Field Notes #004

This year I am putting a ton of energy into systematizing the hell out of my work and life. I have always had a tendency to do that, but I’ve finally come across a process that actually works for me.

In the past, I took a different approach towards how I systematized things. I read a ton of productivity blogs and books, and then attempted to apply the methods in them, sort of in a “solution in search of a problem” kind of way.

Even though I learned a lot of helpful tools and techniques in that process, I always ended up optimizing things that perhaps were not the bottleneck in my daily work. And because trying new ideas always has a cost, I ended up feeling defeated more often than not whenever the novelty wore off and I broke away from a new shiny habit.

These days, I’ve shifted my focus to doing everything bottom up, and it makes a difference. For example, a couple weeks ago I was about to sit down to do some heads down work and my desk looked like this:


Missing from that image is the flat panel display I use as a second screen, because it was sitting on top of a cabinet where I was using it to watch TV the night before. Present in that image is is a mixture of stuff that should be there and stuff that should not, but all I see is a big ball of friction that says “Hey, stay on Twitter for another 10 minutes, that’ll feel a whole lot better than cleaning up this desk so you can get to work.”

And it’s sooooo easy for that ten minutes of procrastination to turn in 30 minutes. Or an hour. Or half a day. I’m not too proud to admit that. It’s the tyranny of having a flexible schedule and not overbooking things!

My process for starting to address this particular issue was to take this picture. It was in part to remind me “This is what you don’t want” and in part to get the wheels turning in my head on a solution.

Soon enough, I remembered two articles I’ve read that address this particular topic:

And you know what, I know the benefits of starting from a clear, well organized state. And I even know how to do it, almost down to an exact level of detail. The challenge is keeping up the discipline needed to make something a daily habit.

In the past, I’d just push myself to rely on self control, and then when things got busy or when the novelty wore off I’d feel guilty for letting the habit slip. I try hard not to do that anymore, because it just makes things worse.

Instead, I try to use systematization to make doing the “right thing” as easy as possible. For me, that meant adding a “Reset to neutral” checkbox to the daily routine tracking tool that I use, and then writing up a checklist for how to do it so that when the time came I just needed to execute the plan without burning any mental cycles to do it.

It keeps evolving, but here’s the checklist I’m using right now:

Screen Shot 2018-03-26 at 9.56.59 AM

I try to follow it in the evenings so that when I get up in the morning I’m all set and ready to go. Whenever I do that, it feels great and reinforces the habit.

An interesting effect of taking this bottom up approach is that solving one problem reveals many others in the process. Here are a couple examples:

  • I was never happy with my current approach for storing checklists like this (They’ve historically been spread across four different wikis as well as paper notes), and that lead me to finally try out Notion. I’m still in the process of evaluating it, but it seems extremely promising as a personal knowledge base tool.
  • I noticed that while I don’t care about doing “Inbox Zero” on a daily basis, it is probably a good idea to do it at least once per week so that I can avoid having an endlessly growing pile of mostly non-actionable emails sitting around. I only started to notice this after I was able to sit down on Monday morning and just start my day, but now I’ve added a Sunday night chore to my routine tracking tool that reminds me to clear my inbox before the week begins.
  • Actually sitting at my desk more often as opposed to giving up on it and working from the couch or dining room table made me realize how much I hated my badly damaged keyboard with its sticking keys. So this new habit of making my desk work-ready had the beneficial side effect of causing me to buy a comfy new mechanical keyboard.

To sum it up, the approach I am now taking is to search for concrete problems in my daily life and then see if there is a very lightweight way to “solve it with a system.”

In doing so, I start to loosen up all the tightly bounded knots around me. But it doesn’t feel like a massive top-down rewriting of my habits, just gradual and continuous improvements that make things flow a bit more smoothly.