Why Do I Feel Like I’m Begging?
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!
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Richard spent 25 years rising through the ranks of a Fortune 500 company. He managed budgets larger than some national nonprofits. He led teams. Mentored young professionals. Flew business class. He knew how to command a room.
Two years ago, he walked away from it all.
He felt an urgent and unmistakable call to start a nonprofit offering vocational training for at-risk youth in his city - welding, carpentry, auto mechanics. He wanted to give teenagers a path toward skilled work, purpose, and dignity.
Today Richard’s work looks very different from the corporate grind. He builds and presents decks. Makes calls. Hosts coffees and dinners - inviting others to help fund the mission.
But one part still gnaws at him. “I used to be the guy people pitched to,” he says. “Now I’m the one asking - and sometimes it feels like I’m begging.”
When Asking Feels Like a Step Down
That feeling - “I’m begging” - often has very little to do with what you’re actually doing.
It’s not about the strength of your invitation. It’s not about the worth of your mission. And it’s definitely not about being annoying. It’s about status dissonance.
Richard once had power. Influence. Control. Now he’s asking people who used to report to him to give generously - and he feels like the one without leverage. That’s jarring.
The Problem Isn’t the Ask - It’s the Story
And that story isn’t usually about facts - it’s about identity. Here’s the lie that creeps in: If I ask for money, it means I need something. And if I need something, I’m not powerful anymore.
It’s an old story - buried deep. That the giver is strong, and the receiver is weak.
But the fundraising I’m talking about turns that story on its head.
In reality:
- Asking requires vision, not desperation
- Inviting someone to join you requires confidence, not shame
- Receiving is an act of dignity, not weakness
The ask is not an admission of failure. It’s an act of clarity, conviction, and co-creation.
You’re Not Pitching - You’re Inviting
When Richard finally understood that he wasn’t asking people to support him, but to join the mission, everything shifted.He didn’t need pity. He wasn’t appealing to guilt. He was offering purpose.
“I realized I’m not actually begging,” he told me later, “I’m offering people a front-row seat to something meaningful.”
Bingo Richard!
That shift - from petitioning to inviting - reclaims your voice. You’re not someone waiting to be rescued. You’re opening a door and saying: “I think you’d care about this. Would you come with us?”
Here are three gentle practices that help reframe what it means to invite support:
A Blessing for Those Who Feel Small When They Ask
You’re not begging.
Not selling yourself.
Not trading dignity for dollars.
You’re inviting them into something sacred. Urgent. Beautiful.
So may you:
- Stand tall in your story.
- Speak with the authority of someone who knows the “why”.
- And remember: when you invite with courage, you dignify the giver, too.
Optional journaling reflection:
✏️ When you ask someone for support, what story do you tell yourself? Is it true?
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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,
