If you missed Part One of my interview with Jesse, check it out here. That’s the set-up. This is the payoff. Please enjoy Part Two (as well as a link to our entire conversation on video) below:
I don’t remember the first question I asked Jesse. I had plenty of them ready. Pages of notes on my phone, all the prompts you keep handy just in case. I figured if the conversation slowed, I would check them. But the conversation never slowed. From the moment he walked in, we were already in it.
He sat down like we had done this a hundred times before, and instead of the stiff warm-up most interviews fall into, we just talked. Where he came from. Why he was running a few minutes behind. The event he had coming up in New York, which was a different kind of show for him, where people were buying a ticket to hear him because they wanted to be there, instead of some corporate gig.
There is a different weight to that, and he felt it. You could hear it in the way he talked about the venue and the planning behind it.
Then we moved into something dads can talk about forever. Kids. Who is home, who is away, what sports they are in, which seasons overlap. Football turning into basketball. Soccer turning into skiing. Surfing when they can fit it in. Proud dad moments. He mentioned he had basketball practice coming up and the whole team was coming over. I looked to my right and saw the court outside. It all made sense.
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About fifteen minutes in he looked at me and asked, almost casually, if we were on. It had not occurred to me that we were not on. This is how I do these. Two people talking like human beings, not performers. I have recorded over 200 conversations and I still do not take any of it for granted. When he asked me what I do for fun, I told him the truth. Sitting in moments like this is fun for me.
But I was not just interested in how he thinks. I wanted to know how he works. How he runs businesses, coaches his kids, prioritizes his marriage, stays healthy, stays curious, chooses the right things to say ‘yes’ to and the right things to say ‘no’ to. That is when the conversation shifted into the foundation of his life, which is planning.
The freedom Jesse has, the travel, the training, the health, the time with his family, the traditions he keeps and the spontaneity he still allows, all of it is supported by a system he actually uses. The Big Ass Calendar grew out of his need to build the life he wanted.
Most people talk about what they should do or want to do. Jesse builds a structure that makes sure he will actually do it. Put it on the calendar. Pay for it. Train for it. See it on the horizon. And when the date comes, you show up.
I asked him if he ever skips something he puts on the calendar. He said ‘no’. Then he told me about the mileage goal he set for the year and how far behind he was. December might end up being a brutal month. For the first time, he admitted this might be the year he does not finish everything he committed to. Not because he does not want to. Life is full. Holidays. Travel. Kids. His show. All the real-world factors that show up whether you are ready or not.
That moved us toward something I think a lot of us feel in midlife. The balance between what is next and what is enough. Ambition does not disappear. It changes its shape. You begin to see the value of choosing well, not just choosing more. I turn 53 in a few weeks. He is now 56. At some point every streak ends. Not because you failed, but because you grew.
So how do you build a year that matches the man you are now, not the man you used to be?
You put the personal things on the calendar first. Time for yourself. Time for your health. Time for your family. Your true priorities. Then you build the professional around that. Your big misogi. Your quarterly Kevin’s Rule challenges. The birthdays, the reunions, the vacations, the trips with your kids, the weekends with your wife, the adventures with your friends.
Once your year is laid out like that you can finally ask the real questions. How much work fits into this life? How many flights do I want to take? How many clients do I truly have space for? What is worth saying ‘yes’ to?
We talked about all of that. Our dads. Our early jobs. The paths we did not take. The risks we did. How you learn to think for yourself. How you measure success when you are old enough to admit that money matters, but it is not the only thing that matters.
Show me your calendar and I will show you your priorities. I have seen Jesse’s. It is dialed. That is why I use it. I wanted to create my own planner until I got his. Every year it gets better. When someone builds something great, you do not reinvent it. You use it.
Towards the end of the time scheduled for our conversation, I asked him what he would be doing if I was not there. He said he would be in the sauna. Then he said we should go. That is how I ended up in a converted trailer sauna with a wood-burning furnace, sitting in 220 degrees while he ladled beer slowly over one rock. The whole thing felt like stepping into one of his stories, and, sure enough, the competitive part of my mind started to wonder if this was a quiet test.
We went sauna, plunge, sauna again. And that is where the real personal conversation began. No cameras. No notes. The early jobs and the lean years. Him selling DVDs out of his trunk. Me logging tape. His jet business. My early films. All the decisions that did not look like strategy at the time but added up to something meaningful later. Two guys from Long Island talking about the turns that changed our lives.
He had to leave first because of basketball practice, not because he was done, which I was grateful for. As he told me to stay as long as I wanted, something clicked. The only reason I could say yes to a full day like this was because I had built my life to allow it. The freedom was not accidental. It was created. Planned. Protected.
What gets scheduled gets done.
Jesse says it often and he lives it. He may make things feel casual and off the cuff, but he is incredibly prepared. That is the part most people never see.
Which brings me to the center of this entire day. The calendar. His Big Ass Calendar. The planner I use every day. Every idea I preach about eliminating surprises, getting ahead, building the year instead of reacting to it came from him.
Here is the moment that tied it all together for me:
I wrote down my meeting with Jesse on the planner I use because of Jesse. The system got me to that room. The system made the meeting real. The system created the moment.
We captured all of it. We did not just film it. We shaped it. Edited it. Finished it. And now we are giving you the entire conversation because I believe you will get something from it. More than something.
This is why we are partnering with them. Why we endorse the planner. Why I want you to use it. Follow the structure, intention, clarity, and accountability because it works. Look at where it got me. Get your Big A## Calendar here with a Midlife Male discount.
Here is the full video. Watch it.
You will understand exactly what I felt that day.
In Health,
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Greg Scheinman
Founder, Midlife Male
52. Husband. Father. Entrepreneur. Coach.
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