

Win the Day
James Whittaker
Ready to Win the Day®?
Hosted by 3x bestselling author, James Whittaker, the Win the Day podcast was created to reveal how the world’s best performers Win the Day … and how YOU can, too.
Featuring exclusive interviews with:
• Billion-dollar founders
• #1 NY Times bestselling authors
• Medical experts
• World champion athletes
• Special forces operators
• And more...
Hit 'subscribe' and let's #WinTheDay 🚀
Hosted by 3x bestselling author, James Whittaker, the Win the Day podcast was created to reveal how the world’s best performers Win the Day … and how YOU can, too.
Featuring exclusive interviews with:
• Billion-dollar founders
• #1 NY Times bestselling authors
• Medical experts
• World champion athletes
• Special forces operators
• And more...
Hit 'subscribe' and let's #WinTheDay 🚀
Episodes
Mentioned books

Sep 30, 2025 • 53min
256. Happy Hustle with Cary Jack (author, podcaster, and founder of The Happy Hustle) 😊
“Choose a job you love, and you will never have to work a day in your life.” — ConfuciusCary Jack is the founder of The Happy Hustle, a top-ranked podcast and movement dedicated to helping people achieve balance, freedom, and purpose.After burning out as a tech entrepreneur, Cary made a radical shift — trading 80-hour weeks for a 20-hour workweek that still generates millions in revenue.Now, through his bestselling book, wilderness masterminds, and global stage presence, Cary is showing people how to align their work with their well-being. In doing so, Cary has proven that you don’t have to sacrifice health and happiness to achieve big goals — you just have to rethink your approach.Cary lives in Bozeman, Montana, with his wife and son, where he can be found fly fishing for rainbows, riding his noble steed, and snowboarding fresh powder. In this episode:• The “More Disease” and how to fill yourself with gratitude.• The limiting beliefs holding you back from the life you want.• Why energy and health are your ultimate performance levers.• How to bring more happiness into each and every day.🍿 Let’s WIN THE DAY with Cary Jack!_🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/256-win-the-day-podcast-cary-jack_Episode links:🎯 Download your FREE Win the Day action plan⚡ Cary Jack website📷 Cary Jack Instagram📚 ‘The Happy Hustle’ by Cary Jack🎤 The Happy Hustle Podcast by Cary Jack🎬 Subscribe to Win the Day YouTube channel💚 Give the Win the Day podcast a 5-star rating on Apple Podcasts🙏 Give the Win the Day podcast a 5-star rating on Spotify_Timemarkers:00:00 Who is Cary Jack1:29 Interview starts2:17 Focus on ONE thing at once4:50 Living a life that’s not yours7:15 Origins of The Happy Hustle 9:12 The 3 types of freedom we all need10:06 Should you stay in a corporate job or start a business13:35 4 questions to build your personal brand16:28 The “More Disease” (know when enough is enough)19:00 Why you’re burned out at work22:18 Know your MVTs (Most Valuable Tasks) every day24:31 The SOULMAPPIN Framework (an operating system for high performance)26:40 Get outdoors more often29:28 How to bring more joy to your life33:26 What it’s like living in Montana36:42 How becoming a parent changes your life — and your marriage38:50 Balance equals happiness40:45 Know what success means to you41:35 Lessons from the most successful people in the world43:40 The best wearable tech is your own mind46:02 Affirmation47:50 Rocket Round_Want to support the show?1. Hit 'Follow'.2. Leave a 5-star rating.3. Share this episode with a friend.This will help the podcast get discovered by more people so they can Win the Day, too.Thank you for your support! It truly means a lot 💕Onward and upward always…#WinTheDayPS — Enjoyed this episode? You'll love this one, too: Episode 250: Masters of Uncertainty with Rich Diviney

Sep 24, 2025 • 19min
255. 11 Lifestyle Changes: What's In — and What's Out 🎡
"They always say time changes things, but you actually have to change them yourself." — Andy Warhol We all have those things that we love, but isn't variety the spice of life?In this minisode, I share what's in and what's out for this season of my life.What are some changes you've been making? Drop a comment and let us know.Onward,JamesPS — Join 20K+ other subscribers on YouTube 🍿_Links and resources mentioned:Episode 233Episode 191Listening on Spotify?Leave a comment to share your thoughts.Want to support the show?Hit 'Follow' and leave a 5-star rating to help others #WinTheDay.💕 Leave a review on Apple Podcasts: https://apple.co/3b29Q2U🙏 Leave a 5-star rating on Spotify: https://spoti.fi/3cKIDT6 Loving the episode? Share it with a friend so they can benefit, too._Your support is greatly appreciated 💜#WinTheDayIn case you missed it: Episode 250: Masters of Uncertainty with Rich Diviney (Navy SEAL Commander)

13 snips
Sep 16, 2025 • 1h 15min
254. Win Monday with Paul Epstein (author; sports leader; executive coach) 🏎️
Paul Epstein, a two-time bestselling author and renowned speaker, shares his expertise in turning high-pressure moments into momentum. He emphasizes how to transform Mondays into powerful launchpads for the week. Paul discusses the importance of clarity in decision-making during tough times and the need to foster a proactive team culture. He advocates for personal accountability and outlines strategies for effective morning routines, encouraging listeners to embrace feedback and build strong emotional connections in leadership.

Sep 10, 2025 • 12min
253. What Conversation Are You Avoiding? 🤔
"Ultimately, the bond of all companionship, whether in marriage or friendship, is conversation." — Oscar WildeWhat's the fastest way to close the gap between your life today and your potential? Have the conversation you've been avoiding.In this minisode, we'll get clear on exactly what this is for you—and how to confront it, once and for all...Onward,JamesPS — Join 20K+ other subscribers on YouTube 🍿_Listening on Spotify?Leave a comment to share your thoughts.Want to support the show?Hit 'Follow' and leave a 5-star rating to help others #WinTheDay.💕 Leave a review on Apple Podcasts: https://apple.co/3b29Q2U🙏 Leave a 5-star rating on Spotify: https://spoti.fi/3cKIDT6 Loving the episode? Share it with a friend so they can benefit, too._Your support is greatly appreciated 💜#WinTheDayIn case you missed it: Episode 250: Masters of Uncertainty with Rich Diviney (Navy SEAL Commander)

Sep 2, 2025 • 46min
252. Transform Your 20s — Helping Young Adults Thrive with Livi Redden (TED speaker, author) 🧠
“When you want something, all the universe conspires in helping you to achieve it.” ― Paulo Coelho (The Alchemist)Why are so many young people struggling to find their way? 🧐As someone who speaks at schools and universities, I’ve seen the mental health crisis up close—apathy, disconnection, and a lack of purpose are real.But one person is on a mission to change that for good...Livi Redden, a TED speaker (2.7M+ views), author, and passionate leader, is dedicated to empowering the next generation to live happy, resilient, and purpose-driven lives.Her mission began at 17, when she held her father’s hand as he passed after a six-year battle with ALS. That moment shaped her relentless drive to help others find peace and purpose.Through her work, Livi inspires young people to build lives they love and embrace who they truly are. It’s hard to imagine a more vital mission for today’s world.In this episode:• The biggest challenges facing young people today—and what to do about them.• How to embrace your full self, even when the world tells you to shrink.• The truth about grief, growth, and finding peace in the hardest moments.• Why your future is brighter—and more in your hands—than you realize.🍿Let’s WIN THE DAY with Livi Redden!_🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/252-win-the-day-podcast-livi-redden_Episode links:🎯 Download your FREE Win the Day action plan🎤 TEDx Talk ‘What Nobody Tells You About Your Twenties’ by Livi Redden📱 Livi Redden TikTok🤝 Livi Redden online community ‘The Sooner, The Better’📚 ‘The Sooner You Know, The Better’ by Livi Redden⚡ Livi Redden website📷 Livi Redden Instagram🎬 Subscribe to Win the Day YouTube channel💚 Give the Win the Day podcast a 5-star rating on Apple Podcasts🙏 Give the Win the Day podcast a 5-star rating on Spotify_Timemarkers:00:00 Who is Livi Redden1:39 Interview starts2:28 When Livi Redden’s father was diagnosed with ALS3:39 Caring for someone with ALS or chronic health issues9:21 How to find the gift in pain11:35 Leveraging pain to find your mission12:38 Life in your 20s (use intention to improve the quality and trajectory of your life)14:24 What teens and young adults struggle with most today (and why your relationship with yourself is most important)16:41 How high schools can be improved20:42 Best advice for young people22:24 What teenagers want from their parents24:26 How parents can encourage their children to open up more27:03 How to become more confident28:40 How your past is holding you back31:22 Take radical responsibility33:00 How Livi Redden secured a TED Talk and made it go viral (2.7M+ views)38:14 Affirmation39:46 Rocket Round_Want to support the show?1. Hit 'Follow'.2. Leave a 5-star rating.3. Share this episode with a friend.This will help the podcast get discovered by more people so they can Win the Day, too.Thank you for your support! It truly means a lot 💕Onward and upward always…#WinTheDayPS — Enjoyed this episode? You'll love this one, too: Episode 208: The Gift of Pain with Brian Bogert

Aug 27, 2025 • 9min
251. What to Do When You Feel Stuck (or Miserable) 🤔
“Happiness is not something ready-made. It comes from your own actions.” – Dalai LamaAre you feeling stuck in your life? Maybe it's a job you're disengaged from, the overwhelm of a young family, or caring for an aging parent.In this minisode, we'll go through a 3-step plan to take back control of your happiness — and your life. Onward,JamesPS — Join 20K+ other subscribers on YouTube 🍿_Listening on Spotify?Leave a comment to share your thoughts.Want to support the show?Hit 'Follow' and leave a 5-star rating to help others #WinTheDay.💕 Leave a review on Apple Podcasts: https://apple.co/3b29Q2U🙏 Leave a 5-star rating on Spotify: https://spoti.fi/3cKIDT6 Loving the episode? Share it with a friend so they can benefit, too._Your support is greatly appreciated 💜#WinTheDayIn case you missed it: Episode 250: Masters of Uncertainty with Rich Diviney

Aug 19, 2025 • 1h 19min
250. Masters of Uncertainty with Rich Diviney (Navy SEAL Commander) 🔱
“Embrace the unknown, for it is in the unfamiliar that we find the most profound inspiration.” — Oscar MaxToday’s a special one — Episode 250 of the Win the Day podcast! To celebrate, I've brought back one of our most iconic guests: Navy SEAL Commander Rich Diviney.Rich first joined us in Episode 124, and clips from that conversation have 10M+ views. Since then, he’s become a close friend and remains the most respected voice I know on leadership, mental resilience, and elite performance.Through his 20-year Navy SEAL career, Rich completed 13 deployments and held numerous leadership roles within the most elite SEAL teams, including DEVGRU (also known as SEAL Team Six). His new book Masters of Uncertainty: The Navy SEAL Way to Turn Stress into Success has just been released.In this episode:• The secrets to elite performance in every domain.• Why you should embrace the traits that make you great.• The best lessons from Rich’s career as a Navy SEAL.• How to become a master of uncertainty.🍿 Let’s WIN THE DAY with Rich Diviney!_🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/250-win-the-day-podcast-rich-diviney_Episode links:🎯 Download your FREE Win the Day action plan⚡ Rich Diviney website📚 ‘Masters of Uncertainty: The Navy SEAL Way to Turn Stress into Success’ by Rich Diviney🎙️ How to Succeed in Uncertainty with Rich Diviney (Episode 124)📷 Rich Diviney Instagram🎬 Subscribe to Win the Day YouTube channel💚 Give the Win the Day podcast a 5-star rating on Apple Podcasts🙏 Give the Win the Day podcast a 5-star rating on Spotify_Timemarkers:00:00 Who is Rich Diviney1:32 Interview starts2:00 How to become a master of uncertainty4:20 Why people fail Navy SEAL training (BUD/S)7:18 How to change your relationship with failure10:13 How to handle stress like a Navy SEAL (“Moving Horizons”)16:00 How to handle anxiety like a Navy SEAL19:49 Prioritizing yourself during Navy SEAL training (BUD/S)23:18 Can a candidate ever game Navy SEAL training?24:45 How Navy SEALs handle the cold26:10 How Navy SEALs use “cunning”28:34 How laughter can build resilience32:23 How to quickly build trust34:44 Seeing SEAL Team 6 for the first time36:18 How coachable are Tier One special forces operators37:58 How intense are special forces operators in real life39:06 How Navy SEALs stay relaxed (and how survive “drown-proofing”)41:20 What Navy SEALs do before an operation43:36 How SEAL Team 6 avoids complacency 45:43 Building a gym for your brain (“Mind Gym”)50:48 The #1 mental struggle for a special forces operator 52:47 How to stand out from your peers54:02 How to build your confidence55:25 Why fear is the #1 thing holding people back57:45 How to reframe your bad days — and use fear to your advantage1:00:03 How to motivate someone in a rut1:01:03 How to build a high-performing team1:02:55 How to handle a creative block1:05:06 How to instantly strengthen your marriage1:10:42 How to raise successful kids1:13:58 Rocket Round_Want to support the show?1. Hit 'Follow'.2. Leave a 5-star rating.3. Share this episode with a friend.This will help the podcast get discovered by more people so they can Win the Day, too.Thank you for your support! It truly means a lot 💕Onward and upward always…#WinTheDayPS — Enjoyed this episode? You'll love this one, too: Episode 154: Prepare to Win with Andrew Sullivan (SEAL Team 6)

Aug 13, 2025 • 13min
249. Thank You Haters 😉
“Learn to use the criticism as fuel and you will never run out of energy.” – Orrin WoodwardHow do you handle the haters? I posted a video recently that has 3.7M+ views on Instagram alone, attracting 5,500+ comments. Here is if you want to check it out: https://instagram.com/p/DH9aWVYTwhjIn this minisode, we dive into why the haters are wrong—and how you can leverage social media for attention.Onward,JamesPS — Join 20K+ other subscribers on YouTube 🍿_Links and resources mentioned:💗 Episode 228: Parenting with Purpose with Bryan Post 💍 Episode 245: Weekly Couples Check-In 🧲 Weekly Couples Check-In [free PDF download]_Listening on Spotify?Leave a comment to share your thoughts.Want to support the show?Hit 'Follow' and leave a 5-star rating to help others #WinTheDay.💕 Leave a review on Apple Podcasts: https://apple.co/3b29Q2U🙏 Leave a 5-star rating on Spotify: https://spoti.fi/3cKIDT6Loving the episode? Share it with a friend so they can benefit, too._Your support is greatly appreciated 💜#WinTheDayIn case you missed it: Episode 228: Parenting with Purpose with Bryan Post

Aug 5, 2025 • 1h 11min
248. Perform Under Fire with Leigh Anderson (paramedic, author 'The Paramedic Mindset') 🚑
“When we are no longer able to change a situation, we are challenged to change ourselves.” ― Viktor FranklLeigh Anderson is a renowned paramedic in some of the most extreme, high-stakes environments imaginable.His diverse operational experience across urban, rural, remote, and marine settings has given him rare insight into how the human mind responds to stress—and more importantly, how to train it to thrive under pressure.Leigh is the author of The Paramedic Mindset, a powerful guide to performing with poise, clarity, and confidence in any situation.Today, through his speaking, teaching, and writing, he brings these life-saving lessons to the public to help people show up stronger in their careers, relationships, and everyday lives.In this episode:• How to lead, adapt, and perform in high-stress environments.• Lessons from life on the front lines.• His best tips for success in everyday life.• How to use failure to your advantage.Let’s WIN THE DAY with Leigh Anderson!_🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/248-win-the-day-podcast-leigh-anderson_Episode links:🎯 Download your FREE Win the Day action plan🧠 ParaMind Online Course (for 50% off, use code: WINTHEDAY50)📚 ‘The Paramedic Mindset’ by Leigh Anderson⚡ Leigh Anderson website📷 Paramedic Mindset Instagram📝 Paramedic Mindset Facebook🎬 Subscribe to Win the Day YouTube channel💚 Give the Win the Day podcast a 5-star rating on Apple Podcasts🙏 Give the Win the Day podcast a 5-star rating on Spotify_Timemarkers:00:00 Who is Leigh Anderson1:26 Interview starts1:54 The injury that crushed Leigh’s athletic dreams5:39 The power of someone believing in you9:13 What does a paramedic do12:00 What being a paramedic teaches you about death14:05 Life is suffering (find purpose in it)16:48 The most stressful part of being a paramedic21:13 The importance of a paramedic telling the patient the truth23:40 What to do if your child is choking25:41 Treating people under the influence of drugs27:19 Do paramedics carry weapons for self-defense 29:50 Australian emergencies (snakes, sharks, box jellyfish, crocodiles)36:00 How paramedics avoid PTSD (and stay focused on the task at hand)39:35 How to become more resilient (lessons from the SAS Regiment)43:05 The gift of stress (challenge vs threat)50:38 How to manage stress in daily life56:18 The #1 paramedic habit to use every day58:40 The luckiest survival stories1:01:28 Affirmation1:02:34 Rocket Round_Want to support the show?1. Hit 'Follow'.2. Leave a 5-star rating.3. Share this episode with a friend.This will help the podcast get discovered by more people so they can Win the Day, too.Thank you for your support! It truly means a lot 💕Onward and upward always…#WinTheDayPS — Enjoyed this episode? You'll love this one, too: Episode 246: The Urban Monk with Dr. Pedram Shojai

Jul 30, 2025 • 23min
247. How I Prepare for Travel (for Business and with Kids) ✈️
"Prepare for the worst, hope for the best." — CiceroIf you travel a lot, but you're not prepared, it can be so much more stressful than it needs to be.In this minisode I’m going to share my best tips for travel so you can stay productive and hit the ground running — whether you're traveling with or without kids.Onward,JamesPS — Join 20K+ other subscribers on YouTube 🍿_Links and resources mentioned:TripItSeatGuru / AerolopaAirpods ProChomps jerkyLesser Evil popcornMack Weldon zipper sweat pantsLumify eye-whitening dropsThorne ThyrocsinThorne Vitamin D + K2_Listening on Spotify?Leave a comment to share your thoughts.Want to support the show?Hit 'Follow' and leave a 5-star rating to help others #WinTheDay.💕 Leave a review on Apple Podcasts: https://apple.co/3b29Q2U🙏 Leave a 5-star rating on Spotify: https://spoti.fi/3cKIDT6Loving the episode? Share it with a friend so they can benefit, too._Your support is greatly appreciated 💜#WinTheDayIn case you missed it: Episode 240: Rewire Your Habits with Kevin Wathey