The Weight of Wealth
This is post #9 of The Clear-Eyed Series: An Exit Strategy from Confusion
If you’re new here, you can start with the first post: “What Counts as a Good Week in Major Gift Fundraising?”
Over several weeks we’re taking a clear-eyed look at the work itself - a steady way of orienting ourselves when anxiety starts to creep in.
And if you’ve been around for a while, consider this your weekly invitation: slow down, take stock, remember what the work really is.
About twenty years ago, I sat with a woman who had inherited significant wealth. In the middle of our conversation, she said something that stopped me.
“Wealth affords you endless options. That can be good, but it can also be very difficult. You don’t have the luxury of saying, ‘I can’t afford that.’”
She wasn’t joking. She certainly wasn’t bragging.
If anything, her tone felt almost pleading - like she wanted me to understand something I hadn’t yet learned to see.
At the time, I remember thinking quietly, “That sounds like a problem I’d be willing to have.”
But as she kept talking, something shifted. I began to realize I had been looking at wealth far too simply.
When affordability disappears
When you don’t have the resources to do something, the decision is often straightforward. “I can’t afford it.” That settles it.
But when you can afford it, the question changes. Now you have to decide why you would or wouldn’t do something. And that question rarely comes with a simple answer. Endless options carry real weight. It took me time to see this more clearly.
As a fundraiser, I’m focused on one cause. One mission. One set of priorities. My work comes with a kind of built-in clarity. The people I’m inviting into generosity don’t live inside that same simplicity. They are holding multiple opportunities at once. Multiple relationships. Multiple requests. Multiple responsibilities - often at levels that are significant and deeply consequential.
These options can feel like freedom. They can also feel like pressure.
Every “yes” creates a set of “no’s.” Every decision carries weight.
The inner world most people don’t see
I began to notice other things as well.
Many of the people I was working with carried a kind of isolation. Wealth changes the nature of relationships. It complicates trust. It introduces distance. It blurs motives.
Even within families, the strain could be significant. Expectations shift. Roles become uneven. Assumptions fill in the gaps. Over time, those small fractures erode connection.
And underneath all of this, life still unfolds as it always does - disappointment and celebration, brokenness and responsibility.
Money doesn’t remove those realities. In some cases, it adds new layers to them.
Where tension shows up
This is where the work can begin to strain. It’s easy to look at someone with capacity and assume the decision should be simple. If they can do it, why wouldn’t they?
And when urgency is tied to a need, that pressure can increase quickly. We begin to project urgency outward, but it isn’t always shared. The gap widens. Pressure builds. Frustration settles in on both sides.
Over time, something shifted in me. Affordability was rarely the real question. Meaning was.
And that realization led to a different posture - more awareness, more curiosity, more kindness.
Instead of trying to move someone toward a decision, I found myself coming alongside them. Paying attention to what was happening in their lives. Listening for what mattered to them. Making space for the complexity they were carrying.
Sometimes that meant conversations with no agenda attached to money.
Just presence.
Just connection.
Just care.
What this might change for you
Think of two or three people in your portfolio. Not in terms of a potential deal, but in terms of their lives.
What are they navigating right now?
Where might they be feeling pressure?
Where might they need encouragement?
Where might a simple, genuine connection matter more than anything else?
Adopting a posture of awareness, curiosity, and kindness won’t just change your outcomes. It will change your experience of the work itself.
My prayers for you this week:
May you see people more clearly than their capacity.
May you move through this work with patience and care.
May your conversations be marked by curiosity and kindness.
And may you be trusted with more than just the ask.
Say it with me:
Reach out to three people today.
* * * * * * * * * *
If you haven’t explored the free resources I’ve created for major gift fundraisers, this is a great place to start:
- Major Gift Fundraising MRI Scan - a short, story-based assessment to help you name your instincts and clarify your posture.
- JappaFry Writer - an AI tool shaped by 30+ years of real-world experience, teaching, and strategy.
- Breakthru Newsletter, Blog, and Podcast - ongoing reflections, conversations, and practical guidance for the work you care about most.
These resources are designed to meet you where you are - and help you move forward with clarity and confidence.
If you’d ever like to talk, you can always schedule a free introductory call. I'd love to get acquainted and hear what you’re navigating right now.
For organizations ready for more structured support:
You may not need a full-time development leader - at least not yet. Sometimes what’s needed is clearer thinking. Sometimes more consistent action. And sometimes, for a season, real leadership.Here are a few ways we can start building momentum together:
* Online Catalyst Course ($199) - A complete brain dump of 30+ years in major gift fundraising - the good, the hard, and the surprisingly joyful. Built around strong fundamentals, the sacredness, and yes, even the fun. Infused with insights from Henri Nouwen. Many who take this course find it gives them everything they need to build healthy, sustainable systems.
* Live coaching ($300-400 / 90 minutes) - Think of this as "brain rental". Focused, strategic, and highly practical. The kind of time that brings clarity quickly and creates real momentum.
* Laser-focused session ($99 / 45 minutes) - For one specific moment that matters - preparing for a high-stakes conversation, navigating an invitation, or working through a decision that needs clarity.
* Fractional Director of Development - For a small number of organizations, I step in more deeply - bringing clarity to your message, movement to key relationships, and structures your team can sustain long after I’m gone.
In the first 90 days, you can expect:
- clearer, more confident communication of your vision
- more meaningful engagement with top givers and prospects
- renewed movement in relationships that may have stalled
- simple, actionable next steps after each interaction
- a sharper sense of who is ready to be invited - and who is not
Most fractional engagements range from $2,500 - $7,500+ per month depending on the level of involvement.Not sure what kinds of support you need? I can point you to a simple Development Readiness Assessment - just reply and let me know.
And don’t miss connecting with my colleague Ivana Salloum - she's wonderful and can help with scheduling, resources, and getting you where you need to go.
Thank you for the work you do. Truly.I’d love to hear what’s unfolding in your world - and how I can come alongside you.
