I built the perfect automated planner and I hate it.

A few months ago, I had finally created the perfect system for planning my week. I'm a paper planner person. Writing on paper helps me think and I might also be a curmudgeon. I wanted to have my plan captured digitally for a couple of reasons. Mainly, I move around a lot between my office, home and coffee shop and sometimes leave my thick quarterly planner behind. Second, digital is where my calendar, to-dos, meeting notes, etc. live. I thought it might be a good idea to have Claude help me validate and automate my plan.

So I wrote an app that I could use to take a photo of my paper planner with my phone and have it transcribed into my notes app. It could then be ingested by Claude as instant context alongside everything else. I gave Claude a routine to run every day of pulling all of this together for me.

I would write my week in preview, a practice I've had for a few years, and then have Claude pull everything together that I might not be thinking of. Commitments from meetings, emails, Notion tasks. I then realized it might be more efficient to flip the order and make sure it reminded me of every commitment and to-do before writing my preview. Seeing everything I had committed to and everything I should get done was pretty overwhelming. Then I realized Claude could probably weight all of those things for me, better than I could! I started asking it, "so what do you think my week should look like?" It always returned a very proper and stoic answer. It seemed achievable and who was I to argue? It can hold way more context at a time than me. The next step was to just have it add everything to my calendar that it knew I needed to get done and bang, I was off to the races. I was now the perfect little transcriber.

The hard problem of planning is admitting that you can't possibly get everything done. And it's even harder to admit that you can't even get done the things you think have to be done. But once you come to terms with that, as Oliver Burkeman has said, "There will always be too much to do – and this realisation is liberating." You can finally let go because you've realized there will always be too much to do and no amount of fighting or ignoring that fact will ever change it. This isn't giving up, it is coming to terms with reality. The act of wrestling with my list and making a judgement call myself, I was reminded, was the point of doing the planning in the first place. And that is exactly what my system had removed.

Even though I know better, I often fool myself into believing that I am one good productivity hack away from solving life. In my more present moments, I realize life is full of uncomfortable tasks that I need to sit with. And I'm more willing to do so when I remember that acceptance is on the other side.

All of this said, there are many things that I should automate away. Technology has improved our lives in many ways but it certainly hasn't made them less complicated and busy. There are many things that are just overhead that don't offer compounded learning from doing them. There are probably even things that do provide compounded learning that I will automate because, well, finite time. But knowing what to automate away requires judgement and, as it turns out, judgement was the very thing I was trying to remove from my process.