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6 Ways I Transitioned Into a New Career Following My Divorce

a New Career Following Divorce

By Stacey Freeman

The ink was not yet dry on my divorce decree when I began seriously thinking about returning to work. Nearly two decades earlier I had graduated from law school but opted into an alternative field in retail and fashion following graduation, never practicing law. Then, just as my career began gaining momentum, I discovered I was pregnant and opted into yet another alternative field – motherhood.


Years later, as the finalization of my divorce loomed near, the logical question of whether I should enter the legal profession reared its head and, for a while, I considered it. However, it did not take me long to realize that what had not made me happy then was not going to make me happy now.

Back as a young and naïve 21-year-old, mounting pressure from family members to pursue their dream instead of my own swayed me, and I passed up multiple acceptances to graduate programs that were more aligned with my interests, choosing law school instead. Newly divorced at 40, I was all too familiar with the feelings of inadequacy and discontent that can come from not following one’s passion and was not about to let history repeat itself. The only difference was that this time, I would be starting over not at the beginning of my earning years but decades into them. Here are six things I did to get started.

READ ALSO: You’re Not a Single Mom Forever: 5 Ways to Plan for Your Empty Nest

1. I focused on work I love

From the time I was small, I wanted to become a writer. And after I didn’t, I always felt like a fish out of water, not doing what I was best at and not excelling as a consequence. When I unexpectedly separated from my husband at 39 years old, I faced the daunting task of reentering the workplace following a more than a 15-year absence. I was at midlife, and though my children were young at the time (11, 10, and 6), I could easily envision a time not so far in the future when my kids would be grown, and my career could take center stage. “So,” I thought, “why not focus on work I love?”

Diary (1)

2. I evaluated my skills

Having not worked outside my home for more than a decade meant I didn’t have an experience-filled resume at my fingertips. As a consequence, I had to think long and hard about what skills I had developed during my career gap that could support my transition into the field I wanted. After recategorizing my work experience from past jobs to fit my current career goals, inventorying the hours I spent volunteering, and then giving myself credit for the managerial and organizational skills honed during my tenure at home, suddenly I had the resume I needed. Like most else, it was a choice of either seeing the glass, ahem resume, as half empty or half full. I chose the latter.


It was a choice of either seeing the glass, ahem resume, as half empty or half full. I chose the latter.


3. I did my homework

Of course, I needed to be realistic in my aspirations. Was there a market for me, and what were my chances of gaining entry to that market? Also, how much was it going to cost me to get started, and how would I finance it? As far as businesses go, the initial startup cost for mine was small and didn’t require much outlay from me. In any event, the expense was not one that I couldn’t cover by making an adjustment to my monthly budget, securing a small business loan, or selling my engagement ring for seed money should I have chosen to go that route. After thoroughly researching the logistics of my business endeavor and how I would go about financing it, I decided it was worth a shot.

4. I developed a plan

Wanting to maximize my chances for success, I developed a plan. Because I had never worked as a writer before, I knew how critical it was for me to set up a platform where I could showcase my skills. To accomplish this, I started a blog, creating for myself an online resume of sorts. In the beginning, I worked entirely for free. However, I treated the time I spent blogging as I would any paid position – with a seriousness of purpose. Whenever possible I also sought out new opportunities that could provide me with the experience I needed to grow. I set both short-term and long-term goals for myself that, with hard work, I could realistically attain but were still ambitious enough to propel me toward my long-term goals of either securing a paid position in a company or starting my own.


5. I set a deadline

As part of my plan, I also included a timeframe during which I expected to achieve my goals. If, after that time had elapsed, I did not progress far enough, I was prepared to shift gears with the understanding that any time I had already invested could be redirected and applied to a different, more promising endeavor. On the flip side, if I had already reached my goals, the deadline would remind me that it was time to move on, effectively preventing me from resting on my laurels.


6. I defined success

Everyone has a different vision of success, which can change over time. I chose to start a business but would have considered finding gainful employment in my field equally as positive an outcome. Success is relative – to others and us – and it has meant something different to me at every stage of my career development, not to mention at every stage of my life. And although every milestone I have reached to date has been a small victory over my past, I know each one has, more importantly, been an inspiration for my future.



About the Author

Stacey Freeman is a writer and blogger from the New York City area, a divorced single mom, a lifestyle editor at, and the founder and managing director of Write On Track, LLC, a full-service consultancy dedicated to providing high-quality content to individuals and businesses. A respected voice for divorce issues affecting both women and men, Stacey has been published in The Washington Post, Good Housekeeping, Cosmopolitan, Woman’s Day, Town & Country, The Huffington Post, xoJane, Scary Mommy, The Stir,, The Good Men Project, and various well-known platforms worldwide. Stacey is frequently called upon for her expertise and insights on the divorce experience and has repeatedly been quoted in The Huffington Post’s divorce vertical. Stacey holds her B.A. in English, summa cum laude and Phi Beta Kappa, from the University at Albany and her J.D. from Boston University School of Law. Email Stacey today at or call 800-203-1946 for a free consultation and proposal. For more information, visit


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