Podcast Summary: The Daily Stoic — "These 3 Rules Will Make or Break Your 2026" Featuring Jesse Itzler

Podcast: The Daily Stoic
Host: Ryan Holiday
Guest: Jesse Itzler
Date: December 20, 2025

Episode Overview

Ryan Holiday interviews entrepreneur, author, and adventurer Jesse Itzler about how to design an exceptional year—specifically, how to approach 2026 with renewed intention, adventure, and personal growth. Jesse breaks down the three rules that have transformed his own life, discusses the importance of intentional planning, building a "life resume," and prioritizing meaningful experiences over routine. The conversation is practical, energizing, and filled with memorable anecdotes and actionable advice for anyone looking to live more deliberately.

Key Discussion Points & Insights

1. The Challenge and Necessity of Creating "Newness" in Midlife

• Routine vs. Innovation: As we age, it's harder to create newness; you must schedule transformative experiences—they won’t happen by accident.
• Quote:
  "As you get older... it's really hard to create newness. Like, where the hell does newness come from? You have to schedule it."
  — Jesse Itzler (08:16)

2. Jesse Itzler’s Three Life-Changing Rules

Rule 1: The Year-Defining "Misogi"

• Inspired by a Japanese ritual: each year, pick one big "year-defining thing”—a major challenge or adventure.
• This could be physical (marathon, mountain climb), mental (launching a business, writing a book), or otherwise.
• The impact is both immediate and lasting:
  "If it's truly year-defining, you're going to learn a lot about yourself and grow from it."
  — Jesse (09:41)
• This challenge brings clarity, pride, and acts as a natural filter, forcing you to eliminate less meaningful commitments.
  • Examples: Jesse completed Ultraman, RIM to rim to rim, lived with monks, launched companies.
• Quote:
  "You should be able to look back and be like, '2025? That's the year I did X.'"
  — Jesse (09:29)

Rule 2: Bi-Monthly "Mini-Adventures" (Kevin’s Rule)

• Every other month, intentionally do one thing you normally wouldn’t—adventure, excursion, unique experience.
• Origin: a friend who, every two months, took on a new small adventure for himself or with family.
• The power of compounding these experiences: If you’re 40 and do this until 80, you’ll have 240 mini-adventures and 40 major ones.
• Quote:
  "If you can't take one day out of every eight weeks and do something for yourself… your work-life balance is out of whack."
  — Jesse (12:18)
• Over time, these accumulate into a vibrant “life resume.”
  • Examples: Fishing instead of watching a game, spontaneous city trips, hiking with kids.

Rule 3: Quarterly "Winning Habits"

• Instead of New Year's resolutions (which fail quickly), introduce one specific, positive habit every quarter.
  • E.g., "I'll drink 100oz of water daily," "I'll never be late to a meeting," "Add 10 minutes of meditation."
• Focus on simplicity and sustainability to allow habits to compound.
• Quote:
  "I'm not trying to do 15 things at once. I'm just trying to slowly layer… If you add one habit a quarter, that's four a year. In just a couple years, that’s transformative."
  — Jesse (15:52)
• Build habit momentum and avoid being overwhelmed by radical change.

3. Practical Strategies for Intentional Living

The Power of Planning & The "Big Ass Calendar" (17:10–18:07; 45:16–46:48)

• Physical, year-long calendar visualizes your entire year, making it easier to fill in and see what actually matters.
• Design life around what matters first (family, health, big challenges), then let work fill in the gaps.
• Quote:
  "Most of us play life on defense... we don't need more time, we need a better system. My calendar is my operating system."
  — Jesse (17:10)

Flipping the Default: Life Before Work (20:15–23:03)

• Most people let work dictate their schedules and fill in personal time with scraps.
• Quote:
  "Work will find a way to fill the cracks for sure. The calendar doesn't lie — you did it all for work and gave the leftovers to your family."
  — Ryan (21:41)

Life by Design and Being "Time Rich" (49:11–52:16)

• Theme: Wealth isn't just money—it's about controlling your time.
• Story of a speed coach who only works as much as he wants because everything is "by design."
• The happiest people are often those in control of their schedules, not necessarily those with the most money.
• Quote:
  "He is insanely time rich... Don't minimize how important 'time rich' is. It's probably the most important thing."
  — Jesse (50:27)

4. The Significance of Personal "Rules" and Family Wisdom

Naming Rules After Influential People (23:03–25:33)

• Jesse names rules after family and friends (Kevin’s Rule, Mom’s Rule, Charlie’s Rule, Ben’s Dad’s Rule).
• Examples include: Never being too tired for your kids, always taking their hand, or supporting their interests even if they're not yours.
• Quote:
  "The people who've had the biggest impact aren’t necessarily the famous ones. They're people you meet along the way.”
  — Jesse (23:03)
• Wisdom passed down intentionally becomes a life compass.

Being Present for Children (24:36–27:27)

• Don't let exhaustion or inconvenience lead to missed opportunities with your children; accept invitations into their world as they come.
• Quote:
  "Whenever your child offers their hand, you have to take it... Whenever they're inviting you into their life, you take it."
  — Ryan, referencing Russ Roberts rule (24:37)

Five-Year View for Life Planning (28:44–29:37)

• Think of life in five-year increments; what changes are coming?
• Motivates prioritizing family and meaningful moments in the present, not deferring them for an uncertain future.

5. How to Close the Year "Light" (33:46–34:47)

• Clean out physical spaces (closet, desk, car), digital spaces (inbox), and eliminate outdated commitments.
• Write 25–50 handwritten thank you notes by year end to close out emotional debts and practice gratitude.
• Quote:
  "I write thank you letters every year... you wrap up the year, you lighten it for yourself by closing it."
  — Jesse (35:12)
• This year-end "audit" mirrors business reviews: balance the personal books.

6. Additional Habits and Practical Takeaways

Practice Gratitude Actively

• "Gratitude isn't just something you feel, it's something you do." — Ryan (36:31)
• Jesse’s thank-you note story: wrote 3,000 postcards in a year at age 22.

Charlie’s Rule: Taking Compliments Well (36:45–39:13)

• Look someone in the eye, accept compliments graciously, and “hit the tennis ball back.”
• Quote:
  "If someone's giving you a compliment... it's important to look them in the eye and hit the tennis ball back and say 'Thank you so much, that means so much to me.'"
  — Jesse (37:31)

The Value of Enthusiasm and Attitude (41:06–42:29)

• Most traits people desire in colleagues ("enthusiasm, honesty") are attitudes, not skills; anyone can choose to be this way.
• Quote:
  "Enthusiasm isn't a skill. It's a choice. It's an attitude."
  — Jesse (41:35)

Journaling as a Foundational Habit (52:16–53:18)

• Ryan journals daily, using a "one line a day for five years" system to observe trends and the passage of time.
• Quote:
  "If you're gonna pick a new habit for 2026: five minutes of journaling will make most people happier, more self-aware, calmer."
  — Ryan (52:35)

7. On Purpose, Wealth, and Life Satisfaction

• Designing for Enough: Focus less on chasing more, or “topping” yourself, more on making every day align with your values.
• Control over one's time (being "time rich") and experiences is more valuable and attainable than ever-increasing income.
• Life design is a practice accessible at every stage, not just once a certain level of success is attained.
• Quote:
  "The happiest people are those in control of their schedules, not necessarily with the most money."
  — Jesse (52:11)

8. Lessons from Extraordinary People: Asking Good Questions (58:45–61:50)

• Jesse became obsessed with learning the habits of ultra-successful individuals, asking them about their routines, not just their achievements.
• Example: A meaningful story about Warren Buffett revealing treasured childhood memories because Jesse asked about meaningful, personal topics (not stock tips).
• Quote:
  "People want to share if you ask them the right questions... If I'd said, 'What stock should I buy?' he'd have turned away, but I asked him something that hit a nerve.”
  — Jesse (61:12)

Notable Quotes & Moments (with Timestamps)

• "As you get older... it's really hard to create newness. You have to schedule it." — Jesse Itzler (08:16)
• "If you can't take one day out of every eight weeks and do something for yourself… your work-life balance is out of whack." — Jesse (12:18)
• "Enthusiasm isn't a skill. It's a choice. It's an attitude." — Jesse (41:35)
• "Work will fill in the cracks for sure. The calendar doesn't lie — you did it all for work and gave the leftovers to your family." — Ryan (21:41)
• "He is insanely time rich... Don't minimize how important 'time rich' is. It's probably the most important thing." — Jesse (50:27)
• "If someone's giving you a compliment... look them in the eye and hit the tennis ball back and say 'Thank you so much, that means so much to me.'" — Jesse (37:31)
• "Gratitude isn't just something you feel, it's something you do." — Ryan (36:31)
• "You want to see: are you getting closer or further away from the life you're trying to live? Because your life isn't someday in the future. This is your life." — Ryan (53:20)

Timestamps for Key Segments

• Jesse Introduces the Three Rules: 08:10–16:39
• On Intentional Planning and the Big Ass Calendar: 16:53–18:07 & 45:16–46:48
• Work-Life Balance & Reversing the Default: 20:15–23:03
• Naming and Sharing 'Rules': 23:03–25:33
• Year-End Reflection & Clean Slate Rituals: 33:46–34:47
• Gratitude, Thank You Notes, and Compliments: 35:12–39:13
• Enthusiasm, Attitude, and “Anyone Can Do This”: 41:06–42:29
• Being 'Time Rich' & Life by Design: 49:11–52:16
• Journaling & Reflective Habits: 52:16–53:18
• Asking the Ultra-Successful the Right Questions (Warren Buffett Story): 58:45–61:50

Final Thoughts

Jesse Itzler's approach urges listeners to actively design their years (and lives), not drift along in routine. His three rules—and the stories and wisdom behind them—make this episode a practical, motivating blueprint for directing your energy, time, and attention toward what matters in 2026 and beyond.

For more info on The Daily Stoic New Year New You Challenge, visit dailystoic.com/challenge.