#3: 'Be Grateful For Every Day That You Have, Because You Never Know When It Might Be Your Last': Vietnam War Veteran Turned Boomer Comedian

In this episode, I talk with Jay, a Washington state-based Vietnam War veteran, longtime benefit auctioneer, entrepreneur, and comedian whose life has been shaped by gratitude, endurance, and the healing power of laughter.

Jay shares the sobering lesson he learned as a young helicopter pilot during the Vietnam War: Every day is a gift, and none of us knows how much time we have. That experience has stayed with him ever since, and it eventually shaped the way he approached work, family, risk, service, and humor.

We also talk about the unexpected school fundraising meeting that changed the direction of his career. What began as a simple effort to help his son's choir travel overseas became the start of a decades-long calling: helping nonprofits raise money with purpose, structure, and joy.

What struck me most is how Jay connects courage and laughter. Whether he's talking about war, entrepreneurship, fundraising, or performing comedy for older adults, Jay always to a series of simple truths: Life is short, fear is real, and some of the best things in life are around the corner if we're only willing to let go.

In this episode, we explore:

• The life-changing lesson Jay learned as a helicopter pilot in Vietnam

• Why gratitude can become a way of living, not just a feeling

• How one school fundraiser became a turning point in Jay's career

• What it means to "let go of the side of the pool" when fear is holding us back

• Why humor helps people focus, connect, and feel alive

• The importance of telling people what they mean to us while we still can

Sincere thanks to Lee Williams for producing this and every episode of Perennial Pen (What Matters Most).

Find Jay online:

Boomer Comedian on YouTube: https://www.youtube.com/@boomercomedian 

LinkedIn: https://www.linkedin.com/in/jay-fiske-0966a/ 

MaestroSoft bio: https://www.maestrosoft.com/jay-fiske 

Reflection question:
Who is one person in your life you'd want to thank, encourage, or honor if you knew tomorrow wasn't guaranteed? (Bonus: Get going and say that thing to them - right now!)

Call to action:
If you or someone you know has a meaningful, life-affirming story to share on Perennial Pen, email me at nate@silvermaplestrategies.com. I reply to every message personally, and I'm always looking for amazing guests and stories to feature.

Until next time, listen for what matters most.