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Launching a Web Series in Midlife: Wendy’s Story

Published on 03/13/2017

Wendy Michaels cover photoReconnecting with an old acting friend and sharing her struggle with her sexual identity led Wendy to collaborate on the new web series, My Sister Is So Gay, just launched in January, 2017.


Tell us a little about your background…

I grew up in Florida, mostly. I say mostly, because at 17 right after high school, I started moving frequently. I’ve moved 35 times in my life—I’m an “army brat” of my own making! Dad and Mom were divorced when I was 13, which was more traumatic for me than I realized at the time. Probably my first big ‘shame’ adventure. I wanted so much to look and feel normal even then. That divorce, in my eyes, branded our family as “something was wrong with us.” Dad and my stepmother and Mom still live in Florida. My sister and her family moved to Colorado recently. My baby brother died in 2003 unexpectedly and this has been a great loss to our family. My mom and I are super close and, I have to say, I probably got my sense of humor from her. When we are together, we see the world the same way and always have a good laugh. She is a rock of support.

Wendy Michaels with her brother and sister

With my brother and sister

My first romantic experience with a woman was when I was 19—and she was my boss! It was 1979 and I was living in Tampa, Florida. I didn’t go to college right away after graduating from high school and I desperately needed a job. So, dressed in my favorite outfit—black floral skirt and midriff top—I headed to the mall. I’m not sure what message I was hoping to send interviewers in THAT outfit. There was a sign at an art gallery entrance that read, “Interviewing, experience needed.” Well, I had no experience in that line of work, nor any desire to work there, but I needed a job, and got hired, much to my dismay. This little decision would change the course of my life forever. During the turmoil of working in a place I hated, somehow this woman—the gallery manager—who appeared so creative, sophisticated, generous, and downright funny, became the focus of my thoughts. We went out a few times after work and both realized we had feelings for one another. We were together three years.

Wendy Michaels With her first girlfriend, 1979

With my first girlfriend, 1979

After we broke up, I wanted to try being with men, but then I met another woman, older than me and completely in control (of everything) and that appealed to me at that time. We were together eight years, building a very successful home healthcare company in Miami, taking care of AIDS patients. CritiCare was the first home care company willing to take care of AIDS patients at the time. My partner was the nurse and I was the operations woman. During this time, I returned to college for a Bachelor of Arts degree in Theatre.

Wendy Michaels Working at Criticare with Tonie

Working at Criticare with Tonie

I built an entire career in acting for two decades while supporting myself in healthcare with the skills I learned at CritiCare. After I graduated from college in 1988, I immediately went to work in our home healthcare business. I was too scared to really put myself out there as an actress full time, but was auditioning.

It all felt and looked normal, except for the “girlfriend” part—I had my own homophobia going on. The problem for me was that I still desired to be “normal,” whatever that means. After I landed my first commercial and then my first stage play, I was encouraged to begin the steps of leaving this relationship. I could finally see myself outside the image of who I was with her. After eight years, my girlfriend and I parted (and I sold my share of the company) and I re-connected with my best friend from high school. We moved to Los Angeles in 1993 and married in 1997, when I was 37.

Wendy Michaels' wedding, 1997

My wedding, 1997


When did you start to think about making a change in midlife?

After acting jobs dried up in Los Angeles and my marriage crumbled, I moved back to Miami in 2001 to be close to my family. I finally felt settled and rooted in a place I loved. I was mostly happy, had found a wonderful church, Church by the Sea, lived in a condo on the ocean that I was looking to buy, and was doing part-time consulting work for physicians, helping them restructure their reimbursement strategies. My left brain was on fire!

Wendy Michaels at the beach

I had semi-retired from acting. It no longer interested me. I thought, “So, this is what it’s going to look like for the next 20 years or so?” I was okay with that. But God had other plans. A friend of mine was in a play and I went to support her and because I still loved being inside of a theatre. Her play was Speaking Elephants by Terry Lawrence and it would change my life, although I would not see the significance of that for years. I was so moved by the play’s story, which told the true-life experience of two elephants, Wanda and Winky, who lived at the Detroit Zoo and were going to be moved to a sanctuary in California called The Performing Animal Welfare Society.

While sitting in the audience, something deep within me felt a kinship and a jolting compassion for the plight of captive elephants. A stirring like I had never felt before. It was like my soul found home. Stage and elephants. As soon as I got home from the play, I devoured the Internet with everything elephant and sanctuary. I was now an activist for captive elephants.

Wendy Michaels volunteering at the Miami Zoo

Volunteering at the Miami Zoo

I volunteered at the Miami Zoo even though it broke my heart to see them on display and behind bars at times. I just wanted to learn more about them and be close to them. I mostly picked up elephant poop because I wasn’t qualified to be a zookeeper. That was fine with me. Exhausting for a 50-something woman, but soul filling to be near them. I would make these little care packages for them and the head zookeeper would let me feed them directly.

An elephant’s trunk is amazing. That’s where they smell you and feel you and will determine if you are a threat or safe. Unfortunately, if you are a threat, there’s nothing they can do in a zoo or circus. A bullhook keeps captive elephants from responding naturally to any outside influences. I started a campaign for Nosey the elephant, who had been part of a small family circus for 25 years, after 33 animal welfare violations by the USDA against her owner brought her attention to me. The fight to have her sent to sanctuary grew into a national campaign. Representative Raymond Lesniak even got involved.

Wendy Michaels with Nosey the elephant


My life felt and looked full. I never saw ACT II approaching.

Was there some event or “aha” moment that precipitated your desire for a change? 

The aha moment did come and it was sort of a burning bush. Now, even though I was “retired” from acting—mainly because jobs had all but dried up for a few years—I was reading plays at night before bed. Just to, you know, keep that pilot light burning low. My spiritual life became huge during this time at the beach. Partly because of the minister at my church, Reverend Barbara Asinger, and partly because I was struggling with my sexuality and was willing to turn to a power greater than myself for guidance with everything.

Wendy Michaels with Barbara

With Barbara

In 2013, at the age of 53, while casually working at my computer for one of my healthcare clients, I heard the message in my head, “This is the year of the artist.” WHAAAAT? That can’t be right. I’m done with that. Finished. Too old. Too fat. Not “bookable.” Someone once told me, when I was doubting this message and the pathway it seemed to be building, that I needed “a bigger God.” That my mind could not conceive of the abundance that my God wanted me to have. So, I learned to have faith that I was being directed this way.

I went for it with my new big God. Sold my luxury car, began to rebuild my acting website, go new headshots, printed resumes. Then a couple of my healthcare clients moved away and I decided not to fill up my time looking for new ones. But then the summer arrived and no new acting jobs and nothing that gave me any sign that this was the “year of the artist.” Still, I kept putting one foot in front of the other.

As September rolled in, a notice in the online trades caught my eye: PLAY AUDITION…. ASPIRINS AND ELEPHANTS. Elephants? Gotta seek this one out. Well, it turned out to be a play at a playhouse in Los Angeles with a playwright I had worked with before in the ‘90s. I sent a taped audition for the role. A week letter I got an email: “Welcome to Aspirins and Elephants.”

I took the role, rented my condo, sent my cats to stay temporarily with my mom, rented a room from a previous roommate in Los Angeles, and headed West again. I’ve been back here ever since.

Wendy Michaels with the Cast of Aspirins and Elephants

Cast of Aspirins and Elephants

What is your next act?

I am a writer, producer, and actor, and captive elephant activist. My acting roles have ranged from a lesbian criminal on the run to a grieving mother losing her 5-year-old son in a car accident to my current role as a homophobic uptight housewife in My Sister Is So gay.

I co-wrote, co-produced and co-star in the web series called My Sister Is So Gay. We launched in January 2017 on Tello Films. Here’s the trailer. It’s the story of Seth, a proud gay man, who’s invaded by his uptight, homophobic sister, Amanda (me!). She just shows up on his doorstep (with luggage) for the first time in 20 years after catching her husband having an affair with her best friend, Katherine. But it seems to Seth that Amanda is way more upset about Katherine cheating on her than her husband. Plus, there’s Seth and Amanda’s boozy, inappropriately sexy mother, Frances, played by the iconic Loni Anderson.

My Sister is so Gay poster

How did My Sister Is So Gay come about?

It’s such a synchronistic story that really re-enforced my faith yet again. My creative partner in this show, Terry Ray, and I were in the same acting class in 1995 in Los Angeles, taught by Broadway veteran director Charles Nelson Reilly. It was a scene study class, which means you choose a partner and then you and your partner pick out a scene from a stage play and present it to the class. Terry and I were each other’s first scene partners. We worked so well together that we were scene partners a lot in his class. I just loved Terry’s sense of humor (still do—he cracks me up) and my dream was to one day do a sitcom with him. We studied together in that class for two years but the opportunity to work together in a sitcom never happened. We also did a casting director workshop together and recently Terry came across a video he had of the two of us working a scene together back in the mid ‘90s in casting director Craig Campobasso’s workshop. What a hoot!

Terry and I had remained friends over the years and we had lunch in early 2014 after I moved back to Los Angeles. We started talking about my struggle with my sexuality (he is gay) and I was sharing some funny instances of that and the conversation sort of morphed into, “Hey why don’t we write something together?” I said, “Let’s write a web series! We can play brother and sister.” To which he replied, “Yeah, we can call it, My Sister Is Gay.” The more we talked, the more ideas about the content seemed to erupt. We decided the sister shouldn’t think she’s gay at all and the brother thinks she is SO gay, hence the title, My Sister Is So Gay.

Wendy Michaels with Terry

With Terry

You also have a new play. Tell us about that.

I have written a play, GOD AND SEX, that I am so proud of and just feeling crazy amazed and blessed that it will have its world premiere next year in early 2017 in Santa Monica. The story started out as my one-woman show titled “10 days” about the 10 days surrounding my wedding experience and how un-special I felt at my own wedding. When anyone would ask me how my wedding went, I would reply with this statement: “It was like driving down a deserted highway all by myself, when suddenly a cow would fling itself at my windshield, like in the movie Twister, and I would be forced to swerve off the road to avoid it.”

Over a decade later, through rewrites and getting slightly more honest about what the story needed to be about (along with some growing up), it became a two-act play named GOD AND SEX with an entirely different story-line. Another synchronistic moment came when I found out that my original writing teacher, Lisa Soland, was coming back to Los Angeles for a weekend to host a writing workshop in July 2014. I had just been cast in another play following Aspirins and Elephants, so I decided to attend her workshop prior to starting rehearsals. That’s where my writing of this show came “out of the closet.” I had been doing rewrites of it in a writing group at church by the Sea in Miami with a few like-minded people but had put it away when I moved back to Los Angeles.

Wendy Michaels with Lisa Soland

With Lisa Soland

This workshop would mean sharing it more publicly. Through Lisa’s workshop, I was able to polish the narrative and really unfold the meat of the story. She always pressured me to tell the story under the story. So the story under the wedding story is: After spending many years in a lesbian relationship, Amy decides it would be easier to “be straight.” The Husband/Target is Tim, her best buddy from high school who has loved her since the day they met. Assuming marriage and living a “normal, straight life” would be as easy as it appears in the movies, Amy commits to her goal of getting married to Tim. Eager to please his parents, Tim convinces Amy to have their ceremony in his parents’ quaint but “intolerant of homosexuals” country church. Amy forges ahead with her own kind of support so she asks Karen, her former lesbian lover, to be her maid of honor. Amy and Tim’s vision of the special day seems destined to go well until important details begin to crumble. Both desperate for their individual sexual and spiritual dreams to be realized, they plow forward and cling desperately to what they think they want, but divine intervention propels change in directions neither of them could have predicted.

It is loosely based on my experience leading up to getting married in 1997 and my first year of that marriage. I reached out to the artistic directors of the Santa Monica Playhouse, husband and wife team, Evelyn Rudie and Chris DeCarlo, asking them to consider my play for production because all of the important benchmarks of that marriage happened while I was performing on their stage. In four different plays!  It seemed only perfect that it premiere there as well. The play is now running on stage in Santa Monica, through May 13, 2017:  “A bride. A groom. A maid of honor (who just happens to be her ex-lover). What could possibly go wrong?!”

Wendy Michaels with Evelyn and Chris

With Evelyn and Chris

How hard was it to take the plunge?

Without the support of the minister of my church, I would not have trusted God the way she taught me. All the arrows seemed to be pointing in the direction of returning to Los Angeles even though it wasn’t on my radar. I basically keep making leaps of faith. How did I prepare? Like I do for all changes and challenges. I stay close to God, listen for that small and gentle voice for direction, and watch. I get messages from books, from billboards, and from different people. Mostly I try and just stay in the day.

How supportive were your family and friends?

Terrific! If it hadn’t been for my mom suggesting that she take care of my two cats, this story would not have been told. I was so nervous about their welfare and uprooting them seemed like such an awful and selfish choice. My mom already had one cat, an elderly dog, and a rescue dog so this was not going to be a breeze for her, but she still volunteered and I took her up on it. By the way, my babies have never been happier.

Wendy Michaels with her mom

With my mom

What challenges did you encounter?

The first was that being back in Los Angeles brought back memories of when I lived there before. By the time I had left the city in the early 2000s, I felt pretty defeated and broken, and all those feelings came rising to the surface as soon as I landed back in town. I spoke a lot to my minister back East, my best friend, and my mom. I’m sober 10 years so my program was front and center.

Then of course there were challenges getting our web series off the ground. We finished writing it in May 2015. The role of our mother we thought would be wonderfully played by Loni Anderson. But how to get a name actress to do our little project? As it turns out, Loni was married to Burt Reynolds and he and Charles Nelson Reilly worked together often in addition to being very close friends. Terry had worked with Loni briefly on a sitcom a decade earlier and, while on the set, he had introduced himself to her. They had a conversation about Charles Nelson Reilly. So, Terry thought, I can try and reach out to her manager. He did and she accepted the role immediately! The script was sent to Sam Irvin, a veteran director and producer and he loved it and said yes right away. Next came cast members Tilky Jones (Nashville) and Debra Wilson (Mad TV). We were set to go. Loni even won a best supporting actress award at the LaWebFest 2016, “the Sundance of web festivals” as quoted by the LA Times. Then we had to work on letting people know about the show before its premiere January 29, 2017 on Tello Films.

Cast photo for My Sister Is so Gay

Cast photo for My Sister Is so Gay

Were there times when you thought about giving up?  

Absolutely! While I was performing in Aspirins and Elephants, the condo that I had been renting and was hoping to buy as a foreclosure was whisked away from me and bought at auction by Fannie Mae and then they kicked me out! I had to put all my stuff in storage and suddenly I was in limbo. I thought, “What have I done?”

But God, my minister, Mom, my acting work, and my best friend kept me going. My relationship with God has blossomed. I believe that my God truly wants a wonderful, abundant, and big life for me. And my mind thinks much smaller than God’s plans. My faith has evolved and my leaps are pretty frequent now.


Wendy Michael with Julie, her best friend

With Julie, my best friend

What advice do you have for women seeking reinvention in midlife?

What worked for me was to enlarge my spiritual life. I have too much anxiety living a creative life to not trust in something greater than myself. I still worry and get scared and wonder if I’m doing the right thing.

My path has been very non-linear (in my mind) and ultra-nontraditional. In walking a pathway that’s off the grid, so to speak, I learned to surround myself with cheerleaders—only people who think what I do is terrific and wonderful and funny and get me. That has been my saving grace. I just let people go who are not with me in a way that fulfills me and motivates me to keep taking risks. Otherwise it’s too much of a drain and I get derailed trying to either please people or get them to like me for who I am. I get just plain exhausted in the relationship. Cheerleaders fuel me and I continue learning to believe in myself.


Wendy Michael with her friends

With friends!

What resources do you recommend in your field?

Pam Grout

James Clear at james@dripemail2.org

Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert

Even The Best Hookers Need Pimps: How to Be a Working Actor in Today’s Hollywood by Sarah Mornell

The Writer’s Motivation by Lisa Soland

Sanford Meisner on Acting by Sanford Meisner

Graphic Artist Julie Palas


Contact Wendy Michaels at wendymichaels6@gmail.com and mysisterissogay@yahoo.com

Website: Wendy Michaels

Website: My Sister Is So Gay

My Sister is So Gay Trailer


Twitter: @wendy_michaels_

Facebook personal page

Facebook My Sister Is So Gay

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. Julieta

    I also improved my life when I expanded my spiritual life. Today I think it is fundamental for any type of Woman.

  2. Joana

    Loved it ! This is such a great inspiration…


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