Gap to Gig
Gap to Gig is for working dads navigating the life in between who we are, what we do, and the life we want to build. Through honest conversations, practical ideas, and grounded perspective, we help dads build meaningful work, stay present for the people who matter most, and make more intentional choices about the life they’re building.
You’re not stuck. You’re in between.
Gap to Gig explores the life in between who we are, what we do, and the life we want to build as working dads. Through honest conversations, practical ideas, and grounded perspective, we navigate fatherhood, work-life balance, meaningful work, identity, relationships, and what actually matters most.
Recent Episodes
42
Aug. 25, 2026
Rob Heller on the Lessons Every Working Dad Shouldn't Leave to School
School plays an important role in preparing our kids for the future. But some of the lessons they'll rely on most aren't taught in a classroom.
Rob Heller is an entrepreneur, author, youth development expert, and founder of Boost, a personal development program that helps teenagers build the people skills, character, and healthy mindset they need to thrive long after graduation.
In this episode, you'll learn how to:
Help kids develop people skills that shape lifelong relationships
Build char
Rob Heller is an entrepreneur, author, youth development expert, and founder of Boost, a personal development program that helps teenagers build the people skills, character, and healthy mindset they need to thrive long after graduation.
In this episode, you'll learn how to:
Help kids develop people skills that shape lifelong relationships
Build char
41
Aug. 18, 2026
Stephen Clifford on Raising Resilient Kids as a Working Dad
Raising resilient kids isn’t about protecting them from every challenge. It’s about preparing them to face challenges with confidence, character, and resilience. Stephen Clifford is an author, youth coach, speaker, and creator of the Forgotten Wisdom children’s book series. Together with his wife, he’s intentionally raising his children to embrace accountability, gratitude, perseverance, and failure as part of growth, while recognizing that every child learns differently. Stephen shares how to
40
Aug. 11, 2026
Natalie Holder on Why Working Dads Need a Personal Board of Directors
Some career decisions are too important to make alone. Whether you’re considering a career transition, navigating a difficult workplace, or trying to find more meaningful work, Natalie Holder believes one of the smartest investments you can make is building your own personal board of directors. As an employment lawyer, executive coach, and former Chief Diversity Officer, Natalie has spent years helping professionals navigate career transitions, difficult workplaces, and high-stakes decisions.
39
Aug. 4, 2026
Andrew Poles on Dad Identity, Ambition, and the Pressure to Succeed
For many dads, ambition starts with a desire to provide. The pressure to succeed, prove yourself, and live up to expectations can quietly shape your identity, your relationships, and the way you experience fatherhood. Andrew Poles knows that tension firsthand. As a single dad, he started his first business at 23 while raising his daughter and trying to build a future for his family. Over the years, he built multiple businesses, coached thousands of entrepreneurs and leaders, and learned that ac
38
July 28, 2026
Carol Enneking on Why Work Life Balance Feels So Hard
For many working dads, the challenge isn’t a lack of ambition. It’s the feeling that no matter how hard they work, there’s always another responsibility competing for their time, attention, and energy. After decades in leadership roles, including serving as a Global VP of Talent and Leadership, Carol Enneking noticed a pattern: many of the most successful people she worked with were also some of the most exhausted. Carol shares how to: Recognize the difference between a demanding season and a
37
July 21, 2026
Chris Woods on Overcoming Fear as a Working Dad
What would your life look like if fear stopped making your decisions? Chris Woods spent decades building a successful career, including leadership roles at Google. From the outside, everything looked like it was working. But underneath the success was a constant fear of failure, loss, and not measuring up. Everything changed when Chris flatlined in a hospital bed at age 40. The experience forced him to take a hard look at what was driving his choices and whether the life he was building was ac
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