Submitted photo Cortland native Diane M. Ross performs stand-up comedy in northern Virginia. Ross’ memoir “First Generation Normal” releases Thanksgiving Day.

CORTLAND — In a life full of improbabilities, unenthusiastic student Diane M. Ross became the lady who motivates unwilling youngsters to love education.

“I wasn’t a great student, a bit of a class clown, and played sports mostly,” the 1990 Lakeview High School graduate said.

An all-county athlete who played softball and basketball, Ross looks back fondly on her childhood in Cortland and how it shaped her journey to becoming a school psychologist, stand-up comedian and author. Now the kid who couldn’t sit still has penned a memoir with humorous stories about growing up in and being shaped by life in Cortland.

“‘First Generation Normal’ came about because I thought my story would resonate with people — overcoming obstacles, working through family dynamics — all through storytelling and humor,” Ross, 49, said. “The book is part stand-up, part therapy. It’s not a ‘how-to’ book, but it does walk a reader through my process of healing and emotional growth.”

When she couldn’t get a publisher to bite on her fiction, she sorted through 30 years of journals and wrote about her own life.

“It was also right around the time I started doing improv and stand-up. I was really getting into humor writing, and people were laughing,” Ross said. “So I pitched a few stories to Olympia, and they loved them and basically wrote back right away that they wanted the full manuscript. I did not have a manuscript at all.

“I had stacks of paper everywhere for months. Every morning I got up at 4 a.m. and wrote until about 7:30 a.m. Then I would work until 3:30, then write a few more hours.

“Finally, in November 2020, the publisher said I had 30 days to finish or they would move on. I submitted the final manuscript on Dec. 18. It’s taken about a year to get it out. Longest. Process. Ever,” she said.

“First Generation Normal” releases Thanksgiving Day at olympiapublishers.com/books/first-generation-normal and Ross’ website, firstgenerationnormal.com, among other outlets.

“Finishing this book is significant for me because, as an ADHD Gemini, things rarely get finished,” Ross said. “A lot gets started. And restarted. But finishing a task such as this is quite the feat for someone who still has to buy winter gloves that get clipped together so one doesn’t get lost.”

CHILDHOOD

“My childhood in Cortland was idyllic in many ways. I had a lot of freedom and room to run wild,” she said.

Her parents, Jerry and Bonnie Ross, “Let us run wild and be free.” After her parents divorced when she was 6, it fell on her older brother and older sister — kids themselves — to “raise” her.

“I was a handful,” Ross said. “I was pulled over by the Bazetta police at 8 years old for riding my go-kart down McCleary Jacoby Road. He happened to be the chief of police and also my great-uncle, which I did not know at the time. I was wearing a motorcycle helmet though, so I did have some sense of safety. Anyway, he followed me home with his lights on.

“I enjoyed skating at the Cortland Roller Rink, which I eventually got kicked out of after a very unfortunate incident involving a ‘skate chase’ with a floor guard. I was pretty hard to catch on foot, let alone skates.

“I was outside so much as a kid. I had a ton of energy,” she said. “We had a fort in the woods. As soon as I got a bike and two wheels, I was all over the place.

“I spent a lot of time water skiing with my dad on Mosquito Lake,” she said. “He is quite the character and the source of much of the book. He raised me (and my siblings) to be fiercely independent and authentic, though you’ll never find his parenting tactics in how-to-parent books.”

She also noted she nearly shares a name with singer Diana Ross, “which has been not only a lifelong joke but the bane of my existence. I can’t even go through airport security without someone asking me if I sing.

“I went to school with a Michael Jackson, so all through school, K through 12, it was Diana Ross and Michael Jackson.”

TEACHING

“I was a pretty terrible student. School was hard,” Ross said. “College was never made a priority in my family or in any way expected, but at the very last minute, I decided to make a run at it.”

She enrolled at Youngstown State University to become, improbably, a teacher.

“As a kid, I felt like school was a fun sponge — it soaked up all of my joy. And I wanted it to be different for other kids like me,” she said.

Ross subbed at Warren G. Harding High School. “I was actually terrible at it. They would call me at 5 in the morning and say, ‘Do you want to work today?’ Nobody wants to work at 5 in the morning.”

She took a full-time teaching job was at the Positive Education Program in Cleveland, where the worst of the worst students were sent. Ross said the main reason she landed the job was because of her ability to remain calm no matter what.

“It was a complete baptism by fire. I was cursed at and called names I didn’t even recognize. But I learned a bunch and grew from the experience,” she said. “And I discovered that I was really good at it.”

She went to grad school at Kent State University and earned a master’s degree in special education.

“After a really difficult divorce in 2000, I resigned from my teaching position to become a United States Peace Corps volunteer. I gave everything away — my car, furniture, etc. — and went to Africa,” she said. She served as an education consultant on teaching students with disabilities.

“I was a terrible Peace Corps volunteer,” Ross said. “I couldn’t learn the language, didn’t pack any skirts, which is a serious requirement, forcing me to wear a tablecloth at one point because you can’t just hop in a car to go to Target and buy a skirt.

“Essentially, for about six consecutive months, I lived in a hut with a dirt floor, thatched roof and no running water or electricity. I became obsessed with outhouses. The title of one of my chapters is, ‘On Finding Peace in Outhouses,'” she said.

Finally, she went back to school the third time to became a school psychologist.

“I tend to work with the kinds of kids nobody else wants, the ones kicked out of class, the ones one step away from being suspended,” Ross said. “It clicked in my head and I know their struggles. I guess the story here is that I ultimately became the person or thing that I needed the most in school.

“I had to overcome a bunch of obstacles, that are weaved throughout the book. But mostly, I had to learn to assimilate to a culture of rules and expectations when I did not grow up with such things. I was a free-range kind of kid, used to running wild and getting my way. Life isn’t conducive to such things, so I needed to learn restraint, compromise and patience.

“For a kid who hated school, I have only ever worked in a school for all of my adult life. This is my 26th year in public education,” Ross said.

Ross now lives in Manassas, Va., with her wife, Kim, and their two dogs, Camp and Kona. And if she’s not home, you likely will find her outside.

“Nature is my happy place. It’s calming. And it forces you to get outside your head because in the scheme of the universe, we are tiny, tiny things,” she said. “I’ve become involved in mental health initiatives, and sit on the board of directors for a mental health nonprofit organization here in the northern Virginia area.

“And yeah, I just love bourbon. I got into it seriously about five years ago and started to collect hard-to-find bottles over the pandemic. Some people bonded with family, explored new talents. I just bought bourbon.”