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Is Becoming an Entrepreneur After Divorce the Risky Business It Seems?

By Stacey Freeman

When I finalized my divorce almost five years ago, I got a do-over. A second chance, not only to find a more suitable partner in love and life but also to find a more suitable career, one which got me excited. Of course, being newly divorced and facing financial challenges, meant that chasing a dream, in my case to become a paid, professional writer and business owner, did not immediately emerge as the most practical option for achieving my goals. The problem was, neither did my so-called realistic one.


Even with a legal education behind me, the fact I had never worked as a lawyer and for more than a decade had not worked outside the home, made my prospects for finding gainful employment in the field bleak. Which meant if I did choose to pursue a career in law despite the apparent obstacles, I would have to start at the bottom, competing with candidates decades younger than me, the majority of whom were not single parents with full physical custody of their three school-age children. More troubling than that, assuming I did get hired, I would run the risk of my worst nightmare coming true: that I would toil away at a job I already knew in my heart wasn’t right for me years earlier.

What to do with your engagement ring after divorce
What to do with your engagement ring after divorce

Still, most of the people whose opinions I sought, and then those whose advice I didn’t, said pursuing a legal career would be the path of least resistance for me. I disagreed, and instead followed advice from a lone voice suggesting I pave my own way by becoming an entrepreneur. In other words, I should take a risk. Today, I’m the founder of a company providing writing services to individuals and businesses and question how much of gamble my decision was. Here’s why.


The risk I took was a calculated one

Like many who are newly divorced, I had some flexibility during the early stages of my settlement to explore various career options without having to immediately worry about how I was going to feed my family and keep a roof over our heads. I wasn’t about to squander that cushion. Because my financial picture necessitates I generate income, an income which must steadily grow as I age, I set a timeframe for myself to earn X dollars by a specific date, as well as laid out other career goals that foretold the possibility of monetary success further down the road. With my finances in mind, I frequently re-evaluate the viability of my business model and continue to tweak and redirect as I see fit, understanding that the experience I accumulate now will serve me in the future, somehow, some way, even if it’s not the way I foresaw initially. That’s because…


All experience is practical

Every skill I hone, every mistake I make, and every milestone I reach adds value to my ever-expanding résumé. Even when I was out of the workforce for more than a decade raising children, I did and learned a lot. I managed all of our family’s daily needs, created and maintained a household budget, supervised numerous construction projects, volunteered, and fielded and resolved pretty much every problem that came up. Without even realizing, I cultivated my managerial, organizational, and social skills for years before ever earning a dime.


Job security is an illusion

Job what? I don’t know many people who are delusional enough to believe they are above getting fired, phased out, or laid off from their current position, no matter how long they’ve worked there. The same holds true for my clients. I’m only as good as my last project or assignment. Except unlike being employed by someone else…


My upside is limitless

Becoming a business owner spells potential. Often, such growth comes in ways I never intended it to or believed it would. There’s always another client. Another opportunity. It’s what makes entrepreneurship exciting and what keeps me plugging away at it each day, even as I meet obstacles and experience setbacks. But when has that ever not been the case?


Divorce, like any other life change, breeds uncertainty. It can feel limiting to us in many ways. Time with our family decreases. Finances dwindle as we face obligations we never had before and with fewer resources available to us following the division of our assets. Titles are stripped away, leaving us “single” and exposed. Entrepreneurship, however, is one place where uncertainty and loss can meet to work in our favor if we allow them. It all depends on how creative we are willing to get to do it. Now, isn’t that a risk worth taking?

About the Author
Stacey Freeman is a writer and blogger from the New York City area, a divorced single mom, 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, Entrepreneur, 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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