When Writing Your Next Chapter is (Literally) Your Next Chapter

Welcome to Career Craft a weekly roundup of expert advice on building your second act career.

Thirty years ago, my husband hopscotched his way to Hawaii after graduating from our New England college, financing his travels with a six-week upstate-New York house painting gig and the sale of his ancient red Nissan Sentra. His goal: become a writer. 

Some of us start out dreaming of being writers – and wind up as digital marketers. Others plot out a path as digital marketers (or as lawyers, accountants, or a fill-in-the-bill-paying-job-blanks) – and then later, often much later, transition into the writing life. 

The beauty (and terror) of the second act is the opportunity to architect a chapter of work, career, or creative endeavor, that doesn’t bear even a passing resemblance to your first. Thinking of making your own big leap?

This week, five writers share how – and why – they made the jump to writing for their career second act.

An Open Book
Becoming an author is my “Michelle 3.0.” After working for decades to end discrimination as a lawyer and a law professor, I realized the limits to legal tools and the constraints of legal audiences. Writing let me reach new constituents who are critical for advancing gender equality: men who are powerful women’s allies, and kids who can challenge gender biases.

The path to authorship required vulnerability and came with more rejections than I can count. But it brought greater rewards than I’d imagined. Writing allowed me to step back, assess what I’ve learned, and hone my message. It connected me with people I’d never have met if I hadn’t faced my fears and sent my first manuscript into the world.

Michelle Travis is a law professor turned writer. She is the author of Dads For Daughters, a guide for male allies who support gender equality, and My Mom Has Two Jobs, a children’s book celebrating working moms. She lives and works in San Francisco, CA.

Must Love Writing
The first thing is to remember, it’s all about the work. Remembering that will make it more bearable if/when you find yourself gobbling peanut butter straight from a jar at 11 a.m. and struggling to remember exactly what day of the week it is. Choosing to make a living writing means losing employer-provided health insurance, not to mention a steady paycheck and a reason to get dressed five days a week. It can be lonely, even frightening. So, focus on what you’re gaining. You get to write fulltime. Presumably, that’s because you love writing. Which brings up the second thing: Write. 

Steve Friedman is the author of four books, co-author of two New York Times bestsellers, and a two-time finalist for the National Magazine Award. He lives and works in New York City.

Get Unstuck
I spent more than 17 years in a career I hated because I doubted whether or not leaving the cage of my own making – the successful career – was possible. I believed I had one expertise, one skillset, one bit of knowledge and that leaving that career would mean I was starting over. I’m here to tell you none of those feelings were true. Those beliefs were ways I kept myself stuck. I turned to writing to find my way out of that cage.  I wrote as a way of sorting my feelings from the facts. Now my book has become the catalyst to the next stage of my career. It became the beginning of the best phase yet and it may just be the same for you too!

Sallie Holder is an award winning attorney turned author & business coach who coined the term “Rock Middle” and founded The BRIMM – The Beyond Rock Middle Movement – where she coaches female entrepreneurs to reach their greatest potential in a collaborative community. She lives and works in Greenville, SC.

An Accidental Career
What started as an accidental side gig eventually became a full-time one. While I was working as a news producer in TV, I sought the guidance of a nutritionist who had a lot of funny words of wisdom (you can eat your dinner or drink your dinner, but you can’t do both). I suggested she write a book and she said she would, but she needed help. So, I helped her, and we sold the book to a publisher. When I was laid off a year or so later, the foundation was in place and a second career was born as a book collaborator. It’s been a decade since I left the TV news biz. I have ghostwritten 20 books, written many articles of my own for various publications, and finally, in 2019, had a book of my own published—Zen Bender: A Decade-Long Enthusiastic Quest to Fix Everything (That Wasn’t Broken).

Stephanie Krikorian is an author, New York Times bestselling ghostwriter, and journalist whose work has appeared in the New York Post, O, the Oprah Magazine, and the Wall Street Journal. She lives and works in East Hampton, NY.

Bring Your Human to Writing
I didn’t set out to be writer. I was a consultant and professional dot connector – connecting great people to each other and to opportunities. In 2009, I connected with an author and ended up working with her on her book. I loved the experience and wondered if this was something I could do. At first, I struggled with the idea of feeling like I didn’t have anything new or special to say. And I wondered who would read anything I wrote? But then, at first through sheer will, I put the imposter in a box and focused on the fact that I brought 20 years of expertise to the table, had a real story to tell, and a way to tell it that I knew would resonate. For those thinking of second act careers, think about ways to leverage what you have done and present it in a personal way. Don’t worry about being unique because if you’re true to yourself you will be. 

Erica Keswin is a bestselling author, speaker, and expert in the business of working human—she helps top-of-the-class businesses, organizations, and individuals improve their performance by honoring relationships in every context, always with an eye toward high-tech for human touch. She lives and works in New York City.

Looking to make work work for you in your second act? Send your career challenges and questions to: careercraft@thisisbrightly.com.