Gap to Gig – Working Dads' Guide to Fatherhood, Meaningful Work, & Finding Balance in Life

Michael Jacobs - Working Dads & Fatherhood Expert

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.

  1. 20h ago

    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: Raise resilient kids without trying to eliminate every obstacleHelp children build confidence by learning from failureAdapt your parenting style to fit each child’s unique personalityTeach accountability and gratitude through everyday momentsModel the values you hope your kids will carry into adulthoodBalance the demands of fatherhood, meaningful work, and being a working dadCreate family traditions that reinforce character over achievementThink beyond today’s parenting decisions to the legacy you’re building for future generationsStephen 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

    Stephen Clifford on Raising Resilient Kids as a Working Dad
  2. Aug 11

    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. 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 decisionsRecognize when it’s time to pivot instead of pushing throughNavigate difficult managers and unhealthy workplace culturesSeparate temporary frustration from deeper career misalignmentIncrease your visibility so new opportunities can find youBuild relationships that support both your career and your personal growthDefine what meaningful work actually means for youMake career decisions with greater clarity and confidenceNatalie 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

    Natalie Holder on Why Working Dads Need a Personal Board of Directors
  3. Aug 4

    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 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 purposeSeparate your self-worth from your professional successIdentify the “shoulds” that are influencing your decisionsBuild a healthier relationship with achievement and validationCreate space for reflection instead of constant strivingNavigate modern dad challenges without losing yourself in workPursue meaningful work without tying your identity to outcomesAndrew 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

    Andrew Poles on Dad Identity, Ambition, and the Pressure to Succeed
  4. Jul 28

    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 misaligned lifeCreate margin for the unexpected instead of operating at full capacityThink about sequencing goals instead of stacking everything at onceBuild stronger relationships through presence and attentionCarol 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/

    Carol Enneking on Why Work Life Balance Feels So Hard
  5. Jul 21

    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 actually connected to what mattered most. Chris shares how to: Recognize when fear is driving your decisions at work and at homeStop catastrophizing worst-case scenariosBuild confidence by bringing fears into the open instead of avoiding themUse gratitude to become more present in everyday lifeChris 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

    Chris Woods on Overcoming Fear as a Working Dad
  6. Jul 14

    Mylena Sutton on the Conversations Working Dads Keep Avoiding

    What happens when the conversations working dads avoid at home start affecting every other part of their lives? Mylena Sutton believes leadership is not something you turn on at work and leave behind at home. The way you handle conflict, stress, shame, communication, and emotional pressure follows you everywhere. For working dads trying to balance career demands, parenting, relationships, and personal identity, that truth can be uncomfortable, but necessary. This conversation explores how emotional avoidance, resentment, shame, and overwork quietly shape fatherhood, parenting, relationships, and work life balance. Mylena shares how to: Handle difficult conversations before they explode into conflictBuild healthier communication patterns inside relationships and parentingCreate alignment between career, family, and personal valuesStop using work as an escape from unresolved problems at homeAddress shame honestly instead of carrying it silentlyCreate healthier boundaries that support long term work life balanceStay grounded in your values during stressful seasons of fatherhood and workMylena’s perspective is direct, thoughtful, and deeply practical. She challenges the idea that dads should simply carry everything silently and instead encourages more honesty, more intentionality, and more alignment between the life you want and the life you are actively building. This conversation offers meaningful insight for working dads navigating parenting, leadership, relationships, and the emotional realities that often go unspoken. Dig Deeper Uno Pink Panther Federal Aviation Administration Rock Steady by Aretha Franklin Follow Mylena On her website: mylenasutton.com/invitations On Instagram: instagram.com/mylenasutton On LinkedIn: linkedin.com/in/mylenasutton On her podcast, The Leadership Drives: theleadershipdrives.com/ 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: rss.com/podcasts/gaptogig/ Sign up for the Gap to Gig newsletter: gaptogig.com Follow Michael On LinkedIn: linkedin.com/in/themichaeljacobs/

    Mylena Sutton on the Conversations Working Dads Keep Avoiding
  7. Jul 7

    Jason VanDevere on Building Generational Habits Through Fatherhood and Entrepreneurship

    What if success is not about building generational wealth, but building generational habits? Jason VanDevere walked away from a future most people would never leave behind. Instead of taking over his family’s successful auto dealership business, he chose to build his own path through entrepreneurship, real estate investing, and coaching. Becoming a father changed how he thinks about ambition, work life balance, and what success is actually supposed to lead to. Jason shares how to: Define success based on lifestyle and values instead of status or incomeBuild work life balance by creating intentional constraints and boundariesStop letting work expand endlessly into family timeCreate businesses that support your life instead of consuming itBuild generational habits that shape your family long after money is goneFor dads trying to balance fatherhood, entrepreneurship, and the desire to build a meaningful life for the next generation, this conversation offers both clarity and actionable perspective. Dig Deeper Ice Bath https://en.wikipedia.org/wiki/SMART_criteria_ Barney The Lion King Stacy’s Mom Follow Jason On his website: https://goalcrazy.com/ On Instagram: https://www.instagram.com/goal.crazy Goal Crazy on Amazon: https://amzn.to/4v8Lo3w Read his book, Dream Driven: https://amzn.to/4dK7lPj Grab the Idea to Profit Blueprint: https://www.goalcrazy.com/blueprint Check out his podcast 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/

    Jason VanDevere on Building Generational Habits Through Fatherhood and Entrepreneurship
  8. Jun 30

    Colin C. Thompson on Mental Fitness for Working Dads

    How do you stay calm, present, and emotionally available when life keeps pulling you in every direction at once? Colin C. Thompson believes the answer starts with mental fitness. As a coach, speaker, and certified Positive Intelligence practitioner, Colin works with people who feel stuck between pressure, responsibility, and the constant demands of work and family life. His approach focuses on helping dads recognize the thought patterns, habits, and emotional reactions that quietly shape how they show up every day. This conversation explores how working dads can build mental fitness instead of constantly operating in survival mode. Colin breaks down the mental habits that create more presence, patience, emotional control, and healthier work life balance at home and at work. Colin shares how to: Create healthier boundaries between work mode and family modeTransition intentionally from work stress into parenting timeRecognize self-sabotaging thoughts before they spiralStop carrying workplace pressure into family interactionsRespond to stressful parenting moments with more calm and less reactivityModel emotional openness and healthy behavior for your kidsReduce comparison and external pressure as a working dadFor working dads trying to balance fatherhood, meaningful work, and the emotional pressure that comes with both, this conversation offers practical ways to build stronger mental fitness, healthier boundaries, and more intentional relationships at home. Dig Deeper Kung Fu Theater Rally’s 24K Magic by Bruno Mars Elmo the President Follow Colin On his websites: https://www.oligye.com and https://www.colincthompson.com On Facebook: https://facebook.com/colin.c.thompson On LinkedIn: https://linkedin.com/in/colincthompson/ 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/

    Colin C. Thompson on Mental Fitness for Working Dads
4.9
out of 5
34 Ratings

About

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.