What Is Win Monday and What Is a Business Athlete?

“Show me your habits and I’ll show you the quality of your life.”
Paul Epstein

Before we talk habits, let’s talk identity.

Nobody commits to a habit before they commit to who they are and what it represents for them. That’s the order. Identity first. Then the reps. How you see yourself determines the choices you make for your health, work, and life.

I spent years inside NFL and NBA front offices. The best people I worked with were not the most talented in the building. They were the ones who showed up like athletes, motivated by performance, growth, and results. I saw the same four traits, over and over:

High performer. They held themselves to a standard of excellence.
Put in the work. They enjoyed the journey and the results.
Drove results. Results weren’t random. They were planned and intentional.
Prepared like a pro. They knew that preparation and practice impacted how they performed when it mattered most.

Winning Monday and being a business athlete is not a title and it’s not a job. It’s an identity. It’s the way you show up.

Winning Monday means taking a meaningful action that creates momentum for the rest of your week. Have that hard conversation you have been putting off, close the sales deal, fix the process issue that’s hurting your team, or simply go for the walk you keep saying you don’t have time for. Whatever it is, winning Monday means you own Monday. You stop drifting into your week and letting meetings and other people manage your calendar for you.

Here is the part most people miss. Business athletes do not wait for January 1st. They do not wait for the perfect week. They start Monday.

A colleague recently shared with me that people’s biggest regrets are the things they wished they had done but never took the chance on. The swings they never took. You’re not going to be successful at everything you try, but you will never regret taking a swing.

So the first questions for you to answer are: Are you someone who wants to Win Monday? Do you want to be a business athlete? If the answer to either is yes, let’s meet at the 50 every week and take this next swing together.

Paul

This Week’s Play: Accountability

Commit to the play

On Monday, I will hold myself accountable for completing one task. That is what a business athlete does.

Pick the task you have been avoiding or the conversation you have been putting off. Then tell someone: your partner, a close friend, a family member, your leader. Out loud, this week.
Write your accountability statement

This week, I will .
Set it up
- What is the first thing you need to do to create accountability?
- Who is going to help you stay accountable?
- How will you make it visible so you don’t forget?

Maintaining momentum

Set dates and times for each step. Pick an action with real consequences and share it with someone else. Win Monday plays run on a weekly template: Sunday plan, Monday execute, Wednesday check-in, Friday reflect.

The Stat Sheet

98%

of people say achieving something meaningful on Monday drives motivation and momentum through the rest of the week.

A Welcome From Paul

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What Win Monday is, what it means to be a business athlete, and why we’ll meet you at the 50 every week.

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Results aren’t random.

See you at the 50,

Paul & Aaron

CEO & COO, WIN MONDAY

Issue #002 · One play. Every Monday.

How You Start Is How You Finish

From Aaron | COO, Win Monday

My wife picked up on the second ring. I was standing alone on top of Grays Peak, 14,278 feet, and I could not get a full sentence out.

“I did it. I love you.” That was all I had. Then my eight-year-old son got on the phone and asked the only question that mattered: “Why did you climb the mountain?”

“Because it was there,” I said. I was completely gassed and it was all I could think of at that moment. The real answer is simpler. Because I made a commitment.

14,278 FT

Grays Peak, ColoradoUnder-trained, anxious, and committed anyway.

01 THE SETUP

I committed to this hike back in July. I built a training plan. Then I prioritized work, the calendar filled up, and most of that plan stayed on paper. I flew to Colorado under-trained. I was anxious. I was not sure how my body would respond.

The night before the climb, Sterling Hawkins, who leads these No Matter What experiences, sat us down at dinner and asked each of us two things.

Before the first step

What do you want out of this?
Why are you here?

01 What do you want out of this? 02 Why are you here?

In the morning at the trailhead, he asked us to say our intentions out loud before we took a step. And he told us the summit was up there, but our own summit did not have to be the top of the mountain.

I did not fully understand why that mattered until I was above 13,000 feet.

02 ABOVE 13,000 FEET

That is where my heart stopped beating in my chest and started beating in my ears. Then my throat. My legs were solid. My lungs were not. Every breath felt like breathing through a tiny straw, and I remember thinking: this is where the mountain asks you if you are committed to the actual summit, or if you just want to stop here.

03 THE KICK

Here is something I have known about myself since I ran track. I start in the back. I stay steady. I keep something in the tank. And I know, from a thousand reps, exactly when to start my kick.

Years ago I tested for the FBI. I was eight to ten years older than everyone on that track. Going into the last lap and a half, I was a full lap behind the leader. Then I kicked into the extra gear I have always had in waiting, the one others do not know is there until they see it. I sprinted the whole way home and finished first by twenty yards.

On Grays, with the top in view, I felt it. Not a decision. An instinct. I knew I was close and I knew I had something left. I decided the actual summit was my commitment and I left the group. When I finally turned around, I was looking down into the clouds and there was nobody in front of me. Nobody behind me. I was alone. Sometimes a commitment can feel that way, and that is okay.

04 WHY IT WORKED

I want to be honest about why that worked, because it was not the training. It worked because of how we started. Sterling built the environment before the first step. Intentions on the table at dinner. Intentions out loud at the trailhead. And when we all got back down, one more question: what did the mountain give you?

THE ENVIRONMENT YOU BUILD AT THE START DECIDES HOW YOU FINISH. NOT FITNESS. THE CLARITY.

05 WHAT THE MOUNTAIN GAVE ME

What the mountain gave me was a commitment. My health is going to be a priority, not the first thing that gets shoved to the back burner the second life gets stressful or overscheduled. That sounds easy. It is not. Wanting it is not enough. I have to build the environment and the weekly habits that make it real, and I am using our own WIN MONDAY® playbook to do it.

I told the group during our debrief meal something I had needed to hear for a long time: taking care of yourself does not mean you care for the people you love any less. It means you plan to be around for them. As Paul, our Founder, always says, "Availability is the best ability."

Aaron

This week's play

Make the Commitment

Ten minutes. Three filters I use for every commitment I make. Use these three filters on the one thing you want to focus on this week.

What is the thing you need to summit (complete) this week?
Name the actual thing. Not “get healthier.” The specific thing you want to make progress on or complete. You just need to make some progress, get it done, or move on.
What is in the way?
What do you need to remove or get out of the way to achieve success? What's blocking you, and how will you remove it?
What does success look like?
What will winning Monday look like for you? What does your “summit” look like? It may not even be finishing the task. It could simply be finally getting started.

Find your intentions at the trailhead (Monday)

Write the answers down. Put them where you will see them every Monday. Then tell one person. That last step is the Monday trailhead.

Now go find your summit this week, starting on Monday.

Momentum starts here

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