Win the Day

“The impediment to action advances action. What stands in the way becomes the way.” — Marcus Aurelius
Caleb Ulffers is the internet’s favorite curator of “little luxuries.”
At his core, Caleb is obsessed with intentional living—designing products, spaces, routines, and even his own mind to create more flow, clarity, and performance.
He’s helped build startup ecosystems, produced nationally recognized conferences, exited companies in health and software, and taught product design to Fortune 500 teams.
More recently, he’s grown a content audience of 250K+ followers by sharing his taste for “little luxuries” and thoughtfully curated consumer products—building both influence and six-figure brand partnerships along the way.
In this episode:
• When it’s time for you to take a different path in your life.
• How your environment shapes your energy.
• The blueprint to consistently go viral on social media.
• Why building in public accelerates trust.
Let’s WIN THE DAY with Caleb Ulffers!
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🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/280-win-the-day-podcast-caleb-ulffers
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Episode links:
🎯 What’s the ONE thing the world’s top performers do to win their day? Download your FREE playbook “50 Ways to Win the Day” and find out
🕺 Caleb Ulffers TikTok
📷 Caleb Ulffers Instagram
📝 Caleb Ulffers LinkedIn
⚡ Caleb Ulffers ⁠website⁠
🎬 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
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Timemarkers:
00:00 Meet Caleb Ulffers: from $5M gym bag company to viral "little luxuries" creator 
2:19 Growing up as the youngest of four in a tiny Nebraska town
4:08 What homeschooling taught Caleb Ulffers — and what it got wrong
8:20 The Starbucks moment: when the dream you were sold turns out to be a lie
12:52 How the startup world gave Caleb Ulffers a new path after corporate life failed him 
15:05 Why experience is the product: lessons from designing a world-class conference 
21:30 How to go viral on social media: the content formula behind 250K followers
30:00 The exact course and cheap home setup that launched Caleb's content career
33:22 How to design your life: AB testing, personality tests, and intentional routines
37:00 Why most people consume self-help content but never actually change
38:32 Too much consumption, not enough digestion — how to learn from what you consume
42:01 Why cutting out news, negative music, and draining people will make you happier 
43:15 Why clarity — not motivation — is what actually moves you forward
46:21 What winning the day really means (and how the answer changes over time) 
47:38 The best coffee products worth knowing about, according to Caleb Ulffers
49:31 The two daily affirmations that will completely change how you see hard times
52:30 Rocket Round
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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…
#WinTheDay
PS — Enjoyed this episode? You'll love this one, too:⁠⁠⁠ ⁠⁠Episode 258: Wealthy & Well Known with Rory Vaden

"If you don't fill your day with high-priority actions that inspire you, your day will fill up with low-priority actions that distract you." —Dr. John Demartini
Three months into writing what was supposed to be my most important project, I was drowning.
The task was to write a modern companion to Think and Grow Rich, the bestselling self-help book of all time.
I had one year, a firm deadline, and interviews locked in with people well above my paygrade: Barbara Corcoran, Bob Proctor, Rob Dyrdek.
The book would be released alongside a multimillion-dollar film. The pressure was immense.
So how do you turn things around when everything is working against you? Let's find out...
Onward,
James
PS —⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Want to bring this thinking to your team? Learn more about how Win the Day helps organizations operate at their potential.
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Listening on Spotify?
Leave a comment to share your thoughts.
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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.
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Your support is greatly appreciated 💜
#WinTheDay

“Whatever we plant in our minds and nourish with repetition and emotion will one day become a reality.” — Earl Nightingale
Dr. Caroline Leaf is a world-renowned neuroscientist and leading expert in mind-management, neuroplasticity, and emotional resilience.
With 40 years of groundbreaking research, Dr. Leaf has pioneered the understanding of how our thoughts shape our brain, behaviors, and overall well-being.
At the heart of her mission is the science of neuroplasticity: the brain's incredible ability to change and rewire itself.
Her bestselling books—including The Perfect You, Switch On Your Brain, and Cleaning Up Your Mental Mess—have sold millions, inspiring countless individuals to take charge of their mental and emotional lives.
In this episode:
• How to shift from survival mode to success
• Why anxiety is a signal—not your identity
• Why most habits don’t stick—and what to do instead
• How to rewire your thinking using neuroplasticity
Let’s WIN THE DAY with Dr. Caroline Leaf!
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🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/278-win-the-day-podcast-caroline-leaf
_
Episode links:
🎯 What’s the #1 thing the world’s top performers do to Win the Day? Download your free playbook ⁠‘50 Ways to Win the Day’⁠ now
 🎁 Get $50 OFF the 21 Day Brain Detox course
⚡ Dr. Caroline Leaf website
📷 Dr. Caroline Leaf Instagram
📝 Dr. Caroline Leaf Facebook
📱 Dr. Caroline Leaf TikTok
📚 Books by Dr. Caroline Leaf
🎬 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
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Timemarkers:
00:00 Meet Dr. Caroline Leaf: 40 years of rewiring the brain
1:35 Interview starts
2:01 Who first believed in you — and why borrowed belief changes everything
3:09 How neuroplasticity was discovered (and why doctors got it wrong)
5:06 Why choice — not knowledge — is what actually heals you
6:05 Why people consume self-help content but never change
8:58 How much control you really have over your thoughts
13:21 How environment, food, and relationships shape your thinking
14:59 Why labels like anxiety and ADHD are holding you back
18:53 How James Whittaker overcame debilitating anxiety — and what finally worked
29:02 How to find the source of your anxiety (and actually heal it)
35:13 The 5-step Neurocycle: how to rewire your brain in 63 days
37:23 Why habits don't stick after 21 days — and what to do instead
41:04 How to make disgust and shame work for you, not against you
43:30 Why you can't change someone else — and what you can do instead
46:26 Parenting tips from a neuroscientist: how to raise strong and motivated kids
50:45 Why you should be more honest with your kids (your kids always think your bad mood is their fault)
56:32 The science of consciousness and what's changing in mental health
58:29 Rocket Round
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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…
#WinTheDay
PS — Enjoyed this episode? You'll love this one, too:⁠⁠⁠ ⁠Episode 176: Your Path to Health, Healing and Happiness with Dr. David Rabin

"Make yourself happy first thing in the morning, and you give yourself the best chance of success." – Chris Voss
I've interviewed 600+ of the world's top performers—Olympic gold medalists, billion-dollar founders, world-class athletes and more.
Many of those interviews have been for this podcast, so you’ve been right there with me.
And you’ll notice there’s a question I include every single time:
"What's the ONE thing you do to win the day?"
It’s so interesting to see the knowledge and experience get distilled into a single response—a ritual.
I’ve learned that these rituals else are specific, repeatable, and available to anyone willing to act on them.
Today, we'll explore that would be worth your time over the next three days.
Onward,
James
PS —⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Want the full list of '50 Ways to Win the Day'? Download it here.
_
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.
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Your support is greatly appreciated 💜
#WinTheDay

"Children are great imitators, so give them something great to imitate." — John Wooden
Sean Donohue is one of the most trusted parenting voices in the world today. Known to millions as The Family Coach, Sean helps overwhelmed parents break toxic cycles, restore peace in the home, and raise strong, emotionally intelligent kids.
Between his high-impact parenting videos, and his podcast The Sean Donohue Show, he reaches 15M+ people each month. His new book The EQ Parent comes out this year.
In this episode:
• How to raise strong kids in a world full of noise and distraction
• Why children copy what you do far more than what you say
• How to set boundaries without damaging trust
• What overwhelmed parents can do today to restore calm in your home
Let’s WIN THE DAY with Sean Donohue!
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🎬 Episode website (including 4K video, full transcript, best quotes, etc.): https://jameswhitt.com/276-win-the-day-podcast-sean-donohue
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Episode links:
🎯 What’s the #1 thing the world’s top performers do to Win the Day? Download your free playbook ‘50 Ways to Win the Day’ now
📚 Free Book: ‘How To Break Screen Addiction and Stop It Before It Starts’
⚡ Sean Donohue website
📷 Sean Donohue Instagram
📝 Sean Donohue Facebook
📱Sean Donohue TikTok
🌎 ‘The Family Coach’ YouTube
🎤’Sean Donohue Show’ Podcast
🎬 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
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Timemarkers:
00:00 Who is Sean Donohue
1:23 Interview starts
2:08 Why Sean Donohue decided to become a parent coach
4:11 Why becoming a dad at 26 revealed everything he didn't know
6:36 Why high achievers struggle to measure success at home
8:24 How a simple nature walk teaches mindfulness to kids
11:22 What you learn in homes that books can't teach you
15:20 Why kids copy what you do, not what you say
16:43 Why yelling at your kids means you've already lost
20:02 How to break generational patterns without a role model
22:09 The toughest season to be a parent
23:11 How to discipline kids without punishment or control
24:18 The power of listening with your eyes, not just your ears
26:36 Never Split the Difference by Chris Voss is actually a parenting book
27:57 The best way to discipline your kids in 2026
30:01 How to speak identity into your children every day
32:49 How to set boundaries without breaking trust
34:40 Solving the bedtime battle: a step-by-step role-play
40:54 Why kids really resist bedtime (it's not what you think)
44:36 How to build a home culture based on mutual trust
48:03 The shared problem-solving conversation that changes everything
53:31 Why sharing your feelings makes kids more obedient
54:20 How to teach kids trust through everyday moments
57:34 When should kids get phones and social media?
1:00:54 Should your kids use screens on an airplane?
1:01:48 Why we're failing to protect kids from screens
1:03:52 Should your kid use an iPad at a restaurant?
1:05:59 Should parents monitor their phone usage of kids
1:08:56 How high-performing parents accidentally create anxious kids
1:10:24 How to parent the child you have, not the child you were
1:12:05 What divorced parents need to tell their kids
1:14:36 How to motivate unmotivated kids (hint: connection first)
1:19:00 What overwhelmed parents need to do first
1:20:02 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…
#WinTheDay
PS — Enjoyed this episode? You'll love this one, too:⁠⁠⁠ ⁠Episode 228: Parenting with Purpose with Bryan Post