Diary of an AI PM is a first-person narrative about building a career in AI product management — written in real time, not in retrospect. Not the polished version. Not the “5 tips I learned” version. The version with the rejected applications still in it.
Who writes this
I’m Michael Kent. I’m a product manager working in production AI systems — and I’m actively transitioning into AI PM roles at high-growth companies in San Francisco. This diary is the record of that transition: the strategy, the preparation, the rejection emails, the near-misses, and (eventually) the landing.
I also run two other channels. ContextWindow covers the strategy and depth of AI product management. PostSynaptic is the technical build log. This is the third piece — the personal one.
What this channel is
It’s a career diary. First-person, chronological, honest. The entries cover what I did, why I did it, whether it worked, and what I’d change. Some entries will be about specific applications or interviews. Some will be about the broader strategy of positioning yourself for a role that most companies are still figuring out how to define.
What this channel is not
It’s not career advice. I’m not in a position to give career advice — I’m in a position to document what I’m doing and let you decide if any of it is useful. If I land the role, the diary becomes a case study. If I don’t, it becomes a cautionary tale. Either way, it’s honest.
It’s also not vulnerability content. I’m not performing struggle. I’m documenting a process. There’s a difference.
The name
A diary is a private record that becomes public. The “AI PM” role barely exists as a defined career path — most job descriptions are either a traditional PM role with “AI” bolted on, or a unicorn that doesn’t exist. This diary is about trying to build the career anyway.
The voice
Sardonic. Specific. Earned. I write the way I think — direct, a little dry, and never performing. If something is going well, I’ll say so without false modesty. If something failed, I’ll say so without performing vulnerability about it.
When does this launch?
The entries are being written now, privately. When the story has enough shape to tell well, they’ll publish with the full timeline intact. Subscribe to get notified.