
Hosted by Jason Wright · EN

The Competitive Advantage of Saying "I Don't Know"What if the greatest competitive advantage in your career isn't intelligence—but intellectual humility?In this Monday Morning Mentor, Jason Wright explores one of the most overlooked leadership traits: the willingness to admit you might be wrong. While most people waste energy defending their opinions, history's greatest leaders built their success by questioning their own assumptions.Drawing lessons from Abraham Lincoln, Charlie Munger, and Ray Dalio, Jason explains why the fastest learners become the strongest competitors and how adopting a "white belt mindset" can accelerate your career, strengthen your leadership, and dramatically improve your decision-making.This isn't about being modest.It's about making your ego irrelevant so your growth becomes unstoppable.

What if the best career advice you ever received came from someone who cared about more than your résumé?Welcome to the first episode of Boss Dad, a new series on The Jason Wright Show where I sit down with young professionals for honest conversations about careers, relationships, ambition, integrity, faith, failure, and figuring out adulthood.My first guest is my former employee and current mentee, Abby Neilson.About a year ago, Abby was a recent college graduate struggling to land her first real job. A phone call that was originally supposed to help her make a few connections unexpectedly turned into a job offer—and eventually into a mentorship and friendship that neither of us anticipated.Abby jokingly calls herself the “personality hire.” But what I saw was something every young professional should understand: you don’t have to know everything when you start. You have to be willing to learn, work hard, accept coaching, and grow.In this first episode, recorded over coffee at our unofficial “satellite office” in Highland Park Village, Abby and I talk about what the first year of a career can teach you—and why the right mentor can change the trajectory of your life.We discuss the pressure young professionals feel to immediately land the perfect job, make six figures, have a prestigious title, and know exactly what they want to do with their lives. The truth is, most people don’t have it all figured out at 22. Your first job isn’t your final identity. It may simply be graduate school that pays you.We also talk about one principle I have tried to instill in Abby from the beginning:Never compromise your integrity.You can recover from a bad decision. You can lose a sale. You can take the wrong job. You can change careers. You can fail and start again.But no job, title, paycheck, opportunity, or relationship is worth becoming someone you don’t respect.In this episode, we also explore:Why your willingness to learn may matter more than what you already knowHow to choose a boss or mentor who is invested in your futureWhy your first job should be viewed as paid graduate schoolThe difference between having a job and abandoning your dreamHow to pursue a passion project while still paying the billsWhy you should ask successful people for advice, not favorsHow to approach potential mentors without asking to “pick their brain”Why rejection is often redirection—and sometimes protectionThe importance of building a network before you desperately need oneWhy young professionals should stop being afraid to send the email, make the call, or ask for the meetingHow faith, family, purpose, and service can redefine what success actually meansAbby also shares how her definition of success has changed over the past year. What once looked like a title or a certain income now looks more like purpose, faith, meaningful work, relationships, and service.That evolution is exactly why I wanted to create Boss Dad.I’m 51 years old. I’ve been an entrepreneur. I’ve worked in corporate America. I’ve hired people, fired people, started businesses, made good decisions, and made plenty of bad ones. I was also once the entitled young professional who thought he deserved the title before he had earned the experience.I can’t go back and change those mistakes.But maybe I can help someone else avoid a few of them.Boss Dad is a place for young professionals to ask the questions they may not know who else to ask. Career questions. Leadership questions. Networking questions. Dating questions. Money questions. Questions about ambition, faith, failure, and the uncomfortable transition from being a student to becoming an adult.Sometimes you need a boss.Sometimes you need a mentor.And sometimes you need a Boss Dad.If you’re a young professional with a question—or you want to join us for a future conversation—we want to hear from you.And if you’re a parent, leader, executive, or mentor, share this episode with a young person who might need to hear it.This is just the beginning.Welcome to Boss Dad.

Go Lay Your Bricks: Staying Busy and Creating to Fight Anxiety and Depression Jason Wright, host of The Jason Wright Show and The Healthy CEO, shares that staying busy and creating something can help fight anxiety and depression. He references Winston Churchill’s lifelong struggle with depression, which Churchill called the “black dog,” and explains how Churchill coped by keeping occupied through painting and even laying bricks to engage his hands and mind. Wright relates this to his own experience of getting into funks and says creative projects like making a podcast or short video help him avoid doom scrolling, overeating from anxiety, and ruminating alone. While noting the value of being comfortable with boredom, he warns against prolonged negative rumination and encourages changing one’s state through movement or activity. He urges listeners to find their own “bricks” to lay and to seek help if needed. 00:00 Welcome and Shows 00:16 Stay Busy Create 00:37 Churchill Black Dog 01:28 My Creative Routine 02:06 Avoid Rumination 02:36 Change Your State 02:46 Lay Your Bricks 03:11 Creative Work Examples 03:44 Wrap Up and Help

Pax Prentiss spent ten years addicted to heroin, cocaine, and alcohol before discovering that addiction was not the root problem—but a symptom of deeper emotional pain.Today he is the co-founder of Passages Malibu, where thousands have recovered through individualized, holistic treatment rather than traditional addiction models.Jason and Pax discuss:Why people relapseChildhood traumaDepressionAnxietyMarijuanaKetamineAlcoholParentingRecoveryAuthentic healthContact Pax for a free consultation

Happy 250th America. I LOVE you!

Digital Minimalism Update: Add Friction to Break Doom-Scrolling Jason Wright shares an update on his digital minimalism effort to reduce dependence on social media and improve focus and cognitive ability, inspired by Cal Newport’s work. He deleted Instagram and YouTube from his phone (leaving them on his iPad), finding the main downside is losing easy interaction with friends via Instagram DMs, not missing the entertainment. Benefits include reading more via Apple News and books (including Ian Fleming’s Casino Royale and Dostoevsky) and feeling “down-regulated” from the urge to scroll; after reinstalling Instagram briefly for a family trip, he felt no desire to scroll and deleted it again. He compares this to quitting drinking and emphasizes environment and context. His key habit advice: add friction (small resistance) to bad habits and remove resistance to good ones. 00:00 Monday Mentor Intro 00:05 Why Digital Minimalism 01:38 Digital Diet Setup 02:30 The Biggest Con 03:33 Reading More Instead 04:22 Weekend Test Reset 06:00 YouTube Temptations 07:06 Habits And Context 09:54 Add Friction Rule 11:09 Remove Resistance To Start 13:28 Brain Wiring Takeaway 14:21 Wrap Up And Sponsor

Self-Control and Divine Masculinity Jason discusses self-control as a vital personal asset, focusing especially on masculinity, drawing on ideas from Robert Greene and Jordan Peterson. He frames self-control as an ancient and biblical principle, citing Galatians 5:22–23 and Jesus’ examples in the wilderness and the teaching to “turn the other cheek,” which he interprets as choosing restraint despite having the power to dominate, not being a doormat. He compares this to martial artists who possess capability without seeking fights, and shares workplace and childhood examples showing how losing emotional control gives others leverage and damages credibility. He argues the most admirable form of control is self-mastery—especially over emotions, words, and actions—and encourages listeners to make self-control a theme for the week, then closes with subscription requests and an Authentic Health sponsorship message. 00:00 Welcome and Theme 00:38 Why Men Need Control 01:14 Biblical Roots 02:52 Turning the Other Cheek 04:17 Dangerous but Disciplined 05:50 Workplace Composure 06:52 Childhood Lesson 07:28 Divine Masculinity 09:28 Weekly Challenge 09:49 Like Subscribe Share 10:25 Sponsor Message

Weekend Review: ‘80s/’90s Nostalgia, Simpler Times, and the Luxuries We Took for Granted Jason Wright reflects on nostalgia for the ’80s and ’90s, noting that older music is popular again and arguing that life felt simpler before today’s intense political division. He cites a Vanilla Ice interview about performers dropping out of a White House 250-year celebration over Trump and praises Ice’s wish to return to a fun, non-political era. Using a BuzzFeed list about “luxuries” from the ’80s, Jason recalls special-occasion restaurant meals (like Red Lobster), traveling to another town just to go to McDonald’s, long-distance phone charges, black-and-white TVs, small servings of orange juice, motel stays and road trips with coolers and roadside picnics, watching MTV only while traveling, wall-to-wall carpeting, real butter, and having your own bedroom. He shares family trip mishaps and vivid music memories, and invites listeners to share their own childhood luxuries and experiences. 00:00 Welcome and Nostalgia 00:21 Music Then and Now 01:54 Politics Took Over 02:37 Vanilla Ice on Fun 05:30 No More Rock Bands 07:11 BuzzFeed Luxury List 08:37 Eating Out Was Special 09:24 McDonalds Road Trip 10:29 Hand Me Downs Story 13:51 Long Distance and TV 15:30 Travel Motels MTV 19:55 Flights and Road Trips 23:22 More Old Luxuries 24:09 Kids Take It For Granted 25:45 Simplicity and Memories 28:52 Summer Memory Lane 31:06 Closing and Comments

00:00 Welcome to Monday Morning Mentor 00:20 The Future Self Concept 00:55 Living Proof of Past Discipline 01:44 Understanding Delayed Gratification 02:16 Financial Discipline and Dave Ramsey 02:56 Finding Your Art 03:54 Making Better Daily Decisions 04:45 Balancing Present and Future 05:11 Looking Back with Gratitude 05:29 Reflections on Getting Older 06:29 Write Yourself Notes 07:32 Finding the Balance 08:42 Final Thoughts and Motivation

Write Your Ideal Self: Lessons from “Rooster” and Monday Morning Mentorship Jason Wright hosts Monday Morning Mentor and shares an idea inspired by the HBO show “Rooster,” in which Steve Carell’s character says he writes for a hero who does what he wishes he could do. Jason encourages listeners to visualize and write down their own “ideal self” (health, relationships, parenting, partnership, presence) as defined by them, aligning with his motto “improve always in all ways” and his Vitruvian Project concept of becoming a more well-rounded human. He suggests journaling or story-form descriptions of an ideal day and asks, if you’re not that person yet, what’s holding you back. He gives a digital detox update, replacing dopamine apps with Duolingo and learning French, and discusses overcoming excuses—like the headache of self-publishing—so he can write more and publish at least one book a year. 00:00 Monday Mentor Intro 01:06 New Show Discovery 01:55 Rooster Premise 03:17 Write Your Ideal Self 04:07 Improve Always Mindset 05:41 Planning the Practice 07:52 Digital Detox Sidebar 09:22 Publishing Roadblocks 10:53 Commit to Daily Writing 11:56 Challenge and Wrap Up 12:19 Sponsor and Sign Off