Annual Review 2020

Writing this Annual Review, I realize that I’m incredibly fortunate. 

While some people spent the quarantine alone, I moved into my childhood home and spent five months with family. While America saw the worst unemployment spike in recent history, my business grew because the pandemic normalized online learning. And while others watched their loved ones suffer from the Coronavirus, I don’t know anybody who had a bad case of it. My fortune was mostly a matter of circumstance and for that, I am blessed. 

This Annual Review has five parts. I’ll start with the highlights, reflect on the goals I set in last year’s Annual Review, set goals for 2021, celebrate milestones, outline what I’d like to improve, and end with a list of open questions.

Highlights of the Year

New Articles Published: 73

Email Newsletters Sent: 114

Website Visitors: 1,379,435

Email List Growth: 13,087 – 45,542 (348% growth)

Twitter Follower Growth: 29,162 – 142,235 (487% growth)

Favorite Book: Leisure: The Basis of Culture

Most Popular Podcast: Balaji Srinivasan

Most Popular Article: 50 Ideas That Changed My Life

Reflecting on 2020 Goals

800 Write of Passage Students: We didn’t meet this goal because we originally planned to run three cohorts in 2020, but only ended up running two because everybody was so burnt out. Personally, running the July cohort was one of the most challenging months of my life, mostly because I re-designed the entire Write of Passage curriculum from scratch. Doing so required 20-30 hours of focused work per week, in addition to the demands of my usual publishing cadence and leading 300 students. But because we exceeded our financial goals for the first two cohorts, we were able to postpone the final cohort of the year and effectively pause business activities between October and December. 

Despite the challenges of running the course, I’m thrilled with the product we’ve built. In terms of revenue and quality, we’ve reached my five-year goals for Write of Passage in less than two years. The student experience improvements can all be traced back to the work of Will Mannon, our Director of Student Experience. Of everything he’s launched, I’m happiest about our Alumni Mentor program. In addition to three-weekday sessions and our “CrossFit for Writing” sessions on Saturdays, students opt into intimate discussion groups, hosted by one of eight alumni mentors. They’re like clubs in colleges, which offer a level of friendship beyond the standard student experience. Because of initiatives like the Alumni Mentor Program, we achieved our goal of having a 60% student completion rate.1 In addition to the Alumni Mentor Program, we launched a mechanics of writing curriculum, segmented video recordings, formalized our Saturday live writing workshops, added an Initiation Week, a student directory, a Write of Passage knowledge base, a media library, a new course forum on Circle, student-led interest groups, and invented the course roadmap diagnostic assessment that’s become standard among Cohort-Based Courses.

Grade: B

120,000 Words on My Website: This year, I realized that word count is a terrible metric for my writing because it creates the wrong incentives. We know this from school, where assignment word counts degrade the quality of your writing. Good writing isn’t necessarily short, but it’s always well-compressed. Superfluous elements are removed so the essential can shine. Knowing that, I abandoned this goal towards the end of the year. 

The catalyst was an essay called The Tyranny of Numbers, which argues that the over-dependence on numbers is the root cause of many societal problems. Striving for 120,000 words put me at risk of Goodhart’s Law, which states that “when a measure becomes a target, it ceases to be a good measure.” Even though my word count has been correlated with my writing progress in the past, knowing about the metric encourages me to game it. Setting an explicit goal breaks the historical relationship between word count and productivity. To date, the best solution I’ve found for improving the quality and quantity of my writing is time — or the number of days I complete a 90-minute writing session. 

Grade: N/A

Secret Biographical Essay: I planned to team up with the founder of a multi-billion dollar company to distill his worldview into a long-form essay, similar to what I did with Peter Thiel’s Religion. But it fell through at the beginning of the pandemic because the company had to shift their attention. I’m already in contact with his team to see when I can resume the project.

Grade: N/A

Visit Three New States and Three New Countries: The Coronavirus looked at this goal, laughed, and said: “Nope!”

Grade: N/A

50 Days of 1-on-1 Time with Friends: The Coronavirus made it hard to see friends for most of the year. My highest concentration of friends is in New York City, but I only lived there for two months this year: January and February. From April to September, I lived with my sister at my childhood home in San Francisco (my parents were absent for the first few months because they were taking care of my grandmother at a retirement home in Florida, but they joined us in June). Though the pandemic made socializing difficult, I spent three months with five friends in particular. Beginning in September, we rented an Airbnb together in Austin, Texas. Together, we enjoyed all kinds of activities: tennis lessons, group dinners, tubing on Lake Travis, and lectures on topics like polling data and quantum electrodynamics.

Grade: A-

Goals for 2021

80,000 email subscribers: Email lists are the blocking and tackling of online business. They’re not sexy, but they’re effective. Growing mine is the most important project in my professional life. Assuming that the quality of my work continues to improve, nothing else correlates as strongly with Internet serendipity and the success of Write of Passage.

The good news is that because my list grew by 348% this year, I’ll end 2020 with 45,542 subscribers. I hope to increase the absolute number of new subscribers in future years, but I don’t think I’ll ever have that kind of percentage growth again. That said, I’m disappointed by the way my growth rate slowed towards the end of the year. When it comes to growing my list, I have three core challenges: (1) I don’t enjoy the work of improving email funnels, (2) I hesitate to implement suggestions because I don’t want to degrade the reader experience on my website with pop-ups and calls-to-action, (3) I haven’t been able to customize my website because I’ve been using Squarespace until recently.

In 2021, I’m going to solve all these problems. (1) I’ll hire an email growth consultant who has built six-figure email lists, (2) I’ll make sure they balance the taste of a brand marketer with the conversion mentality of a performance one, and (3) I’ll work with my website design team to reduce friction in my conversion funnel. As I do, I’ll double down on the growth tactics that already work well for me, such as sharing my free writing courses: a 5-day Twitter course, a 7-day writing one, and a 50-day writing one — all of which I deliver by email. I’ll also keep sharing my Friday Finds links page. People rave about it, and 5.86% of the people who visit become email subscribers before they leave.2 

Email subscriber growth in 2020

40,000 YouTube Subscribers: I spent the second half of 2020 experimenting on YouTube. Doing so felt like a return to my past. YouTube — not writing — inspired me to start sharing ideas online. I originally wanted to be a YouTuber, but I stopped making videos when I realized that writing could help me learn faster. I’m returning to YouTube because it’s becoming such a force in my intellectual intersection of learning, knowledge work, and building online businesses. As my business partner Tiago Forte said to me recently: “The YouTube generation is financially sustainable now.” I uploaded video clips from my podcast, mini-video documentaries, and behind-the-scenes looks into my writing process. Based on view counts and subscriber goals, I wasn’t very successful. 

Through it all, I remained unsure about my goals for the channel. My rational mind wanted me to double-down on my Personal Monopoly and focus on writing for the Internet, while my intuitive mind wanted to focus on whatever I’m excited about. The tug-of-war is on-going, but my intuition now has the upper hand. The conventional wisdom of building a YouTube audience is so soul-deadening that it ruins the fun of making videos. Make your videos actionable, they say. Stay in your niche. Target the masses. Speak like you’re talking to a 5th grader. And if you simply follow your curiosity and wander between ideas, you won’t build a following.

Dumbing down your videos may be the optimal strategy, but I refuse to pursue it. One of the driving ideas behind my work is that smart people are under-served, and geeking out on ideas that intrinsically interest you is the best way to attract those people. Thus, compared to other creators, I don’t think too much about the total addressable market for ideas, and that philosophy is going to drive my YouTube strategy. I’ve already found a part-time production manager and a team of editors to help me. Together, we’re building a creation pipeline to produce each video. The plan is to create video essays inspired by two of my favorite channels: Wendover Productions and CCK Philosophy. I like how they have B-Roll and custom animations, which shift the viewers attention from the creator and onto the ideas they’re presenting. I assume that they take between 15-20 hours to edit, and I’ll be working with a team to make the videos crisp, entertaining, and educational. 

I like to start projects when they’re already 80% done, and these YouTube videos are the perfect example because each one will build upon an article I’ve already written. To begin, I’m making a three-part series inspired by my long-form essay about Peter Thiel. Now that I’ll be sharing the same ideas on multiple platforms, I can invest even more energy into learning and writing which is what I enjoy doing most. 

To record the videos, I’m building a home video studio with decorations, a boom microphone, high-definition camera, professional lighting, and sound-proofing foam panels that’ll make it easy to produce each video.3

700 Write of Passage Students: While the rest of the world is focusing on reducing friction in the learning experience, we want to increase it. Most courses pride themselves on ease of study. In self-paced courses for example, students can learn whatever they want, wherever they want. The idea sounds appealing, but the low completion rates for online courses suggest otherwise. Most students don’t do the work and the drop-off rates are steeper than the face of El Capitan. With Write of Passage, we do the opposite. It’s expensive, not cheap; challenging, not easy; time-limited, not forever ongoing. In this vision, I’m inspired by the Navy Seals. The rite of passage of becoming one inspires memories, life-long friendships, and levels of personal growth you won’t find in friction-free courses.

To increase friction, we’ve raised the price of Write of Passage. Every time we do, the experience improves because the median student is so much more committed. Cheap courses sound great until you realize that the vast majority of students never follow-through on them because the initial investment is so small. That’s why $49 courses don’t have engaged student bodies. But students show up to Write of Passage knowing that it’s going to be one of the most intense online learning experiences they’ve ever had. While internet intellectuals are up in arms about the sunk cost fallacy, big initial commitments are the motivation people need to fight through the challenges of learning a meaningful skill. When you have a group of people doing it together, outcomes improve too. 

It’s like the gym. Everybody knows that you don’t get ripped by paying for a membership. You have to sweat and grind through the pain, which becomes enjoyable when you have a group of committed people to motivate you. This “Soul Cycle Effect” is why people push themselves harder in a workout class than they do on their own. Next year, we’ll double-down on the Soul Cycle Effect. To ensure a group of dedicated students, we’re limiting the number of people who can enroll in Write of Passage cohorts, and our first one of the year will be capped at 350 new students. 

Two Long-Form Essays: I’d like to become one of the world’s best long-form essayists. Doing so is a multi-decade project. As a reader, I like long-form essays because they’re long enough to establish an emotional connection with the author but short enough to enjoy in a single evening. As a creator, they’re long enough to become an intellectual obsession but, as opposed to books, short enough to feel like a temporary stage in your life. As one writer said to me: “Choose your book carefully because you’ll be married to the ideas for a decade.” 

But by demanding my best thinking, each long-form essay alters the direction of my intellectual life. What the Hell is Going On set the direction for my career, The Ultimate Guide to Writing Online laid the intellectual foundation for what I teach in Write of Passage, and Peter Thiel’s Religion sparked my exploration of Judeo-Christian teachings. They’re the truffles of my intellectual life: rare, precious, and delicious when taken care of. Because they’re so long, they attract the highest quality people into my intellectual orbit.

I only published two in 2020: News in the Age of Abundance and the soon-to-go-live Saving the Liberal Arts. 

I ran into a creative block after publishing News in the Age of Abundance, and it took six months for me to find another long-form essay worthy topic after I published it. To prevent such extended stretches of uncertainty in the future, I plan to always have my next one in the pipeline. That way, I can let my subconscious stir on the central ideas for months before I start writing it. For my next essay after Saving the Liberal Arts, I’ll be writing about how time created a culture of anxiety. I’m generating my thesis in a Twitter thread that I’ll return to once I start writing the essay. 

Finish My Private Pilot’s License: Every year gifts me with at least one big surprise. On a personal level, learning to fly an airplane was the biggest one this year. I’ve been mesmerized with flight since childhood. I still remember dragging my father out of bed during middle school to watch the Airbus A380 land at the San Francisco airport for the first time. My childhood room is still covered with well-created airplane magazines (Airports of the World was my all-time favorite). Learning to fly has always been the top agenda on my bucket list, but I knew I wouldn’t be able to pursue it until I left New York City, where the closest airport suitable for recreational flying is 45-minutes outside of Manhattan. 

I started flying in late-October. I’ve been flying out of Austin’s international airport, next to the Boeing 737s and Airbus A319s. Since starting, I’ve been building my skills by flying three days a week and taking an online course (Footnote: In the industry, this course is known as Ground School). To date, I’ve flown for 25.3 hours in the cockpit of a Cessna 172 and landed a plane 50 times. Two months into the process, I’m ready to fly solo. That said, I’ll need another three months to prepare for two Federal Aviation Administration (FAA) knowledge tests (one oral, one written) and a check-ride where I’ll fly with a government official. Once I pass, I’ll be halfway to my ultimate, multi-year goal of receiving an instrument license which will allow me to fly in any weather conditions. 

I credit my Loft House roommate Nick Yoder for pushing me to fly. He lives life more fully than almost anybody I know. Materially, he’s frugal. He buys cheap shoes, rarely splurges, and drives a 15-year-old car. But whenever he’s excited about an experience, he makes it happen. Two weeks before we moved to Austin, he called me to suggest that we learn to fly together. Immediately, I said yes. He did all the difficult work of finding a flight school and showing me how to pass my medical exam with the FAA. Without him, I wouldn’t have pursued flight lessons. 

Working with a Philosophy Tutor: Working with a philosophy tutor was one of my favorite parts of living in New York. Now that I plan to stay in Austin for a while, I’d like to find a new one. Once I do, I’ll recruit a group to join me and split the cost. Ideally, we’d meet twice per month and study one book for three months at a time.4 To find the tutor, I’ll go through friend networks and contact a graduate student at the University of Texas in Austin. PhDs are particularly good to learn from because they tend to say yes to intellectual “side hustles” and are already engaged in the ideas I’d like to study. Or maybe, a reader in Austin will contact me directly. Who knows?

Get Tournament-Good at Tennis: Learning to play tennis was another surprising development this year. I started playing with my roommate at the Loft House. She played in high school, and after seeing her passion for tennis shine during the US Open, I suggested that we start playing. After three nights on the court, I was hooked.5 By taking weekly lessons for two months, I went from a beginner to “good enough to rally, but still has the worst serve I’ve ever seen” in just three months. Next year, I’d like to play in at least one tournament. To do so, I’ll need to find a new instructor who is as analytical and committed as I am. That way, I can train with the seriousness of a college athlete, even though I’ll be playing in casual tournaments.

Things to Improve

Fragmented Attention: Every study I’ve seen about multi-tasking shows how unproductive it is. It’s pernicious not only because it hampers your ability to focus, but also because it makes time go by faster which puts you in an unproductive flow state. It’s what Andrew Sullivan calls “distraction sickness.” Starting immediately, I want to defragment my life and live life in “full-screen mode.”

You enter full-screen mode when you’re focused on one thing at a time. But instant access to the Internet can make that difficult. Do you ever check Twitter on Zoom calls? Or your email at the gym? I do both all the time and I’d like to change that. I wouldn’t be surprised if I shift my attention 300 times per day. In the past, I’ve reduced digital distractions with two strategies: writing down every distraction that I had and doing ten push ups for each one, and keeping a piece of paper next to my computer that says: “There’s nothing more important than the most important thing you can be doing right now.” Next year, I’d like to get back to these habits. 

Morning Commitments: In A Gentleman in Moscow, there’s a clock that only tolls twice per day: once at noon, once at midnight. The Count’s father uses it because he believes that people should be too busy with work in the mornings to hear the chimes between waking and noon. But by noon, having had an industrious morning, he believes that people should be free to enjoy themselves. 

Using a similar philosophy, if I could create my own clock, it’d tick three times: first in the morning when it’s time to start essential work, second in the afternoon when it’s time to stop all work, and third at night when it’s time to go to sleep. During my three-hour essential work window, I’d prioritize “The Magical Three,” a three-hour window where I tackle my two daily priorities: 90 minutes of writing and 45-minutes of fitness. The rest of time would serve as a buffer for food and travel. 

The Ruthless Elimination of Hurry: Derek Sivers likes to tell a story about the time he lived on the beach in Santa Monica, where he used to ride his bike on the 15-mile path next to the beach. For years, he sprinted whenever he traveled the path. No matter how hard he cycled, it took him roughly 43 minutes to ride the tail. But after a few months, all that effort made him less excited about the ride. One day, he decided to do the same ride, but chill. Instead of going all out, he took it easy — 50% of his usual effort. Instead of grinding his teeth as he looked at the finish line, he looked around at the dolphins in the water next to him and the pelicans flying over him. When he finished, he looked at his clock: 45 minutes. 

As he reflected: “Wait — what?!? How could that be? Yep. I double-checked: forty-five minutes, as compared to my usual forty-three. So apparently all of that exhausting, red-faced, full-on push-push-push I had been doing had given me only a 4 percent boost. I could just take it easy and get 96 percent of the results. Which then makes me realize that half of my effort wasn’t effort at all, but just unnecessary stress that made me feel like I was doing my best.”

I think about Sivers’ story all the time because I’m such a hurrier. And that hurry comes from seeing wealth and achievement as cures for my own feelings of inadequacy. But hurry and presence are incompatible. By definition, you can’t give somebody your undivided attention if you’re thinking about something else and all my worst mistakes come from being in a hurry. Given the shortness of life, how can I live efficiently without hurrying? And at what point does the desire to maximize my days interfere with my ability to enjoy them? 

A desire for movement is in my nature. I’ve always been hyperactive. I relish the opportunity to pursue inspiring, self-chosen goals. But no matter how strong the allure of productivity is, working so hard that it turns into a battle isn’t sustainable, which is why I burned myself out after the recent Write of Passage cohort. But at the same time, the sacrifices I’ve made have put me on a career trajectory that I’m very proud of. Balancing the two is the daily challenge of every ambitious person. Ultimately, I’d like to adopt a more focused approach to work where I move deliberately instead of hurrying, and maintain my ambition but drop the anxieties behind it. If Sivers’ metaphor holds, I can accomplish almost as much with a considerable increase in happiness levels. 

Things to Celebrate

Time with Family: I spent more time with family this year than I have in the past five years, combined. My sister and I lived together at my childhood home in San Francisco between April and June, while my parents were in Florida taking care of my grandmother. But after my parents came back in June, we all lived together for the first time since 2013. 

In late March, when the pandemic peaked in my former home of New York City, I was on a work trip in Mexico. With the pandemonium at its peak, I flew back to San Francisco to wait things out with my sister. I unexpectedly stayed there for five months until the end of September. Through it all, the forced quarantine brought our family closer. We’re an active bunch so it can be hard to get us all in the same room, but the forced quarantine made it easy for us to enjoy walks, meals, and long conversations together.

Twitter: Twitter’s been the center of my intellectual life since 2014. In college, I still remember a friend making fun of me for refreshing TweetDeck so often. But I didn’t crack the code on building an audience there until mid-2019.

Twitter’s the only social network that rewards you for the quality of your thinking, and it’s fast-becoming the intellectual hub of Silicon Valley and the investment community. In April, when I had some spare time during the pandemic, I created a course called How to Crush it on Twitter. It focuses on how to use Twitter to learn faster, create career opportunities, and spark real-world friendships. They say that teaching is the best way to learn, and my experience validates that claim. Since launching the course in June, I’ve already doubled my Twitter audience using the tactics I explain in it. For an introduction, I recommend this YouTube workshop, and this five-day email series.

With that said, I spend wayyyyyyyy too much time on Twitter. Ten years into using it, I still haven’t found a way to tweet regularly while also resisting the magnet of notifications and the never-ending feed of new ideas. I check Twitter compulsively. If I have 30 seconds free, I pop open my phone and tap on that little blue bird. Next year, I’d like to change that. I already put my phone out of arm’s reach when I write and in another room when I read at night. For now, I’ll leave this as an open question: How can I use Twitter instead of letting it use me?

Website Redesign: You can file this story under the “I didn’t deserve it, but I’m extremely grateful” category. During the summer, while walking with a friend in Marin County, I ran into WordPress CEO Matt Mullenweg. Though we’d only met once, when I interviewed him on my podcast, few people have been more helpful in my career. Back when Write of Passage was just an idea, Matt and his team at Automattic led and funded all the web development for the business. It was transformative at the time because I didn’t have the money to build a course-worthy website. Because of his generosity, every Write of Passage student also receives a free full year of WordPress Premium.

This time, when I saw Matt, I was looking to build a cohesive visual identity. Colors, shapes, logos. You name it. While doing so, I also wanted to build a new personal website. Unfortunately, I didn’t know any designers or web developers who I trusted with my brand. When I spoke with high-end design agencies, their cost proposals were way beyond my budget. Once again, Matt offered to lead and fund the project. He connected me to WordPress’ Director of Special Projects and their team of designers and engineers. Together, we embarked on a three-month branding and web development project that led to the website you’re reading this on right now. 

We wanted something distinct, sophisticated, and instantly recognizable. Once we found the right shape of purple and the drop shadow boxes to support the images, we implemented them across the site. By keeping things simple, we simplified the design decisions for future projects. 

Studying Philosophy: I’ll remember 2020 as the year that I seriously started studying philosophy. I’m less interested in “meaning of life” philosophy, and more interested in economic systems and political theory. My motivation to engage with it was spurred by friendships with two former Columbia philosophy students: Jeremy Giffon and Johnathan Bi. At the beginning of the year, I audited one of their classes, which focused exclusively on Max Weber’s ideas. Though the class ended early due to the pandemic, it was one of my first introductions to the rigor of philosophical discourse, partially because the processor was the former Director of the Frankfurt Institute for Social Research, which was one of the most important philosophy hubs in the 20th century.

Philosophy is notoriously difficult to learn, both because the canonical texts are poorly written and because they require so much context to understand. While living in New York, I learned it by working with a tutor who is receiving his PhD at Columbia. And to explore it on my own, I listen to podcasts like Philosophize This and lecture series from people like David Harvey and channels like CCK Philosophy and Yale Courses.

Angel Investing: I experimented with angel investing this year, and backed six companies: Roam Research, Primer, Everything, Rize, Circle, and a still-unnamed education company. They fall into the three categories that define my career: education, knowledge work, and the creator economy. 

Assuming that most of my investments will go to zero (and they will), angel investing has two benefits: learning and relationship-building. 

First, I’ll focus on the learning part. Investing helps you learn faster because it gives you a stake in the outcome. There are two ways to make money as an investor: betting that the world will stay the same and betting that the world will change. Warren Buffett has made his money betting that the world will stay the same. The less the world changes, the more he succeeds. BNSF Railway, where Buffett recently invested $44 billion is the largest non-financial company in the Berkshire Hathaway portfolio. But angel investors tend to back companies that are trying to change the world. For example, my portfolio company Primer is betting that homeschooling will be a much bigger part of the future. There are 54 million students in the United States, and if 2% of them switch to homeschooling, the market will grow by 40%. Backing Primer is a bet on that change. Each investor update gives you a window into the ways the future is going to be different from the present. 

Relationship-building is the second benefit. Professional relationships are often fuzzy. Are we friends or competitors? Could we ever work together? By aligning your interests, angel investing is one of the fastest ways to solidify relationships. As a practitioner, when you make investments, you also stamp yourself into the social structure of an industry. You gain admission into group chats with the kinds of people you’d never be able to meet otherwise. In this case, I wish the world worked differently because angel investing creates an industry aristocracy where the rich get richer by having exclusive access to the hottest investments.6

Podcast Production: One of the main benefits of writing an Annual Review is to make my frustrations explicit. Last year, I wrote that I wasn’t enjoying the podcast anymore: “I’ve fallen out of love with the podcast. Each recording is a logistical pain, it doesn’t feel innovative enough, and it’s not growing as fast as I’d like it to.” I’m happy to say I’ve changed that. As I wrote in How I Produce a Podcast, my assistant and I spent the first half of the year building a production system for each episode. Furthermore, I didn’t enjoy lugging equipment from Brooklyn to Manhattan and back whenever I recorded an episode. But the pandemic normalized virtual recordings, which are much easier to produce and almost as good as in-person ones. 

Next year, I’ll shift my attention to growing the podcast. In my opinion, the podcast’s popularity doesn’t reflect its quality and I’d like to change that. I’ve tried sharing clips on YouTube, but they have low retention rates. YouTube experts tell me that viewers don’t want videos of two people talking on Zoom, even though the in-person equivalents are quite popular. The surest way I know to grow the podcast is to grow my audiences on YouTube, Twitter, and email which gives me a taller stage to share the podcast from. In the email domain, I also added a weekly newsletter that I publish alongside every episode with quotes, clips, and highlights from every episode (you can subscribe below). 

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In the name of growth, I’m thinking about changing the name of the show and doubling-down on a theme. Doing so will give listeners more predictability with what to expect. To date, the podcast’s been one of the best serendipity vehicles in my life and any change should encourage that. I’ll also change the podcast introduction to encourage reviews, which will improve the podcast’s placement in search algorithms. Right now, I have 76 ratings on the iTunes Podcast app. By the end of next year, I’d like to have 500. 

Email Consistency: I didn’t miss a single edition of Monday Musings or Friday Finds. Every week, no matter what else was happening, I sent an email. I’m very proud of that. 

50 Days of Writing: The challenges of running July’s Write of Passage cohort put me into a writing slump. To snap out of it, I started writing short articles about the writing process. Since they came so easily when I started, I set a goal of publishing 100 articles in 100 days. But by Day 20, it became such a grueling challenge that I was no longer able to prioritize my Liberal Arts essay. 

Note: If you’d like to receive 50 lessons about writing in the next 50 days, enter your email here and I’ll send them to you. 

Open Questions

Operationalizing Write of Passage: It’s time to build systems that make it easier to run Write of Passage. The more the course can run on auto-pilot, the easier the cohorts will be to run and the more attention we can give to students. 

To date, I’ve been responsible for the curriculum. In July, we re-designed every idea, every slide, and every example from scratch. Because of all that work, we now have a foundation to build upon for the next few years. We even designed each session as if it’ll become a chapter in a book I eventually write about the Write of Passage methodology.7 For the beginning of 2021, we’ve also hired a professional video team to re-record every module and make them suitable for the next few years.

When it comes to operationalizing the course, we plan to build a repeatable series of launch emails, polish the Alumni Mentor Program, and write our emails to students in a way that we can re-use them between cohorts without losing the personal touch that makes Write of Passage so distinct. We’re hiring a full-time Director of Course Operations who’ll be responsible for automating our back-end systems. Done right, these initiatives will make our lives easier and improve the student experience.

To date, when it comes to online education, partnering with Tiago Forte is the best decision I’ve made. Most courses have spiky workloads which makes it hard to hire full-time employees. Tiago and I avoid the problem by using the same team for Write of Passage and his course, Building a Second Brain. By doing so, we effectively double our rate of learning and cut our expenses in half. And at the beginning of every year, we come together and co-host an Annual Review Workshop.

The Sabbath: In a marvelous essay called I Used to Be a Human Being, Andrew Sullivan writes about the tension between noise and silence in the Judeo-Christian tradition. The tension between motion and reflection, getting through the day and getting a grip on your whole life. For centuries, the Sabbath defined Western life. It offered a weekly moment of calm and a chance to reflect on your place in the world without life’s usual distractions. Then, it suddenly disappeared. 

As recently as the 1960s, Blue Laws forced businesses to close on the Sabbath. Only the Church was open. John Mark Comer calls them a “government-mandated speed limit on the pace of American life.” The malls were closed and there were certainly no brunches. But Sundays are no longer reserved for rest and worship. They’re now a chance to eat out, finish errands, and get a jump-start on the work week. To be sure, I would vote against the details of the world I just mentioned. We’ve gained a level of freedom and we should celebrate that. But at the individual level, religious or not, we owe ourselves a chance to reflect on where we’ve been, where we are, and where we’re going.  

Beginning in the fall, I committed to a weekly Sabbath. One day per week, usually on Sundays, I keep my calendar open to slow down and reflect on life’s most important questions. To my chagrin, I haven’t taken it seriously enough. I’ve skipped a few Sundays when life got busy. Next year, I’d like to be more deliberate about blocking the time and postponing all productive activities. Though I’m exploring a number religions, particularly Judaism and Christianity, I don’t yet subscribe to any particular creed. As a non-believer, the best word I’ve found to describe my philosophy of the Sabbath is otium, a Latin word for leisure. But it’s not the American kind where you sit around and do nothing. It’s the Roman kind where you play sports, contemplate life, and consume transcendent art. 

A Consistent Revenue Stream: Write of Passage launches are the thing I enjoy least about my work. Since I only earn income two times per year, so much of my livelihood rides on each one. And it isn’t just me. I have two full-time employees and a bunch of contractors to pay as well. To reduce the stress of launching new cohorts, I’m looking for ways to supplement my income with a more consistent revenue stream that’s worth the opportunity cost of not focusing on Write of Passage. That extra financial security would give me the liberty to make bolder bets in my career and enjoy the process of launching the course instead of fighting the emotional weight of volatility.

As important as this goal is, I didn’t make it a goal because I don’t want to rush towards it. Rather, I want it to be an open question that looks in the background of my subconscious mind. So far, I’ve considered raising an investment fund, acquiring a software company, starting an eCommerce company, and launching a subscription to my podcast.8

Organizing My Writing: Structuring ideas is my biggest writing challenge. I’m good at making a lot of specific arguments, but struggle to tie them all together into a coherent thesis. Since my essays aren’t well-structured, I also tend to repeat myself. To fix this, I’m studying logic with my writing coach. Doing so, we believe, will help me fit my ideas into logical chains of arguments that’ll give direction to my essays.9

Fitness: I don’t enjoy weight lifting as much as I used to. I’d like to change that, either by finding a new fitness routine or maybe even diversifying the kind of music I listen to during my workouts.10 Right now, I devote 2.5 hours per week to weightlifting. Any more than that bores me. Beyond the steel, I also walk for 1-2 hours per day, usually with friends or while taking phone calls. But fitness automatically becomes more enjoyable when you start training for something. Training for a Spartan Race in 2019 was the most motivated I’ve felt in the gym as an adult. If they come back in 2021, I’ll run more of them. For cardio, I’ll keep playing tennis twice per week with lessons on Monday mornings. 

Being Prolific: The Internet rewards people who are prolific. Due to the structure of online information platforms, the people who publish the most, grow the fastest. Committing to a consistent publishing schedule has brought me to where I am. But now that I have a sizable audience, I’d like to switch my focus away from continuous output and towards excellence. My two favorite examples are Paul Graham, who has been publishing stellar essays for more than a decade. He is prolific, but mostly because he’s been writing for so many years. Last week, a friend sent me one of his essays from 2003. When it comes to long-form essays, he’s the model I’d like to follow. In the words of Anthony Trollope: “A small daily task, if it be really daily, will beat the labors of a spasmodic Hercules.”


1 Measured by the number of people who attend the final live session. Another 10% of students watch the live sessions asynchronously.

2 In the world of email marketing, that is a very high conversion rate.

3 The investment is worth it because I can also reap the rewards of it in Write of Passage.

4 Similar to the learning process I advocate for in Learn Like an Athlete.

5 My mind comes alive in solo pursuits with enough variety to stay fresh, but enough consistency to reward obsessive knowledge and a mastery of technique. Golf, flying, writing, and tennis all share these traits. 

6 It’s the Matthew Principle: “For to every one who has will more be given, and he will have abundance; but from him who has not, even what he has will be taken away.”  —Matthew 25:29

7 I’ve spoken with numerous publishers, but am not close to finalizing anything. Though it’d be good for the school, I don’t enjoy writing about writing as much as I enjoy synthesizing random ideas.

8 For now, I’ve decided against launching a podcast subscription because I don’t want to limit the reach of my ideas. I’d rather optimize for growing my audience, and use that reach to invest or monetize products.

9 The process of clarifying what I’m trying to say begins with two questions: (1) what is my pain point? and (2) what reasons do I have for believing it’s true? 

10 I usually listen to electronic music because it’s tailor-made for workouts, but I could switch into rock or hip-hop.