Happy Holidays, you wonderful Human Being!

Somehow, we’ve arrived at the end of 2025.

The inbox is overflowing.

The group texts are chaotic.

Half of you are in transit or hiding from a relative in a guest bedroom.

So this is a soft landing issue, not a homework assignment.

Before we log off, I want to say thank you, share three big lessons we practiced together, and leave you with a few gentle questions for your own reflection.

And yes, the title is a nod to Mariah Carey.

Don’t worry—I’m not about to sing.

You’re safe.

What We Practiced Together in 2025

Three Big Lessons

1. Kindness Needs a Core, Not a Costume

This was the year we stopped treating kindness as “being nice” and started treating it as a leadership operating system.

Radical Kindness isn’t about avoiding hard conversations or keeping everyone comfortable. It’s kindness with a core:

  • Clear boundaries

  • Honest feedback

  • Decisions made with both head and heart

We talked about leaders who set the bar high and stay deeply human. Cultures where people feel safe enough to tell the truth, ask for help, and admit:

That’s the kind of kindness I’m asking Santa for.

Authentic Kindness is more important than being right or first!

2. Ask for An Answer (Instead of Pretending You Have One)

If 2024 was the year of hot takes, 2025 felt like the year of exhaustion.

Everyone was supposed to have a stance, a strategy, a solution—instantly.

We pushed back on that.

Ask for An Answer is my antidote to performative certainty:

  • The words you use (Language)

  • The time you take (Latency)

  • The way you close the loop (Loops)

We explored what happens when leaders stop playing “heroic fixer” and start playing “curious guide” instead:

  • “What are you seeing that I’m not?”

  • “What would a brave decision look like here?”

  • “What do you need from me to move forward?”

Respect, trust, and growth thrive when we trade ego for honest questions. That’s the work.

3. Belonging as a Leadership Choice (Not a Poster)

This year, across campuses, boardrooms, and your stories, one truth kept echoing:

Belonging doesn’t happen because we print a value on a wall.
It happens because leaders make daily decisions that say:

We talked about:

  • Higher education under pressure

  • Scholarships and students studying democracy at its birthplace

  • Teams navigating fear and fatigue

  • The power of chosen family and real allyship

Belonging is not a “nice to have” in times like these.
It’s a business imperative, a moral imperative, and a leadership test we’re all retaking—every single day.

A Personal Note From Me

On a personal level, 2025 has been one of the fullest years of my life.

I stood Up North with the man I love and said “yes” to a new chapter.
I recorded a podcast in a studio that teenage-me would never have believed he’d sit in.
My work deepened—from All Pride, No Ego to Ask for An Answer, from 1:1 coaching to bigger conversations about culture, kindness, and power.

I also had moments of doubt, grief, anger, and sheer overwhelm—just like you.

What I know now is this:

Every version of me that showed up this year—executive coach, author, podcaster, chairman, groom, jet-lagged traveler—felt held by this community.

When you read, reply, share, or carry an idea from Field Notes into your own leadership, you’re not just “supporting my work.”

You’re co-creating it with me.

Thank you for that. Truly.

Three Questions for Your Own Year-End Reflection

No worksheet. Just three questions you can tuck into your carry-on or your quiet moment on the couch:

  1. Where did I practice Radical Kindness this year—toward myself and toward others?
    Where did I choose empathy and honesty over avoidance or performance?

  2. What question changed the way I led, loved, or showed up in 2025?
    What did I ask—or finally say out loud—that shifted the story?

  3. What am I ready to leave in 2025—and what am I committed to growing in 2026?
    Habits, stories, roles, expectations… it all counts.

If any of these land, hit reply and share.
I read your notes—often with coffee, sometimes with tears, always with gratitude.

A Glimpse at 2026

In 2026, I’m doubling down on practical tools for leaders who want:

  • Kind cores and clear boundaries

  • Better questions and faster, cleaner decisions

  • Cultures that are courageous, inclusive, and actually sustainable

You’ll see more on Ask for An Answer, more voices on the podcast, and more ways to engage with the League of Radical Kindness as a living, breathing leadership community.

Same heart. Evolving containers.

If there’s something you’d love to see from me in 2026—workshops, retreats, deeper dives on certain topics—let me know. This community is at its best when it’s a conversation, not a broadcast.

A Holiday Wish For You

However this season finds you…

In a full house, a quiet apartment, an airport, a hospital, a boardroom that refuses to slow down, or somewhere in between—

I hope you give yourself permission to be human.
To rest when you’re tired.
To cry if you need to.
To laugh loudly when joy sneaks in.
To remember you are not behind. You are not broken. You are not alone.

Thank you for walking this year with me.
Thank you for leading—with all your imperfections, all your courage, and all your heart.

I hope Santa brings your everything you wish for………

With Radical Kindness and so much gratitude,
Jim

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