Accepting technology means accepting ourselves, Pt. 2

Today’s newsletter is the second part of an essay on how I learned to embrace my internal contradictions, and embrace technology in the process. If you haven’t read the first part, please start here.

💭 Good systems make us proactive, not just productive

My internal contradictions followed me throughout college, even after I gave up my system. The best I could do was pick one side and stick with it, even if it meant temporarily shutting off the other parts of myself. So I picked emotion — the better to make friends and avoid another dining hall disappointment.

As a consequence, I struggled to focus on my assignments; whenever I’d study away from my dorm, I’d see someone I knew and feel bad if I didn’t make conversation. I feared that if I allowed myself to be engulfed by work, then I’d quickly become a stone-faced productivity machine instead of an approachable, smiling friend. So I'd be in the library, constantly aware of nearby friends, making sure I acknowledged them when they wanted to chat or got up to leave.

Then I graduated, and I was slapped across the face with the obvious fact that the working world, unlike college, doesn’t revolve around making friends, sharing anxieties, and having deep conversations. A month after commencement, I found myself in a fast-paced newsroom in Seoul where being stone-faced was an asset.

Emotions, off. Logic, on.

Not that it was as easy as flipping a switch. The transition was gradual; it took until the following year, when I moved to Washington to work at a think tank, to shut down my emotional side in earnest. There, my first boss required the team to maintain a granular, public to-do list in a Google Doc and update her on it every day. Part of me couldn’t stand the rigidity. But another part — the rational — felt that its eyes had been reopened.

Five years after the dining hall encounter, I finally had a new system to follow. And I was happy.

How to save a life

A few months after joining the think tank, I became the speechwriter for its then-director, and I brought my nascent task management system with me.

As a result, a job that would’ve flummoxed my college self, with its requirement to master and write intelligently about a new foreign policy topic every day, suddenly felt manageable. I set up recurring tasks, made speech and op-ed templates, and learned to break assignments down into steps so easy I couldn’t procrastinate them (e.g. “duplicate the template,” “Google this topic and read the first five articles”).

Sure, my new boss occasionally thought my talking points were a bit robotic and uncreative, and my emotional side noticed that, too. But my rational side had the wheel, and man, being less anxious and more productive than ever felt good.

My to-do list migrated from a Google Doc to various task management apps: Apple Reminders, Wunderlist, Trello, Todoist. With each evolution, I fell more in love with productivity software. And then, in July 2020, with nothing to do during COVID summer, I discovered an app called Notion.

I’ll spare you the nerdy details, but here’s what mattered most about Notion: Unlike everything else I’d used, it was great at linking long-term goals (”read 24 books this year”) to monthly tasks (”read 2 books in July”) to daily to-dos (”read 10 pages today”) so that I could climb mountains one step at a time, knowing that the path to the summit was clearly paved.

Previously, long-term goals were the exclusive domain of emotion: I’d dream big, but have no idea how to execute. I’d think about Marisia, the woman who saved my grandmother during the Holocaust, and aspire to recreate her impact — but what did that mean practically?

Short-term to-dos, meanwhile, were the exclusive domain of logic: I’d succeed at the little things, but have no idea how they got me closer to fulfilling my purpose. I got really good at “optimizing my workflows” — but to what end?

Now, I could get them to work together. I could create a visual link between my abstract aspirations and the concrete actions by which I’d achieve them. For the first time, my rational and emotional sides could see what life might look like if they were no longer at odds.

Digital love

Then, another setback.

The pandemic gave me some moments of solitary productivity, but for most of it, my family and/or girlfriend were working from home alongside me. Particularly for my girlfriend, whom I hadn’t been dating for long, seeing me in the thick of my work was new.

Her main observation? How I’d shift, abruptly and without warning, from soft and sweet during breaks to stern and stoic at my desk. One minute I’d joke around, and the next, I couldn’t be bothered to chat. I must’ve been annoyed, she assumed — but I asserted that I was fine, which only made her more confused. Then the repeated questioning would upset me, and things would spiral from there.

Just like that, I caught a whiff of the old fear. Was she right? Was there something wrong with me?

No. I had come too far since the dining hall to undo my work so easily. I was both deeply emotional and deeply rational — I just didn’t know how to explain it., Eventually, we came up with a name — “focus mode” — for my mood at work. Focus mode didn’t invalidate how silly and playful I could also be, but now we both understood that each side had an important role to play.

Both sides now

In the years since I discovered Notion, my systems have kept evolving, each time bringing my emotional and rational sides closer together.

My rolodex tracks when I last spoke to my friends and reminds me to get back in touch. My rational side tees up conversations for my emotional side to show up to and enjoy.

My notebook stores everything I’ve written and most of what I’ve read, watched, and listened to. My rational side captures my thoughts so that my emotional side can let its imagination run free.

My task manager assigns an effort rating to all my to-dos, then organizes them into one-week “sprints.” My rational side enforces deadlines — for doing my chores, texting my parents, even writing this newsletter — so that my emotional side can achieve anything it sets out to.

In these ways, my systems — my technology — have made me only more human.

In other words, if emotions and logic can be reconciled, then so can humans and technology.

For that to happen, we need new vocabulary and new examples that reflect the middle ground between rejecting our devices and being addicted to them.

That shift is already underway. My generation came of age along with technology; we’re not helpless to it, nor do we deny its potential. We’re thinking about how we want to live with it, and how we want to raise our kids with it. And we pride ourselves not on being productive for unquestioned ends, but on being proactive in pursuing the joy of life.

We already know the future we want. All we need is a system to get us there.