The Long Game
This is post #7 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.
In the early 2000s, I became friends with a guy named Jared.
At the time, he was building a new business with significant promise - but it hadn’t yet broken open. He was also investing in his local community, testing ideas, hosting conversations, and trying to contribute in ways that mattered.
I walked alongside him in those early days. I joined his podcast a few times. Encouraged his listeners. Showed up when I could.
In terms of fundraising from him, I didn’t have a clear pathway. There was no transaction waiting to happen. It was a good relationship - grounded in shared curiosity and mutual respect.
As time passed, his business grew. Eventually, it led to a significant exit. His capacity expanded. His philanthropic world widened substantially almost overnight.
But still - nothing immediate between us in terms of his giving. Just the continuation of a relationship that had already been formed.
Years later, when I was helping launch a global initiative, Jared stepped in as a patron funder. It made sense.
The alignment was real.
The trust was already there.
The timing - finally - was right.
From the first conversation to that moment of partnership, more than a decade had passed.
That’s the long game.
The Lie About Speed
One of the most persistent lies in major gift fundraising is the belief that things should move faster.
If someone is truly interested, they would have decided by now.
If this were real, we’d be further along.
We must be behind.
These thoughts slip in quietly. And over time, they begin to erode otherwise good work. But major gift fundraising is layered work.
We need to remind ourselves that wealth doesn’t simplify decisions - it complicates them.
When someone has significant resources, they are not short on opportunities. Each week brings a fresh wave: new invitations, new ideas, new causes, new requests.
For people who are not wealthy, “I can’t afford it” serves as a clear and necessary filter. But for someone with means, that filter largely disappears. The question is no longer about affordability. It becomes something deeper:
Alignment…
Meaning…
Timing…
Trust…
Legacy…
Impact…
Discernment Takes Time
When a giver takes eighteen months to decide, something starts to stir beneath the surface for us fundraisers:
Impatience creeps in.
Self-doubt follows close behind.
And if we’re not careful, subtle judgment begins to take shape.
Did I misread the relationship?
Were my instincts off?
Should I have moved faster?
In those moments, it helps to remember: delay is not the same as disinterest.
Sometimes it is discernment.
Sometimes it is competing priorities.
Sometimes it is simply life unfolding in ways we cannot see.
What gets damaged when we rush the timeline isn’t just the immediate opportunity. It’s the relationship itself. Trust begins to erode. Tone tightens. Future capacity narrows. Reputation quietly shifts - often without a word being said.
The long game protects all of that.
And the long game asks something deeper than strategy ever could.
It asks for humility - the recognition that we do not control the timeline.
It asks for trust.
It asks for hope.
Because even when nothing seems to be happening… good things are still forming beneath the surface.
Leaders have to internalize this too.
If your team is working the system - staying connected to active givers, building a healthy pipeline, strengthening relationships - you are not behind. You are building something durable.
There may be seasons when things feel thin. But thin is not the same as fragile.
Here’s your daily commitment: We are not going to go out of business for a lack of networking and connecting.
Resources form over time. Connections deepen over time. They grow where disciplined activity and relational integrity are present - paired with optimism that steady work actually leads somewhere meaningful.
So, be clear about your weekly activity. Stay present in the lives of the people you serve and invite. Let time do some of its quiet work.
You do yours.
Say it with me friends:
Reach out to three people today.
* * * * * * * * * *
As many of you know, I am now working fulltime to rally resources and attention to the work of Sinapis.
Sinapis equips entrepreneurs in frontier markets to build redemptive businesses that create jobs, restore dignity, and transform communities. I get a front row seat to watch leaders in Africa and other emerging markets build companies with courage, excellence, and deep faith. It’s humbling work. And I’m all in.
Because of that, I’m taking on fewer paid coaching and consulting engagements than in previous years.
But here’s what hasn’t changed. I still care deeply about major gift fundraisers. I still believe this work is sacred. And I still want to give generously of my time and tools. Especially to leaders in the global south and those serving in frontier markets.
If that sounds like you, I encourage you to take full advantage of what’s freely available. Here's where you can access a lot of content for free:
* Major Gift Fundraising MRI Scan - A story-based self-assessment to help you name your instincts, clarify your posture, and grow with intention. Takes about 20 minutes and provides a customized coaching summary.
* JappaFry Writer - A freely available AI writing partner built from 30 years of my teaching, frameworks, stories, and strategy in major gift fundraising.
* Follow me on LinkedIn - You'll get short pro-tips and reflections on major gift fundraising every day between 5-7am pacific.
* Breakthru Blog - Weekly reflections and practical guidance for those navigating the fundamentals, sacredness, and fun of major gift work.
* Breakthru Podcast - Audio readings of the blog and interviews with high-capacity givers and reflections to help you strengthen your messaging, systems, and storytelling.
If you’re serving in a frontier market or the global south and want to connect, please reply to this email. I am especially eager to encourage leaders building sustainable fundraising systems in emerging contexts.
If you’re interested in paid coaching, I still offer a limited number of sessions each month. You can find details on my website or reach out to Ivana Salloum for scheduling support.
Thank you for the work you do. I look forward to hearing about the good things unfolding in your world!
