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

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 [https://en.wikipedia.org/wiki/Brazilian_jiu-jitsu] Barney [https://www.youtube.com/shorts/oeiO19qaDmQ] Back That Azz Up by Juvenile [https://www.youtube.com/watch?v=FYqmQPklI_0] Follow Rob On his website: robcapili.com [http://robcapili.com] Lovers Quarrel: https://www.kickstarter.com/projects/robcapili/lovers-quarrel-a-graphic-novel [https://www.kickstarter.com/projects/robcapili/lovers-quarrel-a-graphic-novel] Follow Gap to Gig On Instagram: instagram.com/gaptogig [http://instagram.com/gaptogig] On TikTok: tiktok.com/@gaptogig [http://tiktok.com/@gaptogig] On X: x.com/gaptogig [http://x.com/gaptogig] On YouTube: youtube.com/@gaptogig [https://youtube.com/@gaptogig] On your podcast player of choice: https://rss.com/podcasts/gaptogig/ [https://rss.com/podcasts/gaptogig/] Sign up for the Gap to Gig newsletter: gaptogig.com [http://gaptogig.com] Follow Michael On LinkedIn: https://www.linkedin.com/in/themichaeljacobs/ [https://www.linkedin.com/in/themichaeljacobs/]

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 [https://drgabormate.com/addiction/] Naraka [https://en.wikipedia.org/wiki/Naraka_(Buddhism)] Pink Panther [https://www.youtube.com/watch?v=wy0ZoiJVmQk] Tom and Jerry [https://www.imdb.com/title/tt37522729/] Wonderland [https://www.sixflags.com/canadaswonderland] Scare Away the Dark by Passenger [https://www.youtube.com/watch?v=cWKTFuAFcOY] Follow Faisal On his website: https://www.faisalensaun.com/ [https://www.faisalensaun.com/] On his podcast: https://open.spotify.com/show/2IhYB1waklQjJWPkDKeU66 [https://open.spotify.com/show/2IhYB1waklQjJWPkDKeU66] On X: https://x.com/faisalensaun [https://x.com/faisalensaun] On Instagram: https://www.instagram.com/faisalensaun/ [https://www.instagram.com/faisalensaun/] On Facebook: https://www.facebook.com/faisalensaun1 [https://www.facebook.com/faisalensaun1] On TikTok: https://www.tiktok.com/@faisalensaun [https://www.tiktok.com/@faisalensaun] On YouTube: https://www.youtube.com/@faisalensaun [https://www.youtube.com/@faisalensaun] On LinkedIn: https://www.linkedin.com/in/faisalensaun/ [https://www.linkedin.com/in/faisalensaun/] Follow Gap to Gig On Instagram: instagram.com/gaptogig [http://instagram.com/gaptogig] On TikTok: tiktok.com/@gaptogig [http://tiktok.com/@gaptogig] On X: x.com/gaptogig [http://x.com/gaptogig] On YouTube: youtube.com/@gaptogig [https://youtube.com/@gaptogig] On your podcast player of choice: https://rss.com/podcasts/gaptogig/ [https://rss.com/podcasts/gaptogig/] Sign up for the Gap to Gig newsletter: gaptogig.com [http://gaptogig.com] Follow Michael On LinkedIn: https://www.linkedin.com/in/themichaeljacobs/ [https://www.linkedin.com/in/themichaeljacobs/]

Anthony Kuo on Escaping the Success Trap and Building a Career That Actually Fits

What happens when you do everything right on paper… and still feel like something is off? Anthony Kuo knows that feeling firsthand. From performing at Carnegie Hall at 17 to climbing the corporate ladder after graduating from NYU Stern, he checked every box most people chase. But underneath the external success, something never quite clicked. Now a career satisfaction coach and founder of Untamed Career, Anthony helps high achievers untangle the gap between success and satisfaction and build careers that actually align with who they are. This conversation explores what many working dads quietly wrestle with. The tension between providing and feeling fulfilled. The pressure to keep going even when something feels misaligned. And the challenge of figuring out what you actually want when the answer is not obvious. Anthony shares how to: * Understand the difference between success and satisfaction and why both matter * Recognize when your work is draining energy instead of fueling it * Break down the overwhelming question of “what do I want?” into something actionable * Avoid burnout by paying attention to the process, not just the outcome * Navigate career changes without blowing up your life or risking stability * Understand how your career choices impact your presence as a parent Dig Deeper NYU Stern School of Business [https://www.stern.nyu.edu/] Carnegie Hall [https://www.carnegiehall.org] ADHD [https://www.nimh.nih.gov/health/topics/attention-deficit-hyperactivity-disorder-adhd] The Song That Never Ends from Lamb Chop [https://www.youtube.com/watch?v=xz6OGVCdov8] Follow Anthony On his website: https://untamedcareer.com [https://untamedcareer.com] On Instagram: https://www.instagram.com/untamedcareer/ [https://www.instagram.com/untamedcareer/] On Facebook: https://www.facebook.com/anthony.c.kuo [https://www.facebook.com/anthony.c.kuo] On YouTube: https://www.youtube.com/@untamedcareer [https://www.youtube.com/@untamedcareer] On LinkedIn: https://www.linkedin.com/in/untamedcareer/ [https://www.linkedin.com/in/untamedcareer/] Follow Gap to Gig On Instagram: instagram.com/gaptogig [http://instagram.com/gaptogig] On TikTok: tiktok.com/@gaptogig [http://tiktok.com/@gaptogig] On X: x.com/gaptogig [http://x.com/gaptogig] On YouTube: youtube.com/@gaptogig-gtg [http://youtube.com/@gaptogig-gtg] On your podcast player of choice: https://rss.com/podcasts/gaptogig/ [https://rss.com/podcasts/gaptogig/] Sign up for the Gap to Gig newsletter: gaptogig.com [http://gaptogig.com] Follow Michael On LinkedIn: https://www.linkedin.com/in/themichaeljacobs/ [https://www.linkedin.com/in/themichaeljacobs/]

Shaun Dawson on Fatherhood, Identity, and Redefining Work-Life Balance for Dads

What does it really mean to succeed as a dad when work, ambition, and identity are all pulling in different directions? Shaun Dawson, tech leader, father of two, and host of the Raising Men podcast, challenges the idea that success is defined by output alone. He shares a more grounded perspective on fatherhood, work life balance, and what working dads often get wrong when they focus too heavily on providing financially while overlooking emotional presence. Shaun shares how to: * Redefine success beyond income and external achievement * Build emotional security for your kids, not just financial security * Separate identity from output and rethink what actually gives your life meaning * Recognize when ego is shaping your parenting decisions * Stay present during everyday moments that are easy to overlook but impossible to get back * Navigate the tension between guiding your kids and letting them become who they are This is a thoughtful and honest conversation for working dads trying to build a life that balances fatherhood, meaningful work, and a deeper sense of identity. Dig Deeper Conan the Barbarian [https://en.wikipedia.org/wiki/Conan_the_Barbarian] Raising Men by Eric Davis [https://amzn.to/3OaHLu4] Bluey [https://www.bluey.tv/] Dairy Queen [https://www.dairyqueen.com/] Piano Man [https://www.youtube.com/watch?v=gxEPV4kolz0] Follow Shaun On his website and podcast: https://raising.men/ [https://raising.men/] On Instagram: https://www.instagram.com/raisingmen_podcast/ [https://www.instagram.com/raisingmen_podcast/] On Facebook: https://www.instagram.com/raisingmen_podcast/ [https://www.instagram.com/raisingmen_podcast/] On YouTube: https://www.youtube.com/@RaisingMen_Podcast [https://www.youtube.com/@RaisingMen_Podcast] On LinkedIn: https://www.linkedin.com/company/raising-men/ [https://www.linkedin.com/company/raising-men/] On TikTok: https://www.tiktok.com/@raisingmenpodcast [https://www.tiktok.com/@raisingmenpodcast] Follow Gap to Gig On Instagram: instagram.com/gaptogig [http://instagram.com/gaptogig] On TikTok: tiktok.com/@gaptogig [http://tiktok.com/@gaptogig] On X: x.com/gaptogig [http://x.com/gaptogig] On YouTube: youtube.com/@gaptogig-gtg [http://youtube.com/@gaptogig-gtg] On your podcast player of choice: https://rss.com/podcasts/gaptogig/ [https://rss.com/podcasts/gaptogig/] Sign up for the Gap to Gig newsletter: gaptogig.com [http://gaptogig.com] Follow Michael On LinkedIn: https://www.linkedin.com/in/themichaeljacobs/ [https://www.linkedin.com/in/themichaeljacobs/]

Paul Comfort on Finding Meaningful Work and Work-Life Balance as a Dad

What if the reason work feels off is not the job itself, but a lack of clarity about what you are actually built to do? Paul Comfort has spent decades helping people identify their strengths, align their careers with purpose, and build lives that feel both successful and meaningful. His work centers on the idea that most people never take the time to understand what they are uniquely wired to do. For dads trying to navigate fatherhood, career decisions, meaningful work, and work-life balance, lack of clarity can lead to frustration, burnout, and a constant feeling of being pulled in too many directions. Paul shares how to: * Identify your natural strengths and use them to guide career decisions * Recognize when you are in the wrong role versus the wrong season * Align your work with your values, personality, and long-term goals * Make better decisions about transitions, promotions, and opportunities * Help your kids think about their own strengths and future paths Dig Deeper Command & Conquer [https://www.ea.com/games/command-and-conquer] PEG Channel [https://www.fcc.gov/media/public-educational-and-governmental-access-channels-peg-channels] DiSC Profile [https://www.discprofile.com/what-is-disc] Maslow's Hierarchy of Needs [https://en.wikipedia.org/wiki/Maslow%2527s_hierarchy_of_needs_] Barney [https://www.youtube.com/shorts/oeiO19qaDmQ] Free Fallin’ [https://www.youtube.com/watch?v=1lWJXDG2i0A] Follow Paul On LinkedIn [https://www.linkedin.com/in/paulcomfort] On Instagram [https://www.instagram.com/paulwcomfort] On his show, Transit Unplugged TV [https://www.youtube.com/c/TransitUnpluggedTV] On his podcast, Transit Unplugged [https://transitunplugged.com/transit-unplugged-podcast/] Check out his book, Find Your X Factor, and take the assessment [https://findyourxfactor.ai/] Pre-order his book from B&N [https://www.barnesandnoble.com/w/find-your-x-factor-paul-comfort/1148750775] Follow Gap to Gig On Instagram: instagram.com/gaptogig [http://instagram.com/gaptogig] On TikTok: tiktok.com/@gaptogig [http://tiktok.com/@gaptogig] On X: x.com/gaptogig [http://x.com/gaptogig] On YouTube: youtube.com/@gaptogig-gtg [http://youtube.com/@gaptogig-gtg] On your podcast player of choice: https://rss.com/podcasts/gaptogig/ [https://rss.com/podcasts/gaptogig/] Sign up for the Gap to Gig newsletter: gaptogig.com [http://gaptogig.com] Follow Michael On LinkedIn: https://www.linkedin.com/in/themichaeljacobs/ [https://www.linkedin.com/in/themichaeljacobs/]