What Faithfulness Looks Like
This is post #10 (and the final post) of The Clear-Eyed Series: An Exit Strategy from Confusion
If you’re new here, 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 to reorient when anxiety starts to creep in.
And if you’ve been around for a while, consider this your weekly invitation to slow down, take stock, and remember what the work really is.
Several years ago, I spent 24 hours with a friend at his lakehouse.
We had first met on a trip through Asia, introduced by a mutual friend. After that, we stayed loosely connected. We spoke when it made sense. When we did, the conversations had weight. Over time, something steady formed between us - unforced, undefined, and, importantly, unhurried.
For most of those years, I didn’t know if our relationship would ever turn toward a conversation about giving. And I found that I was genuinely at peace with that. The relationship didn’t need an outcome to validate it. The relationship had its own integrity.
Eventually, though, an opportunity emerged - one that aligned with their interest and convictions. I reached out and asked if I could spend some time with him and his wife to explore it together.
He said yes. Then he added something I didn’t see coming:
“What if we made it a prayer retreat?”
I can still feel my reaction. Something in me expanded. Not because of the potential gift, but because of what he was naming.
This is what I am always looking for in this work - moments where the relationship becomes more human, more whole. Where there is room not just for conversation, but for presence. For prayer. For laughter. For shared meals, for something that feels, unmistakably, like blessing.
Even when the stakes are high, it doesn’t have to feel transactional.
Letting the time unfold
So I said yes - and we let the time unfold.
Over those 24 hours, we moved at an unforced pace. We prayed, sometimes together, sometimes apart. We talked about their lives, the things they care about, the commitments they were already carrying. We shared a great meal. We laughed. We simply enjoyed being in the same space.
There was a quiet sense of purpose to the time, but it never felt managed. Nothing was rushed. Nothing was overly curated. (I wrote more about that experience here, if you want to explore it further)
We both understood why I was there. That didn’t need to be inserted into every conversation. For the most part, I let him guide the rhythm, trusting that if and when the moment came, the invitation would emerge naturally.
And it did.
Not as a dramatic pivot, but as a continuation. The invitation to consider a gift felt like the next honest step in a relationship that had been forming for years. There was clarity in it, but also a noticeable freedom. I was prepared for either outcome, and I believe he knew that.
They ultimately chose to move forward with a significant gift, and I’m deeply grateful.
But that isn’t the part of the story that stayed with me.
What actually makes this work
What has stayed with me is everything that made that moment possible: The years of steady connection, the absence of pressure, and the shared understanding that the relationship itself mattered, whether or not a transaction ever occurred.
Faithfulness in major gift work often looks ordinary in the moment and becomes meaningful over time.
It would be easy to point to that 24-hour retreat and treat it as the defining moment. It wasn’t. It was simply a window into what had already been built. Trust had formed slowly. Clarity had emerged through consistent, honest conversation. The relationship had grown strong enough to hold a meaningful decision without strain.
For most of those five years, I hadn’t asked them for anything. I was willing to let the relationship exist on its own terms. That willingness changed me. It made me more attentive. More patient. More present to what was actually unfolding in their lives.
That posture matters more than any tactic.
Because for most of us, a 24-hour retreat that culminates in a significant gift is not the norm. Most of this work looks far more ordinary - a thoughtful conversation, a follow-up that demonstrates care, a well-timed word of encouragement. Small moments repeated with intention.
And over time, those moments accumulate. They form something durable. The kind of relationship where a meaningful invitation can be offered without pressure - received without resistance.
If there is one idea I hope stays with you, it’s this: you don’t need to rush this work to do it well, but you do need to remain present within it.
That means continuing to show up. Placing yourself in environments where you can meet people with both capacity and genuine interest. Building relationships through consistent, meaningful engagement.
Service, quality, love, and persistence - these aren’t abstract ideals. They are daily practices.
So as you look at the week ahead, consider two or three people in your world - not in terms of capacity, but in terms of their lives. What are they carrying? Where might encouragement matter? Where might clarity help? Where might a simple, thoughtful connection make a difference?
And perhaps most importantly: What does it mean to see them - and to love them?
That question will shape your work in ways that no strategy ever could.
My prayers for you this week
May you find steadiness in the work you have been given.
May you trust the pace at which relationships grow and decisions take shape.
May your presence bring clarity, encouragement, and care to the people around you.
And may your work be marked by faithfulness, even when the results take time to appear
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:
- 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.
