The Power of One Winning Habit Per Quarter

Most people start the year with a list of New Year’s resolutions.
By February? Most of them are gone.

Why? Because trying to overhaul your entire life at once is a recipe for failure.

Flip that script with a simple framework:
Instead of chasing 10 new habits at once, add just one winning habit every quarter.

That’s 4 new habits a year—sustainable, realistic, and powerful when compounded over time.

What Is the Winning Habit Rule?

The framework is simple:
Every 3–4 months, pick one habit you know will improve your life—and master it.

That’s it.

Instead of spreading yourself thin, you stack habits slowly, giving each one the time and focus it needs to stick.

Why It Works

1. Sustainable Pace
   One habit every quarter is doable. You don’t need willpower overload or a total life reset.

2. Deep Integration
   By focusing on a single habit for 90 days, it becomes automatic. You’re not juggling 5 changes at once.

3. Compounding Over Time
   4 new habits a year.
   40 new habits in a decade.
   That’s how small, consistent upgrades become a completely different life.

Examples of Winning Habits

Winning habits don’t have to be complicated. Think small, high-impact, and repeatable.

• Drink 100 ounces of water daily.

• Walk 10,000 steps a day.

• Read for 20 minutes every night.

• Journal each morning.

• Cold shower or breathwork practice daily.

• Go to bed at the same time every night.

• No phone for the first hour of the day.

Each one, by itself, seems small. Stack them year after year—and you’re unstoppable.

How to Apply the Winning Habit Rule

1. Pick Your First Habit

Ask: What’s the one thing that would create the biggest ripple effect in my life right now?
Examples: better sleep, more movement, less distraction.

2. Commit for 90 Days

Make it non-negotiable. Track it. Build it into your daily rhythm until it sticks.

3. Add the Next One

At the start of the next quarter, keep your first habit rolling, then add another.

4. Celebrate the Stacking

At the end of the year, you’ll look back and see 4 new habits woven into your life.

The Compounding Effect

• Year 1 → 4 winning habits.

• Year 5 → 20 winning habits.

• Year 10 → 40 winning habits.

That’s 40 automatic behaviors working in your favor without you even thinking about them.

Now imagine layering this with:

• 100 Hour Rule → building a new skill every year.

• Misogi → one annual stretch challenge.

• Kevin’s Rule → six mini adventures every year.

Habits. Skills. Adventures. Challenges.
That’s how you engineer a life of growth and unforgettable experiences.

The Takeaway

Forget trying to change everything at once.
Focus on one winning habit per quarter.

Do it for 90 days, make it stick, then move on to the next.

👉 Four habits a year. Forty in a decade. A completely different life.