Winning Seasons

Experience

Apr 21

I’ve been wrestling with balance.

Not the tactical kind - juggling meetings, workouts, and family dinners - but the deeper craving for comfort.

The quiet belief that after years of pushing, I somehow deserve ease. And while that feeling is human, I realized it can be dangerous when I’m in a true Build Season.

“Winning doesn’t ask if we’re tired. It asks if we’re ready.”

In the middle of this internal conversation, I found myself thinking back to Tim Grover’s book Winning.

Grover reminded me that living a "good, balanced life" isn’t the result of random harmony — it’s the byproduct of hard work, relentless effort, and the discipline to stay committed when it’s easier to slip into comfort.

That reminder pulled me back to why I’m sharing this today: winning isn’t about chasing daily balance. It’s about honoring the seasons that make long-term balance possible.

This is the realisation I collided with:

When I’m in a Build Season, craving daily comfort becomes a dangerous distraction.

Comfort isn’t evil.

Joy, peace, and rest all have their rightful places. But when the vision I’m chasing demands everything, the pursuit of balance can quietly sabotage momentum.

The Bigger Realisation: Winning is Seasonal, Not Daily

Balance isn’t something we manufacture every day like clockwork.

True balance — the kind that builds legendary lives — happens over seasons. Over years, even decades.

It’s a marathon made up of brutal sprints and measured rests.

Stories of the Season: It’s Everywhere

Sara Blakely didn’t build Spanx from a “balanced” 9-5.

She worked alone for two years, selling fax machines by day, perfecting her prototype by night, pouring every spare minute into a dream no one else could see yet.

J.K. Rowling wasn’t “balanced” when she was writing Harry Potter in cafes, broke, heartbroken, raising a child as a single mother.

She lived through a season of sacrifice — trusting that the harvest would come.

Elon Musk didn’t create Tesla while enjoying leisurely weekends.

He famously slept on the factory floor, obsessed with survival, while critics called him crazy.

None of them lived in perfect balance.

They lived through seasons of focused imbalance for something bigger.

The Seasons Framework: Choosing Wisely

We can’t operate the same way all the time.

We have to know our season based on our personal Vision — and commit fully to it.

• Winning Season: Extreme focus. Building. Sacrificing. Expanding.

• Healing Season: Repairing. Reflecting. Regathering strength.

• Harvesting Season: Enjoying victories. Realigning. Reinventing.

If we’re in Build Mode but expecting Healing rewards, we create resentment.

If we’re in Harvest Mode but behave like it’s Battle Mode, we miss the joy.

Wrestling Comfort: A Necessary Internal Battle

Here’s the uncomfortable truth:

When we’re building something transformational, deserving isn’t the currency.

Discipline is.

We aren’t wrong for wanting comfort. We aren’t weak for craving balance.

We’re human.

But greatness demands a higher conversation with ourselves.

One that sounds less like, “I deserve easier,” and more like, “We choose harder now for easier later.”

Trust Framework: How to Operate Seasonally

Radical Honesty: Declare the truth of your season to yourself.
Strategic Sacrifice: Consciously give up comforts that dilute focus.
Scheduled Restoration: Plan for recovery after periods of intense work.
Macro-Alignment: Think in 6, 12, and 24-month cycles, not daily snapshots.

Personal Application Lens
(Self-Mastery)

When I step back and look at my life through the lens of seasons, it’s clear that personal mastery demands efficiency and internal consistency. I can afford to be brutally honest with myself, trim distractions, and push forward without needing external applause. It’s about doing what’s necessary, even when it’s not immediately gratifying, because the version of me I’m building depends on it.

Reflection Exercise:

What season are we truly in right now? Not what we want — what we need.

Mini Inventory:

Identify 3 comforts we’re willing to temporarily sacrifice in service of our vision.

New Habit:

Build 1 daily ritual that reinforces the season we’re committing to (e.g., 90 minutes of deep work before social media).

Vision Audit: Write down your 5- to 10-year vision.
Season Check-In: Based on your vision, what season are you in?
Identify 3 Comforts to Sacrifice: (Examples: binge-watching, oversleeping, saying yes too often.)
Design Your Rituals: Build daily habits that match your season.
Honor Your Restoration Time: Schedule future "healing" blocks after intense "winning" pushes.

"What personal discomfort am I willing to endure today for the life I want a decade from now?"

Professional Application Lens
(Leadership)

Professionally, the application shifts. Efficiency with ourselves must become effectiveness with others. Leading a team or an organization through seasons requires clear communication, deliberate structure, and the ability to rally people toward a shared outcome. It’s not enough to grind personally; we have to align others without burning them out or creating confusion. Seasonally-driven leadership requires pacing and vision management at scale.

Team Audit:

What season is our business/team truly in? Building? Healing? Harvesting?

Strategic Communication:

Declare the season clearly to our team. Align performance expectations.

Restoration Plan:

Schedule seasons of “off-field” restoration before burnout forces it.

“Balance isn’t found. It’s earned over decades of disciplined seasons.”

Declare the Organizational Season: Is your company/team in a build, heal, or harvest phase?
Communicate Seasonal Expectations: Set clear internal language: "We are in a Winning Season until [date/event]."
Align KPIs to the Season: Aggressive targets during Winning seasons; stability metrics during Healing; innovation metrics during Harvesting.
Protect Focus Ruthlessly: Eliminate low-priority initiatives that conflict with your declared season.
Plan for Team Recovery: Build intentional "off-seasons" to prevent burnout and retain high performers.