Plan Your Life, Not Your Schedule

Why most people plan their year the wrong way – and how one entrepreneur wants to change that with a giant wall calendar.

Most of us know the feeling: the year is over, and we ask ourselves where the time went. The calendar was full of meetings, deadlines, and obligations. But what did we really experience? What stays in our memory?

Jesse Itzler has found a radical answer – a wall calendar bigger than most office desks, and a philosophy that turns our idea of scheduling on its head.

Who Is Jesse Itzler?

Jesse Itzler is not a typical entrepreneur. His career began in the early 1990s as a rapper on MTV – under the stage name "Jesse Jaymes," he actually landed in the charts with songs like "Shake It Like a White Girl." He managed Run-D.M.C., one of the most influential hip-hop groups of all time, and wrote the official anthem of the New York Knicks.

But that was only the beginning. Itzler founded Marquis Jet, the world's largest prepaid private jet company, and sold it to Warren Buffett's Berkshire Hathaway. He then built up Zico Coconut Water – and sold that too, this time to Coca-Cola. Today he is co-owner of the Atlanta Hawks, an NBA team.

What really sets Itzler apart, however, is not his business success. It is his approach to life itself.

The Family Behind the Entrepreneur

Jesse is married to Sara Blakely, the founder of Spanx and one of the most successful self-made billionaires in the world. Together they have four children and live in Atlanta. In interviews, Itzler emphasizes again and again that his family is the most important part of his life – and that his planning system is designed precisely to create time for the people who matter most to him.

"Most people fill their calendar with Zoom calls and appointments," says Itzler. "At the end of the year, they don't have much to show for it."

The Books: Lessons from Extreme Experiences

Itzler has captured his life philosophy in two bestsellers:

"Living with a SEAL" (2015) tells the story of how Itzler invited the Navy SEAL David Goggins – often called "the toughest man in the world" – to live with him for a month and train him. The book is hilarious and inspiring at the same time. The central lesson: when you think you're at your limit, you've only reached 40 percent of your capacity.

"Living with the Monks" (2019) documents Itzler's time in a monastery, where he learned from monks how to find calm and focus in a hectic world. The mantra he took away: "Remember Tomorrow" – with everything you do today, consider how you will feel about it tomorrow.

Both books show Itzler's method: he learns not from books, but through radical immersion in new worlds.

The Big A's Calendar System

The heart of Itzler's planning philosophy is a physical calendar – 365 days on a single, giant sheet of paper hanging on the wall. He calls it the "Big A's Calendar."

But the revolutionary part is not the size. It is the order in which Itzler fills it in.

First, he plans what he wants to experience. Only then, what he has to do.

Most people do it the other way around: they enter the work appointments first, then the obligations, and hope that some time is left over for "real life" at the end. Spoiler: it rarely is.

Itzler reverses the process. Before a single business appointment goes into the calendar, he enters:

• Misogi (one big, life-changing challenge per year),
• Kevin's Rule (six mini-adventures, one every two months),
• Winning Habits (four new habits, one per quarter),
• family time (individual trips with each child, couple time with Sara),
• and personal priorities (exercise, recovery, friendships).

Only when all of that is in place do the business obligations come in. They have to organize themselves around life – not the other way around.

The Three Pillars of the System

1. Misogi – The Annual Boundary Experience

The term comes from a Japanese purification ritual. For Itzler, misogi means: once a year, do something that fundamentally challenges you. Something you're not sure you can pull off. That can be an ultramarathon, an expedition, or a completely new project.

The rule: it should have a 50/50 chance of success. Too easy brings no transformation.

2. Kevin's Rule – Regular Mini-Adventures

Named after a friend of Itzler's, this rule says: plan a small adventure every eight weeks. Something you wouldn't normally do. That can be a spontaneous camping trip, a cooking class, a local half marathon, or a day trip to a place you've never visited.

Six such experiences per year add up. By the age of 50, you'll have collected 300 additional adventures you otherwise never would have had.

3. Winning Habits – Sustainable Habits

Instead of making ten new resolutions on January 1st and having broken them all by February, Itzler adds just one new habit per quarter. Q1 could be daily meditation. Q2 adds a fitness ritual. Q3 maybe more mindful eating. Q4 a morning routine.

At the end of the year, you have four new, solidified habits – without the pressure of a radical overhaul.

Why It Works

The system works for a simple reason: it makes life the priority and work the remainder.

When you look at a full calendar filled with experiences, adventures, and conscious moments, you won't ask at the end of the year where the time went. You will remember.

Itzler sums it up like this: "If you do one misogi, experience six mini-adventures, and establish four winning habits, you've won at life."

Conclusion: From Schedule to Life Calendar

Jesse Itzler's approach is an invitation to actively shape your own life instead of passively letting it happen. The Big Ass Calendar is more than a planning tool – it is a visual reminder of what really counts.

The question is not whether you have time for the important things. The question is whether you schedule them first.

Want to implement Itzler's Winning Habits approach in your everyday life? The Yeap Habit Tracker helps you build new habits step by step – entirely in the spirit of Itzler's philosophy of sustainable rather than radical change.