What Day One of the Kickstart Actually Looks Like

Tomorrow morning, a group of dedicated nonprofit leaders will log in for day one of the Kickstart.

I've been doing this long enough to know exactly what that first session looks like — and I still get a little keyed up the night before.

Here's what's actually on the agenda.

Day one isn't about tactics. It's about expectations. Before anyone touches last year's appeal or opens a planning template, we get clear on what "done" looks like in 30 days. Not vague hope — a specific, written picture of the plan each person will walk away with.

Then we go bigger. What's the actual goal for this year-end appeal? Not "raise more than last year" — a number, tied to a reason. Big-picture goals are easy to skip past because they feel obvious. They're not. Most of the fundraising plans I see are missing this step entirely, which is exactly why they fall apart in November.

Last, we take stock of resources. Staff time, board involvement, existing donor data, whatever's already half-built from last year. You can't plan a route without knowing what's in the car.

That's day one. Expectations, goals, resources — in that order, on purpose.

Week two is where it gets sharper: we pull apart last year's appeal and ask what actually worked, what didn't, and what needs to change for this year's goals to be realistic instead of aspirational.

I'll be honest — this is my favorite part of running the Kickstart. Not the finished plans at the end, though those are satisfying. It's day one, when a room full of people who've been quietly overwhelmed all year finally get a structure to work inside.

If this isn't the year you're in a program like this, that's fine — you'll see plenty from us here either way. But if you've ever wondered what actually happens inside something like this, now you know.

Now go ask fearlessly.