Every year starts the same way.
Big goals. Fresh intentions. A sense that this year will be different.
And yet, if we’re honest, most years do not fall apart in December.
They lose momentum much earlier than that.
Usually on a Monday.
That thought has sat with me since my recent conversation with Paul Epstein, the former NFL and NBA executive behind the Win Monday movement. On the surface, the idea is simple. Win Monday. Build momentum. Let it compound.
But the reason this conversation landed so deeply for me is not because it was clever or motivational.
It is because it forced me to confront how I have been starting my weeks and, by extension, how I have been building.
Change Isn’t the Problem. Drift Is.
I have spent my career working in and around constant change.
Technology shifts. Industries transform. Organizations reorganize.
Even personally, the last few years of building my own work have been full of uncertainty.
So when Paul said, “Change is never going away. Uncertainty is never going extinct,” it did not feel theoretical. It felt obvious.
What hit me harder was what followed.
If change is constant, then waiting for clarity is a losing strategy.
Momentum does not come from certainty. It comes from ownership.
That reframing matters.
Because too often, we treat Monday like something to survive instead of something to use. We spend Sunday night rehearsing the week’s problems, and by the time Monday arrives, we are already playing defense.
We have lost before we have started.
The Moment That Shifted My Thinking
There was a specific part of the conversation that stayed with me.
Paul talked about owning the morning before the world gets loud. Not as a productivity hack, but as a way of protecting agency. Before emails. Before notifications. Before everyone else’s priorities show up uninvited.
It was not about waking up at some heroic hour.
It was about designing the start of the day intentionally.
And that is when something clicked.
I realized I have been building big things, important things, while letting the start of my weeks stay loose. Strong effort. Good intentions. But not enough structure around the moments that actually determine momentum.
If Monday is where momentum is born, then being casual about Monday is not neutral.
It is a liability.
What Winning Monday Means for Me in 2026
This is not about doing more.
It is about doing a few things on purpose.
As I think about what I am building in 2026, my work, my voice, my commitments, my family rhythms, I do not need a more ambitious plan. I need a more deliberate starting line.
Here is what winning Monday looks like for me this year:
1. Protecting the first part of Monday, no matter what.
Not reacting. Not scrolling. Not negotiating with the day. Starting with work that actually matters before the noise shows up.
2. Defining one meaningful win for the day.
Not ten tasks. One action that moves something forward. Momentum comes from progress you can feel.
3. Treating Monday as a tone setter, not a hurdle.
If I start the week grounded and intentional, the rest of the week responds differently. Not perfectly, but differently.
This is not about perfection.
It is about responsibility.
As Paul put it in our conversation, adversity is not your fault, but it is your responsibility. That idea applies just as much to how we start as it does to what we face.
Why This Matters Beyond January
This is not a New Year’s resolution.
Resolutions are fragile. They depend on motivation.
Habits are sturdier. They survive bad days.
When we do not win Monday, the cost is not dramatic. It is subtle.
We drift. We react. We let the week decide for us.
And over time, that drift compounds just as reliably as momentum does.
Winning Monday is not about hype or discipline theater. It is about creating a repeatable way to reassert agency in a world that constantly pulls it away.
Momentum is built gradually.
Then suddenly.
And most of that work happens on Mondays.
So that is where I am starting 2026.
Not with a resolution.
With a decision.
Made on Monday.
This work is meant to be lived, not just read.
Through The Future of Human Experience podcast and my ongoing book project, I explore how leaders build momentum and stay grounded amid constant change.
I also work with organizations through keynotes and facilitated conversations when these ideas need to move from reflection to action.
If you are planning an event or gathering where this conversation matters, I would welcome the opportunity to be part of it.