Episode 259- Mastering the Winters of Life

Our entire philosophy at Personal Mastery Training is built on one radical idea: In order to achieve mastery, we cannot simply get through challenges. We must strategically seek to get something from them.

We understand the seasons of nature perfectly. Spring is for growth. Summer is for harvest. Autumn is for beautiful decay and letting go. But then there is the fourth season: Winter.

Winter shows up in our personal lives, and it often leads us to panic. It’s not always cold outside, but it is freezing inside. It’s the season of unexpected layoffs, financial downturns, health setbacks, profound loss, or a nagging creative block.

It is that time when the lights dim, the external noise goes quiet, and we are forced into deep introspection.

My Personal Winter

I’m sharing this with you not from a place of theory, but from the trenches. 2025 has been a season of deep winters for me. Earlier this year, I lost my son to cancer. Recently, I lost a dear friend and co-host of the Alliance, Dr. Charlie Cartwright.

I am in the deep winter. But this pain has become my motivation to share the philosophy of the seasons—wisdom I learned from the modern-day philosopher Jim Rohn—so that we can navigate these dark times together.

The "Summer Mode" Trap

The primary source of suffering during winter comes from the narratives we cling to. We are culturally conditioned to believe we should always be in "Summer Mode."

Thanks to social media and FOMO (Fear Of Missing Out), we think we should always be growing, always achieving, and always producing a visible harvest. When winter hits, an unhelpful inner voice screams: "Why haven't I figured this out? Why am I not happy? I am failing because I have nothing to show."

We try to manufacture a summer feeling. We fill our calendars and double down on external effort, even though our environment is screaming at us to stop.

Winter is Not a Punishment; It’s Preparation

We have to accept the purpose of winter. It is not a punishment. It is a vital, non-negotiable phase of life.

Think of a seed. It cannot grow until it is broken open in the dark, cold ground. The deep, transformative work of life happens in the dark.

I love this wisdom: "We won't rise to the occasion when something happens; we will fall to the level of our preparation."

My family and I are surviving this tragedy not because we are superhuman, but because previous winters prepared us. We are falling to our level of preparation.

How to Navigate the Cold: Strategic Stillness

If you are in a financial, mental, spiritual, or existential winter, how do you handle the stillness without falling into paralyzing stagnation?

1. Practice Essentialism Winter is the time to cut dead branches. In business, you consolidate resources. In life, you declutter. This season has forced me to become brutally non-negotiable about what I say "yes" to. Ask yourself: What foundational belief about myself is dying off so something stronger can take its place?

2. Turn Pain into Purpose Stagnation is avoidance. Productive stillness is intentionality. I could have gone "zero dark thirty" and hidden from the world after losing my son. Instead, we chose to turn pain into purpose. We raised $65,000 for a foundation in his name. We focused on helping others get healthy. The way I grieve is to be of service.

3. Set a Winter Intention Don't set a goal for an outcome (like "get a new job" or "be happy"). Set an intention for a skill.

• Example: "My intention is to learn how to sit with discomfort without seeking a destructive escape."

The Power of Protective Habits

In the summer, your habits are focused on output. In the winter, your habits must pivot to input and protection.

• Protect your time.

• Protect your energy.

• Prioritize rest.

We have a toxic narrative that says, "I'm too busy to rest." You must replace that with: "Rest is my most productive activity right now." It is an act of proactive self-mastery. You are stocking your internal pantry for the coming spring.

The Ultimate Gift of Winter

If we leverage this season correctly, we gain two things we can never get from summer:

1. Unshakable Resilience: Summer teaches you how to enjoy the harvest. Winter teaches you that you can survive when the field is barren. It teaches you that your worth is not tied to your productivity.

2. Profound Self-Intimacy: In the quiet of winter, you finally hear your authentic voice. You stop worrying about who the world expects you to be and align with who you truly are.

This Too Shall Pass

It is always darkest before the dawn. If you are in the cold right now, know that the light will return. But don't just wait for it—utilize the dark. Let the pain change you. Let it be the incubator for your greatest future self.

Don't just get through it. Get from it.

To my son, and to Dr. Charlie Cartwright—one love.

Peace, love, and a sprinkle of soul.

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