“You have to stop getting ready to get ready. Just get on with it.”

When tragedy strikes, do we retreat into safety or leap boldly into the unknown? For Sheryl Tullis, the answer became crystal clear after receiving devastating news that would forever change how she approached life. In this deeply moving yet inspirational episode of Good Life Stories, host Tracy Crowley sits down with Sheryl to explore how a devastating personal loss became the catalyst for one of the most adventurous chapters of her life. Sheryl’s “50 Adventures by 50” challenge wasn’t just about checking items off a bucket list—it was about fundamentally reimagining how to live with intention and purpose.

The genesis of this adventure-filled journey traces back to a tragedy that occurred 13 years ago. Sheryl’s youngest brother Justin, serving in the National Guard, was killed in a helicopter crash during a routine training mission. The timing made the loss even more poignant—he died on his birthday. This devastating event forced Sheryl to confront mortality in a way that permanently altered her perspective on life’s priorities.

“Life is super short,” Sheryl reflects. “He was lucky enough to die doing what he loved. And when it’s my time, am I going to die doing what I love or am I going to have wasted a whole bunch of time doing things that I don’t love?” This profound question became the driving force behind her commitment to living more boldly and intentionally.

Each year since Justin’s death, Sheryl has honored his memory with a “Justin Day”—a celebration where she tries to do something amazing, epic, or serendipitous. This annual tradition of adventure and remembrance laid the groundwork for what would become her most ambitious personal challenge yet.

As Sheryl approached her 50th birthday, she recognized it as a significant demarcation point. “How much do I have left? And what am I really trying to do here?” she wondered. The answer came in the form of a commitment to try 50 new things, inspired by the movie Walter Mitty—the story of a mild-mannered man who lived in fantasies while his real life passed him by, until circumstances forced him into an epic adventure that revealed his true capabilities.

“I wanted a Walter Mitty experience,” Sheryl explains. Her adventures ranged from simple pleasures like trying new foods and attending different concerts to truly epic experiences. She hot air ballooned over 3,000 ancient temples in Bagan, Myanmar, climbed Mount Rainier, and tried parasailing and paragliding. The key was intentionality—actively seeking experiences that would push her outside her comfort zone.

The support of her community proved crucial to the project’s success. “I told people this was my intention, and they came to me with ideas,” she shares. “So it was really about saying yes to those.” This collaborative approach to adventure not only helped her exceed her goal—she completed over 80 adventures—but also revealed something deeper about her purpose.

“My Walter Mitty moment was realizing that what I’m about is adventuring with people I love and helping people get outside their comfort zone,” Sheryl discovered. This insight has continued to shape her approach to life beyond the original challenge. She’s developed a system called “Momental”—combining momentum and intentionality—to help herself and others focus on adventures, financial goals, relationships, and skill development.

The episode takes a delightful turn when Tracy asks about Sheryl’s superpower. With characteristic humor, Sheryl reveals an “underappreciated superpower”—having “a lyric for everything,” no matter how inconvenient the timing. This musical inclination leads to spontaneous song breaks that, while sometimes eye-roll-inducing to her husband, demonstrate her ability to find joy and connection in unexpected moments.

Her more practical superpower is remaining “calm under fire.” Drawing from her military experience and crisis communications background, Sheryl explains, “I always just look for the next thing to do and don’t get very wrapped around the axle about things that are turned upside down or ambiguity.”

Tracy’s personal testimony adds another layer to understanding Sheryl’s impact. She describes how Sheryl’s encouragement and belief helped her overcome self-doubt about a book project, demonstrating the ripple effects of Sheryl’s commitment to helping others step outside their comfort zones.

The conversation beautifully illustrates how tragedy, when met with intentionality and courage, can become the foundation for a more vibrant, connected, and purposeful life. Sheryl’s journey from grief to adventure serves as a powerful reminder that our greatest challenges often reveal our greatest capacities for growth and joy.

About Sheryl Tullis

Sheryl Tullis is known for challenging boundaries.

She graduated from West Point in the first decade of women graduates. While a cadet, she qualified Airborne and interned as a speechwriter for General Colin Powell. Her first assignment as an Army officer was Deputy Director of Information Management in Germany, during the early days of the world wide web.  A few years later Sheryl pioneered Procter & Gamble’s first e-commerce business. At Microsoft, Sheryl served as chief of staff and speechwriter for the Chief Marketing Officer, and created new digital marketing capabilities for 7700 marketers.

Excited by emerging tech, she leapt to exec positions on the mobile agency side — earning 11 industry awards in two years. An advocate for helping others smash ceilings and break boundaries, Sheryl founded Women in Wireless – Seattle and Mobile Mixers, and she earned the Mobile Growth Summit / Bolden “People’s Choice” award for her work as global president of the non-profit which champions women in digital.

Sheryl then joined a private equity firm and rose to Partner and Chief Marketing Officer. A strong proponent of military veteran hiring, she helped pioneer the Microsoft Software and Systems Academy, the first tech transition program for transitioning service members.  

Last year she left the corporate world to co-found The Line Experience, with a goal of breaking down barriers to cycling and more inclusive access to public lands. The Line Experience provides affordable mountain, gravel, and e-bike rentals; instruction, and trail guidance, with a particular focus on newer riders of all ages and backgrounds.

• Website: https://thenextstage.co/ | https://theline.bike
• LinkedIn: https://linkedin.com/in/sheryl
• Instagram: https://instagram.com/thelinebike

About Tracy Crowley

Tracy Crowley has always been an entrepreneur. Whether it was making gowns for fellow Army wives, taking portraits in black and white, or working on her other businesses, she is always learning something new.

That passion for learning something new and giving something back collide nicely in this podcast.

Join Tracy for Good Life Stories, where simple curiosity brings out great stories, every single time.

Check out Tracy’s new book! https://tracycrowley.life/