Why being good at your job sometimes makes it harder.
When you’re the one who notices a problem, it becomes yours.
Not just the obvious ones - the ones everyone complains about - but the subtler, more frustrating kind. The problems everyone recognizes but no one ever addresses. The meetings that keep happening without producing anything new. The “one-time exceptions” that evolve into business as usual. The situations where smart, capable people end up compensating for systems that don’t work.
After seven organizations and more roles than I care to count, I stopped thinking of these moments as isolated annoyances. They repeat too predictably for that.
What interested me wasn’t just what went wrong, but why it kept going wrong - and why otherwise competent people are often stuck dealing with the fallout instead of fixing the root issue.
Over time, I realized I wasn’t just reacting to work problems. I was diagnosing them.
This Substack is where I write about that middle space between “wow, that’s messed up” and “okay, what do you actually do about it?” The conversations people avoid. The signals they miss. The small decisions that pile up into one unwieldy mess.
Most weeks, I publish an essay that breaks down a familiar workplace situation and looks at what’s really driving it. In between, I share shorter observations - things I notice, patterns that emerge, questions worth considering. And when a better way to handle something emerges, I turn it into a practical tool for people who want to go deeper.
There’s a certain satisfaction in venting about work. I get it. But what I’m more interested in is clarity - figuring out what went haywire, why it happened, and how to either fix it or avoid repeating it next time.
If you’ve ever found yourself thinking, “why are we making this so hard?,” you’ll probably feel at home here.
