A world-class delayed gratifier who spent five years pointed the wrong way, CJ breaks down how to know when you're on the wrong path, why your work should feel like play, the "4 out of 7 days" framework, and his AAA framework for accomplishing almost anything.

A conversation about identity change and building a life you don't want to escape.

Connect with CJ: Instagram @cj.finley

I Offer Personal Skills & Mindset Coaching: https://thatryangray.com/

Connect with me on Socials: https://www.instagram.com/thatryangray/

This is a solo reflection on my conversation with Jack Lesser, and the line of his that's lived in my head ever since: the opportunity is coming, and when it gets here, I'll kick the door down.

I get into three things that conversation pulled loose. First, what it takes to get off someone else's path and onto your own — and why the moment you're finally on the right path is the moment the tracks disappear and it's just you.

Second, the borrowed voice running the narration in your head, and how I've learned to quiet it long enough to hear the one underneath that's actually mine. Third, why presence, agency, and accountability are muscles — they build, but they atrophy the second you stop using them — and the creative pilgrimage I took to rebuild mine.

This isn't a story about having it figured out. It's about sitting in the tension of not knowing, doing the work anyway, and finding some balance between who you are and who you're trying to become.

The Stupid Gap is the space between who you are and who you need to become in order to build a life that you don't want to escape.

Watch the full conversation with Jack Lesser on YouTube. I offer personal skills and mindset coaching to help you connect to your purpose, build agency, and navigate your own stupid gap — book a vibe check at https://thatryangray.com/

Instagram: https://www.instagram.com/thatryangray/

Jack walked away from a "golden handcuffs" corporate job, got dragged to the floor by his first breathwork session, and went to a 5-day retreat in Costa Rica that took the person he used to be apart and rebuilt him.

We get into identity change and the fear-based decisions that kept him stuck, what a real breathwork experience actually feels like, why focus is the superpower of 2026, proof of work as a way to live, and the strange moment he realized the intention he'd written for himself was almost word-for-word this show's tagline.

The Stupid Gap is a podcast about identity change — the space between who you are and who you need to become to build a life you don't want to escape.

Did you know I'm a personal skills & mindset coach?

If you want to know more check out my personal website below.

🌐 thatryangray.com

🔗 Get in touch with Jack: https://jacklesser.me/

This is a solo reflection on what stuck with me after sitting down with Marcus Fein — a man who spent 22 years in addiction and found the courage to start over. His story isn't the subject here (that's the full episode, linked below); it's the mirror that made me look hard at where I'm acting with courage and where I'm hiding from it.

I get into why agency isn't something you're handed — it's something you build, one act of courage at a time. I unpack how courage is a skill rather than a trait, why awareness (journaling, meditation, self-inquiry) is what lets you catch your own growth and turn it into fuel, and the harder question underneath all of it: where am I living in alignment, and where am I still numbing, avoiding, and running from my own life.

If you've ever wanted more agency over your life but didn't know where it actually starts, this one's for you.

The Stupid Gap is a show about identity change — who we become, and how we change, in order to build a life we don't want to escape.

▶ Watch the full conversation with Marcus Fein: HERE
🔗 Work with me — book a vibe check: https://thatryangray.com
📲 Follow on socials: @ThatRyanGray

If you or someone you know is struggling with substance use, the SAMHSA National Helpline is free, confidential, and available 24/7: 1-800-662-4357.

Marcus Fein got sober in his late 30s after 22 years of drinking and using, and discovered that quitting was only step one. In this conversation, he shares how childhood trauma he didn't remember until age 30 shaped two decades of addiction, what finally made him ask for help, and what rebuilding your identity after sobriety actually looks like day to day.

Now an actor in Austin, Marcus explains how acting, meditation, and daily structure became his tools for starting over — and why, at 40, he feels like a kid seeing the world for the first time.

The Stupid Gap is the space between who you are, and who you need to become, in order to build a life that you don't want to escape.

New episodes weekly at thatryangray.com.

Follow on all socials: @ThatRyanGray

If you're struggling with substance use, the SAMHSA National Helpline is 1-800-662-4357 (free, confidential, 24/7).

Robin is someone who performs at an elite level across multiple arenas — pro sports, business, and a strong committed relationship. The throughline isn't talent. It's the conscious choices he's made about who he surrounds himself with and how he deals with what's broken inside him.

In this episode, I share what that conversation stirred up for me — personally, honestly, and without the polish.

In This Episode:

• Why your choice of partner is the single most important decision you'll ever make
• My own path through avoiding commitment, exploring ENM/polyamory, and finding clarity
• What Robin's level of athletic discipline exposed about my own excuses
• Turning pain into fuel — Robin's story about his father, and mine about abuse and abandonment
• The cost of numbing yourself — and what happens when you stop
• Why "one percent better" is the goal, and why grace matters when you fall short

🎧 Full Robin Perségol episode: https://youtu.be/wV8qxj-2CLw?si=Y4aOTSQCQwXcU_iB

🌐 Personal Skills & Lifestyle Coaching with Ryan: thatryangray.com

00:00 Why I'm Making This Episode

01:00 Robin's Relationship: The Real Cheat Code

03:00 The #1 Life Decision Most People Get Wrong

05:00 My History With Relationships (ENM, Polyamory, Fear of Marriage)

08:30 Learning to Move Slower in Love

11:00 What Robin's Athletic Level Did to My Excuses

14:00 Stop Letting Tiredness Win

16:00 Turn Your Pain Into Fuel

19:00 Robin's Vulnerability: Father's Neglect, Insecurity, Growth

22:00 My Own Story: Abuse, Abandonment, Numbing

26:00 Stepping Into the Light

29:00 Why I Started This Show

31:00 Subscribe & Links

This conversation goes well beyond sport. Robin is a HYROX pro athlete with multiple Sub-60 finishes and a top-20 finish at the Pro World Championships. But that's not what this episode is about. We dig into what happens when the sport ends and your identity goes with it, what it looks like to use fitness as a crutch instead of a cure, and what it actually takes to become someone you respect.

In This Episode:

• Losing your identity when rugby ended — and the years of drift that followed
• Using CrossFit to numb instead of heal
• The divorce that forced him to look in the mirror
• Why your romantic relationship is the most important arena
• Going one layer deeper — understanding why you react the way you do
• Where "I'm not enough" really comes from
• How to create space in high-emotion moments instead of reacting
• Advice for anyone who feels completely lost right now

Find Robin:

📸 Instagram: @RobinPersegol

🏢 RPG Design — Gym Design & Architectural Consulting

👉 https://www.rpgdesign.co/

Books Mentioned:

📖 Clarity and Connection — Yung Pueblo

📖 Before and Laughter — Jimmy Carr

In this episode, JP opens up about the voice in his head that told him he wasn't enough — a narrative he traces back to age 12 — and the years it took to stop running from it. We go deep on depression, therapy, the burnout of chasing external validation, and what it actually looks like to rebuild yourself from the inside out.

JP is also a passionate mental health advocate. His personal battle with depression led him to co-create Move For The Mind — a community movement in Austin that raised over $1,500 for the Sims Foundation. He's the kind of guest who makes you want to go do the work.

If this conversation resonated with you, please subscribe and leave a review. It means more than you know.

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IN THIS EPISODE

- The narrative JP built at age 12 that told him he had to perform to be loved

- Burning out six months into professional golf with no one to celebrate with

- Hitting rock bottom and finally deciding to change the voice in his head

- How meditation built his muscle of self-awareness

- Reframing nerves as excitement under competitive pressure

- What manhood actually looks like to him

- Creating emotional safety in relationships

- His work with the Sims Foundation and the Move For The Mind event

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FIND JP

Instagram: @PCLE6522

SUPPORT THE SIMS FOUNDATION

Instagram: @simsfoundation

BOOKS MENTIONED

- Before and Laughter — Jimmy Carr

- White Mirror — Tinkered Thinking

- The Secret Language of the Body — Jennifer Mann & Inna Segel

In this episode of The Stupid Gap, Yash walks us through the full journey — from growing up in a top-10 ranked high school in Cupertino where the pressure to perform was relentless, to being forced into a computer science degree he hated, to showing up on day one of his corporate job at Fidelity already planning his exit at 30. He talks about picking up a camera, building a podcasting business from a gym in Austin, getting cheated on and choosing accountability over bitterness, and what it finally took to have an honest conversation with his family about the life he actually wanted to live.

This one is packed — risk, identity, emotional intelligence, the sunk cost fallacy, mimetic theory, the FIRE movement, and one of the most honest takes on infidelity and personal responsibility we've had on the show.

If you've ever felt the weight of other people's expectations pulling you away from who you actually are — this episode is for you.

📚 Book left for Yash: The Subtle Art of Not Giving a F*ck — Mark Manson

📚 Yash's recommendation: White Mirror — Tinkered Thinking (Twitter collective)

Full conversation with DJ Father Glass on the channel.

I Offer Personal Skills & Mindset Coaching: https://thatryangray.com/

Connect with me on Socials: https://www.instagram.com/thatryangray/

Full conversation with DJ Father Glass on the channel.

I Offer Personal Skills & Mindset Coaching: https://thatryangray.com/

Connect with me on Socials: https://www.instagram.com/thatryangray/

Seth — known around Austin as DJ Father Glass — spent six years too afraid to chase the one thing he actually wanted. When he finally started DJing, the same fear followed him into the booth, and so did the drinking, the all-or-nothing thinking, and a run of relapses that cost him gigs, relationships, and nearly his life. In this conversation he walks the whole arc: getting in trouble with the law as a kid, going in and out of sobriety for eight years, a night that ended with him held hostage over money he owed, and the small window of willingness that finally made him choose to live.

We get into why community beats willpower, why he books more shows sober than he ever did high, how he lost 39 pounds rebuilding his life around structure instead of chaos, the idea of building your "boardroom," and the one skill he credits for all of it — the willingness to actually look at himself.

The Stupid Gap is the space between who you are and who you need to become to build a life you don't want to escape. Honest conversations about identity change, fear, and the work of becoming.

I Offer Personal Skills & Mindset Coaching: https://thatryangray.com/

Connect with me on Socials: https://www.instagram.com/thatryangray/

CHAPTERS

0:00 Who is DJ Father Glass

2:04 From San Francisco to Austin

3:23 Six years too scared to start

7:25 Fear, the stupid gap, and not getting started too late

11:00 Why community beats doing it alone

17:28 Checking the ego and stepping back

20:11 AA, ego death, and helping the next person

24:16 The moment he decided to get sober

26:58 Relapse, willingness, and pouring out 100 beers

28:38 The sober toolbox: coaches, schedule, accountability

34:46 Looking at yourself honestly

38:28 Surrender: admitting alcohol won

41:00 Being a sober DJ in nightlife

46:57 Fitness, depression, and losing 39 pounds

51:35 Setting real goals and flexible structure

55:41 Building your boardroom

58:34 Self-awareness as the master skill

1:01:34 Spirituality, prayer, and being "religious curious"

In this episode of The Stupid Gap, Alexandra walks us through the moments that changed her — from sobbing over pizza in a Roman hostel on night one, to sitting in silence for a week at a Buddhist monastery, to a simple but powerful shift in language that transformed how she relates to her emotions.

We get into solo travel and how it forces presence, the difference between expectations and intentions, why meditation isn't a quick fix, the role of ritual in building a mindfulness practice, and how to reframe your experience so that it creates space between you and your emotions.

If you've ever felt stuck, anxious, or like you're waiting for permission to go do the thing — this one's for you.

📖 Book recommendation from Alexandra: The Miracle of Mindfulness by Thich Nhat Hanh

Chapters

00:00 Intro: Alexandra's Journey & What Brought Her Here

01:43 Moving to Italy at 21: Renaissance Studies & Finding a Purpose

04:40 Solo Traveling for the First Time: Taking the Leap

07:28 The Rush of a New Idea: Excitement, Anxiety & Wanting Change

11:56 Mentors, Planning & Overcoming Pre-Trip Doubt

15:38 Crying in Rome: The Reality of Solo Travel vs. The Dream

18:14 How to Survive the Overwhelm of Solo Travel

20:44 Failing Forward: Why the First Rep Is Always the Hardest

24:02 How to Stop Yourself From Backing Out of Hard Things

28:37 Finding Community & Why Accountability Doesn't Have to Be Loud

30:31 What Is Zen Buddhism? A Beginner's Overview

35:10 How Alexandra Found Buddhism: Breakups, Books & a Silent Retreat

39:28 Life Before & After Meditation: Anxiety, Therapy & Real Change

44:07 Why Meditation Isn't a Quick Fix (And What It Actually Is)

46:00 Expectations vs. Reality: How to Hold Them Loosely

48:37 Intentions Over Expectations: Controlling the Controllables

54:16 The Power of Ritual: Using Your Senses to Get Present

57:56 Training for Hard Moments in Easy Ones

01:01:12 Recognizing Emotions Before They Become Reactions

01:05:03 "I Am" vs. "I Feel": The Language Shift That Changes Everything

01:07:10 Witnessing Your Emotions Without Becoming Them

01:10:54 Closing: Life as an Experiment & Book Recommendation

Keywords

meditation, mindfulness, mental health, intentional living, zen, zen buddhism, buddhism, solo travel, female solo travel

Takeaways

• Starting a podcast can be a fulfilling creative outlet.
• Personal growth often comes from self-awareness and curiosity about others.
• Small talk can lead to meaningful connections if approached positively.
• Overcoming fear of rejection is essential for personal growth.
• Compliments among men can foster a supportive environment.
• Uninformed optimism can lead to personal and professional growth.
• Navigating entrepreneurship involves managing self-doubt and expectations.
• Brotherhood and mentorship are crucial for men's mental health.
• Positive reinforcement can significantly impact morale and motivation.
• Balancing masculine and feminine energy is key to healthy relationships.

Chapters

00:00 Introduction to the Stupid Gap Podcast

02:49 Personal Growth and Self-Awareness

06:06 The Art of Small Talk and Connection

09:08 Overcoming Fear of Rejection

12:07 The Importance of Compliments Among Men

14:51 Uninformed Optimism and Informed Pessimism

17:48 Navigating Entrepreneurship and Self-Doubt

20:48 The Role of Brotherhood in Men's Lives

24:00 Mentorship and Support in the Fire Service

27:12 The Impact of Positive Reinforcement

29:49 Navigating Masculinity and Vulnerability

33:01 The Balance of Masculine and Feminine Energy

35:49 The Importance of Self-Discovery

39:08 Expectations vs. Intentions in Life

41:58 The Protector vs. Predator Dynamic

45:06 Building Healthy Relationships

48:06 The Journey of Self-Acceptance

51:05 Champion Mindset and Self-Confidence

53:49 Conclusion and Final Thoughts

Keywords

podcast, personal growth, self-awareness, small talk, fear of rejection, compliments, brotherhood, masculinity, vulnerability, self-acceptance