Everyday I’m Hustlin’
Each week, I write this Breakthru Guide as a small act of devotion:
to the vocation, to the givers, and to the brave souls who keep asking.
Welcome to the newcomers! You can see all previous guides on The Breakthru Blog.
Carve out 45 minutes to read “Gifted: A Fable About Fundraising (aka Awkward Invitations)” by J.Paul.
This is a special early peek reserved just for subscribers of The Breakthru Guide - and the friends you’d love to pass it along to.
If you’ve read Patrick Lencioni’s fables (The Five Dysfunctions of a Team, Getting Naked), you’ll recognize the style - short, story-driven, and practical. Gifted is 45 pages and 7,700 words. You’ll find both a PDF and audio files in this Google Doc link, so you can read or listen.
When you’re done, I’d appreciate your honest feedback. You can:
- Email me directly (no need to hold back), or
- Fill out this quick 7-minute survey (anonymous feedback)
This book will be a free resource for charity leaders and major gift fundraisers. Your insights will help make it as compelling and useful as possible!
* * * * * * * * * *
(This post is part of the 👻Spooky Season Series: The questions that keep us up at night😱)
Jennifer started her new role as a major gift officer on September 1 - excited, eager… and tossed straight into the fire.
It was the 4th quarter. Year-end campaigns were already looming.
She barely had time to set up her email signature before someone asked for her top 10 prospects. By day three, she had a badge, a laptop, and access to a Google Drive full of half-finished proposals.
By week two, she was being pulled into board meetings, sent to networking events, and asked to qualify new leads for a November pitch.
Meanwhile, the CRM had just been overhauled - and no one really knew how it worked.
Jennifer was smart, warm, and deeply committed to the mission. But the pace was unrelenting. The expectations were unspoken.And the rules? Unclear.
“I keep asking myself,” she told me, “Am I doing enough? Or am I already behind?”
The Invisible Weight of “Enough”
That question - Am I doing enough? - rarely comes from laziness or entitlement. It comes from pressure. From ambiguity. From the quiet fear that you're letting someone down.
In major gift fundraising, it can be hard to know what’s working:
- No one applauds you for the conversation that didn’t lead to a gift.
- You don’t always hear back after sending a proposal.
- Big gifts can take months - sometimes years - to materialize.
So you start tracking everything.
Measuring everything.
Comparing yourself to the person who “already hit their number” or “just closed a six-figure gift.”
And then the whisper starts:
🫢You’re not doing enough
😱You’re already behind
😬They’re going to find out
The Slow Burn of Guilt-as-Motivation
Let’s be honest: guilt can be motivating - for a while.
It makes you stay late. Work harder. Say yes more.But eventually, guilt becomes your operating system. And when guilt runs the show, everything starts to feel like failure. A “not now” feels like a no. A pause in momentum feels like collapse. A day without activity feels like wasted time.
You stop seeing purpose - and start seeing only deficiency.
The Question Behind the Question
“Am I doing enough?” often hides deeper questions:
- Am I doing this right?
- Do I belong here?
- Will anyone notice if I burn out?
You don’t just want to hit goals. You want to feel like your work matters - and that it’s leading somewhere.
And when that connection breaks, the pressure doesn’t fade. It grows teeth.
Reframing “Enough” in a World Without Finish Lines
Let’s try something gentler. Instead of asking: Am I doing enough? Try asking: What would “enough” look like this week if I defined it by presence, purpose, and momentum - not just hitting dollar goals?
Here are three practices to help you reframe “enough” when the pressure builds:
A Blessing for the Guilt-Weary
If this question keeps you up at night, it’s not because you’re broken. It’s because you care.
You were never asked to be superhuman.
You were asked to show up - present, faithful, and real.
So may you:
- Lay down the need to prove your worth.
- Trust that seed-planting is real work.
- Remember: even when you can’t measure it… you are making a difference.
That, my friends, is enough.
* * * * * * * * * *
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,
