Deep work and the reverse todo list

I recently finished reading Cal Newport’s Deep Work: rules for focused success in a distracted world. While it’s pretty reasonable advice (like the nugget “When you work, work hard. When you’re done, be done.” p. 154), there are a few really powerful parts that I found very affecting and reasonable. Since I bet most folks take one message from Newport’s very well-publicized media appearances, and that’s his digital minimalism message. While that’s a pretty important concept, it actually isn’t the main message in Deep Work. Instead, what does appear prominently is the philosophy of work mindfulness or intention. Presaging recent discussions of millennial burnout, Newport recommends that people

1. take work seriously,
2. remain self-aware about how work time is spent,
3. but then ensure that leisure time is spent mindfully, too.

This concept of “mindfulness” is really interesting to me. It’s cropped up on research about depression & anxiety. Apps like Calm and Headspace have built up reasonably-large, dedicated communities. Guided meditations on YouTube can often hit millions or tens-of-millions of views. But, like many buzzwords, the precise definition of what counts as mindfulness isn’t clear.

For Newport, work mindfulness is intrinsically-connected to quantification, which makes sense as a computer science professor. But, what’s really heartening about his perspective on mindfulness as quantification is that it’s a descriptivist, not a prescriptivist approach to the practice. By this, I mean that Newport’s overtly Taylorist suggestions (like “Schedule every minute of your day”) are made not to suggest that folks actually stick to that schedule. Instead, Newport describes processes by which you can review and revise your detailed daily schedule to account for bursts of inspiration or pressing and unforeseen matters. Thus, instead of committing yourself to rigid, extrinsically-motivating structures that often bind too tightly to be realistic, Newport recommends you simply externalize your work practices (through scheduling) to be aware of what you are spending time doing. By constructing a detailed schedule beforehand but revising that schedule throughout the day, you effectively “set your intention” for chunks of your time, but you don’t beat yourself up if you fail to complete specific markers.

*This kind of work mindfulness has been really helpful for me, too. Before I ever read Newport’s book, I used a “reverse to-do list.” I struggled to manage my time when I was split between being a PhD student at Arizona State & working at Nextdoor. I tried using systems like Todoist, but found them to be overly punitive. The concept of every task having a deadline that was prominently displayed was pretty overwhelming. Further, if you didn’t get done something on your todo list, clicking that “Reschedule” prompt always felt so defeating. Further, if you fell out of practice checking the app every day, the disappointing red Overdue: 5 days text felt pretty bad to see. This kind of prescriptivist thinking about work is inherently evaluative. It carries judgements on when tasks ought get done and suggests a kind of moral penalty for them having not been done. Indeed, their “karma” concept is inherently moralizing, suggesting that every single deed had moral weight. No thanks.

Instead, I took a non-evaluative approach to to-dos. I’m by far not the first to think of this, but one thing I learned to do for myself is to state a few things I intended to get done each day, and then to record everything I did in that day in a separate list. In this manner, I’d set an intention for what I wanted to do. I’d get balance in tasks or load by ensuring that that intention reflected a healthy mix of the things that I needed to get done in the near term and some things I needed to get done in the medium-to-far term. Then, recording separately what was actually completed, regardless of whether it was something I’d intended to complete, helped me connect how I actually spent my day to how I’d intended to spend my day. Something like:

I find this to be extremely helpful, and can reach into my [dynalist] (https://dynalist.io) and pull these lists (daily) back to 2014. There’s no graph, no running score, and no overdue. But, by reviewing these each day, I can build awareness of the things that I’m not accounting for that take up my time. I can discover the stuff that I tend to get done easily, as well as the things that stay on the today I want to list forever (and thus, might not really be things I want to do!). This, while not as directly quantitative as Newport’s suggestion to schedule every minute and revise that schedule often, is still a work mindfulness technique to develop self-awareness of how you spend your working hours.

I find these kinds of mindfulness strategies to be very helpful, especially when they’re non-evaluative. If you spend enough time making yourself feel like a failure, it disincentives the process of measurement itself. So, I find that practices that focus on building awareness, rather than evaluating progress, are the best form of productivity tracking & management. And, I’m definitely pleased to find that Newport’s suggestions about metacognition and mindful, attentive work align with the single best thing I’ve found to help my own productivity and self-esteem as a 28-year-old Assistant Professor.