The Magic of Boredom

🦊 #62 — Benefits of boredom, the future of AI-assisted creativity, and an ode to procrastination.

Hey friends,

I had to push this newsletter by a week, but I’m glad to be here with you now. I’ve been hard at work on my upcoming book of fables, and recently finished drafting its fifth fable. There’s still lots more writing to do, but this is a big milestone, and I’m proud of myself for continuing to honor my own goals.

Thus far, I’ve managed to juggle writing the book alongside this newsletter, but a recent revival of my social life pushed my schedule over the edge. I’m incredibly grateful to be seeing friends in person again, but it’s clear that my social battery has shrunk over the course of these pandemic lockdowns. I’ve been feeling a hint of burnout as I’ve tried to juggle all the things.

Luckily, I’m headed on a vacation next week! It’s the first time I’ll be on a plane since before the pandemic. I’ll be taking a break from all of my work — part-time startup work, newsletter and essays, and yes, even my book writing. Usually, I take a break from one and keep doing the other, but not this time. My mind, body and soul need a real break, and I’m going to give it to them.

I’ll be back in your inbox in mid-August. Until then, take care and be well!

P.S. If restrictions are lifting in your area, how has the transition been going for you? What were the first activities you jumped at the chance to resume? Do tell! I’d love to hear from you.

The Magic of Boredom

In this new essay, I share the story of how, back in the early 2000s, I turned my dead-end internship into a career-launching experience.

You might be working in a place that feels barren, empty and without hope. But perhaps somewhere, hidden in the depths of its soil, there is a budding seed of opportunity.

Let yourself be bored enough to search for it, curious enough to water it, and patient enough to tend to it. You might be amazed by what bears fruit.

By embracing boredom and chasing curiosity, I unearthed a spring of opportunity amidst a barren desert.

Read the essay: The Magic of Boredom

AI-Assisted Creativity

In a prior newsletter, I wrote about the explosion of AI-assisted tools that have been built on top of the the machine learning framework, GPT-3:

There is incredible potential but we need to temper our expectations. Personally, I find myself oscillating between excitement, bewilderment, and anxiety whenever I deeply consider the implications of GPT-3 (and beyond). Can artificial intelligence replace human creativity?

I wrote that almost exactly a year ago today. It’s been interesting to follow the evolution of the space since then. One of the tools I’ve been able to play with hands-on is Sudowrite, which presents a compelling offering: “Bust writer’s block and be more creative with our magical writing AI.” I’ve used the tool on a few occasions while writing fables. I don’t outline my stories, but I usually have a rough idea of what happens next. In the rare cases where I don’t, I look to this tool to spark some ideas. I provide it with a few paragraphs of my own writing as “prompts”, and then it does its magic.

I haven’t found the results to be directly usable in my stories. But there is occasionally an unexpected direction, character, or phrase that it generates which gives me an idea to further explore. In that sense, the tool serves as a kind of slot machine for random thoughts in the theme of whatever you give it. I pull the lever, and see what it yields. This is fine, since the tool gives get infinite “pulls”, charging a fixed monthly subscription price. Typically, my turn at the machine yields no winnings, and I return empty handed. But sometimes, I’ll find a nugget to work with, and scamper back excitedly to my cave of solitary writing. I expect the tool’s rate of return to improve over time as it evolves.

Eliot Peper, published author of many wonderful novels exploring technology and climate change fiction, recently noted how the tool has supported his own writing for almost a year. The tool was also recently profiled in New Yorker:

Whatever field you are in, if it uses language, it is about to be transformed.

I believe there is a strong potential for growth of such creative tools, along with the AI-assisted creatives that use them.

The robotic elephant in the room is the potential risks of these technologies getting out of hand. But what does it mean to get out of hand? What is the line to be crossed, and when might we cross it? These are fascinating questions that we haven’t even begun to frame clearly, let alone answer. Zach Cohen’s article on the risk of artistic creation explores these questions, not from a purely technical perspective, but rather that of someone simply trying to understand what all of it means for creativity: 

I believe that there will probably be three categories of art in the future – human-made, human + machine-made, and machine-made. What does machine-made art look like?

This week, the anxiety around this thread bubbled up during a New Yorker interview with the director of a controversial new documentary, Roadrunner, about Anthony Bourdain. In the film, the director chose to use deep-fake technology to generate dialogue in the late Bourdain’s voice. As it turned out, Bourdain had in fact said those words, just not in recorded form.

Is this a violation of ethics? Is it a horrific act to bring a dead man’s voice to life with technology? Would it be different if it was a voice actor doing an excellent impression? Is the issue that it was technology, not the act itself? Or was it that the technique was not disclosed as the voice was playing? What would have made it okay, and to whom?

There is a lot to unpack here, but this bit stood out to me from Helen Rosner’s piece:

Gregory suggested that much of the discomfort people are feeling about “Roadrunner” might stem from the novelty of the technology. ”I’m not sure that it’s even all that much about what the director did in this film—it’s because it’s triggering us to think how this will play out, in terms of our norms of what’s acceptable, our expectations of media,” he said. “It may well be that in a couple of years we are comfortable with this, in the same way we’re comfortable with a narrator reading a poem, or a letter from the Civil War.”

When it comes to new technology, whether it is considered “right or wrong” is rarely decided on its arrival. Instead, as it is launched into society, it triggers discourse and discussion in hopes of reaching a consensus.

What we are “comfortable with”, a vague notion as fickle as fashion, will likely determine what is acceptable. But what we consider acceptable ethically does not limit what is possible technologically.

We are in complicated, ambiguous and uncharted territory. If the space of technology’s future were a universe, it is firmly in the beginning of its Big Bang phase. There are nebulas of optimism, and galaxies of fear. Every potential future is a star in its collection — enormous and compelling to our eye, yet tiny and trivial in its infinite expansion.

Might as well grab some popcorn and enjoy the show while it lasts.

P.S. On the theme of coping with ambiguity, you might enjoy my essay Embracing Uncertainty, in which I share the guidance and wisdom of Pema Chödrön, who gently offers lessons on how to sit with discomfort.

Quick Links

Bo Burnham & Surviving Social Media — A new monologue video in which I explore the challenges of staying present in a world dominated by social media. I’ve been fascinated by Bo’s ideas on this topic (especially his comments in this interview clip). It made me question how I’m showing up online, when and to what degree I’m “performing”, and how to strike a healthy balance.

The Work Item Podcast — This was one of my best interviews, I think. Mostly because Den is a wonderful host with such genuine, infectious energy. I shared a lot of my thinking on creativity, work, playfulness & more. I think you’ll enjoy it.

An Ode to Procrastination — I resonated with this piece on “existential exhilaration of playing chicken with Time”. (I conveyed a similar sentiment in a short essay last year, Last Minute Circus. In the evolution of my writing, I think of that essay as the marker for when my writing began to take more of a poetic bent. Like the ode, it’s short and sweet.)

Wolf’s Way

I’ll leave you with a draft illustration from a fable in my upcoming book:

A dancing wolf skips along the grassy fields, singing and howling her morning chants. She relishes the tickle of fern upon her unkempt fur. Perched atop a hill, she scans the horizon surrounding her. Her rumbling belly focuses her loose gaze. For her, the chase of prey is a form of play.

Until next time,


🌎 | 🐦 @daretorant