A weekly letter for people who think the work matters.
Aggressive Optimism is a free weekly newsletter for purpose-driven leaders who are done with cookie-cutter advice — and ready to think differently about fundraising, brand, and legacy.
This is not a tips newsletter.
Every week I write you a letter.
It starts with a story. Something I saw, something that happened, something that made me stop and think.
Then I look at it differently and I invite you to do the same.
That's the whole thing. One story. One reframe. One question to take back to your work.
I write the way I talk. Which means it's honest, it's a little unexpected, and it's never going to tell you to "leverage your synergies."
If you've ever sat in a fundraising training and thought "this doesn't feel like us," you're my people.
Let's figure out what actually will.
Here's what will land in your inbox every week.
💛 A real story — something I've learned or observed that made me see things differently.
💛 A pattern — the thing underneath the story that shows up everywhere, not just in that one situation.
💛 A reframe — a different way of looking at it that might just change how you approach your work.
💛 A question — specifically for my nonprofit friends, designed to take straight back to your organization.
💛 A closing line — because every good letter deserves one.
No fluff. No templates. No "10 tips to transform your fundraising." Just one perspective shift, delivered every week, free.
You'll love it here if:
💛 You're a purpose-driven leader who thinks about more than just the numbers.
💛 You believe your organization's story is its most powerful asset, you just haven't figured out how to use it yet.
💛 You're tired of advice that works for someone else's organization and want to think differently about what's actually yours.
💛 You're a nonprofit leader who wants to raise more money without losing what makes your organization worth donating to in the first place.
💛 You're not ready to hire a consultant yet , but you want to keep thinking.
This is the place for that.
Why I write it.
I've spent years watching mission-driven organizations borrow strategies that weren't built for them. Tactics that work great for someone else's community, someone else's team, someone else's story. And I've watched those organizations burn out trying to make something fit that was never going to.
Aggressive Optimism is my weekly attempt to offer a different way of thinking. Not a formula. Not a framework. Just a perspective shift rooted in real stories, delivered with honesty, and designed to make you think "I never looked at it that way before."
It's free. It's first person. And it's never noise.
I'd love to have you in my world.
Jenna 💛
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