Born in Bridgeport, Connecticut in 1958, Cindy Eastman was raised in Louisville, Kentucky. She attended undergraduate schools in Austin, Texas and graduate school in Springfield, Massachusetts and holds a Master’s degree in Education. After writing a weekly column for the Waterbury Observer, she began publishing essays on her website, Writing Out Loud.

Her career in education has taken a wide and diverse route from teaching computer skills to elementary schoolchildren to facilitating professional learning communities for teachers and teaching English as an adjunct to college freshmen at a community college.

Currently, she coordinates a supervised visitation service with her husband in his counseling practice and does diversity and anti-bullying trainings for the Anti-Defamation League. She also teaches a writing course for the Osher Lifelong Learning Institute at the Waterbury campus of UConn. Eastman makes her home in Connecticut with her husband, Angelo, and their cat. She is working on a second collection of essays when she is not babysitting her grandson

The collection of essays in Flip-Flops After Fifty will immediately amuse, enlighten, and provoke the reader to think about the topics that affect all of us. This writer has experienced some of life’s painful jabs and has come through it all with strength, humor, and having learned a lesson or two. And she’s happy to share these lessons with others. Who hasn’t dealt with the emotions from family events, stress from lousy jobs, or the bittersweet feelings when the kids leave home? Not to mention body image, high school reunions, and parenting. It’s all covered here in this first collection of personal and insightful essays. Chapters include: “Family”, “The Holidays” and “Fifty.”

Eastman’s conversational style and easy humor tackle the sublime and the ridiculous, the sacred and the profane. After a certain age, and it’s no secret that it’s fifty, Eastman’s essays argue that attitudes change for the better. Making decisions gets easier, although there’s no guarantee that life does. Even so, her writing allows us to take a look at our own issues with the reassuring handholding of a confidante. This is a collection that you will want to keep for yourself as well as give to a friend.

At first grateful to be able remodel the dining room of her family’s modest home in Connecticut to accommodate her eighty-six-year-old father for what everyone felt would be a short duration of care, Cindy Eastman ultimately experienced a whole gamut of feelings over the course of what turned out to be four years of caring for her dying dad. Caregiving impacts everyone, and this account—told in essays recorded before, during, and after the time Eastman’s father was with her—details that impact, not just on the primary caregiver but also the rest of the family.

One of the reasons Eastman committed to writing down her experiences was because she predicted that once her dad died, there would be a tendency to soften or even deny any of the negative and challenging times—and there were many. As of 2020, more than 53 million adults provide homecare in this country, and the reality of that arrangement is different for every family. It is not, as some might suggest, a “noble gesture” but rather an elegant conflict—an intricate reassembling of the family dynamic that many people don’t ever see coming. In these candid, often poignant essays, Cindy Eastman brings all the emotions of taking on the challenging responsibility of caregiving a parent at the end of their life to the surface.