Chapter 3: From cloud computing to soaring in the clouds

Roman Sochan spent an entire career in technology services and cloud computing. Now at age 58, he’s changing his career to work in the clouds—literally. In only four years he went from zero experience as a small-planes pilot to logging more than 400 hours of private aviation, recently acquiring his instrument-rating (for flying in the clouds) and his commercial-rating (to work as a paid pilot.)

Sochan’s journey into the skies wasn’t without turbulence. Growing up in Sarnia, Ontario, he took an introductory flight lesson as a teenager but couldn’t afford to continue. Life quickly took over—school, a master’s degree, marriage, kids, and a demanding career. His childhood dream was grounded for decades.

Then came COVID-19. The upside to the pandemic was that it allowed for more free time when work commutes, appointments and social commitments were eliminated. With grown kids and money saved for flying, Sochan signed up for lessons at a local airport near his home in Redwood City, California. What began as a hobby quickly became a passion—and then a potential new career. 2025 is the year Sochan plans to start teaching others to fly.

“I’m shocked now that I’m even sitting here telling you that I’m on the verge of becoming a flight instructor,” he says.

“Work that’s something you love to do isn’t really work.”

Greg Davidson echoes Sochan’s sentiment. “I feel good coming to work every day,” says the high school math teacher who spent 30 years as a corporate attorney before pivoting to education.

Unlike many midlife career changers, Davidson’s leap into a new career wasn’t from burnout — more like curiosity. As a partner at the prestigious Los Angeles-based firm Gibson, Dunn & Crutcher, he enjoyed his work and respected his colleagues.

Davidson managed high-stakes transactions, including Intel’s billion-dollar investments in Clearwire and defending PeopleSoft during Oracle’s hostile takeover. Yet, after decades with the same firm, which he joined straight out of law school, he found himself wondering: What if?

“I thought, would I regret not trying something new and different?” he says via video call. “I realized that now was probably a good time to try something new, while I have the aptitude and energy.”

The question was…what? A program at his alma mater — the Stanford Distinguished Careers Institute — helped guide him to teaching, a path he had never considered. Davidson’s knack for math, honed during high school and later as a lawyer calculating financial transactions, resurfaced as a potential calling.

His timing to become a first-time teacher was the absolute worst possible. His first day of work was exactly the day his new employer — Sacred Heart Preparatory in Atherton, California — went to remote learning. They couldn’t accommodate him right away. Davidson was ready to teach, so he found a role at Our Lady of Mount Carmel grammar school in Redwood City, California.

Being a first-time teacher for anyone is hard, teaching remotely via Zoom as a newbie even harder. While his students attended class virtually, Davidson was at school, limited to waving at colleagues and interacting from a safe distance due to strict social distancing protocols.

The world came back online. Sacred Heart called him back. Now in his second year of teaching high school math Davidson humbly admits, “I’m still new at this and still learning.” He even half-jokingly asks me to help him grade finals.

Davidson agrees that shifting from corporate law to the classroom isn’t the usual path, but he says it doesn’t have to be so unusual. Watching students light up when they “get” the math, learning and sharing with fellow teachers, going to school sporting events—all confirm that his leap into the unknown was worth it.

He says midlife career pivots can be far less daunting than one might imagine. You just have to look for them. “The opportunity to give back is there.”

The unsung heroes behind our “second acts”

It must be said that pursuing midlife passions requires the assistance, sacrifice and sometimes financial support of our loved ones. I once overheard my wife at a party, talking to a friend about my many “dueling pianos” shows (I spent a whopping 73 nights away from my family in 2021 alone.) I started to cringe, thinking a rant was about to start, but she said something along the lines of “I support him because it’s what makes him happy. I can’t keep him from that.”

Greg Davidson’s wife and kids love that he became a school teacher during his prime earnings years. Matt Jones says his wife was a “bit concerned” when he became a full-time artist, but is nonetheless supportive. Benefits from her teaching job cover their family. He even shows her his Profit & Loss statements to track his art sales.

Scott Johnson supplements his income with contract work for a bank, giving him more flexibility to paint outdoors when the weather is clear. His wife, also supportive, holds down a successful career in corporate real estate services. Rink and Sturgis have retirement savings and the encouragement of their thriving Greenville art scene.

Sochan’s wife also works, and was understandably nervous about the risks of flying small planes when he decided to take lessons. She got comfortable when he made a point to share the intricate details of his safety training protocols, and checklists. Now he regularly flies with his kids.

No matter where we are in life, our dreams are built on the foundation of those who believe in us. I know I’m grateful for the support of my wife, my family and friends.

“Facing the music” of the other side of 50: jammers find joy and connection

Carl Katz didn’t wait until midlife to reinvent himself. He spent his whole career doing that.

Katz is a trained attorney who got his start at a D.C.-based law firm. He’s been senior in-house counsel at a major wireless corporation. Co-founder of a digital advertising agency. COO of two craft breweries. University guest lecturer. Not-for-profit board member. Partner in a software company. Dad, husband, consultant, silver medalist at the 2022 Great American Beer Festival.

But now, Katz just wants to rock.

It stemmed from a “bucket-list” idea he and seven other friends came up with just a year ago. Learn an instrument (none have ever played.) Study for six months. Assemble in the spring and rock-out.

Only he and the drummer stuck with it. But they found new players at the adult band program at a “School of Rock” franchise near his home in Tustin Hills, California. Katz is the lead singer and resonates joy even when he’s just talking on speakerphone about taking the stage with his bandmates, with no illusions of stardom or even securing paid performances. “We’re never going to get a legit gig,” he laughs.

But that’s beside the point. For Katz, it’s about the magic of collaboration—different instruments coming together like a “team sport” to create something greater than the sum of its parts. “When you’re sitting on the edge of the stage, and people are looking at you, singing along—it’s total connection, and it feels incredible.”

Katz is so inspired by his midlife foray into music that is planning to open his own “School of Rock” location. The performance-based music education program for kids has 300 national locations and bills itself the “number one childhood education franchise.”

It’s not just a business decision for Katz—it’s a chance to make his next career move, maybe his final one, into a meaningful encore.

“If you’re in your 50s, you probably have one more at-bat,” he says, citing the appeal of being his own boss, the scalability of a subscription-based model (students pay a monthly fee to play), and the thrill of helping kids discover the joy of music.

“I don’t want to wait until I retire to do something that’s truly fun,” he says.

Coming in the final installment of “Rocking the Second Act”: From a retired college chancellor who escaped Zoom hell by playing piano, to a big tech attorney rediscovering joy in a 90s cover band, to two longtime friends building a creative clubhouse for grown-up musicians—this final chapter celebrates the power of music to heal, reconnect, and rewire what midlife can look like.

Spoiler: it involves jamming, joy, and a cool space called Sound Union. Don’t miss it.