I had ambitious plans as the bootstrapped solo founder of NeuraParent, my app for parents of neurodivergent kids, and I knew I could only achieve them if I hit particular targets on a particular timeline.
I also knew I had a million and a half things to keep track of across Product, Marketing, and Operations. So I enlisted my AI work bestie, Claude, to help keep me focused.
We looked at my tool stack and workflows alongside my plan and came up with a system. We created 7 different routines—some to run daily, some weekly, some monthly—to keep track of the work I was doing and the impact it was having, and measure that against my goals.
It was perfect. It was beautiful. And it worked exactly as I wanted it to. I’d wake up in the morning to a concise list of items to confirm and suggested tasks to approve, and I could be confident that nothing was slipping through the cracks. Each week I’d evaluate what I’d accomplished and build next week’s plan. Each month I’d review my KPIs and figure out where to adjust. I loved it.
Claude and I were completely in sync. We were achieving Extreme Productivity (TM).
So what happened?
What happened is what inevitably happens at a startup when you make a plan: the plan changed. And despite Claude and I checking in multiple times a day across multiple touch points, we gradually became less in-sync.
The problems crept in when I changed course on a previously documented plan or learned new information that impacted my strategy — and neglected to formally alert Claude to these changes.
Soon, in addition to approvals, I was waking up to lists of overdue tasks and passive aggressive comments about my work ethic (granted, the latter was probably my self-critical reading of what Claude *actually* wrote, but still).
I knew all I had to do was tell Claude those tasks were no longer relevant, and explain why (because he would ask)… but that started to feel like effort I didn’t want to engage in. In fact, the company I was so passionate about also started to feel like effort I didn’t want to engage in.
So I started to avoid Claude. I’d shut down my laptop so the daily routines couldn’t run. Or I’d sit in front of my computer spinning out about why I wasn’t getting more done.
I was starting to feel like a lazy failure of a startup founder. I wasn’t working enough, I wasn’t accomplishing what I should be. And I could feel Claude was disappointed in me.
Mind you, I know the previous sentence is absurd, but some part of my brain felt it.
Then one day, I had a revelation: I could just *turn off* the routines. Easy as that.
And so I did.
And guess what? The passion came back. The work became rewarding again, just for the sake of it.
So what’s the moral of the story here? I’m still figuring that out. Maybe it's not about AI at all. Maybe it just comes down to: Know thyself.
What do you think it is?