A short history lesson, a powerful question, and a simple framework to design a year that actually means something.
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Hey Friend,


Happy New Year!


I wish you much happiness and success in 2026. 


And my goal is that this newsletter can play a small part in you achieving that. 


There are only a few email newsletters I’m subscribed to that if they don’t show up in my inbox, I miss them. And my north star is making this newsletter meet that same standard for my readers. 


(I’d love it if you’d take 30 seconds to hit reply and tell me what I could do to make this newsletter be unmissable for you.) 


Over the last couple days I’ve been sharing questions that help me reflect on 2025. Better questions = better results. 


Today, I want to share my favorite question for looking ahead.


This one question will help you unlock an incredible 2026…





MAIN FEATURE


What Will the Headline Be for Your Life in 2026?

Before I give you the question, I want to share a short history lesson I think you’ll find fascinating.


Just down the hill from Mount Rushmore is something most people don’t even know exists.


The Crazy Horse Memorial. A massive sculpture blasted into the side of a mountain to honor the famous chief.


The project was started by Korczak Ziolkowski, an artist from Boston who had been an assistant on the Mount Rushmore construction. 


When Ziolkowski was commissioned to carve Crazy Horse, he didn’t just take on a sculpture.


Before he ever drilled into the mountain, he had to build a life from scratch. A log cabin. Roads. Outbuildings. Crops. Power. Water. Everything required just to begin the work.


Inside the museum at the base of the mountain, there’s an exhibit dedicated to Korczak. And on the wall hangs a massive animal hide, covered in simple drawings.


It’s called a winter count.


This was a tradition used by Plains tribes. Every winter, when the weather forced people indoors, they would sit around the fire and reflect on the year that had passed.


They didn’t record everything.


The elders chose one moment that defined the year.


That symbol was drawn onto the hide.


Over time, the hide became a visual record of an entire life. Births. Losses. Setbacks. Victories.


Ziolkowski’s family kept a winter count of their own, and that’s the one hanging in the museum today.


You can see when children were born. When major breakthroughs on the sculpture happened. When disaster struck and buildings burned down. When progress stalled. When it surged forward.


One year. One defining story.


Most people can’t clearly remember what happened just a few years ago. Everything blurs together.


What a shame.


How much richer would your life feel if every year actually stood for something?


So while everyone else is thinking about resolutions, I want you to think in terms of headlines.


Here’s the exercise...


Finish this sentence as if it’s already December 31st:


“2026 was the year that I __________.”


This can be big or small. Abstract or concrete.


It might be the year you ran your first marathon.


The year you bought your first investment property.


The year you reached one whole Bitcoin.


Most people let the year write its own headline. And when they do, it usually sounds like this:


“2026 was the year I worked hard but nothing really changed.”


I want the opposite for you.


You decide the headline first. Then you engineer your decisions to make it true.


Because once the headline is clear, clarity shows up everywhere else.


If the headline is “2026 was the year I created freedom for myself,” certain meetings disappear from your calendar.


If it’s “2026 was the year my money finally started working harder than I did,” saving alone no longer makes sense.


If it’s “2026 was the year I stopped living by default,” systems matter more than effort.


Here’s the core idea to sit with:


A year is a precious unit of measurement.


You don’t get many of them. And they compound, whether you design them or not.


So instead of asking, “What do I want to accomplish in 2026?”


Ask a better question.


“What do I want 2026 to be remembered for?”


That answer becomes the headline.


And once the headline is clear, everything else becomes easier to design.





Wealth Is Not Earned… It's Engineered.

Wealth isn’t measured by income. It’s measured by what you build with it. January 7–9, 2026, I’m hosting a live 3-day virtual workshop where you’ll build your complete Wealth Operating System from the ground up. Hands-on tools. Custom worksheets. Real-time coaching.

Start 2026 with a plan that actually makes you wealthier.

GRAB YOUR SEAT

TODAY'S VISUAL





This is what the sculpture looks like today, and what it will look like someday.


Progress has been insanely slow. But keep in mind it’s 600 feet tall! 


Mike Rowe talked about it when he was on the Joe Rogan podcast. He said all of Mt. Rushmore could fit on the forehead! 






CLIENT WIN


A Ninja ChatGPT Idea You Can Steal


One of my coaching clients had an awesome win recently that was just too cool not to share.


He dabbles in business brokerage on the side. He enjoys it but it takes up a ton of his time. 


He spends hours on the phone with potential buyers, answering questions about the businesses for sale. 


So he started taking transcripts of all of his conversations with the sellers, along with all of the financials and other documentation, and feeding everything into a custom GPT. 


Now he just sends a link to prospects and they can ask basic questions to the GPT instead. 


Plus he programmed it to be friendly and encouraging. So he doesn’t have to be “on” all the time. 


It took him an hour to set up, and now it saves him 4 hours every week.  


I always say, anything you do twice, you need to build a system for. 


Well this client proves you can do that with conversations too. 


Ask yourself what things do you find yourself explaining over and over again. What questions do you get asked all the time. 


Can you create a GPT to just repeat these things for you and send a link instead? 


Wealth isn’t just about earning more. It’s about engineering leverage.


When your time is the bottleneck, growth stalls.


When systems replace you, suddenly you have more options.


That’s exactly the kind of thinking we develop inside WealthOS. And it’s what we’ll be breaking down at the upcoming 3-day live event. We’d love for you to join us.





TODAY’S LIST


Want to Go Deeper on the Crazy Horse Story?


If that winter count story grabbed you, here are three rabbit holes worth your time:


The Crazy Horse Memorial today

Scroll down this page. There’s a video of Korczak’s grandson explaining where the project is today and there is some incredible drone footage.

Crazy Horse’s Winter Count

This is a winter count based on Crazy Horse’s life. Fascinating to look at.


1977 Interview with Korczak Ziolkowski

He has a crazy Polish name but this is the most American guy ever. In this YouTube video he’s dressed like Daniel Boone, detonating TNT on the mountainside, and talking about what it means to leave a legacy. Great video.