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Getting Outside Her Comfort Zone with Weekly Adventures: Sherry’s Story

Published on 01/14/2019

An epiphany in midlife convinced Sherry to shake up her life. She embarked on her 52/52 Project: 52 weekly projects outside her comfort zone. And published a book about her adventures!

Tell us a little about your background.
I grew up in Toledo, Ohio and, with the exception of one year in Chicago, I remained in this way underrated area my whole life. I was the youngest of three stair-step aged girls, whom my mother in her late-life maternal soft spin now refers to as being “spirited.” I experienced a happy yet unremarkable childhood—not the atypical or dysfunctional life that leads many individuals to become writers. What did set my family apart, however, was our collective sense of humor. With a houseful of three other strong, independent, and funny females—and a father who referred to dinner time as “sarcasm hour”—I quickly realized that making people laugh was the key to forging my own role both within my family and my social circles. By the third grade, I had channeled my wit and my way with words into becoming the class clown and also an above-par writer.

While her older sisters DC (middle) and Lori (right) may have always better grasped the art of modeling, Sherry learned early that she could make people laugh–even if it was unintentionally.

My senior class awarded me the titles of “Best Sense of Humor” and “Best Party-Giver.” Oddly, neither of these accolades led to any college scholarships. Regardless, I graduated with honors from The University of Toledo with a degree in communications and then embarked on a successful journalism career—later seguing into nonprofit communications—with the last twenty-eight years working at my alma mater. Following the protocol of the eighties, I married my college sweetheart soon after graduation and started a family, resulting in two sons, now in their late twenties.

All went according to plan. Until my divorce.

Sherry says Son #1 (right) and Son #2 (left) have noted their mother’s escapades and writing have made them almost as proud as embarrassed.


When did you start to think about making a change in midlife?
The failure of my marriage was jolting. I made the most of it by returning to my love of creative writing. On the nights and weekends my children spent with their father, I began to blog and write books, finishing four (unpublished) novels. Although this proved to be a productive and rewarding coping mechanism, most of my life remained very standard and routine. I stayed in the same house and at the same job for more than twenty years. I spent those two decades taking part in the same ordinary daily activities and living the same, ordinary life. I wasn’t exactly unhappy, but I wasn’t truly fulfilled, either.

When I turned 52, I suddenly realized I needed to climb out of the rut—or more accurately, the crater—I’d dug for myself. Perhaps it was a midlife crisis. Maybe hormonal psychosis. Or possibly I subconsciously recalled that my father died a week after he turned fifty-three.

I decided I needed to shake up my life. Rather than taking on the typical bucket list, which I didn’t feel would truly change me or my world, I chose to embark instead on an “unbucket list.” My 52/52 Project, at the age of fifty-two, consisted of fifty-two weekly experiences outside my comfort zone—which would either frighten me, embarrass me, or made me squirm in some way.


What is your next act?
I am the author of Finding My Badass Self: A Year of Truths and Dares, published last year by She Writes Press. My year of new challenges changed my life forever. My memoir chronicles my escapades ranging from the scary and crazy, like baring it all at a nude beach, to the frightening and enlightening, such as going on a raid with a SWAT team and vice squad.

My next act is to continue living my life with more spontaneity, less worry, and a newfound ability to laugh at myself. This has led to a number of other amazing experiences that continue to shape my life. I published my first book at the age of 55, met readers and new friends across the country to engage in more new ventures, and found myself at the red carpet at the Screen Actor Guild Awards.

I’ve found new venues for my writing, and I gradually began receiving invitations for motivational speaking gigs across the country. Me: a motivational speaker? The woman who has always been far more of a cautionary tale? Talk about a next act and a life reinvention!

It’s astounding how your life can change when you simply open the door to a world of strange newness, and surprisingly find yourself greeted by pure serendipity.

Following the publication of her book, “Finding My Badass Self: A Year of Truths and Dares,” Sherry continues to be amazed at being hired as a motivational speaker–when she’s always considered herself more of a cautionary tale.


How hard was it to take the plunge?
Once I decided to take the plunge and came up with a partial list of new life challenges, I immediately dove into the first one and then began blogging about my adventures and misadventures. I decided that putting this out there in public was necessary in order to hold myself accountable. Considering my uncertainties and fears, it was the best way to ensure I’d see this whole project through. It helped build my confidence, provide me with an early audience, and assure me there was even a book in this.


How supportive were your family and friends?
My family—particularly my elderly mother and young adult sons—didn’t truly comprehend or embrace my 52/52 Project for several weeks. But once they understood the scope of it, they were all in. My mother told me she was now living vicariously through me. My twenty-something sons felt simultaneously embarrassed by the stories of my more personal exploits and yet proud of my new lifestyle. Son #2, in a Facebook post, said, “OK, so here’s the latest post from my mother: who is obviously way cooler than I am.” Son #1, after watching a TV interview with the host of Jackass, told me he saw some similarities in our escapades and approach to life. “So,” he said. “I’ll bet you never thought your life would mirror Johnny Knoxville’s.” I had to Google Jackass and Johnny Knoxville. Umm… No, indeed.

Sherry’s mother, Gloria Stanfa, is the source of much of the humor in her daughter’s writing–and in Sherry’s life.


What challenges did you encounter?
Challenges? Well, crashing a wedding (accidentally catching the bouquet), going on a raid with a SWAT team and vice squad, taking a homeless stranger to lunch, and going au naturel at a nude beach—with my elderly mother in tow—were challenging, no doubt. I’ve never felt so unsure of myself, so frightened, and so humiliated, as I did during this year of new life challenges. Yet… (see below)

After her Big Fat Greek Party, Sherry wanted to enroll at Marquette University and pledge Sigma Chi–fresh off of its double-secret probation.


What did you learn about yourself through this process?
… Yet, I have never felt so self-fulfilled—or had so much fun. Because pushing yourself outside your comfort zone is empowering. And learning to laugh at yourself is liberating—and it’s also a helluva survival tactic. Most of all, I learned that the anticipation of what we fear is almost always worse than the reality.

If I could do anything differently, I would have embarked on this new approach to life thirty years sooner. Just imagine what else I may have experienced through the years!

Sherry headed out one day in pajamas, slippers, and a headful of curlers. Breakfast was at a restaurant called “Chowders ‘n Moor,” a fitting venue for a fish out of water.


What advice do you have for women seeking reinvention in midlife?
With a new approach to life—in my mid-fifties—I changed my outlook, changed my daily way of living, and changed my whole world. While I’ve made an effort to hang onto the very best qualities of the young woman I was at sixteen or even thirty, I’ve also evolved into someone different and new.  I’ve learned it’s never, ever too late to reinvent yourself.

As Sherry embraced her weirdness during her public mime performance, the passersby and she seemed to agree–in an unspoken understanding–that we’re all weird, really.

What advice do you have for would-be writers?
For wannabe writers, I suggest you seek out and follow online advice from professionals and at writing workshops or conferences. Write. Edit. Submit. Write, edit, submit again. Never, ever give up.

For those of you who want to reinvent yourself in some other way: Do whatever makes you most afraid. You’re likely to discover the most rewarding experiences in life are the ones you’ve been sidestepping all along.


What resources do you recommend?
For writers, my favorite workshops/conferences for learning and networking purposes are the Erma Bombeck Writers Workshop and the Midwest Writers Workshop. For anyone simply looking to shake up or reinvent their life, I’ll shamelessly recommend my book, Finding My Badass Self: A Year of Truths and Dares. However, my most helpful advice is to live your life fully—far outside your comfort zone.  It’s how you’ll learn the most about yourself and the world around you.

Some of my favorite women who write about midlife, with humor and poignancy, include Carrie Fisher, Anna Quindlen, Nora Ephron, and Elizabeth Berg. I’d recommend practically everything by these authors, but here are some to start with:
Carrie Fisher: Wishful Drinking
Anna Quindlen: Lots of Candles, Plenty of Cake: A Memoir of a Woman’s Life
Nora Ephron: The Most of Nora Ephron
Elizabeth Berg: The Day I Ate Whatever I Wanted: And Other Small Acts of Liberation

Sherry’s menagerie–especially Ringo the Wonder Retriever–has been a source of support and encouragement in everything she does, except for any long trips precluding pets.

What’s next for you?
I’ve recently embarked on several new acts, including moving (for the second time in five years), beginning to make plans for retirement from my communications career, and writing a new book. I’m seeking out every way possible to change and grow.


Connect with Sherry Stanfa-Stanley
Email: sherry@sherrystanfa-stanley.com
Website: sherrystanfa-stanley.com
Facebook: Sherry Stanfa-Stanley, Author
Amazon Book Link (but also please consider ordering from your local indie store): Finding My Badass Self: A Year of Truths and Dares

HeleneTStelian Musing
I’m Hélène Stelian, the Midlife Mentor with a passion for facilitating personal development in women 40+. Through my THRIVE Courses, I help introspective, curious, action-oriented women 40+ deepen their journeys of self-discovery and growth—and create their next chapter with courage and intention.



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  1. LorieAnne

    Thanks for writing. I am inspired by your adventures and attitude. Fear of what others(family) will think is what holds me back from getting out of my comfort zone.
    Today I promise to do one thing that I am fearful to challenge but really want to do. Thank you again for your words.
    Ps getting the book!!

    • Sherry Stanfa-Stanley

      Thanks, LorieAnne! Yes, do that one thing today–and then maybe one more again next week. It gets easier, and you become a bit desensitized to what others think. Have fun!

  2. DC Stanfa

    Fantastic interview. Proud to claim her as my sister. I’ve attended many of her events, and her inspirational speeches are also hilarious.
    The “passerby” in the mime photo is actually me. She really threw herself into that one. There’s a YouTube video of that!

    • Hélène Stelian

      I know, so awesome!!

  3. Dani

    Terrific story! Thanks for sharing

  4. lisa

    Thanks for having the courage to take this ‘plunge’! Your experiences reinforce what you said at the of this post and that is to Do whatever makes you afraid.

  5. Gloria J. Stanfa

    I am so proud of you, not just because you are my daughter, but because you are the woman you turned out to be! Thank you for sharing your life, your success, your goodness and your love with me, your mom.

    • Sherry Stanfa-Stanley

      Thanks for providing love and support, as well as the occasional fun fodder. 😉

  6. Camille


    Your story is an inspiration. I am at a crossroads in my life and need to make decisions. Fear has kept me in a state of immobilization for as long as I hate to admit. Your story nudges me to muster up the courage to step out there to fulfill my dreams regardless of the limitations that I place on myself. I just ordered your book through my local independent bookseller and can’t wait to read it. Thank you for sharing your story. It matters!

    • Sherry Stanfa-Stanley

      Forge ahead, Camille! Hope your journey is interesting, enlightening, and fulfilling!

  7. Jessica Jolly

    What a great story! I haven’t done exactly tge 52/52 but have definitely left my comfort zone as I gave reinvented myself in my 50s. And you are sooo right—you have to go towards the things that scare not away from them. I hope you will join Heles closed Facebook group “Empowering Women in Midlife”. There are a bunch of us on there engaged exactly on this quest!

  8. Charisse

    I’m so glad I stumbled upon this article. You are an inspiration Sherry. I’m going to have to go and order your book now. I can’t wait to read about your adventures. God bless and keep up the good work.

    • Sherry Stanfa-Stanley

      Thanks, Charisse. Hope it encourages you to pursue some adventures of your own!


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