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

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 per...

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 ...

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 overloo...

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 fatherhoo...

What if the way you show up after the game matters more than the game itself?

After more than three decades coaching and mentoring young people, Antwaun Thompson has seen a clear shift. Kids today are facing more pressure, less confidence, and more noise than ever before. And for many parents, especially working dads trying to navigate fatherhood and work-life balance, it's not always clear how to support them the right way.

This con...

Why does work that once energized you start to feel like something you can’t turn off?

Dr. David Shar studies what happens when people fall out of love with their work and why that shift often happens long before anyone notices. His research shows that for working dads, the challenge is not just workload. It is how work connects to identity, purpose, and the life you are trying to build at home.

This conversation reframes passion in ...

What if the biggest gap between your work and your life is not your schedule, but how you define success?

Alan Lazaros built what most people would call a successful life. High income, fast growth, and clear upward momentum. But after a near-fatal car accident at 26, he was forced to confront a harder question. Was any of it actually meaningful?

For working dads trying to balance ambition, work-life balance, and presence at home, thi...

Why do so many working dads feel disconnected from their kids even when they are physically present?

Modern fatherhood comes with pressures that did not exist a generation ago. Constant work demands, two-income households, packed schedules, and technology that never turns off have pushed many families into reactive mode. And when stress builds, connection is often the first thing to break.

Dr. David Marcus, a clinical psychologist wi...

What happens when you realize the career you built doesn’t actually align with the life you want?

Scott Maderer built a successful career in finance, checked the right boxes, and did the things ambitious professionals are supposed to do. But eventually he realized something important was missing. The work that once looked impressive on paper no longer felt connected to his values, his purpose, or the kind of impact he wanted to make...

What happens when your self-worth quietly becomes tied to your output?

After nearly two decades leading digital transformation work for major brands, Loren Silverman realized that success on paper didn’t equal fulfillment in real life. The titles, the grind, the constant responsibility all looked right from the outside. But underneath, something felt off.

That realization didn’t lead to a dramatic overnight reinvention. It led to som...

What does meaningful work actually look like once you become a parent?

For many professionals, the answer changes. Priorities shift. Energy changes. The things that once felt exciting or important can suddenly feel disconnected from the life you want to build.

Career strategist Julia Toothacre works with high-performing professionals who look successful on paper but quietly feel stuck, burned out, or misaligned. Her work focuses on h...

What if the key to balance is not working less, but working with intention?

Alex Tuck runs a remote-first consulting firm from a farm in Vermont while raising four young kids with his wife. His approach is simple but disciplined: block the time, protect the priorities, and design work to fit life, not the other way around.

From quarterly OKRs to daily timeboxing, Alex has built both a company and a family rhythm around clarity and st...

What happens when the job you thought would carry you to the finish line disappears overnight?

Two months into what she believed would be her final role, Merry Korn was let go. She was a single parent with two teenagers, college tuition looming, and no clear path forward. The fear was real. The pressure was immediate. Staying in bed was not an option.

What followed was not an overnight success story. It was a series of hard conversat...

What happens when health scares, job loss, and family tragedy collide all at once?

After having part of his lung removed, being laid off during the pandemic, and losing his father-in-law the same day he was discharged from the hospital, Tony Berardo was forced to confront a hard truth: work was taking up too much of the wrong space in his life.

Instead of chasing security, status, and a bigger paycheck, Tony rebuilt his life around s...

What does leadership look like when the mission is your family and the stakes are emotional, not tactical?

Brad Leeman is a retired U.S. Marine Corps Lieutenant Colonel, combat aviator, and F-35 test pilot who spent nearly two decades leading in environments where preparation, clarity, and execution were non-negotiable. After transitioning out of the military, Brad became an entrepreneur and founder of SwingSesh, a company built aro...

How do you communicate in a way that builds trust, connection, and confidence with your kids, your partner, and the people you work with every day?

Danny Brassell has spent decades teaching, coaching, and speaking around the world about storytelling, reading, and communication. This conversation explores how communication is not about polish or performance, but about meeting people where they are and staying present in the moments t...

Jon Merlin is a longtime designer who left agency life to start his own creative studio while raising two young daughters. Instead of letting work bleed into every hour, Jon drew a hard line around family time and rebuilt his business around clarity, intention, and values.

This conversation explores what it really looks like to pursue entrepreneurship without losing presence at home, and how letting go of perfection can unlock both ...

Why does work keep crowding out family time even when no one is explicitly asking it to?

Doug Fleener is an author, coach, and former corporate executive who has lived both sides of the work equation. After years of leadership roles and constant pressure, he intentionally redesigned his work around presence, health, and family. As a dad to grown daughters and a teenager, Doug brings rare perspective on how seasons of fatherhood chan...

What do you do when your career looks successful on paper, but something quietly feels off?

Stephanie Cordes is a career ownership coach who works with people at the exact moment when professional success and the life they want to live stop pointing in the same direction. She knows this moment personally. After building a successful corporate career, Stephanie realized that checking all the boxes did not automatically mean she was b...