On 40.

Sit back, enjoy the journey, and trust the process! And wear a ridiculous hat!!

On 40.
One time, about eight months ago, I told one of my teammates that I wanted a giant foam cowboy hat like Yosemite Sam. I don't remember saying this, but I am not surprised. So guess what I got for my birthday last week because my team is actually The Best?

I remember when my dad turned 40.

I was in junior high school. My mom threw him this bananas-bonkers surprise party at a restaurant with friends and family. There was karaoke. I think I was at a sleepover at Michelle R.'s house that night so I wasn't at the party. I just knew it was a big deal.

He was 40.

"Over The Hill."

He came home with cheeky, funeral-themed birthday cards.

He was old. OLD!

Practically seconds from death, if you didn't know any better.

And that sentiment seems reasonable — until you turn 40.

ARRIVING AT LEADERSHIP UTOPIA

I turned 40 on February 28.

I woke up that day, no wiser than the day before.

I probably (definitely) hit snooze too many times.

There was no ceremonial declaration of reaching adulthood, or being reminded that I was halfway done with living my life. No mysterious envelope from the Universe stamped, "Congratulations — you now understand everything."

It's quiet. Kind of sneaky. And generally without fanfare.

Yet, appropriately I find myself reflecting on some hard questions now that I am here:

What have I learned?
What actually matters?
Why did I spend so much of my thirties bearing burdens that weren't mine to carry?
Stop Worshipping at the Altar of The Grind
Everyone’s tired, and no one’s getting saved.

I've learned that leadership cannot be taught from a tidy, corporate-slide-deck. Leadership is messy, human, emotional. Complicated. Sometimes delightfully ridiculous.

It's altogether Odd.

And it was only in the last year that I've realized something important.

The leaders who change lives aren't the polished ones.

They're the weird ones.

The curious ones.

The ones brave enough to lead with humanity and not from a management textbook.

LEADERSHIP LESSONS LEARNED ON THE ROAD TO 40

1️⃣ Leadership is not — and never was — about you.

One of the most freeing realizations as a leader? It's not about me.

It's a vow, not a crowning achievement. A responsibility to be taken seriously, not a title on a business card.

When I first stepped into leadership, I thought a lot about whether I was doing it right. Whether people respected me. Whether I looked like a real leader.

But eventually reality taps you on the shoulder and whispers the truth:
It's not about you.

If you're doing it well, the spotlight shifts to the people around you — the team doing the work, solving the problems, and bringing the mission to life.

The Oddball Leader understands this on a deep, visceral level: your role is about stewarding people and creating an environment where those you serve can thrive.

Seen. Heard. Valued.
Oddball Leaders build a culture of belonging

Once you let go of needing leadership to validate you, you tend to become a lot better at leading.

2️⃣ Belonging is the real foundation of great teams.

The best teams I've ever worked with had something powerful in common:

People felt safe to be themselves — not the "work-appropriate" version. Or the polished, professional avatar. Their REAL selves!

When people feel a true sense of belonging, the extraordinary is possible. They ask better questions. They challenge assumptions. They bring creativity and courage to the table.

Psychological safety is not a buzzword — it's oxygen for good work.

Oddball Leaders create that oxygen. #imatree 😆😆

Oddball Leaders make it safe to say "I don't know," to challenge the boss, and try weird ideas.

And sometimes the weird ideas are the ones that change everything!

3️⃣ Leaders are nothing without gratitude.

In my twenties, I thought leadership meant having all the answers.

In my thirties, I learned it meant asking better questions.

In my forties, I'm convinced it means saying thank you — often and sincerely. Because no leader succeeds alone. EVER.

Every win a leader gets to claim is the result of someone else's effort, insight, persistence, or courage. Oddball Leaders understand that success belongs to the team, and they lead with genuine for appreciation for the people doing the work.

Yes, it seems simple and almost cliche to have gratitude. But appreciation is a wildly underrated leadership strategy, because it doesn't transform teams unless it's practiced consistently.

People who feel valued bring more energy, more creativity, and more commitment to the mission.

4️⃣ Curiosity beats control every time.

If there is one thing leadership guarantees, it's encountering conflict.

Miscommunication. Bad days. Mistakes and frustrations.

Earlier in my career, my instinct was to solve problems quickly. React and try to fix things.

Experience has taught me a better approach:

Get curious first.

Curiosity changes the entire tone of a conversation. Instead of, "Why did you do that?" the question becomes "Help me understand what happened."

It creates room for reflect instead of defensiveness.

The Oddball Leader uses curiosity as the framework for difficult conversations — seeking understanding before judgment. Because most problems aren't caused by bad intentions.

They're caused by misunderstandings, assumptions, or humans being humans. (And remember: you're human, too.)

Curiosity makes space to solve those problems together.

Workplace grace
Oddball Leaders uphold the dignity of ALL people

5️⃣ Joy is not optional!

Work can be frustrating, and fundraising can be especially exhausting.

There are the unrealistic fundraising goals from board members and leadership, tight deadlines, emotional stakes, and quite often the humbling experience of asking someone for support and hearing "no."

So somewhere along the way, I learned a vital Oddball Leadership truth:

If there's no joy, the work won't last.

Scattering a Hundred Griefs
Great Leaders choose joy.

Choosing joy doesn't mean ignoring the hard things. It means remembering the humanity in the middle of them. It means laughing when something ridiculous happens, celebrating the tiniest of wins, and occasionally embracing the absurdity of the work we do.

Joy keeps teams resilient, and it reminds us why we showed up in the first place. And it may be the one thing that carries you through a tough season.

6️⃣ Oddballs like us change the world.

At 40, I've noticed the most impactful leaders are rarely the most conventional ones.

They are curious thinkers, empathetic listeners, and willing to challenge the status quo.

They are the Oddballs. The people who lead with heart instead of ego. The ones who ask questions others are afraid to ask, even at great personal and professional risk.

Do-Over: When Oddball Leadership demands sacrifice
Let’s talk about what really happened in February 2025.
But most importantly, they build cultures where people can bring their full selves to the work. Which means the work becomes, bigger, braver, and more meaningful.

IN CONCLUSION

Dear Bri,

This is you, a.k.a. Bri from the Future™️.

One day you will arrive at the ancient, crusty age of 40.

But before that, you will become a leader of the people. And there's something important you should remember:

There's literally no point in fitting into someone else's idea of leadership or professionalism.

You will spend a good portion of your thirties worrying about whether you were doing it "right." Whether you looked like a real leader. Whether you were professional enough, polished enough, and composed enough.

Eventually you will learn a beautiful truth; the world doesn't need more perfectly polished leaders. It needs more human ones.

It needs leaders who are curious instead of defensive, and who create belonging instead of maintaining hierarchy. It needs leaders who are thankful, and who laugh when things get weird — because things will 100% get weird.

The world needs more Oddball Leaders.

So don't be afraid to lead in a way that feels honest. Protect joy, your joy and the joy of those around you. Ask the uncomfortable questions. And never stop building and preserving spaces where people can show up fully as themselves.

You will lead differently. And that's the whole point.

Peace out,

Bri from the Future™️