I’ve always said that if it’s not on the calendar, it doesn’t happen. So I decided to go big or go home for 2026 (literally). I’m supersizing my planning obsession this year with Jesse Itzler’s ‘Big A## Calendar.’ Join me in this new experiment as I attempt to outsmart my own busy schedule and become more “time rich.”

I have to admit…I have an odd obsession with planning. Color-coded calendars, to-do lists, perfectly executed spreadsheets…it’s all deeply satisfying to me. My mantra is simple: If it’s not on the calendar, it doesn’t happen.

But here’s the catch: a calendar that is ‘full’ isn’t necessarily ‘intentional.’ If I don’t take the wheel, those empty boxes will quickly fill themselves with meetings, errands, and other life demands. None of these are ‘bad’ things, but they can easily turn a year into one long marathon of ‘busy’ unless I make space for the things that actually make it meaningful.

The “Supersized” Solution

I wanted to try something new for 2026, so I finally pulled the trigger and purchased the Big A## Calendar created by Jesse Itzler. If you don’t follow Jesse, he’s an entrepreneur (and husband to SPANX founder Sara Blakely) who lives life at about 200 mph.

The calendar itself is just a tool and yes, it is BIG (4’x 3′ to be exact). But beyond Jesse’s infectious energy, what I love about it is his simple three-step planning framework to designing an unforgettable year. Instead of reacting to the year as it unfolds, he plans it from the top down. A much more proactive approach.

Here is the simple framework, and why I think it’s actually workable for people with busy lives.

The 3-Step Framework

Step 1: Close the year before you plan the next one

Jesse starts by fully closing out the year that is ending. Not with a complicated, soul-searching retreat, but with an honest review.

• What worked?
• What did not?
• What mattered more than expected?

One thing he suggests is imagining putting every area of your life into a blender…work, health, relationships, finances, and happiness. Then, give yourself a score of 1 to 10. The value isn’t the number; it’s noticing which two or three things are dragging the average down. Those are your signals for where to focus next.

Step 2: Choose one “Misogi” and six mini-experiences

This is the part I am most excited about. A Misogi is one big, meaningful challenge you choose for the year. It’s something slightly outside your comfort zone that gives the year a clear anchor.

It might be training for a race, launching that creative side-hustle, or something you have been dreaming about but it’s stuck in the ‘someday’ camp.

In addition, he uses something he calls ‘Kevin’s Rule’: mapping out six “mini experiences” for the year (one every other month). These are small adventures…could be a day trip, a local workshop, or simply a hike. They are realistic enough to actually happen but different enough to stand out in your memory.

Step 3: Add one steady habit each quarter

Instead of a laundry list of failed New Year’s resolutions, Jesse adds habits in layers. One habit per quarter. Start with one and every three months, add a new habit.

• Q1: Drink more water.
• Q2: Walk daily.
• Q3: Meditate for ten minutes.
• Q4: Actually be on time.

Four habits a year doesn’t sound like much, but layered over time, they quietly rewrite how your life runs.

The Color-Coding Magic

The calendar comes with a dry erase pen and a pack of color coded stickers. Each color represents a focus area so you can visually see how you are prioritizing various areas of your life.

• Orange (Work): Travel, deadlines, launches, and big “don’t-interrupt-me” meetings.
• Green (Health & Energy): Workouts, rest days, and those doctor appointments we always reschedule.
• Yellow (Family & Relationships): Birthdays, school plays, and actual quality time.
• Red (Non-negotiables): Vacations and personal commitments (i.e. wedding, graduation etc).
• Purple (The “You” Category): Creative projects, thinking days, and personal goals.

Here’s a short 12 min video of Jesse walking through the framework so you can see how it all comes together.

Why the “Visual” Matters

The Big A## Calendar is simply a way to see the entire year at once. The goal is to put the Red and Yellow priorities on the calendar first.

Work will always expand to fill the space you give it. This calendar is designed to help you set the boundaries before the “daily grind” takes over. Seeing the whole year makes the trade-offs clearer and saying no to things that don’t fit a lot easier.

Cheers to 2026!

My hope is that when I look back next December, the year will feel memorable and intentional. I want to remember what mattered, not just what filled my days.

The good news? You don’t need a giant wall calendar to adopt the methodology (though if you want to join the “Big Calendar Club,” you can grab it here). You just need the intention to put yourself on the schedule first.

For now, that feels like a pretty great place to begin.

Thanks for reading and sharing. xx