Preston Cherouny was born in Atlanta, Georgia in 1965 and grew up in Canton, Connecticut. His parents, Richard and Mary, taught him the values of humility, honesty, and hard work—principles that have guided him throughout his life. After attending Avon Old Farms School, Preston earned his degree in American Studies from Skidmore College in 1988. While there, he played a season on the golf team, sparking a lifelong love for the sport.
In the early ’90s, Preston moved to Washington, D.C., where he built both his career and his family. He married his wife, Merrell, in 1993 at St. John’s Church—the same church where he would later serve as Chief Operating Officer. Together they raised two children, Grace and Hayden, who remain his greatest joy.
Preston’s career path at St. John’s began in 2017, first as Financial Secretary, then as Interim Parish Administrator, and eventually as COO. His leadership is rooted in patience, humility, and persistence. “Success to me—it’s in the work,” he says. “It’s the process, not the outcome.”
Outside of work, Preston is an avid golfer and fitness enthusiast. He is also dedicated to giving back—supporting education and community spaces through donations to his alma mater and the University of Maryland.
His story is one of quiet strength, reflection, and balance. Through ups and downs, Preston has learned to slow down, stay present, and focus on what matters most—family, community, and the simple act of doing your best every day.
What is your typical day, and how do you make it productive?
Most mornings start early for me—usually around 5:30 a.m. I like the quiet. I use that time to read, check the day’s schedule, and get a quick workout in before heading to St. John’s Church. Once I’m at the office, I spend the first hour walking through the building, greeting staff, and checking in on operations. It’s not just about oversight; it’s about connection. I find that a brief, honest conversation can prevent big misunderstandings later.
I block time for deeper work mid-morning—budgets, planning, or reviewing reports—before the day starts pulling me in different directions. I try to write down three goals every morning. Hitting all three isn’t always possible, but the act of writing them keeps me focused. Productivity, for me, is less about speed and more about clarity.
How do you bring ideas to life?
I’ve learned that ideas don’t come to life through big moments of inspiration. They come through small, steady progress. I start by writing things down—always by hand first. I sketch out the idea, what it might solve, and who it might help. Then I test it in conversation with my team.
At St. John’s, for example, when we were considering a new financial reporting system, the idea began as a simple note about transparency. It became real only after talking it through with staff and parishioners, understanding their needs, and adapting the plan to fit them.
What’s one trend that excites you?
The renewed focus on community-centered leadership. In a world where everything feels digital and distant, I find it exciting that people are rediscovering the value of local connection—churches, schools, neighborhoods. It’s something we’ve always known but sometimes forget in the rush of modern life.
What is one habit that helps you be productive?
Writing things down. I keep a small notebook with me at all times. It’s not digital—it’s pen and paper. I jot down goals, reminders, even frustrations. The process of writing slows me down enough to think clearly.
What advice would you give your younger self?
Slow down. When I was younger, I thought success was about momentum—always moving, always achieving. But life has taught me that it’s about consistency and reflection. I’d tell my younger self to listen more, forgive faster, and not measure worth by career milestones.
Tell us something you believe almost nobody agrees with you on?
I think failure is one of the best teachers, but only if you sit with it long enough. Most people rush past failure or try to forget it. I think you need to study it. I’ve learned more about myself through my mistakes than through my successes.
What is the one thing you repeatedly do and recommend everyone else do?
Take time each week to be fully present with your family. No phones, no distractions. Just dinner, a walk, or even sitting together. It’s simple, but it changes your outlook.
When you feel overwhelmed or unfocused, what do you do?
I go for a walk, usually on the golf course if I can. Something about being outside, seeing the open space, resets my thinking. I’ve also learned to forgive myself for needing breaks.
What is one strategy that has helped you grow your business or advance in your career?
Honesty and humility. When I took on leadership at St. John’s, I realized that people don’t expect you to know everything—they expect you to listen. I’ve found that transparency builds loyalty, and loyalty builds strong teams.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Early in my career, I made a major financial oversight that affected a project’s timeline. It was my responsibility, and I had to face it head-on. The experience taught me two things: communicate early, and don’t try to fix everything alone. Admitting the mistake and asking for help turned it into a learning moment.
What is one business idea you’re willing to give away to our readers?
Create a “Community Audit” app—something that helps small organizations or churches track their local impact: volunteer hours, donations, attendance, and outreach. It could visualize how small acts add up to big results.
What is one piece of software that helps you be productive? How do you use it?
I use Evernote for quick notes and document storage. It syncs between my phone and laptop, so I can capture ideas wherever I am. But I still prefer writing by hand when I can.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
I’ve read The Road to Character by David Brooks several times. It’s about humility and how inner strength often comes from struggle. It helped me rethink what success really means.
What’s a movie or series you recently enjoyed and why?
I recently rewatched A Man for All Seasons. It’s about integrity and the cost of standing by your principles. That theme never gets old for me.
Key learnings
- Writing down daily goals creates clarity and helps maintain focus.
- Failure, when studied rather than avoided, can become a powerful teacher.
- Genuine leadership comes from listening and honesty, not authority.