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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 episodes
- 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 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
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55 min - 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 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/
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On LinkedIn: https://www.linkedin.com/in/themichaeljacobs/
53 min - 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 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
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On LinkedIn: https://www.linkedin.com/in/themichaeljacobs
53 min - 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 conflict
- Build healthier communication patterns inside relationships and parenting
- Create alignment between career, family, and personal values
- Stop using work as an escape from unresolved problems at home
- Address shame honestly instead of carrying it silently
- Create healthier boundaries that support long term work life balance
- Stay grounded in your values during stressful seasons of fatherhood and work
Mylena’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/
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On your podcast player of choice: rss.com/podcasts/gaptogig/
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On LinkedIn: linkedin.com/in/themichaeljacobs/
51 min - 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 income
- Build work life balance by creating intentional constraints and boundaries
- Stop letting work expand endlessly into family time
- Create businesses that support your life instead of consuming it
- Build generational habits that shape your family long after money is gone
For 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
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On LinkedIn: https://www.linkedin.com/in/themichaeljacobs/
46 min - 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 mode
- Transition intentionally from work stress into parenting time
- Recognize self-sabotaging thoughts before they spiral
- Stop carrying workplace pressure into family interactions
- Respond to stressful parenting moments with more calm and less reactivity
- Model emotional openness and healthy behavior for your kids
- Reduce comparison and external pressure as a working dad
For 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/
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On LinkedIn: https://www.linkedin.com/in/themichaeljacobs/
45 min - Matt Campbell on Rebuilding Energy, Presence, and Work Life Balance in Fatherhood
Why do so many working dads feel exhausted even when they’re doing everything "right"?
Dr. Matt Campbell believes the problem is not that most people are broken. It’s that they’re depleted.
Matt is a clinical psychologist and creator of the Primal Five Framework, which focuses on five foundational areas that shape how we show up every day: sleep, sunlight, movement, connection, and consumption. His work explores how modern life quietly pulls us away from the things our minds and bodies were built for and how that depletion affects everything from patience and anxiety to parenting and meaningful work.
Matt shares how to:
- Recognize when exhaustion is really a capacity problem instead of a time problem
- Improve work life balance without trying to overhaul your entire life overnight
- Build routines that reduce decision fatigue and make healthy habits easier
- Find practical ways to incorporate movement into an already busy schedule
- Create meaningful connection instead of surface-level social interaction
- Break cycles of depletion, irritability, anxiety, and overwhelm
Matt brings a thoughtful and deeply practical perspective to fatherhood, parenting, and the reality of trying to stay healthy while balancing work, family, and daily responsibilities.
Dig Deeper
Our Epidemic of Loneliness and Isolation
Scooby-Doo Theme Song
Thunder Road
You Never Even Called Me by My Name
Follow Matt
On his website: https://www.ourprimal5.com/
On his newsletter: https://our-primal-5.kit.com/9b41ee5325
On Instagram: https://instagram.com/ourprimal5
On LinkedIn: https://www.linkedin.com/in/matt-campbell-a5b22910/
Get the Our Primal 5 Workbook: https://amzn.to/48Qoe9h
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On LinkedIn: https://www.linkedin.com/in/themichaeljacobs/
1 hr 1 min - Mike Weyandt on Presence, Identity, and Navigating Fatherhood Through Uncertainty
What happens when your life changes faster than you can process it?
For Mike Weyandt, the shift into fatherhood came all at once. A long, uncertain adoption process suddenly turned into bringing home a newborn in a matter of weeks. At the same time, his career path was in flux, and shortly after, the world shut down.
What followed was a season filled with constant change, new responsibilities, and very little time to step back and make sense of it all.
Mike brings a rare combination of perspectives. As a former opera performer, he understands what it means to be fully present when it matters most. As a talent leader and executive coach, he has helped others navigate uncertainty in their careers. And as a dad, he has lived through the reality of balancing meaningful work, identity shifts, and the everyday demands of parenting.
Mike shares how to:
- Recognize and interrupt reactive patterns in both work and parenting
- Build awareness around the thoughts that drive stress and overwhelm
- Stay present when everything around you feels uncertain
- Balance ambition with the realities of fatherhood and daily life
- Move from constant reaction to more intentional decision-making
- Let go of “should” thinking and challenge inherited assumptions
- Handle career uncertainty without defaulting to ineffective busy work
- Accept that growth as a parent and professional is an ongoing practice
Mike’s perspective is thoughtful, honest, and deeply practical. Especially for working dads trying to figure out work life balance while navigating change, pressure, and the desire to be more present at home.
It’s a reminder that not every season needs to be solved immediately. Sometimes the real work is learning how to stay grounded while everything is still unfolding.
Dig Deeper
ADHD
Never Eat Alone
Bluey
Crazy by Patsy Cline
Follow Mike
On his website: analogpractice.work
On LinkedIn: https://www.linkedin.com/in/mweyandt/
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On LinkedIn: https://www.linkedin.com/in/themichaeljacobs/
1 hr 4 min - Rob Capili on Rebuilding Life After Divorce and Raising Resilient Kids
What does it actually look like to rebuild your life after everything falls apart?
Rob Capili has lived through it. Divorce, career pivots, identity shifts, and the long process of starting over while still showing up as a father. His path has never been linear. From tech to filmmaking to music to entrepreneurship, he has followed curiosity, taken risks, and learned the hard way what matters and what doesn’t.
But some of his most important lessons didn't come from success. They came from failure, from relationships that didn't work, and from the responsibility of raising kids through difficult transitions.
This conversation is raw, honest, and grounded in real experience. Especially for working dads trying to navigate fatherhood, work life balance, and the pressure to get it right while figuring it out in real time.
Rob shares how to:
- Rebuild your identity and direction after divorce
- Balance honesty with protecting your children during difficult seasons
- Let go of perfection and focus on being present as a parent
- Give kids the space to make their own decisions while still guiding them
- Shift from outcome-based thinking to focusing on effort and process
- Recognize what you will and will not tolerate in relationships moving forward
- Use failure, setbacks, and painful experiences as fuel for growth
- Follow curiosity and creativity while still carrying real responsibility
Rob’s perspective is direct, thoughtful, and often unexpectedly funny. A reminder that even in the hardest seasons, there is a path forward.
Dig Deeper
Brazilian Jiu-Jitsu
Barney
Back That Azz Up by Juvenile
Follow Rob
On his website: robcapili.com
Lovers Quarrel: https://www.kickstarter.com/projects/robcapili/lovers-quarrel-a-graphic-novel
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51 min - Faisal Ensaun on Taking Ownership of Your Life and Redefining Success as a Dad
What if the life you’re building is the very thing draining you?
Faisal Ensaun’s journey spans survival, addiction, reinvention, and ultimately building a life rooted in purpose, ownership, and alignment. From immigrating out of a war-torn country to hitting personal rock bottom, he rebuilt his life by asking harder questions than most people are willing to face.
Today, as a coach, entrepreneur, and father, Faisal works with high performers who look successful on the outside but feel disconnected underneath.
Faisal’s perspective is intense, honest, and grounded in lived experience. Especially for dads trying to navigate fatherhood, meaningful work, and the pressure to provide without losing themselves in the process.
Dig Deeper
Gabor Maté
Naraka
Pink Panther
Tom and Jerry
Wonderland
Scare Away the Dark by Passenger
Follow Faisal
On his website: https://www.faisalensaun.com/
On his podcast: https://open.spotify.com/show/2IhYB1waklQjJWPkDKeU66
On X: https://x.com/faisalensaun
On Instagram: https://www.instagram.com/faisalensaun/
On Facebook: https://www.facebook.com/faisalensaun1
On TikTok: https://www.tiktok.com/@faisalensaun
On YouTube: https://www.youtube.com/@faisalensaun
On LinkedIn: https://www.linkedin.com/in/faisalensaun/
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59 min
About Gap to Gig – Working Dads' Guide to Fatherhood, Meaningful Work, & Finding Balance in Life
From the publisher's feed
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.