Ben and the Big A## Calendar

This past year, I tried something new that quietly changed the way I think about time. I don’t have a traditional 9 to 5 job, I volunteer a lot of my free time, and I have three boys and a wife with their own busy schedules that I want to be present for. So life feels very busy all the time! Back in 2019, I attended a conference where the keynote speaker was Jesse Itzler. If you don’t know who Jesse is, he’s an entrepreneur, endurance athlete, and speaker who spends a lot of time thinking about how we use our time. Google him, it’s worth it.  

This year, I started using Jesse Itzler’s Big A## Calendar, and for the first time, I didn’t just plan my work. I planned my life. At a basic level, it’s exactly what it sounds like. A massive wall calendar that forces you to see the whole year at once. But the real value isn’t the size. It’s the mindset Jesse encourages behind it, to be intentional with your time, because time is the one thing you don’t get more of. Jesse talks a lot about designing your life instead of reacting to it. Seeing the year all at once changes how decisions feel. You stop saying “someday” and start asking, “Where does this actually fit?”

The calendar is just a tool, but the purpose is clarity. When everything lives in one place, you can’t hide from how your time is actually being spent. For me, keeping it in my home office made a big difference. I see it every day. It’s not buried in an app or hidden behind reminders or the productivity planner I use every day. It’s right there on the wall, quietly holding me accountable to the people I want to spend time with and the things that matter most to me. The goal isn’t to cram more in. It’s to make sure the right things don’t get squeezed out.

Here’s how it works in practice. The most useful part of the Big A$$ Calendar for me is the color coding. Each major part of my life has its own color: work, family, personal time, date nights, community (basketball), and adventure (more on that in a second). When you step back and look at the year, patterns jump out immediately. Too much of one color over a long stretch is hard to ignore. And that’s probably what surprised me most; this helped with balance, not just awareness. I could see busy work periods coming, and I could intentionally follow them with personal breaks or lighter weeks. Instead of burning out and then reacting, I was planning recovery ahead of time. Honoring the calendar meant honoring the commitments I’d already made to myself and others. I still have work to do when it comes to holding the line, but fewer date nights got pushed, fewer personal retreats were rescheduled, and family time stopped feeling optional.

About that adventure thing…

One of Jesse’s core ideas is the Misogi. A Misogi is one big, audacious event you plan for the year. Something that stretches you far beyond what feels comfortable. It should be challenging enough that there’s a real chance you won’t succeed, but meaningful enough that you’re excited to try anyway. The outcome isn’t what matters. It’s who you become in the process.

I didn’t do a Misogi in 2025, my first year using the calendar, but I’m excited to figure out what my challenge will be in 2026. I trust that seeing it on the calendar will help me refocus on my health and wellness. I’ll train differently. I’ll prepare differently. I’ll think differently.

Another idea Jesse shares is Kevin’s Rule, which is closely tied to his idea of planning six mini-adventures each year. The rule is simple: don’t miss important moments with the people you love because of work or obligations. Named after an adventure with his friend Kevin, Jesse encourages building a “life resume” made up of experiences, not just achievements. For me, those mini-adventures might look like a hiking trip, a camping or kayaking weekend, visiting a new city, or seeing a new baseball stadium. I’m excited to think about these adventures and, just as importantly, who I might invite to join me.

After a year of using the Big A$$ Calendar, I felt more balanced, more intentional, and less guilt about taking “me time.” When something felt off, I could usually see it on the calendar before I felt it emotionally. The size and visual nature of the calendar made it impossible to lie to myself about where my time was going. And honestly, that’s what made it work.

I’ve already started blocking time for 2026. I’m thinking about what my next big Misogi might be and what smaller adventures I want sprinkled throughout the year. I’m protecting time before it gets taken. If time is the one asset we all share equally, how we choose to use it might be the most important decision we make all year.

If this resonates – check it out! I hope it’ll work for you too.  

Inestment Advice offered through Great ValleyAdvisor Group, a RegisteredInvestment Advisor. Great Valley Advisor Group and Haas Financial Investment Advice offered through Great Valley Advisor Group, a Registered Investment Advisor. GreatValley Advisor Group and Haas Financial Group are separate entities. This is not intended to be used as tax or legal advice. Please consult a tax or legal professional for specific information and advice. are separate entities. This is not intended to be used as tax or legal advice. Please consult a tax or legal professional for specific information and advice. 

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