Or: A field guide for working in the messy middle of operations.
What This Is (and Isnât)
Three years into my first ops role, I was stuck. The work was getting harder, and I wasnât improving fast enough. I could feel it. I'd solved the same forecasting problem three times in six months, each time like it was the first. I knew there had to be patterns, but I couldn't see them clearly enough to learn anything from them.
So I went looking for help. I found finance books that taught me how to build models and think about how cash moves through a business, but not how to build trust in the models themselves. Operations guides that explained how to design a process, but not how to get people to use it. Communities full of people asking tactical questions about tools, but no one talking about the judgment calls that really mattered.
Everything I found treated the work as either fully tactical (build a dashboard) or fully strategic (design a business model). Nothing lived in the space I actually worked: the messy middle, where the forecast keeps breaking or two teams canât agree on what âcustomer successâ even means.
The books assumed you either knew nothing or knew everything. The communities assumed your problems were just like everyone elseâs. None of it felt like the work I was doing.
Who This Is For
This is for people who work in that messy middle. It turns out I wasn't alone there. I've often been asked for advice on what to read, and I've never known what to say. Hopefully this helps.
You might be called Finance, RevOps, BizOps, or something else entirely. Your job description probably doesn't capture what you do.
The work involves debugging numbers and the processes behind them. It means sitting in meetings where everyone agrees the system is broken, but no one can explain exactly what is broken or how. It's noticing how small inconsistencies compound into big problems and learning to spot the early signals.
It's asking, "Wait â how does this actually work?" when everyone else is ready to move on. It's caring about getting it right, not just getting it done.
If solving the same problem repeatedly feels like your specialty, or if you've struggled to find writing that reflects this kind of work, this might help.
What You'll Find Here
These are essays about patterns, not playbooks about processes. Real things that broke, and what they taught me. Quiet observations about systems that kept working when everything around them changed.
Some will be structural: how forecasts drift, why cash flow models break, what makes operating rhythms stick.
Others will be cultural: how trust accumulates, why ownership matters, what happens when systems lose their believers.
Most will live in the overlap between structure and culture, because that's where the interesting problems usually are.
Nothing here will solve a lack of clarity for you, but it might help you notice it sooner. There is no magic dashboard waiting at the end. Just better questions and sharper instincts.
What to Expect
These essays will show up when they're ready, not on a schedule. They are meant to be useful, not comprehensive. Each one stands alone, but they will build on each other over time.
They won't teach you to blitz-scale or unlock hypergrowth. They won't offer frameworks that solve everything. They assume you already know the work matters. You just want better tools for doing it.
If you've spent time inside a company trying to keep the gears aligned while everything shifts around you, this won't feel novel. It will feel familiar. Thatâs the point.
The goal is not to offer answers. It's to name the shape of the work and make it just a little easier to do it well.
