Introduction to 👻Spooky Season for Major Gift Fundraisers

Before we get started, check This Out:
‍I’m writing a fable about fundraising and looking for some readers to give me comments, critiques, etc. If you’ve read any of Patrick Lencioni’s fables like “5 Dysfunctions of a Team” or “Getting Naked”, this will look familiar in structure. It’s about a 45m read (7,700 words and 45 pages) and I believe it’s relatable, funny, and profound…
BUT I need to see if you agree! Send me a direct message and I'll send you both audio and written drafts to review.

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The other night I had a strange dream. I was lying on a hard floor, tossing and turning to find relief, but no position felt right. My neck ached, my side throbbed, and I kept asking myself: Why am I here?

‍Then I woke up, in my bed, warm, comfortable, properly cushioned. Yet my brain had convinced me I was somewhere cold and unrelenting and my whole body remained tense from a dream that wasn’t real.

It struck me: this is exactly what it feels like to be a major gift fundraiser wrestling with the questions that keep us up at night.

‍These questions? They’re like that hard floor.

‍They show up in the quiet. They hum beneath the surface. They trick your body into tightening. They whisper that something’s wrong… even when you’re safe. And they refuse to leave us alone until we face them.

So, a new series is born (a spooky🎃one) for the Breakthru Guide: The Questions That Keep Us Up at Night.  Each week, I’ll explore a question I’ve heard in real conversations with fundraisers who live this work every day.

Here’s what’s ahead:

‍What if they say no?
‍Rejection stings, even when we’re “just inviting.” How do we hold our confidence - while staying kind and bold?

‍How do I ask someone who has more than I’ll ever have?
‍There’s a sacred weight to inviting a wealthy, influential person to give. It takes soul work, not just scripts.

‍Am I doing enough?
‍The hustle is real. But when is it faithfulness - and when is it just fear?

‍Why do I feel like I’m begging?
‍Fundraising isn’t supposed to feel manipulative. But some days, it does. Let’s dig underneath that.

How do I measure my professional value when gifts are delayed or disappear?
‍When the numbers dry up, so does the dopamine. What anchors your sense of worth?

‍Can I be fully myself in this work?
‍Professionalism, authenticity, faith, strategy - must they always be in tension?

‍What is this job doing to me?
‍Exposure to wealth, long travel days, impossible goals… Is your soul still intact?

‍Will I still believe in this ten years from now?
‍Burnout is one thing. Losing conviction is another. What does it take to sustain joy in this sacred and strategic calling?

I don’t claim to have all the answers. But I’ve lived every one of these questions - and more.

I want to walk through them with you, not as an expert handing out solutions, but as a fellow traveler on the same road.

What about you? Which of these questions has haunted you lately? Reply and tell me. Or better yet - send me your own reflection. I might feature it in the series.

See you next week for the first one. Until then, may your dreams be soft… even when the questions linger. You’re not alone.

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‍If you haven't taken advantage of some of the resources I've created to help major gift fundraisers, take a look now!  Initial calls with me are free and "no strings attached".  Sometimes folks feel like they need to wait and not 'bother' me until they have a pressing issue.  No need for that...just make the call. 🕺

‍Here's where you can access a lot of content for free:

* Major Gift Fundraising MRI Scan - A story-based self-assessment that helps you name your instincts, clarify your posture, and grow with intention. Takes less than 20 minutes and gives you a custom coaching summary based on your responses.

* JappaFry Writer - A freely available AI tool that draws from over 175 pages of original teaching, storytelling, frameworks, and strategy from my 30 year career 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 Newsletter - As you've seen here, these are longer weekly posts (audio and written) sent directly to your email.

* Breakthru Blog - the newsletter from the previous week gets posted here each week for everyone (so email subscribers get it a week early).

* Breakthru Podcast - Interviews with high net worth givers about how we as fundraisers can get better at inviting them to the party.  And audio readings of Breakthru Blog posts.

‍Before getting to the PAID stuff: My opinion is that no small ministry with a tight budget should be spending more than $3-5k (total) for major gift coaching/consulting.  Most of you will be good-to-go spending far less than that.  This was a major issue for me when I was a frontline fundraiser - major gift consultants were an expensive 'black-box-of-confusion' for me.  That stops now.

‍Here's the PAID stuff:

‍* Online Catalyst Course - This is a full brain dump of my 28+ years of experience - good, bad, ugly.  It's built around the fundamentals, the sacredness, and the fun, of major gift fundraising.  It's infused with Henri Nouwen reflections.  Many people can take this course and they will be 'cooking-with-gas' and not need any additional coaching from me on the core systems.  I'm grateful that this course has gotten *great* reviews.

* Live coaching with me - I refer to this as "brain rental".  The ROI on live coaching, as you might imagine, is extraordinary.

Finally, be sure to connect with my colleague Ivana Salloum.  She's super awesome and can help with scheduling and access to resources, etc.

I look forward to hearing about your good work!

Blessings,