Wednesday Wisdom #14

Issue 14: Digital Minimalism, Where to Blog, WikiRoulette, Knowledge Workers

Hey everybody 👋,

Greetings from Chicago.

I had an enlightening conversation with my friend Adam Tank on Saturday after our Crossfit for Writing session. We were talking about weekly newsletter burn out and whose newsletters we look forward to reading each week. I can count on one hand those that have a 100% open rate for me. Some—while interesting—are not in the ‘can’t miss’ category.

Those that do meet that ‘can’t miss’ criteria have something in common. My writing teacher, David Perell calls this a ‘Personal Monopoly’. You want to be known as the best thinker in a skill or topic. Personal Monopoly is the unique intersection of your knowledge, personality, and skills that nobody else can compete with. Personal Monopolies aren’t found—they’re created.

Packy McCormick’s newsletter Not Boring meets the ‘can’t miss’ criteria. He has been able to combine business strategy, technology, and pop culture and write about it interestingly and uniquely Packy.

While I’ve settled into a consistent weekly writing routine here and am proud of the essay I published last week, I’ve had a harder time than I expected to figure out my own ‘Personal Monopoly’. When I spoke to Packy about it this week, he said it took him 10 months before focusing in on what he’s doing today. The secret is not forcing it and just putting in the reps (keep publishing).

Other work that’s consistently in the ‘can’t miss’ category is Ben Thompson’s Stratechery and Nick Maggiulli’s Of Dollars And Data. Both writers are extraordinary and are the best at what they do.

Packy’s work stands out for me because he hasn’t been writing for that much longer than I have. For the same reason enjoy playing golf with better players than me, it’s inspiring to see someone so good at what they do that it motivates you to keep working at it.

Feedback always helps to know how I’m doing with these newsletters. It allows me to know what topics to focus on and what not to. Just reply to this email and I would love to have a conversation with you about what you liked and where you think I can improve.

Send me a note

If you missed last week’s newsletter, you can check it out here. I shared my published essay about Chicago and discussed Worldconnectors, the Mere-exposure Effect, Netflix, and more!

Digital Minimalism

Cal Newport’s Digital Minimalism has been on my reading list for some time and I was excited when it finally became available to borrow through Libby.

Digital Minimalism is a philosophy in which you focus your online time on a small number of carefully selected and optimized activities that strongly support things you value and then happily miss out on everything else. We should be conscious of the apps we need and don’t need and be able to control our usage so that we are no longer slaves of our technology.

Newport offers practical advice and frameworks for thinking about the role that technology and social media should play in our lives.

Digital Minimalism: Choosing a Focused Life in a Noisy World by [Cal Newport]

When Steve Jobs introduced the iPhone in 2007, he sold it as an iPod that can make phone calls. His vision of disruption was much more modest than what happened.

The devices we use every day were originally designed to help improve our lives and stay connected with the people we care about. Instead, they became digital slot machines that began to dominate our time and attention. The “Like” button became the foundation on which companies like Facebook rebuilt themselves in the mobile world. This introduced a rich new stream of social approval indicators that arrive unpredictably—creating an impulse to keep checking our accounts.

Facebook’s notification symbol was originally blue, to match the palette of the website. Due to low engagement, they changed the notification color to red—an alarm color—and clicking skyrocketed.

With Google worth $995 billion and ExxonMobil worth $225 billion, extracting eyeball minutes has been significantly more lucrative than extracting oil.

“The tycoons of social media have to stop pretending that they’re friendly nerd gods building a better world and admit they’re just tobacco farmers in T-shirts selling an addictive product to children. Because, let’s face it, checking your “likes” is the new smoking.”

Interesting Things I Learned This Week

Where to Blog

Ben Thompson is the author of my favorite business strategy newsletter Stratechery. His analysis is unquestionably the best $120 I spend each year—like getting an MBA lecture delivered to your inbox each morning.

I was so happy to discover that Ben started writing a personal blog along with his business analysis. Ben wrote a great post over the weekend called ‘Where to Blog’. This has been top-of-mind lately for me as I’ve started publishing my writing here in a weekly newsletter and on my website.

In his post, he offers this advice:

  1. Own your domain (rules out Medium and Substack for personal websites)

    • This matters more than the service you use because it allows switching in the future.

    • Buy your domain independently from where your blog is hosted.

    • Don’t feel like you need a ‘.com’ domain; it’s too hard to find one with a pronounceable name.

  2. Have an open-source alternative (rules out Squarespace and Wix)

    • It’s generally not a good idea to be a customer of a monopoly.

    • Using a service built on open-source gives you options on hosting.

    • Easy switching options if you are unsatisfied.

  3. Consider optionality

    • Ben recommends Wordpress over Ghost due to the ecosystem of developers, plugins, and themes.

    • The entire point of having your own site is to be independent, but it’s easier to be independent if you are one of many.

My domain is hosted through GoDaddy and has gone from being on Blogger, Tumblr, and now Wordpress. I’ve considered switching to Squarespace since their templates and themes look so good, but after reading Ben’s post I’m inclined to stay with Wordpress for the foreseeable future.


I can’t believe I’ve never seen this but WikiRoulette is a tool that lets you learn something new on Wikipedia each time you hit refresh.

Here are the last 5 random items that popped up:

  1. Hyposmocoma barbata

  2. Battle of Polesella

  3. Seibel S-4

  4. Trickle-bed reactor

  5. Voorcompagnie

Knowledge workers are like professional athletes

  1. Clear on and off-seasons.

  2. Highly specialized training regimen.

  3. A dedicated team of coaches and trainers.

  4. Vastly unequal pay.

  5. Recruiters and scouts will scour the globe for them.

Companies will be like pro teams that will disproportionally overspend for the best talent.

Tweet of the Week

Photos of the Week

The restaurants and businesses in our neighborhood got boarded up after the protests last week. Now the boards are covered in amazing artwork. This is a small sample of many murals we’ve seen on our walks around the neighborhood. ❤️

Sometimes it’s easy to feel helpless about what’s going on—seeing these positive messages so soon after businesses were covered in plywood as protection gives some hope to a city and world that’s hurting right now.

"No matter the color of your skin, race, gender. I think it's important that you take the time out of your personal bubble and express that you're here to help whoever is in your community" - Chicago mural volunteer Jori Harland

Thank you for reading and until next week,


If you would love to discuss anything I’ve covered, please reach out to me by replying to this email or sending a direct message on Twitter at @levnaginsky

If you’re reading this because someone shared this newsletter with you or you clicked a link somewhere, welcome! Please subscribe to receive future updates.

Share Wednesday Wisdom