To have and to have not

Chris,

You asked me the other day if, given the chance, I’d do all of this again. Not the signaling, not the doors it opened, but the actual learning. Whether it was worth it.

I keep thinking about a coworker I once heard complaining about the “alphabet soup” at the end of people’s names on LinkedIn. All those certifications and degrees, and still no real sense that they knew what to do when an actual problem showed up. I have my education on LinkedIn, but I don’t promote it much. I think they were mostly right. Just because I can put letters after my name doesn’t mean I suddenly have answers.

If anything, education has mostly given me more questions.

I’ve learned everything I know about management from three places: school, books, and community. That’s probably how we learn most things, if you’re loose with the definitions. None of them gives you answers on their own. They just give you different ways of looking at the same mess.

You know I failed out of art school. Some of that was me being young and bad at navigating bureaucracy, some of it was absolutely my color blindness. I couldn’t hand-mix paints the way the color theory class required, and I couldn’t figure out how to explain to the instructor that I literally couldn’t see what they wanted me to see. By the time I realized there was no way through it, my grades were already shot.

Coming home felt like failure. It was you handing me t-shirt designs for the conferences you were starting to organize that gave me a way back in. That turned into my first tech job, my first Agile role. I read that first Scrum book obsessively because I didn’t want to fail again and end up stuck. When I got the job, they sent me to a three-day certification course.

I sat in a conference room across town while someone taught me what I’d already read, only now there were corporate games. Passing a ball around to demonstrate information flow. I passed the exam with almost a perfect score—two questions off, exactly what the instructor guessed I’d get. What I’m still not sure about is what I actually learned. Mostly it confirmed that I’d read the book correctly.

Get up in the morning and out to school
Mother says there be no work next year
Qualifications once the golden rule
are now just pieces of paper

Lars fredrickson and the Bastards (To have and have not)

Then I got my first team, and it turned out I knew almost nothing about the problems they were facing. I could recite the framework, but it didn’t map cleanly onto reality. Worse, it exposed contradictions in what I’d been taught. When I went back to the trainer months later with questions, I mostly got shrugs. That’s when books really entered the picture.

I read every Scrum book I could find around 2014. There weren’t that many then. Each one gave me maybe one or two useful ideas, and the rest was just the same thing reframed. The investment felt huge for such a small return. That’s when I realized I needed more than just books about the thing I was already doing.

I went back and finished my undergraduate degree, switching from photography to IT management at an online, self-paced school. I thrived there. I could apply what I was learning immediately. I finally understood the history behind the bad practices I was seeing at work. I learned how teams fit into organizations, not just how ceremonies were supposed to run. School didn’t give me answers so much as it gave me more rocks to turn over.

Between classes, books multiplied. Not just Scrum anymore—project management, psychology, organizational behavior, even cookbooks. I was teaching mise en place before starting work, pulling from IO psychology to create safety on teams, borrowing wherever I could find something useful. That’s around when I started going to Lean Coffee.

Community did what neither school nor books could do on their own. Sitting in rooms with other people trying to solve similar problems grounded all that abstract knowledge. You’d hear someone describe a situation and think, oh, I read something about that once. It was also humbling. You start to see how easily jargon traps you, how far into the weeds you can get without realizing no one else can follow you there.

At those meetups, I noticed two kinds of people. Those who were there because it was their job, and those who were there because they loved it. The first group shows up to network, to stay employable, to find the next thing. I respect that. The second group shows up because this weird niche thing is where they feel most like themselves. That’s where I started to feel like I belonged.

I collected certifications along the way—sometimes because they were required, sometimes between jobs because they couldn’t hurt. They opened doors occasionally, but mostly they were proof that I was still learning. When I was unemployed again, I went back to school for an MBA. This time I was honest with myself: it probably wouldn’t open doors. I’ve been told too many times that I’m “not technical enough” to manage technical people. That’s its own rant.

I did it anyway because I like this stuff. I love learning how organizations work. Managerial accounting fascinates me. Behavioral economics and IO psychology never get old. I read business books now because I’m genuinely curious, not because I think the next one will finally give me the answer.

There’s a spectrum of people who do this job. On one end, it’s just a job: make the plan, get the work done, go home. On the other end, it’s a calling—not just making plans, but making people. I started on the job end, wanting a life better than bartending as an art school dropout. Somewhere along the way, I fell in love with the science of management.

So was it worth it?

I don’t think I can answer that cleanly. I don’t have answers now that I didn’t have then. What I have are better questions, more places to look, more ways to help when something isn’t working.

At this point, I’m probably too deep in it to be objective. I’ve drunk enough of the Kool-Aid that it’s just my life now. But if the question is whether the learning itself was worth it—yes. Even if all it did was teach me how much I still don’t know.