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 with dads, experts, leaders, and people who have navigated their own twists and turns, host Michael Jacobs explores fatherhood, work-life balance, meaningful work, parenting, identity, ambition, relationships, and what actually matters most in modern life. Most of life's biggest decisions don't belong exclusively to work or family. They live somewhere in between, where the challenge isn't simply succeeding at work or showing up at home, but figuring out how all the pieces fit together. How do you build a meaningful career without losing yourself in it? How do you stay ambitious while remaining present for the people who matter most? How do you navigate career changes, setbacks, uncertainty, and new opportunities while still showing up for your family? How do you know if you're spending your time on the right things? This show is for working dads who feel pulled between responsibility and fulfillment, ambition and presence, work and the rest of life. The dads who don't want to wake up ten years from now wondering where the time went. Every conversation is designed to help you make more intentional choices about your work, your relationships, and the life you're building before the years have a chance to pass you by. Along the way, you'll find practical ideas, fresh perspective, and the confidence that comes from knowing you're not the only dad asking these questions.
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What is Gap to Gig – Working Dads' Guide to Fatherhood, Meaningful Work, & Finding Balance in Life?
Gap to Gig – Working Dads' Guide to Fatherhood, Meaningful Work, & Finding Balance in Life is a business podcast hosted by Unknown Host, with 0 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.
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Episode #41
Stephen Clifford on Raising Resilient Kids as a Working Dad
Aug 18, 20261h 1m
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: Raise resilient kids without trying to eliminate every obstacle Help children build confidence by learning from failure Adapt your parenting style to fit each child’s unique personality Teach accountability and gratitude through everyday moments Model the values you hope your kids will carry into adulthood Balance the demands of fatherhood, meaningful work, and being a working dad Create family traditions that reinforce character over achievement Think beyond today’s parenting decisions to the legacy you’re building for future generations Stephen offers practical encouragement for working dads navigating fatherhood, modern dad challenges, and the responsibility of raising children with character in an increasingly comfortable world. Dig Deeper The Berenstain Bears Running of the Bulls - Pamplona Teenage Mutant Ninja Turtles Ninja Rap Zombie by The Cranberries Follow Stephen On his website On Amazon On Instagram On YouTube On LinkedIn Taylor’s Job Safari on Instagram Taylor’s Job Safari on YouTube Follow Gap to Gig On Instagram On TikTok On X On YouTube On your podcast player of choice Sign up for the Gap to Gig newsletter Follow Michael On LinkedIn
Natalie Holder on Why Working Dads Need a Personal Board of Directors
Aug 11, 202657 min
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. Her personal board of directors framework provides a practical way to gain perspective, challenge your assumptions, and make better career and life decisions. Natalie shares how to: Build a personal board of directors that helps you make better career and life decisions Recognize when it’s time to pivot instead of pushing through Navigate difficult managers and unhealthy workplace cultures Separate temporary frustration from deeper career misalignment Increase your visibility so new opportunities can find you Build relationships that support both your career and your personal growth Define what meaningful work actually means for you Make career decisions with greater clarity and confidence Natalie offers practical advice for working dads navigating career transitions, meaningful work, and the challenge of building a career without losing sight of what matters most at home. Sometimes the best next step isn’t having all the answers. It’s surrounding yourself with people who help you ask better questions. Dig Deeper Starwood Hotels Stanford's National Accelerator Laboratory American Bar Association National Speakers Association Sesame Street Losing My Religion Follow Natalie On her websites: https://www.questei.org and https://www.natalieholderspeaks.com On YouTube On LinkedIn Follow Gap to Gig On Instagram On TikTok On X On YouTube On your podcast player of choice Sign up for the Gap to Gig newsletter Follow Michael On LinkedIn
Andrew Poles on Dad Identity, Ambition, and the Pressure to Succeed
Aug 4, 202654 min
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 achievement alone doesn’t answer the deeper questions about who you are and what truly matters. Andrew shares how to: Recognize when ambition is being driven by pressure instead of purpose Separate your self-worth from your professional success Identify the “shoulds” that are influencing your decisions Build a healthier relationship with achievement and validation Create space for reflection instead of constant striving Navigate modern dad challenges without losing yourself in work Pursue meaningful work without tying your identity to outcomes Andrew offers a thoughtful perspective on dad identity, fatherhood mental health, parenting and ambition, and the pressure many men feel to prove themselves through achievement. This conversation is a reminder that success is most fulfilling when it’s connected to who you are, not who you think you’re supposed to be. Dig Deeper University of Texas at Austin Baby Shark Ted Lasso Jamie Tartt James Taylor Tim Curry as Dr. Frank-N-Furter Sephora Follow Andrew On his website On Instagram On Facebook On YouTube On LinkedIn Follow Gap to Gig On Instagram On TikTok On X On YouTube On your podcast player Sign up for the newsletter Follow Michael On LinkedIn
Carol Enneking on Why Work Life Balance Feels So Hard
Jul 28, 202653 min
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 misaligned life Create margin for the unexpected instead of operating at full capacity Think about sequencing goals instead of stacking everything at once Build stronger relationships through presence and attention Carol offers practical wisdom for working dads trying to navigate fatherhood, meaningful work, and the tension between professional ambition and personal priorities. Dig Deeper Stephen Covey Sharpen the Saw Insperity The Brady Bunch Barney My Best Friend’s Girl Follow Carol On her website: https://carolenneking.com/ In her community: https://carolenneking.com/join-community/ On Facebook: https://www.facebook.com/carolenneking On Instagram: https://www.instagram.com/carol.enneking On YouTube: https://www.youtube.com/@CarolEnnekingSpeaker On LinkedIn: https://www.linkedin.com/in/caroltenneking/ Get her book, The Rebalancing Act: https://carolenneking.com/book/ Follow Gap to Gig On Instagram: instagram.com/gaptogig On TikTok: tiktok.com/@gaptogig On X: x.com/gaptogig On YouTube: youtube.com/@gaptogig On your podcast player of choice: https://rss.com/podcasts/gaptogig/ Sign up for the Gap to Gig newsletter: gaptogig.com Follow Michael On LinkedIn: https://www.linkedin.com/in/themichaeljacobs/
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 actually connected to what mattered most. Chris shares how to: Recognize when fear is driving your decisions at work and at home Stop catastrophizing worst-case scenarios Build confidence by bringing fears into the open instead of avoiding them Use gratitude to become more present in everyday life Chris offers a practical perspective for working dads trying to balance fatherhood, career growth and the pressure that comes with providing for a family. You don’t need a life-altering event to start asking better questions about your work, your priorities, and the life you want to build. Dig Deeper Cardiac Lyme disease Enneagram Peter Crone Clifton StrengthFinders The Brady Bunch Follow Chris On his website: https://chriswoodscoach.com On Instagram: https://www.instagram.com/chriswoodsleadership On YouTube: https://www.youtube.com/@chriswoodscoach On TikTok: https://www.tiktok.com/@chriswoodsleadership On LinkedIn: https://www.linkedin.com/in/chriswoods His book, Balls & Brains: https://amzn.to/4x7kzhD Follow Gap to Gig On Instagram: instagram.com/gaptogig On TikTok: tiktok.com/@gaptogig On X: x.com/gaptogig On YouTube: youtube.com/@gaptogig On your podcast player of choice: https://rss.com/podcasts/gaptogig Sign up for the Gap to Gig newsletter: gaptogig.com Follow Michael On LinkedIn: https://www.linkedin.com/in/themichaeljacobs
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