When I was about eight years old, there was a trend at my school: kids were starting clubs. So, I decided to start one too.
I invited my friends Lisa and Mary to join. I don’t remember what I called the club or what it was supposed to be about. But I do remember exactly what happened when they arrived at my house.
They walked in, looked at me, and waited.
And I realized…I had no plan.
No agenda. No activity. No idea what I was doing.
What I did have was an immediate wave of panic and embarrassment.
I suddenly felt completely exposed and inadequate. The feeling stuck with me for years.
Fast forward a few decades and I’m in a client meeting.
A high-level philanthropy leader is looking to me for guidance. And even though I’m a seasoned philanthropy advisor, I’d feel this flicker of self-doubt. Not often. But enough to notice.
And eventually, I realized something important:
That eight-year-old girl was still showing up in the room.
Not literally, of course. But the shadow of that moment, the belief that I might be unprepared, the fear that I didn’t have a “real” plan, the worry I’d be found out…was lingering underneath the surface.
It wasn’t until I saw this clearly that I could start releasing it.
Why This Matters for Philanthropy Leaders
Wealth doesn’t erase these shadows. In fact, it can amplify them.
I’ve worked with ultra-high-net-worth individuals and foundation leaders who carry their own childhood echoes into the room:
- Fear of disappointing others
- Guilt about having too much
- Uncertainty about being taken seriously
- Worry that “the bottom could drop out” at any moment
- A sense of needing to earn their right to lead
And here’s the thing. These patterns don’t always show up as emotions.
They show up as energy:
- Saying too much or not enough in a meeting
- Overcomplicating simple decisions
- Avoiding strategic moves because something feels “off”
- Getting stuck in cycles of overthinking
- Holding back from bold ideas out of fear they’ll seem silly or “too much”
You Can’t Lead Powerfully from a Place of Unconscious Doubt
Whether you’re advising a family, leading a corporate giving program, or directing your own giving, you bring your whole self into the room. Even the parts you think you’ve outgrown.
And those parts—the ones you haven’t yet acknowledged—can quietly run the show.
That’s why part of evolving as a philanthropy leader and donor isn’t just about better strategies or clearer goals. It’s about recognizing and releasing the shadows that keep you from showing up fully.
It could be the eight-year-old club founder who didn’t have a plan.
It could be the teen who learned to keep their voice down.
It could be the parent who felt judged for giving “too much.”
Once you see it, you can change it.
The Lesson Here?
As a philanthropy leader if you’ve ever walked into a decision feeling uncertain, even when you “should” feel confident, ask yourself:
- What part of me is really feeling this way?
- Where did that part learn to doubt itself?
- And is it still true now?
Acknowledging the energy you bring into the room is one of the most overlooked tools for philanthropic leadership and success.
Because when your energy aligns with your clarity, your giving becomes unstoppable.
If you’re ready to stop second-guessing and start making bold, effective decisions in your philanthropy, I offer a 12-month advisory partnership called the Philanthropy Impact Accelerator. It’s designed for ultra-high-net-worth donors and philanthropy leaders who want expert guidance, clear priorities, and fast progress—without the overwhelm. You’ll get direct access to me as your trusted advisor, two strategy days to jumpstart your work, and ongoing support to help you move forward with clarity and confidence.
Spots are limited—book a call or email me if you’d like to explore whether it’s a fit.
