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I’m a software engineer and entrepreneur focused on modern web technologies and AI.

Here's an ongoing autobiography, which also shares the story of my by-the-bootstraps "unschooling" education: now the subject of a chapter on grit and resilience in the bestselling book Mindshift by Barbara Oakley.

An angel investor once described my core soft skill in the role of founder or early team member as: "The ability to perceive exactly what needs to be done. And then to do it."

My experience working in difficult environments around the world means that I can be trusted to get things done, even when things go wrong.

In the past, I coined the term "Startup Cities" as co-founder of StartupCities.org and a startup spinoff, both of which focused on why startups should build cities. I now write about Startup Cities at StartupCities.com

I've won several awards for economic research and have been published or interviewed in Virgin Entrepreneur, a16z's Future.com, The Atlantic's CityLab, Foreign Policy, and in academic volumes by Routledge and Palgrave MacMillan.

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Building Tools to Change Yourself

Lifedash - A Microapp Suite

It's a New Year and that can only mean one thing: too much time spent ruminating about one's own shortcomings and all the things you failed to accomplish last year.

I'm experimenting with a new approach to positive behavior change: encode behavior in a tool that you build.

Here's my reasoning:

  1. Building a tool is costly. It's not cheap talk. I will have spent at least a few hours programming the tool. This raises the stakes and connects me more deeply with the behavior I want to change.

  2. I spend most of my productive hours in front of my computer. So I'm more likely to interact with a tool that's omnipresent on my desktop than I am with some accountability website like stickk.com. Think about if something that haunts you all day, like Slack, could make you a better person.

  3. Each time I interact with the tool, I'm mentally taken back to the behavior change that it represents. The tool itself stands in for the original motivation to change, which is so easily lost to the vagaries of time.

These tools have taken the form of a desktop app I call Lifedash. It's not really one app, more a loosely organized collection of microapps, each focused on a particular area I'd like to improve. Each app is dead simple and the suite is wrapped by an interface built with Electron.

Let's go one by one.

Commitment Monitor – Fight The Tendency to Say "Yes" Too Often

Commitment Monitor is three text boxes and a brief reminder:

../assets/blog/img/tools-for-change-1.png

That's it.

This tells me that I have three slots for commitments. One contains my primary work obligation (day job). One might contain a side-project. One might contain a hobby I like.

This radically simplifies the questions like "do I have time to work with X on Y", "can I take this consulting project", "should I sign up for Mandarin classes"?

In the past I would reason in blocks of time. I would say things like: "hmm well maybe on Wednesday nights I can fit in a meeting..." and "if it's only a 5 hour per week engagement I can probably fit it in..."

I've come to see this as too prone to self-delusion.

With this tool my reasoning becomes: "Is there an empty slot on this screen?"

If there is, perhaps I can say yes. If there isn't, then the answer is a definite "No" until I finish or quit something else.

Interestingly, this has given me strong motivation to finish projects. I feel guilty quitting something before it's complete, especially if it was important enough to put on this page. So this leads to saying "No" far more often. Good!

So far I prefer reasoning about commitments as these discrete blocks rather than trying to ration out time. The reality is that the creative mind does not always deliver on a perfect schedule. These blocks align better with the phenomenology of creative work. When I ask myself "what should I work on right now", I easily grab something off this list and get going.

I also like it better than a 'task list' because a big list of todos gives me anxiety, whereas a short list of relatively open-ended commitments fills me with inspiration and possibility.

Instant Confidence – Fight Depression, Ennui, and Self Doubt by Brainwashing Yourself with Positivity

Since I've always been nominally unqualified for everything I've ever done, I'm plenty familiar with the feeling of being an imposter. What am I doing in this fancy world of tech with all these Harvard people? What if someone finds out how often I forget the same few Bash commands?

I believe that social reality often behaves like a self-fulfilling prophecy. Confidence begets achievement, which begets confidence, which begets further achievement etc. It can go the other way too, so it's important to fight the drumbeat of negativity and self-doubt/loathing that so often accompanies creative work.

Enter Instant Confidence.

../assets/blog/img/tools-for-change-2.png

In Unleash Your Inner Company (recommended) serial entrepreneur John Chisholm writes that the most effective strategy in low moments is to overwhelm your subconscious with positivity. In other words, just force yourself to think of a vivid memory where you were smart, charming, a good leader, kind, or whatever other positive trait you care to imagine.

I think of this as brainwashing yourself.

The subconscious tends to spiral in the direction it's pushed. Without action, a moment of doubt or negativity can compound until you're absolutely certain all your woes are because when you were 7 all those kids laughed at your class presentation about Macchu Picchu... and maybe if you had never discovered World of Warcraft you'd be in MIT and... and... and that's why you can't fix this bug right now.

Chisholm's advice is to plant the Righteous Fist Of Positive Thinking right between the eyes of the subconscious and send it spinning in the other direction.

Great advice. But... it's actually quite hard to think of a positive memory when you're spiraling into negativity.

With Instant Confidence I can fill up a library of anecdotes and memories from my life where Good Stuff (TM) occurred and where I was Not Such a Bad Person After All. Then I can click a button and the app will serve me a random memory. That's it.

(I originally wanted it to text me the memory on mobile. But AWS SNS text messages were too short for the detail of many of the memories. Plus, I've been fine just opening my laptop.)

Notifications – Use Spaced Repetition to Support Creative Discipline

A hypothesis: a lot of creative failure comes from commitments and intentions that fail to move from short-term to long-term memory.

In other words: What if you're not especially undisciplined, just forgetful?

Tell me if this sounds familiar: you start, inspired, with the real intention to "write more in 2020". Something happens to throw you out of your routine. It's hard to get back into it and you don't feel as inspired, so you procrastinate a bit. Things get in the way.

You wake up six months from now and nothing was written.

It's easy to blame a lack of self-discipline in situations like these. But I wonder if the brain basically just forgets the commitment. That's certainly how it feels.

I've followed this disappointing pattern many times. But I never really "give up" exactly. I just wake up one day and suddenly remember that I said I would "insert-desirable-habit-here" but that commitment has vanished.

Your brain is ruthlessly prioritizing and that special moment between you and your blog posts last Thursday doesn't make the cut.

The new creative commitment, which is vulnerable and neurologically weak, is never reinforced enough in your mind to move it to long-term memory. As the intention moves from near-term to long-term, it fades and dies.

Where did it go?

A Digression on Cues, Rituals, and Triggers

I once had a co-worker who would write down the people, locations, and main events of each day in a journal. He swore that with only this data he could more or less remember any day in detail. I believe him. Think of how long-forgotten memories can flood your mind when you encounter a certain smell or location.

The habit changes that I have sustained are usually because there is an environmental cue – a memory trigger or ritual – that reminds me of the long-term commitment. Or it's a behavior that I've done for a long time and already see as a part of my identity.

In other words, it's either being popped into short-term memory by the outside world, or it's already in my long-term memory.

One theory of memory posits that memory is like a hash table. We store vast quantities of data. To access the underlying value, we use a key. Following this "hash table" theory of memory, forgetfulness is less that the memory fades and more that we lose the key. And without the key, we can't get at the value.

A fully-formed habit that's part of your identity is like having the key always at hand. Something about your identity and the narrow scope of your day-to-day psychology generates the key you need to access the memories that align with the commitments. "I'm just not someone who steals" you think when you find a stranger's wallet on the street. "Time to cut this out and get to the gym, because I'm a guy who exercises" says your subconscious after a day of Netflix binging.

It's hard to get a new key into your identity and day-to-day behavior.

It's much easier to encode the keys into your surrounding environment.

End of Digression.

../assets/blog/img/tools-for-change-3.png

Notifications sends push notifications at certain time intervals that science suggests will move nearly anything into long-term memory. This is the pattern of "spaced repetition" that Jeopardy champs use to memorize trivia.

../assets/blog/img/tools-for-change-4.png

In other words, the microapp is trying to get me to memorize my long-term commitment. (For the nerds, the algorithm fights the exponential forgetting curve).

It has only been about 20 days since I started this, so it's too soon to tell if this will work.

Focus – How Goes the War For Your Attention?

I'm a card carrying member of the Attention Resistance. In other words, I think we're all engaged in long-term guerrilla warfare with tech companies who want to seize control of all our conscious moments.

My 'Attention Resistance' stack includes using Brave Browser (ad blocking by default), blocking my Facebook feed with a browser extension, leaving my phone on Do Not Disturb for 4 years, and obsessively monitoring my time online with RescueTime.

I love RescueTime and recommend it. But I really just want to know if I've been focused overall. So the Focus microapp uses a cloud function (AWS Lambda written in Go using Serverless) to grab some "is Zach focused today" data and show me relevant numbers. I see little blocks like this one for a rolling period of 14 days:

../assets/blog/img/tools-for-change-5.png

That's it!

Reconnect – Long-Distance Friendship for Introverts

It's 2020 and you probably have that friend in Japan/Bolivia/Ethiopia that you met at that Leadership Retreat/Study Abroad Course/Ayahuasca Ceremony a few years ago.

Too often in the past I've let these friendships wither and fade. The worst part is that the tree of friendship needs only a little bit of water to stay alive, so there's no excuse for losing touch with these wonderful people.

Reconnect is a big list of everyone that I want to stay in touch with and the last time I spoke with them. Every three months the microapp will surface those who I haven't talked to. They go away when I click "Mark As Done", which saves the current date as the last time I spoke to them.

../assets/blog/img/tools-for-change-6.png

If I've contacted everyone on my list recently, it shows this boring screen:

../assets/blog/img/tools-for-change-7.png

Now this one must surely seem hopelessly nerdy.

But as a typical introvert, I only ever think about reconnecting with someone if the environment happens to remind me of them. Unless Tom is in my day-to-day environment, I will never autonomously think "I want to have a phone conversation with Tom!" (This, by the way, is a great reason for an introvert to find an extroverted best-friend/co-founder/partner).

This makes me sad, because when I am reminded of someone, I recall how fond I am of them, how much I value the relationship, and how I wish I spoke to them more. There is a mismatch between my true desire and my default behavior.

Let's hope Reconnect can make 2020 full of friendship.

Conclusion

I keep having new ideas for tools in Lifedash. The microapp format makes adding new tools very easy – I made Reconnect while eating breakfast today. This suggests I'm having a good time.

And if I can make facing my own weaknesses and struggling against them a good time — well, this will have been worthwhile.


Have you built any tools to improve yourself? Send me a note at hello@zach.dev

Jan 06 2020
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