It’s Happening Again…

This is post #2 of The Clear-Eyed Series: An Exit Strategy from Confusion

‍If you’re new here, you can read the first post here: “What Counts as a Good Week in Major Gift Fundraising?”

Over several weeks we’re taking a clear-eyed look at the work itself - not a checklist to complete or a new system to master, but a steady way of orienting ourselves when anxiety creeps in and the work starts to feel elusive.

And if you’ve been around for a while, consider this a weekly invitation to slow down, take stock, and remember what the work really is.

Over the last couple of months, I’ve been having a lot of good conversations.

Meetings. Phone calls. Text threads. Emails. Coffees. Meals. The kind of relational work that actually matters in major gift fundraising.

And yet, sometime in mid-January, I noticed something strange happening in my body. Every time I reached out to someone, I winced.

Not because the outreach was wrong.
Not because the relationship was strained.
But because I knew the conversation wasn’t fully documented yet.

Which led to a very honest internal question: Really? I’m wincing for doing my job?‍

Here’s the context. I’m still relatively new at Sinapis, and for a stretch of time I didn’t have full access to our CRM. So I did what I know how to do. I met with people. I listened. I followed up. I connected. The relational work was real - but the documentation lagged behind.

Part of me was annoyed at that gap, and another part of me, surprisingly, was calm. I knew help was coming. Ivana, my assistant, is a lifesaver. She has an incredible ability to take texts, screenshots, voice notes, and half-formed thoughts and put them into the CRM in a way that actually reflects reality. Knowing she was in this with me kept the anxiety from tipping into panic.

Still, eight weeks of good relational work eventually demands a reckoning.

So Ivana and I are now staring straight at an eight-hour documentation sprint. Not as punishment.  Not as shame.  But as cleanup. As alignment. As finishing the work we already did.

I know how it’s going to feel when it’s done.
Peace.

Here’s the thing I keep (re)learning in this work. The work is not finished until it’s documented. A good week has both.

Which raises a very practical question: How do I structure my week so this doesn’t keep happening?‍

Because confusion in major gift fundraising often comes from good relational work that isn’t supported by consistent weekly disciplines. And that’s when anxiety comes dancing in to fill the gap - mine, for reasons I don’t fully understand, usually does the salsa.

So before we talk about calendars, systems, or next actions, it’s worth slowing down and asking a more foundational question:

What should I actually be doing in a given week to do this work well - and stay human while I do it?

That’s what this week’s guide is about. Not squeezing more productivity out of already tired people. Not layering on new expectations. But naming the few weekly practices that protect relationships, preserve your soul, and keep you from slowly drifting into transactional habits you never intended to adopt.

Let’s talk about the work beneath the work. My hunch is that you’re not looking for more ideas. You’re trying to discern whether the things you’re spending time on actually matter - or whether you’re quietly falling behind while looking busy.

So I’ll say it plainly. A clear-eyed week in major gift fundraising is built around a small set of activities that protect relationships, preserve your humanity, and keep the work from drifting into something transactional.

Start with connecting activity

If you strip the work all the way down, the heart of a good week is simple: are you having conversations with people?

Not every conversation is about money. Not every conversation moves something forward in visible ways. 

But conversations are the unit of progress in this work.

If you’re consistently engaging people and paying attention to where those relationships actually are, you’re doing the work.

That’s why I care so much about having a clear sense of strength of relationship and the next action for each person in my portfolio. It keeps me honest about reality.

When I know where a relationship stands - and what the next faithful step might be - I can relax.

Finish the work you start

Here’s where anxiety sneaks in for a lot of us (4 fingers pointing squarely back at myself). 

We have the conversation.
We do the visit.
We send the follow-up.
And then we move on.

But unfinished work lingers.

Documentation isn’t bureaucracy. It’s registering the work so your brain - and your team - can exhale and move on, too.

When Ivana and I do our weekly touchpoints, we always raise our cups for a little “cheers.” I thank her for her good and hard work, and she thanks me for my brain.

It’s a small ritual. And it always reminds me of something important: it’s not good for anyone if I’m hoarding things in my head.

‍Let prayer set the pace

For me, prayer and meditation are what keep me human in this work.

Prayer slows me down enough to see people clearly. It softens the edge that pressure creates. It keeps me from turning people into outcomes.

When prayer is present, I’m more patient with silence. I’m less likely to assume bad intentions. More curious. More generous in how I interpret what’s happening.

When prayer slips, I notice it quickly. My thinking narrows. My posture hardens. And I start pushing in ways that don’t actually serve anyone.

A clear-eyed week includes specific prayer for the people you’re working with and the invitations you’re carrying - even if nothing visible happens yet.

Measure what you can actually control

One of the most freeing shifts fundraisers can make is learning to celebrate what’s within their control.

You don’t control decisions.
You don’t control timing.
You don’t control responsiveness.

You do control whether you reach out.
You do control whether you prepare well.
You do control whether you document what matters.
You do control whether you stay grounded.

When leaders and fundraisers align around connecting activity instead of just outcomes alone, something healthy happens. Anxiety goes down. Integrity goes up. And relationships have room to grow at their own pace.

When our weeks get crowded and our disciplines slip, we drift toward becoming transactional. We rush conversations. We force money into moments that aren’t ready. We start interpreting silence personally. 

A note for CEOs and board members: You face an important choice here, you can either calm the system - or inflame it.

These clear-eyed weekly practices exist to protect you from that drift. They help you stay oriented.

So if you’re wondering what you should actually be doing this week, start here:

👉🏻 Have a few meaningful conversations.
👉🏻 Pay attention to where relationships really are.
👉🏻 Finish the work by documenting it.
👉🏻 Stay grounded in prayer.

Clear-eyed weekly practices don’t make the work easier. They make it truer.

And also this (say it with me):
‍Reach out to three people today.

* * * * * * * * * *

‍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,