Adjacencies: Underhead, free traits, hunt before you eat

adjacent • possible (noun): an innovation that acts as a building block, enabling additional breakthrough discoveries.

Here are this week's building blocks! This is an experimental new newsletter, so I'd love to hear your thoughts on whether the format/ideas are useful or "meh."

Underhead: I made an app that turns your to-do list into a life coach

To-do lists suck. This quote captures why. From The Distracted Mind by neuroscientist Adam Gazzalley and psychologist Larry D. Rosen:

The conflict is between our goal-setting abilities, which are so highly evolved, driving us to interact in high-interference environments to accomplish our goals, and our goal-enactment abilities, which have not evolved much at all from our primitive ancestors, representing fundamental limitations in our ability to process information. It is this conflict that results in… a tension between what we want to do and what we can do.

To-do lists are all about planning. But what I ultimately care about is doing. Stuffing a bunch of tasks into a long and complicated list doesn't make me want to do them. It makes me want to open a new tab and watch YouTube videos.

I'm supposed to keep these posts short, but I realized I couldn't make this one work without sharing a true story:

More than a decade ago I discovered an app that somewhat solved the to-do list problem. It was called NowDoThis. Here's how it worked:

1. You wrote your big hairy to-do list in a text box and clicked "Ready." Then…
2. Your to-dos got displayed one task at a time on distraction-free pages as you checked them off. This allowed you to focus on the current task and removed the cognitive overhead of worrying about the whole list.
3. If you included units of time in the text of your to-dos (e.g. "Spend 30 minutes reading The Distracted Mind") a countdown timer would get added to the pages for those to-dos. When the timer expired, NowDoThis would make a pleasant "ding" sound.

I loved NowDoThis. I conquered a lot of projects with it. Then one day, about 10 years ago, the site just went offline. I panicked for about ten minutes until I remembered I could code. A few days later, I was using my own functionally complete version of the app. I called it Underhead because, just like working memory which lies under your head, this app reduced cognitive overhead.

In the months that followed I tweaked and refined the app, making it incrementally better. But one of those refinements became a small revolution which transformed Underhead into a fundamentally new kind of tool: I implemented a text-to-speech feature which read the tasks aloud. This meant that after writing the to-dos in the box and pressing "start," I no longer had to even look at it anymore; the software voice would "coach" me through the tasks and even prompt me with spoken reminders about how much time was remaining on a given task. Now I could minimize the Underhead window and let it guide me in the background. I could even use it from the smartphone in my pocket and listen to the instructions through my earbuds. Underhead became a central pillar in the way I worked, and I became the most effortlessly productive person I know.

Fast forward 10 years to the present. I still use Underhead every day. I never intended to release it publicly. But I think the time has come: Underhead is one of the secret weapons behind many of the productivity approaches I write about in my newsletters. It helps power things like plan-do-learn loops, procedures, TEA management, warm-ups, timeboxed reading, and more. So I'll probably discuss it in more depth in the future, publish some guides, and spend a month or two on product development.

Here it is if you want to kick the tires, suggest new features, or tell me how much you can't stand text-to-speech voice technology: https://underhead.io.

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Acting out of character as an entrepreneur

From Brian R. Little's excellent book Who Are You, Really?:

Are you confined only to projects that suit your inborn traits? Not necessarily. … We sometimes want things that require us to stretch ourselves to achieve them. So an agreeable person may act disagreeably to book an urgent appointment with an in-demand physician, or a biogenically anxious person may appear poised and unruffled when first meeting her in-laws. These people are engaged in what I call “free traits.” And they are doing so to more successfully pursue a personal project.

The phrase “acting out of character” actually has two meanings. It means acting away from our characteristic way of behaving. But it also means acting from character. We often act out of character in the second sense when we guide our actions by our values. You may not be naturally open and extraverted. But given an important occasion or project you have little choice but to act out of character, to rise to the occasion and be an alternative you — in a sense, perhaps, an optimized you.

Little's concept of "free traits" applies to indie hackers more than to any other demographic I can think of.

Years ago I went on record saying I think the ability to become who you need to become to achieve your goals is the single most valuable skill for running a business. I went on:

In practice, this means if I ever catch myself asking, "How do I do this thing I don't like to do?" I reframe it to, "How do I become the kind of person who enjoys doing this thing?" And only then do I solve for X.

Looking back on it today, I'd say that those lines do a good job of capturing my philosophy of task-level work and many of the approaches I write about.

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Artificial scarcity, artificial fatigue

From the neuroscientist Andrew Huberman on the Jocko Podcast:

We can now access dopamine release without any effort at all. High-flavor, high-calorie food, right? That was probably rare in nature at one point. We had to work hard in order to get game, get grains, get berries. So it used to be: "effort, dopamine, relaxation, repeat." But now…

It's fair to say that high levels of dopamine achieved without effort will destroy a person. Whether or not that comes through a high-potency drug or a high-potency food, if it comes with an intensity and a frequency that doesn't require effort, it will destroy a person.

I've done a lot of reading and thinking about dopamine over the years because of its central role in energy management. And in four simple words — "effort, dopamine, relaxation, repeat" — Huberman captures the two most important insights I've found for managing my motivation over the long term.

First, by consistently going out of your way to exert effort before rewarding yourself with dopamine, you leverage a kind of self-imposed "artificial scarcity" (to borrow a term from economics) that makes it easy to stay hungry and proactive in those moments when projects become difficult. I think of it as always hunting before you eat, even if you've already stored a bunch of food.

The second insight, "artificial fatigue," is less intuitive. It's when you go out of your way to recharge with low-stimulation activities immediately following those exciting hunts and feasts — even if you aren't exactly "tired." Most high performers in disciplines with well-defined measures of success have incorporated full nights of sleep and even afternoon naps into their deliberate practice regimens. But these conventions are a lot less common in knowledge-work disciplines where it's harder to measure success, like entrepreneurship, fiction writing, etc.

In Plan, Do, Learn, I described my own convention of looping through 90- to 120-minute "sessions" of intensive project work, then self-imposing 30- to 60-minute cooldown periods where I relax and recharge. What I didn't mention was that I usually restrict these cooldowns to low-stimulation activities like walking in nature, meditating, showering, and reading physical books, and that this almost always brings me roaring back to my workstation with enthusiasm and countless fresh ideas.

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