200,000 Words Later: What I’ve Learned About Strategy, Leadership, and Building
This is post #200. Here is what happens when you stop theorizing and start diagnosing.
Today is kind of a big day. This is post number 200 since Backstory & Strategy first published on May 15, 2025.
If you were feeling particularly generous and counted each individual word, I am likely well over 200,000 words. But where does that leave us? For starters, it means this newsletter is now long enough to rival novels like Moby Dick or Crime and Punishment. The difference is that each of those books had an outline before the first word was written. Writing Backstory & Strategy has been an experiment in throwing myself into the deep end.
One trend that I noticed in looking back at analytics was that you guys really did show up for news about news. But more than that, the pieces that resonated were the ones where I pulled apart an engine to figure out why it wasn’t running. And again, it didn’t matter if that engine was a newsroom, a nonprofit board, or a leadership team.
From all those words, a few core truths have really crystallized for me about what is going on and how the industry can start to turn it around.
Revenue is treated like an appendage.
Whether it is a hard paywall on a news site, an annual gala, or an end-of-year donation push, fundraising is just slapped on the end of the real work, completely disconnected from the mission. The problem is, the traditional “subscribe to support our mission” model is bankrupt for two reasons: economics and trust. Newsrooms keep asking audiences to buy into a relationship that most modern people can’t afford. Deep institutional loyalty just doesn’t compute when a generation can’t afford to be loyal to their favorite brand of toilet paper. But it isn’t just about the money. Organizations are also asking for absolute trust at the exact moment when faith in institutions has completely cratered. No pitch letter or subscription discount is going to fix that double bind. The product has to be unbundled.
The industry waits for a hero.
The single biggest lie told in the nonprofit world is that someone will save it. Sure, there’s a small army of consultants out there waiting to sell the dream of a billionaire, federal grant, or shiny new tech platform to solve all the problems. The biggest takeaway from the posts that you shared over and over was that bullshit doesn’t cut it anymore. When I wrote about what a real newsroom for Cheltenham would look like or took aim at the white noise of good intentions, you roared back. You are tired of theory. You want blueprints. The future isn’t going to resemble a miniature version of NPR or the New York Times. It is going to look hyper-local. Hyper-specific. Built by and for the communities that live there.
Everyone forgets just how human this all is.
One post I never expected to receive such a huge response to was What Parenting a Neurodivergent Child Taught Me About Newsrooms. People love to nerd out on strategy and Key Performance Indicators, but what about the human OS? Burnout isn’t just long hours in newsrooms and nonprofits. It’s a symptom of executive dysfunction. Leaders are using management practices from the mid-century on teams who work completely differently. It’s time to build systems that take into account just how human the workforce is.
Lesson Four: Talking about leadership isn’t enough.
In order to write about leadership and systems, I had to build my own infrastructure to actually support it. Every link I covered with regard to board development and strategic alignment wasn’t rhetorical. They were mechanical problems. Which is why I started expanding from words to building actual tools. AgendaFlow and The Board Translator weren’t a side project from this newsletter. Developing those tools felt like its natural progression. Nonprofits shouldn’t just pray for better boards or wish their staff knew how to create alignment. Someone needs to build the tools that make those things the baseline.
Paywalls, Amigos
With subscriber numbers steadily climbing, the question I get from pretty much everyone who follows my work is: why haven’t I charged for this? It makes sense. Who doesn’t love the idea of a little side hustle, and who doesn’t feel like they could use a few extra bucks at the end of the month? Every time I’m about to click that magical button, I pause and ask myself why. Putting a paywall on Backstory & Strategy doesn’t fit with why I started this. Sure, it’s one thing to chronicle how and why these giant legacy models are failing. But my mission with this newsletter isn’t just to watch from the sidelines. It’s to empower the people inside those rooms to meet these challenges head-on.
Journalism and the nonprofit world are basically in the middle of a gut renovation. There is a real chance here to build something that actually works. But that requires strategy with teeth, leadership that doesn’t burn people out, and tools that make the job easier. Putting a paywall on this newsletter feels like telling a crew to go build that future and then charging them to look at the blueprints.
That said, just because I don’t use a paywall doesn’t mean I turn away the occasional tip. If a particular piece really resonated with you over the last 200 posts, or if you just want to help me celebrate this milestone, I definitely will not say no to a token of appreciation.
To the Future
In my first 200 posts, I think I’ve done a pretty good job identifying the holes in the dike. Now it’s time to start filling them in. I know what doesn’t work. I know the cavalry isn’t coming. Let’s start building for the teams that need it most.
Since today is a bit of a celebration, I do have one small ask. I would love it if you could join me in this moment. Hit reply and share some words of encouragement, or let me know what you have liked most about Backstory & Strategy so far. And yes, full disclosure, if you say something particularly brilliant, I may just use it in future marketing.
Thank you to everyone who has read, shared, and challenged me since May. Now back to the work at hand.
-Yoni
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