I work from home a lot in the summer. On a recent trek into the office, I ran into a friend I hadn't seen in a while on the walk downtown. She asked how work was going. I told her work has been great at Ateko, lots of fun challenges, and that I'm really enjoying myself. She said hers was great too, and filled me in on where she was at.
She's about three years into her job now. The first couple of years were spent learning, absorbing, and solving problems as they came. More recently she's moved into a bigger role, she understands the business better than ever, and she's gotten good at knowing what actually deserves her attention. She told me she's probably only "busy" about 60% of the time these days.
She paused after that, and we kind of tumbled into a conversation about it. Having time on your hands is supposed to feel like a reward, but for us, at least, it doesn't quite. There's a kind of oomph that comes from having real things pulling at you, and when it's not there, something feels off.
When I ran my own agency, chaos was the baseline. I was figuring out how to run a business from scratch: managing people, balancing the books, doing sales, keeping clients happy. I had no idea what I was doing for the first few years. I made plenty of mistakes, learned from them, and eventually got pretty good at it. But every couple of years, there would be a real crisis. The business would be circling the drain, and sometimes a potential buyer would show up. I wanted out during those moments too, though for a very different reason: selling felt like a lifeline, a way out of the stress. Each time, the due diligence process helped us name the single biggest problem we were facing, and we'd take real measures to fix it. We'd carry on, hit the next stretch of hard problems, and then the next crisis.
The last of those big fixes was different. The whole team worked on it together, and it changed everything: how I ran the business, how I managed people, how we sold work, how we marketed. It was the best thing we ever did, and it made us great. The 18 months after that were about as close to perfect as a small business can get: we were profitable, we had no major fires left to fight, and clients were coming to us. I went from working 80 or 100-hour weeks down to 30 or 40. I had all the time in the world and nothing hard enough to spend it on.
And then something weird happened: I got bored. Everything was going well, and I still couldn't find the energy to engage with it the way I used to. I was approached to sell, and I took the offer. If I'm being honest, I wanted out, and the reason was the opposite of every other time: the business was doing great. There wasn't anything hard enough to make me care.
I've been on a bit of a high with my own role lately. I'm managing three teams, working through two big client projects, and building some systems to help my teammates save time and work with less stress. I've been talking with friends for months about how much I love it. It's full-on, but I'm managing it in a mostly controlled way. AI has been a great unlock on that (more on that below). Part of what feels right is that I'm constantly having to be quick on my feet, responding to things from clients and internally as they come. That's exactly the mode I was in at my best during the agency years.
Three kinds of chaos
Throughout my career, I've worked in three kinds of environments, and I react to each one differently.
The first is what I'd call engineered chaos: when things are going well, certain people in the organization manufacture turbulence anyway. They're usually bored themselves, or they feel left out and want to put their mark on something. It's demoralizing, and I've worked in places like that. They do a lot of damage.
The second is the opposite: stable, smooth, and predictable. On paper, that sounds ideal. In practice, the last stretch of my agency was exactly this, and I've described above what it did to me. When the big problems are gone, the energy that came with solving them doesn't find somewhere else to go.
The third is controlled chaos: a handful of big, solvable problems at once, where I have real control over the outcomes. My ADD thrives in this kind of environment. The work has weight, the problems are real, and I'm moving things forward rather than waiting for something to go wrong.
We parted ways about halfway to my office. I spent the rest of the walk thinking about the conversation. I've been telling people a lot lately how fantastic my job is right now, and it's been hard to pin down exactly why. Part of it is the people. I work with a really good team at Ateko, and I probably don't say that enough. The other part is how I've been working, and that's what the walk helped me finally name.
What my days look like now
I have Cursor open every day with three to five projects running at once. All of them are big, solvable problems. I start each morning moving between windows: I explain what I want to get done on a problem today, hit enter, and move to the next window. By the time I loop back, the first window has thought through my task and has a plan or a set of questions ready. I give it feedback, push back on anything that's off, and ask my own questions before moving on. By lunch I'm usually focused on two of the five, but I've moved all of them forward in a way that feels like several days' worth of work from before I was working this way.
The honest part
I want to be clear about what this actually feels like, because it's not a productivity story. By the end of most days I'm wiped. I've spent the whole day thinking, directing, questioning, testing, reviewing, and course-correcting, and there's very little downtime. The difference from the last 18 months at the agency is that the problems have weight and I'm the one pushing toward them. What makes the work feel right isn't the tool. It's having the right kind of problems to work on and real control over the outcomes.
My friend and I put a name to the same thing on that sidewalk, coming at it from completely different points in our careers. When the right kind of chaos is there, the kind built around big, real problems you actually have the ability to solve, some people do their best work. I don't think we're unusual. If you know your version of it, I'd be curious to hear what it looks like.