we can’t get that vision for our future without stepping out.” 

It seemed impossible to take such a risk earlier in my life, though I thought about it many times. I was married without a dowry at age 25; a stay-at-home mom at 30; and at 40, a self-supporting divorcée with young children. Between my obligations and a history of mood swings and depression, I felt stuck.

This whole “clean break” approach to a professional life pivot was a revelation to me, a once deeply artsy, brainy kid from the Bronx who dabbled in creative professional pursuits along the way, but who later leaned into sensible corporate work. I was an editor for publishers, an editor who worked in marketing and, most recently, a brand marketer with editorial expertise. I’m good at this work and followed the opportunities that came to me. But like Keisha “TK” Dutes said in her recent “Secrets to a Career Change” TueNighter class, being good at something isn’t a good enough reason to keep doing work that lights no fires inside.

It’s not like I’ve lacked ideas about what I might want to do next. I’ve had a million and one over the years — from becoming a chef to opening a menswear store to starting a fitness business for the fitness-averse, and more — but then I’d hear my mother’s sensible voice ringing in my ears: “You can do anything you want in life… as long as you have medical benefits and save for retirement.” 

This practicality used to torment me. I’ve held a lot of shame about all the paths not taken. I’ve completely lacked any empathy for myself about what I’ve done and what I’m fortunate to have as a result. We’re a society that fetishizes “Do what you love!” but doesn’t want to talk about, or validate, all the quotidian — and not-so-quotidian — details that affect that path and process.

“After years of ambitious ideas left unfulfilled, my big risky move is to stop thinking about what’s to come and start dreaming more and living for what moves me right now.”

So let’s talk about that. I’ve come through the pandemic privileged to have more money in my bank account and fewer financial obligations. My kids are mostly grown — I still have two years of college payments left, but between some savings and modest loans I’ll be fine — I have no credit card debt and my parents are financially independent. Thanks to my mom’s advice, I have enough retirement money that I’m able to dip into some of it without imperiling my later life savings. I waited until my birthday to give notice because of a little-known Rule of 55, which allows me to draw from my 401K without the 10% penalty typically assessed for withdrawals made before age 59-½. 

Another benefit of making this change at 55? My mood is more even and I’m kinder these days, surely aided by those fewer obligations, therapy and probably menopause. When my parents or children say things I disagree with, I don’t reflexively sneer or judge. Instead of jumping to defensive anger when my buttons are pushed at work, I actually use a tip from a career coach I worked with last year and keep a QTIP on my desk to remind me: Quit Taking It Personally. 

Of course, the big question is: “What will Dori do next?” After years of ambitious ideas left unfulfilled, my big risky move is to stop thinking about what’s to come and start dreaming more and living for what moves me right now. 

My kids think it’s my destiny to open a restaurant or other food business. I’m not convinced that’s the case. Still, I may go up to the Catskills this summer to work some events for a chef friend, just because it sounds like fun.

I’ve planned my midlife gap year in broad brushstrokes, mapping it out in sticky notes a few months ahead at a time. First thing I’m going to do is chill out, go to art museums and gardens and walk aimlessly down my hometown’s streets. I’m planning to launch a podcast that explores big life changes and how people navigate them. And if I have one career-focused inkling right now, it’s to do meaningful work to better people’s lives.

I’m equal parts excited and terrified about what this year will bring. People have called me brave for leaving a good job at my age. Of all the things I fear right now, my ability to support myself isn’t one of them. What really scares me? Living an unfulfilled, unexceptional life.

Tell Us in the Comments

If you could take a "gap year," what would you do?

9 Responses

  1. laura

    Dori, Brava! Beautifully expressed. And you are navigating this midlife gap year (and life leap) with an ideal balance of intention and whatever-happens-next openness. Enjoy!

  2. Shannon

    I so relate to this and feel like I am on the precipice of doing the same. I look forward to following your journey!

  3. Valerie Yoder

    Dori, what a great article. I’m sort of in the same place as you, trying to figure out my next move.

    • Dori Fern
      Dori Fern

      Glad it resonated, Valerie. All the best to you on your next move!

  4. Carole

    Great to read ! Following a similar path !

  5. Susan Jahns

    Thank you so much for writing this. We’re on similar paths (married at 20s, kids by 30, and divorced at 42) and I’m exploring what’s next now that my youngest is a college junior. I own a small marketing agency so that adds an extra layer as I’ve built up a 20-year business that will require an exit plan (which I’m only beginning to explore). I’ll read up on Dutes as this gets to the heart of it: “being good at something isn’t a good enough reason to keep doing work that lights no fires inside.”

  6. Leeloo

    Of course I got here, because I to am looking into a gap year. I make 6 figures, I have been saving and working 2-3 jobs most my adult life to save and help my family. I have been waiting for someone to give me permission for once, to do something that is entirely about me. I have a year o expenses saved and will not need to touch my retirement. I have zero debt , no kids and a husband who supports my decision. I am still petrified. But I have achieved a point where I feel empty inside. Aimless. I will 45 and I thought what better way to enjoy my midlife crisis than to travel, spend time with family and wonder aimlessly for a while

    • Dori

      Leeloo: I heard a podcast episode about creativity recently with a famous writer (I’ve forgotten her name) who, when a caller asked how to get over the fear of starting to write, fear of failure, said: It never goes away; you just have to do it and know you are not alone. This was so helpful to me–wandering aimlessly is a great start. Wishing you scary, wonderful days ahead!


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