The Shape Of Competition
I love winning. Maybe a little too much.
Recently I was playing cornhole with my sister. I sunk the bag on a clutch toss to win the game and you would have thought I won the Powerball jackpot. I yelled. Beat my chest. Strutted in a circle around her. It was quite a performance.
She wore the same mildly amused expression the entire time.
And I’m pretty sure we haven’t played cornhole since.
The truth is, I feel that same competitive energy in fundraising. I want the organization I’m serving to win. I want to succeed. I want to build a reputation for doing good work. And if I’m honest, there were times early in my career when that desire to win was shaped as much by ruthless competition as anything else.
I’ve gotten better over time. Thirty-plus years in the industry will do that. But I still cringe a little when I think back about how I carried myself early on. About five years into my first fundraising role, a wealthy friend sat me down and, in a very gracious way, said something along the lines of: “Hey Captain Intensity… why don’t you take it down a few notches?”
It stuck.
At the time, I didn’t fully agree with him. I thought I was doing my job. I reasoned that competition was necessary. That I was being a good steward by pushing hard, closing gifts, and trying to win.
Underneath it all was a simple assumption: If we don’t win, someone else will.
That was the logic I was operating from
But over time, something didn’t quite hold. I began to notice that giving doesn’t seem to follow a zero-sum equation.
Certainly, there are moments when resources are limited and decisions have to be made. But over the long run, something else appears to be happening.
A rising tide.
When people are invited well, engaged thoughtfully, and given space to respond freely, giving tends to expand. It grows.
More recently, I’ve been looking at the word competition itself. It comes from the Latin competere - to strive together. To seek something alongside others who are pursuing the same goal. That shifts the picture.
The other organizations are no longer the opponents. They become part of the environment that shapes the work. Their presence raises the standard. It exposes gaps. It challenges us to communicate more clearly, serve more thoughtfully, and steward relationships more carefully.
Competition, in this sense, becomes a shared pursuit. A way of refining what we are doing in the presence of others who are also trying to do it well.
That doesn’t eliminate the tension. There are still choices to be made. There are still opportunities we don’t receive and outcomes we wish had gone differently.
But It does change the posture
It moves us away from trying to win at the expense of others and toward trying to do the work well in the presence of others.
That shift has changed how I approach fundraising in a few practical ways.
👉 I pay closer attention to the giver’s full landscape - what else they care about and where they are already engaged.
👉 I’m more willing to make connections that don’t directly benefit the organization I’m serving. Introducing someone to another leader.
👉 Pointing them toward a different opportunity. Supporting their giving elsewhere when it’s a better fit. I pay attention to how I speak about other organizations, especially those working in similar spaces.
There’s a way of talking that subtly diminishes others in order to elevate your own work. People hear it. And there’s a way of talking that reflects respect for the shared pursuit. Those small decisions accumulate. They shape how people experience you. They shape how they experience the work itself.
The desire to win is still there. I still want to do good work. I still want the organizations I serve to thrive. But my definition of winning has changed. Winning is no longer measured solely by outcomes. It’s measured by the quality of the work. The integrity of the relationships. The way we show up alongside others who are also aiming at something worthwhile.
If you’ve been reading along over the past few weeks, you know I’ve been thinking about some words that I believe matter deeply in major gift fundraising: service, quality, competition, and love.
Service keeps us close to the person.
Quality keeps us close to the work.
Competition reminds us that we are not doing this alone.
And love shapes how all of it is expressed.
When love is present, competition doesn’t disappear. It becomes something else. A shared pursuit.
Which leaves us with a couple of important questions:
* What are we really trying to win?
* And who are we becoming in the process?
* * * * * * * * * *
If you haven’t explored the free resources I’ve created for major gift fundraisers, this is a great place to start:
- Follow me on LinkedIn for daily pro tips and reflections.
- 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.
