This is my first time writing a mid-year review.
This year has brought so many unexpected changes that I needed to gather my thoughts and reflect on the ways my life has transformed.
I had planned to spend the year living in New York, but the Coronavirus put a wrench in my plans. I’ve spent most of the year living with my family in San Francisco. I’ve ended my New York lease, and will be moving to Austin, TX in the fall.¹
In quarantine, I’ve had more time alone than ever before, which has helped me make meaningful progress on my goals. I’m writing this review during my second Write of Passage cohort of the year.
In this essay, I’ll review all aspects of my work life. I’ll begin with strategies for working with a personal assistant, an update on my writing and podcast, and end by focusing on the future of my online writing school.
Personal Assistant
Hiring a personal assistant has been one of my biggest wins of the year. It’s my second attempt at hiring one. The first one didn’t work, mostly because I didn’t take the process seriously enough. Since I wasn’t ready to hire somebody full-time, I didn’t give my first assistant the attention he deserved. For my second go-round, I did things differently. I worked with Great Assistant and paid them a hefty fee to source and train my assistant.
It seemed like a crazy decision at the time, but I’m glad I did it. My assistant is a pillar of my life now. Instead of handing her low-value tasks and expecting her to figure things out on her own, I have two weekly meetings with her. Together, we draft standard operating procedures for course operations, newsletter editing, and podcast production. In the first three months, she’s written 30+ standard operating procedures, mostly focused on Write of Passage and publishing newsletters, the podcast, and YouTube videos.
I think of company operations like a bucket. First, you have to build the bucket. Then, you have to fix the leaks. Until now, most of our attention has gone towards building the bucket. We’ve covered leaks up with duct tape, but haven’t had the time to make structural reinforcements. For the second half of the year, I’d like to fix leaks with long-term solutions. Doing so will require a new kind of leadership because slowing down to focus on details is against my temperament, but across the business, we need to streamline our systems.
I’m reminded of Steve Yegge’s Google Platforms rant where he talks about how teams at Amazon are internally separate. Bezos’ kingdom is a meeting-light culture where teams communicate through service interfaces. No other forms of interprocess communication, such as direct-linking and communication back-doors, are allowed. The teams’ service interfaces work with developers in the outside world, which is the essence of Amazon’s service-oriented architecture. Even if the company operates at a much bigger scale than Write of Passage, I want to borrow their simplified communication principles.
In our business, every urgent text message indicates an upstream leak in our standard operating procedures. For example, when my assistant asks me for the title of an upcoming podcast right before it goes live, we know that we need to add that step to the document I send her right after we record the podcast.
As a remote work company, we should all write down our repeated processes. Otherwise, we will be so dependent on back-and-forth communication that everybody in the business will be tethered to their phones. Onboarding, too, will be difficult because new hires will have to adapt to so many implicit organizational norms.
As humans, we should do as little work as possible. Our minds should be occupied by systems design, so software can execute tasks on our behalf. Software never sleeps, rarely breaks, and even the most expensive software-as-a-service platforms cost a fraction of what it takes to find, hire, and onboard an employee. Everybody on our team should look for ways to automate their own work. Each team member is an architect with a huge influence over thousands of students’ experiences, so we must hire brilliant people. As Alfred Whitehead once said: “Civilization advances by extending the number of important operations which we can perform without thinking of them.”
In the long-term, the less we have to think about repeated tasks, the better. But don’t mistake that as an excuse for sloppiness. We should take copious notes whenever we execute a task for the first time. We should answer questions like: What took surprisingly long? Where did we make mistakes? What didn’t we like working on? Taking consistent notes will prepare us for the postmortem we do after every launch and cohort. These postmortems come in long lists of tasks to fix and projects to work on, and we also write long-form memos to accompany major strategic decisions. In sum, in the second half of the year, my assistant Becca and I will focus less on giving her more responsibility and more on making her more efficient with the responsibility she already has.
North Star Podcast
To date, podcast operations are the biggest success I’ve had with my assistant. At the beginning of the year, I I was burnt out on recording it. Dealing with my audio engineer, testing for quality, and uploading the podcast took four to five hours per episode. Since that time wasn’t as enjoyable as writing essays, I stopped publishing interviews. Then, Becca arrived. She now edits every episode and works directly with my engineer. My only responsibilities are sourcing guests, recording episodes, and recording the introduction. She manages everything else.
Our standard operating procedures for the podcast fall into four steps. I record the podcast, send the episode to my audio engineer, who sends it to my assistant so she can publish it to my website.
With a simple system in place, we’ve been able to maintain a weekly publishing schedule. Along with the consistency, I’ve upgraded my audio quality with purchases such as the Shure SM7B, the same microphone that Joe Rogan uses. Now that the podcast sound is up to my standards and is easy to produce, I can move on to higher-order projects such as growing the show’s audience, rebranding it, and eventually launching a subscription.
Growing the podcast is a priority because of the access it brings. It’s an effective way to meet people I’d never otherwise meet. For example, I interviewed Tiago Forte in 2017 and now he’s my business partner. Sara Dietschy, Jennifer Morrison, and Steve Cheney have also become friends. Now that my newsletter is growing by ~1,000 subscribers per week, my pitch to potential guests is more attractive than it’s ever been.
For example, here’s a recent email I sent to Seth Godin (the interview will be published in November).
Oops! There’s a typo in my email. But I think that proves my point… in the most embarrassing way.
Most people who follow me still don’t know I have a podcast. After all, it’s not what I’m known for. Compared to essays and Twitter, the tactics for growing a podcast have never been clear to me. Doing so begins with consistency, so I plan to maintain a weekly publishing cadence. But that’s just the first step. Before the end of the year, I’d like to publish the episodes to YouTube (with video whenever possible). As the world’s second-largest search engine, the platform will attract new listeners and improve search visibility. I’ll also target guests with large audiences, especially ones who are promoting their books and therefore grateful for the invitation. Thus, I plan to promote the podcast with micro-content such as quotes and short videos to share on Twitter and YouTube.
I may eventually launch a podcast subscription, but I’m on the fence about it because the podcast may be more productive as a marketing engine for Write of Passage, rather than a direct monetization channel. Monetizing it directly, however, would push me to hire a full-time producer which would accelerate growth for the podcast. At a high level, the subscription would include detailed show notes and transcripts for each interview I record. For listeners who want to hear more from me, I’ll create subscriber-only Ask-Me-Anything episodes and an audio complement to all my essays where I’ll add context to the main ideas. For now, if I do launch the podcast, I won’t create a forum or any additional subscriber-only essays.
My Writing
First, the good news. I’ve published 23 articles so far this year, which is almost one per week. I’m happy with that cadence, but I’ve fallen off a bit in the past two months due to the demands of running Write of Passage.
The average quality of my essays is rising. Of all the ones I’ve published this year, I’m most proud of a short article called The Price of Discipline and a long-form one called News in the Age of Abundance. I’m proud of the former because it reflects the progress I’ve made with my coach, Ellen Fishbein. She’s pushed me away from “the share a fact, add a quote, and prove it with data’‘ writing style I’ve leaned on until now, and towards a more playful style inspired by personal experiences.
Now, the bad news. Teaching others to write has ironically given me less time to write myself. I haven’t been able to maintain a daily, 90-minutes-per-day writing practice. Doing so is easy to neglect because it isn’t urgent. But over the long-term, it’s an essential habit to maintain because it promotes my business and brings me so much satisfaction. My writing practice demands a level of intellectual rigor that no other activity can provide. Contrary to every piece of conventional Internet advice, the longest essays are the most productive ones, as long as they’re exceptional. I welcome that challenge. As my ambitions for length grow, the bar for clarity, coherence, and interestingness does too. Luckily, there’s a fix: waking up earlier, writing before the day begins between 8 am – 10 am, and creating systems that allow me to delegate work.
In the second half of the year, I’d like to shift my focus towards long-form essays.²
Along with the podcast, long-form essays attract the highest-quality people into my life. Write of Passage benefits too. Without high-quality people, it’s just another writing school. With them, it can blossom into an alternative to a traditional MBA, with a community as intelligent as an Ivy League university.
Writing is nature’s way of showing you how sloppy your thinking usually is. My mind tends to skip between topics, and the quarantine has made it worse because my Twitter usage has increased. At its worst, I develop BuzzFeed Brain where I find myself skimming instead of reading, secretly hoping my next intellectual breakthrough is just a thumb-scroll away. Long-form writing, however, re-activates my focus muscle and that’s why I do it.³
You can’t write 10,000 intelligent words about a topic until it has lived in your mind for an extended period of time. Only then can you explore the contours of an idea and analyze it from every perspective. Whenever I start an essay, the main idea is tangled like a pair of old headphones. I don’t find momentum until I can draw the main idea simply and summarize it in the length of a tweet.
Angel Investing
I don’t know what my investing future looks like, but I enjoy doing it. To be sure, angel investing isn’t a smart financial decision on a risk-adjusted basis, but that’s okay. I don’t really invest to make money. I do it to learn and support admirable people who work in my areas of interest: education, productivity, and the creator-economy.
Write of Passage is a Venn-diagram of all three areas. Since we educate people to become productive creators, I have a unique window into all three sectors. I’ve now invested in a creator-economy business and two education-related ones.
My investment thesis is fueled by rapid improvements in creator-focused tools: Stripe, Patreon, Shopify, Substack, Zapier, Teachable, and Supercast come to mind. At the same time, intelligent people are under-served by the information economy. Information may be abundant, but high-quality public thinking is scarce. Just as Stripe wants to increase the GDP (Gross Domestic Product) of the Internet, I want to increase the Internet’s GDC⁴ (Gross Domestic Content). The world needs more people like Rhonda Patrick, Jason Crawford, Maria Popova, and José Ricón, so I intend to invest in businesses that help creators monetize.
I’ve made two investments in the education industry. The first is focused on higher education, the second on homeschooling. The higher education one, my biggest investment, is still in stealth mode. The founders describe the company as “Amazon Web Services for college degree programs.” The team has already implemented 37 degree programs at 10 non-profit, accredited, four-year universities and now have ~80 more colleges pursuing these programs through their faculty governance process. Reading the quarterly investor reports makes me feel like I’m on the ground floor of a still-secret, soon-to-be skyscraper.
To shake up the homeschooling market, I’ve also invested in Primer. An increasing number of children are learning from home, despite the challenges of starting a homeschool and building a curriculum. From 1999 to 2012, the percentage of students who homeschooled doubled from 1.7 percent to 3.3 percent, and today, there are 2.4 million homeschoolers in America.
Parents say a “lack of community” and not being able to stay home to teach are the main reasons why parents don’t homeschool their children. But if 2 percent of the 54 million students in the U.S. switch to homeschooling after Coronavirus, the market will grow by 40 percent, which makes now the right time to place a bet. As the founders explained in their mission statement, Primer’s first product is a series of interest-based communities designed for students, with built-in homeschooling compliance for parents.
Deep Reading
You can tell a lot about who you want to become by the people you admire. Nassim Taleb tops my list. For years, he spent 30-60 hours reading per week and it shows. Same with Tyler Cowen, whose erudition comes to life in his Conversations with Tyler podcast. Both have taught me that the more you learn, the more color you see in the world. For example, New York City skyscrapers stopped being utilitarian objects after I learned about the Art Deco architectural style. Knowing the history turned those monuments of capitalism into towering works of art. Whenever possible, I visited 30 Rock and the Chrysler Buildings to marvel at the Deco-style lobbies. In them, I saw the optimism of the Roaring ‘20s, an age that worshipped steel that kissed the heavens and the airplanes that soared above them.
But building a business makes deep reading difficult because the move-fast neuroticism I need to build Write of Passage is the opposite of the contemplative mindset I need to soak into a 17th-century work of philosophy. In reflection, the hours I’ve spent grappling with Marx’s Das Capital and Weber’s The Protestant Ethic and the Spirit of Capitalism have simultaneously been my most challenging and rewarding moments of the year thus far.
Ultimately, I’d like to devote at least 10 hours per week to deep reading. That time would be devoted entirely to books and long-form essays. Right now, I’m lucky to get five. I hesitate to add deep reading to my calendar because I don’t want to make it a chore, but leaving time unscheduled should solve the issue. Paradoxically, finding the time begins with improving business operations, which takes away time from deep reading. Or maybe, I’m caught in the same pernicious cycle that plagues our industrial society: We keep inventing things that save us time, but it feels like we have less free time than ever before.
Write of Passage
The school has been a smashing success. I never dreamed that my work would be so fulfilling, especially as a 25 year-old. As a three-person team, we’ve already taught more than 500 people from more than 30 countries how to write this year.
Write of Passage is transforming in surprising ways. When I built the first version of the course in February 2019 with Tiago Forte, we set out to create an online writing course. Now, it’s transitioning into an educational, online social club. Unlike other courses, it’s not about watching a bunch of videos. It’s about publishing consistently, building friendships, and making writing a collaborative experience.
In the early days, the course was limited by a sparse curriculum and a lack of knowledge about running online courses. Since starting full-time on January 1 this year, Will Mannon (who is responsible for the quality of the student experience) has raised the bar with an obsessive commitment to student needs. As an alumnus himself, he understands their psychology in ways I never will.
We balance each other well. I prefer long stretches of productive solitude, but Will jumps to the social responsibilities of our work. As a duo, we are weakest in the organization bucket. Both of us are quick to take action, which often comes at the expense of systems design. To date, we’ve compensated for our nascent processes with sheer willpower.⁵ We both work our asses off. During the current cohort, each 90-minute live session requires 5-7 hours of planning, rehearsal, and slide design. But if I’m being realistic, our cadence isn’t sustainable. I’d like to shift our attention towards simplifying the business and making it easier to run, even if it comes at the cost of 2020 revenue. When in doubt, we’ll choose the system with the fewest moving parts.
Until now, Write of Passage has felt like an experiment. For most of 2019, I mumbled when I spoke about it because the student experience had so much room for growth. Spurred by all the improvements we’ve made and the intimidating quality of people in the course, I now stand up straight and speak confidently about the business.
Maybe I just needed a vision for it. In August 2019, I had dinner with economist Tyler Cowen in Manhattan’s SOHO district. When I shared my long-term vision for what I’d like to do with my career, he encouraged me to clarify my goals and raise my ambitions. That’s exactly what I’ve done.
I now have a 10-year vision for Write of Passage, which will become the business school of the future. The long-term student journey will follow a seven-step process: Start with the Write of Passage cohort, take Building a Second a Brain with Tiago Forte, return for future cohorts, become an alumni leader, join the club, launch a business, and graduate once it’s profitable — all while growing your audience.
Ultimately, I’d like to help launch hundreds of niche Internet businesses. In order to do that, I want the community to have the camaraderie of a CrossFit gym, the commitment of CrossFit participants, and the global reach of the CrossFit brand.
The success of the school is limited by email marketing, launch operations, student quality, student experience, and long-term student success. I’ll take each in turn.
Email marketing
Email is the center of everything we do. Most businesses have one central metric, where everything else works out if you get it right. For example, in the early days of Facebook, the entire company was oriented around growing its active user base. When I visited Facebook HQ in 2014, I remember seeing a large wall showing its up-to-the-minute growth in daily and monthly active users. For me, the equivalent metric is the number of quality email subscribers. Quality is measured by email open rate, the number of interesting email responses I receive, and likelihood to join Write of Passage.⁶
To send emails, I use an email service provider called ConvertKit. Until now, I’ve built the system haphazardly and done what was most convenient in the moment. The system works for simple tasks like writing weekly newsletters and running writing workshops, but unfortunately, it doesn’t support launches well. The point of an email service provider is to help people opt in and out of certain email lists depending on their preferences. That way, I can offer casual readers and potential Write of Passage students different experiences.⁷
Beyond email, the business is profitable enough that we can afford to reduce technical debt instead of focusing solely on revenue growth. If we don’t simplify our systems now, we’ll pay the price later.
One of the biggest challenges in running a business is knowing when you should double down on your core strengths and when you need to suck it up, improve your weaknesses, and work on important projects that aren’t in your wheelhouse. It pains me to say this but designing email systems does not suit my strengths. The slow, detailed nature of architecting systems claws at my soul. But this is a high-priority project that must get done, so it falls in the “Damn, I gotta suck it up and do it category.” Details matter. I’m going to rope in my assistant Becca, my business partner Tiago, and maybe even a ConvertKit consultant to re-architect the system.
Just as product subscriptions give you recurring revenue, email subscribers give you recurring attention. Compared to Twitter followers and podcast listeners, people who join my email list are much more likely to stick around and join Write of Passage. From my newsletters, they can opt-in to learn more about the school, which raises the chance they’ll sign up. The same principle applies to almost every online creator: Writing online without building an email list is like playing Monopoly, passing GO, and not collecting $200. Publish consistently, grow your email list, and you have a winning formula.
To date, I’ve never missed a single edition of Monday Musings or Friday Finds. Not one. I set a goal of 50,000 email subscribers with a 50% open rate by the end of the year, and I’m proud to say I’m well ahead of my pace. I now have 35,864 email subscribers and a 53.26% open rate. The list is growing by almost 1,000 people per week, so if I can sustain that pace and grow at 150 subscribers per day, I will finish the year at 60,000 subscribers.
I didn’t anticipate the steep growth trajectory because I came into the year disappointed with my 2019 email list growth. It wasn’t a consistency problem. It was a lower conversion rate one. Lots of people were reading my tweets and visiting my website, but only a small percentage were signing up for my email list. To remedy the situation, I focused on lead magnets which did little for list growth at the beginning of the year. Email subscriber growth trajectory exploded after I re-designed the home page on my website and launched my email courses: a writing-focused one and another Twitter-focused one. Beyond the courses, I’ve grown the list by adding free writing workshops with online writers like Matthew Kobach, Anne-Laure Le Cunff, and Sahil Lavignia.
To continue growing my list, I plan to host a writing workshop with an online writer every two weeks. In addition to being fun, they double as an email growth channel because the majority of attendees subscribe to my email list. My writing workshops will serve as an unprecedented window into people’s creative processes. Even though the Internet is littered with superficial productivity content such as “8 things successful people do every morning,” people are starving for an in-depth look into how people perform their craft. Knowing that, I’ll ask each guest to codify their writing process by creating slide decks or sharing live demonstrations.
Everybody will benefit. Guests will benefit from the show’s reach, viewers will benefit from a detailed window into the writing process, and I’ll benefit from learnings I can share with my Write of Passage students.
Launch Operations
Running launches is fast-becoming one of our core competencies. Most businesses make money every day, but when you run an online course, you only make money a few times per year. Thus, every launch is high-stakes, especially when you have full-time workers to pay.
We’ve had two launches so far this year. The uncertainty of outcomes made both launches emotionally challenging, especially the February one when the stress and anxiety caused my health to collapse. It was the sickest I’ve been in my entire professional life. Worse, since we had no automated launch procedures set up, Will had to pull all-nighters just to get our students enrolled. I’m not proud of that. As a leader, that’s the last thing you want to see. Part of the problem was that we held our major launch events during the live enrollment period, which compressed three weeks of work into one. To be fair, it was Will’s first time running a course as a full-time employee, so he had a steep learning curve, but after the launch, we brainstormed a plan to reduce stress for future launches.
To prepare for our latest one, Will and I spent a week together in Los Angeles. I was in charge of curriculum improvements, he was in charge of student experience improvements, and we teamed up on launch-related tasks. Like always, we went to Walgreens to purchase pens and Post-It notes. Then, we planned. We audited every live session and assignment. I built a new writing curriculum from scratch. Will designed our alumni mentor program, architected the course forum, and made a list of ways to automate internal launch operations. At the end of the week, we put together a full launch plan with every email, workshop, and podcast we’d publish in the month of June.
If the February launch required 10/10 effort, the June one required an 8/10 — enough stress for everybody on our team to have a small emotional breakdown during the 8-day window when students can enroll in the course. We gave ourselves six weeks to focus on the launch, but 80% of the work still happened during the last week. We executed too slowly in the last week of May and first week of June, in part because I spent those two weeks moving from Brooklyn to San Francisco. Due to the nature of the business, launches will always be stressful, but I’d like to get them to a 5/10.
For the June launch, my new assistant worked with Will on a number of behind-the-scenes launch maneuvers. For example, Will delegated crucial operations to my assistant, such as editing the workshop videos, and making both the course calendar and the Zoom links for the course. Moving forward, we will show her how to enroll new students, test integrations, and help with unforeseeable customer service issues such as launch emails not going to students who’ve changed their email address and no longer receive my newsletter.
These edge cases are a thorn because so much of our knowledge is tacit. For example, email addresses are our unique identifier for students. Whenever a student changes their email, we have to update every internal system manually. Since we still don’t have a standard operating procedure for email updates, it takes a lot of time. Individually, these edge cases are not a big deal, but collectively, they create lots of stress. To lower our cortisol levels, I need to give Will time to build systems and back-end infrastructure. Until then, the business will overly depend on him, which means more work for him and more key-man risk for the business.
Student Quality
Improving the quality of the Write of Passage community is now a bigger priority than increasing profit. Don’t get me wrong: profit is the lifeblood of the business. Without it, I can’t support my students or the people who work for me. But for the foreseeable future, when we often have to make tradeoffs between growing revenue and increasing the quality of the community, I’ll tend towards the latter goal. We don’t just want smart students. We want people who are curious, generous, and optimistic. That way, Write of Passage can continue to be a beacon of hope in a world of cynicism.
Write of Passage’s moat is exceptional students. Our school can only compete with traditional MBA programs if the student body is superb because post-collegiate education is as much about the network you build as what you actually learn.⁸ Fortunately, it is trending in the right direction. In the current cohort, we have a senior vice president at a major Silicon Valley company, the CEO of a $100 million company, and a two-time New York Times Best Selling author.
In the words of a returning student: “For some reason, the first 2 weeks of this Cohort have felt exceptional compared to the last one (even though I really liked the last one too). I’m not sure how to describe it, but there’s a different energy to it, and like 90% of my breakout rooms have been better than the ones I had in the previous Cohort. I’m not sure if it was something you guys did differently, if it’s the fact that I know what to expect, or if it’s the selection of people this time around.”
We also have students from more than 25 countries, which makes it a global experience unlike anything most students have ever been a part of. To give you a sense of the global flavor, we have people from Panama, Bahrain, Singapore, Holland, South Africa, Germany, India, Malaysia. Hong Kong, Australia, England, Scotland, Portugal, Spain, Thailand, Nicaragua, Saudi Arabia, Japan, Guatemala, Belgium, and the United Arab Emirates.
We are still in the early days of creating the Write of Passage culture. As I said to our team of seven alumni mentors last week, “We picked you because you will have an outsized influence on our culture.” As stewards of the community, we all have a duty to set the tone for good behavior and intellectual standards.
To improve the culture, I’m drawing inspiration from institutions and creators. Of all the young educational institutions I admire, Y Combinator has done the best job attracting the right people for its goals. I’m particularly interested in the early cohorts, which attracted people like Brian Chesky and Patrick Collison, who went on to build Airbnb and Stripe respectively. Likewise, I want Write of Passage to be a blazing fire of ambition where we students encourage each other and build lifelong friendships. That begins with attracting the right people online.
Of all the creators I admire, Patrick O’Shaughnessy has the best job building a kind and intelligent audience. His Invest Like the Best podcast is superb. He dives deep into the weeds of business topics and doesn’t stop to explain ideas you can Google like disruption theory and price elasticity. Last year, he hosted a conference called “Capital Camp” for podcast listeners which had the best selection of people of any conference I’ve ever been to. Every attendee was intimidatingly intelligent, which made every conversation fruitful. If we succeed, Write of Passage will blend the ambition of Y Combinator with the curiosity of Patrick’s podcast audience.
Student Experience
Earlier this year, I audited a course at Columbia University. I joined because the entire semester was focused on a single philosopher, Max Weber, so I knew it’d make me learn about him. To my surprise, the class was terribly run. Since it lacked energy, I spent more time looking at the clock than the professor — who was a renowned philosopher, but a terrible teacher. To understand why he was able to teach so poorly at one of the world’s top universities, follow the incentives. Tenured professors are divorced from the demands of the market. They won’t lose their job, even if their teaching is poor. Their reputations are built on the quality of their research, so teaching students isn’t always a priority.
Online teachers are different. If they do a poor job, their bank accounts will dry up. As a result, the rate of improvement for online schools is much faster than the rate of improvement for Ivy League ones. Fortunately for them, the Ivy Leagues will stay around because their reputations are so strong. However, mid-tier liberal arts universities have a grim future. Without a culture of innovation or technical competence, hundreds of them will go out of business in the next decade.
Just as Ivy League schools offer more than classrooms, online education is moving beyond the realm of learning. Like the top universities of today, the best online schools of tomorrow will have thriving alumni networks and in-person social events. Write of Passage will lead the way. On the surface, it is an online writing school, but it’s really a vehicle for changing identity at scale. You can’t possibly complete all the Write of Passage assignments and still feel like the same person. It is already an intense experience with many moving parts, such as live sessions, the community forum, mentor groups, live meetups, and CrossFit for Writing (a weekly session where students go through a nine-step rapid fire process to draft an article in two hours). It’s like a writing-focused Coachella, where you can’t possibly attend every event in a single cohort.
With ~300 students in the current cohort, it’s big enough to help people push through the fear of writing to an audience. If publishing an article on your website is like recording a TED talk, sharing an article with the Write of Passage community is like speaking at a Toastmasters event. Speaking on a smaller stage helps you work out the kinks before an audience of acquaintances, just like Write of Passage.
For most students, the psychological blocks to writing online are a bigger roadblock than the physical ones. Many students are plagued by a fear of writing online. Their struggles are paradoxes which exist beyond the realm of logic. For example, students are simultaneously annoyed that nobody reads their work and worried that once they publish their next article, their friends will laugh at them and expose them as an intellectual fraud. According to logic, both of those things can’t be true at the same time. But human emotion exists beyond the realm of logic.
I’m fluent enough in the logical realm that stepping into the emotional one feels like learning a new language, and right now, I only understand the basic vocabulary. In search of a new arena of wisdom, I plan to spend more time in personal coaching and growth experiences over the next decade. I’ll focus less on tactical challenges and more on psychological ones.
Until today, I’ve built Write of Passage for the mind. Now, it’s time to start building it for the heart. In order to do that, I’ll need to venture beyond the black-and-white domain of logical truths and into the subtler, multi-colored realm of emotional ones. To be frank, I don’t know how to do that, mostly because so much of modern coaching and psychology seems like a nugget of gold buried under a pile of bullshit.
Long-Term Student Success
Every cohort is emotionally taxing, so we plan on running fewer ones but making the ones we do run bigger and better. In the past 14 months, I’ve run five of them. But in the next 18 months, I plan to only run two. The scale and rarity of cohorts means Write of Passage may lose some of its intimacy. In the early cohorts, the course had the cohesion of a secluded log cabin because there were so few people. By the final live session, we often had only 20 people on the live calls. This cohort, we will have more than 150. Though I won’t miss the high drop-off rates of early cohorts, I already miss the small-group interaction I had with students in the first few cohorts.
Nevertheless, the student experience has vastly improved. To re-create the small group environment as the class has grown, we’ve added eight Alumni Mentor groups with 20-40 students each. At the surface, they’re designed to help students stay consistent with their writing. Students who attend every week meet people who hold them accountable for writing consistently and attending their live sessions. Together, they exchange feedback, share encouragement, and learn from an alumni mentor who has built a consistent writing habit of their own. The groups are open to everybody, but we encourage students to attend the same one every week. I think of the groups like a 6 am Tuesday morning SoulCycle class. Even though reservations are open to everybody, the majority of cyclists attend that same class every week, so many of them know each other. That’s the familiar experience we want to create for our students.
Our first glimmer at alumni-run consistency happened with CrossFit for Writing. In the four months between Cohorts #4 and #5, two alumni ran a session every weekend and had 10-15 students on every call. That’s the kind of initiative I want to see from our alumni. If we’re going to fulfill the Write of Passage vision, it needs to become way bigger than myself. I want to shift the spotlight away from me and onto our community leaders. Already this year, I watched Charlie Bleeker lead the chat during the first Cohort 5 live session and Ana Lorena Fabrega turn the Write of Passage ideas into a full-fledged curriculum for 9-to-11-year-old kids.
The school’s culture hinges on the leadership of our alumni. We need them to step up and model etiquette for the chat, article feedback, and breakout rooms. New students will follow what they do because even though it’s hard to be the first person to do something, it’s easy to be the tenth.
As of now, mentors can only officially help a few times per year when we run the live cohorts. In the next few years, I’d like to create a year-round community where students can help each other publish continuously. With it, Write of Passage will become like a fitness group. In CrossFit, for example, you start by learning basic exercises, such as squats, deadlifts, and bench presses. But everybody knows you don’t get ripped by learning the exercises. You get ripped by consistently working out, and that’s why people sign up for memberships.
Write of Passage is the same. Joining the course makes you familiar with ideas like Personal Monopolies and the Paradox of Specificity. But like fitness, you can’t become a successful online writer until you put in the reps. Doing so is easier with a peer group, which is why so many students return for many cohorts. Writing consistently will never be an easy task. Nobody is expecting it to be. But by giving people a community of people to work with, we can make writing more rewarding and enjoyable.
To deliver on that promise, we need to build a more efficient organization. Back in the early days of Amazon, Jeff Bezos asked the entire company to focus on an acronym called “GOHIO” for one year. It stood for “Getting Our House in Order.” As Eugene Wei wrote, every group spent the year learning how to scale volume without linearly scaling headcount or spending. Bezos wanted to see how systems would break and which ones needed to improve most. By doing so, Bezos could identify economies of scale. For example, he asked the support team to find alternative solutions to frequent, labor-intensive customer service inquiries like printing returning labels. We are a small business so unlike Amazon, we can tackle the most important “get our house in order” projects in three months, hopefully by the end of 2020.
The July Write of Passage cohort will likely be the last one of the year. The Annual Review Workshop is my only other big event this year, but other than that, the business won’t earn any more revenue until 2021.
Strategically, we have two options: hire more people or accomplish more with the people we already have. Even though it means less short-term profit because we have to solve problems by creating efficient systems instead of adding people to our team, the second option is much more attractive to me. That’s okay because I want to maintain our cozy and quirky company culture where everybody works hard, but trusts each other. I have a wonderful relationship with everybody I work with, so I’d rather scale with the team I have than immediately build a bigger one.
Ambassador Program Experiments
While planning for 2020 at the beginning of the year, Will and I decided to start an invite-only Write of Passage ambassador program for our most committed alumni. The program was an experiment, so we made it free. I contacted participants directly and encouraged them to pitch a project of their choosing. There was only one rule: “Make your project so ambitious that it scares and excites you.” We encouraged students to develop their ideas with the help of our resources by choosing one of three paths: build an online education business, develop a program to complement Write of Passage, or create a project inspired by the course material. The program was particularly impactful for Suthen Siva and Ana Lorena Fabrega.
Suthen and I ran a Write of Passage Fellowship where we worked with eight writers to publish a long-form essay on a topic of their choice. In February, Suthen flew to New York to plan it with me. We received dozens of applications and put together an exceptional group of fellows. For our first time running the program, it went pretty well. The essays are superb, and most of them wouldn’t have been published without the fellowship, which was our top success metric.⁹ Nevertheless, I don’t think we are going to run another fellowship. When we started it, Write of Passage wasn’t buzzing like it is now. Since building the school demands my complete attention, I’d like to focus on fewer projects and devote more energy to the ones I choose.
Rather than “give back” through the fellowship program, I’d like to devote those resources to student scholarships for Write of Passage. This year, we’ve given more than $50,000 in scholarships, mostly to young adults in developing countries. Most of them see the Internet as their greatest shot at economic success. Even if they don’t have access to first-world banking and infrastructure, the Internet puts them on a near-equal playing field when it comes to learning and audience building. In future cohorts, major corporations will subsidize student scholarships. In fact, I’ve already spoken to representatives from multiple $1 billion companies who are interested in funding students.
My surprise partnership with Ana Lorena Fabrega was the highlight of the ambassador program. Every couple of years, you will meet somebody so talented that they’ll knock you off your feet. You’ll know it when they inspire you to action and surprise you with fresh ideas. Vision is a rare and valuable thing, so when you find somebody who has it, trust your instinct, and do everything you can to work with them.
Ana Lorena is Exhibit A of this type of person. She’s always wanted to start a school for 9-11-year-olds, so we decided to create one together. As we wrote in our manifesto, we want to help kids explore their curiosity by helping them become prolific creators. To make that happen, I’ve helped Ana grow her audience and refine her vision. Since taking Write of Passage herself, she’s built a four-digit email subscriber list and grown her Twitter audience by more than 10,000 followers. We’ve also launched a weekly YouTube series called Show & Tell. Our show is still small, but I’m confident it will attract the parents of our future students, in part because early feedback has been positive and we have so much fun recording it.
But when it comes to building a business, we’re frozen. Unfortunately, our personality types are so similar that we will struggle to build a business together without a third person. We need somebody who can conquer operations and complement our hyperactive personalities. Instead of pulling hairs over the technical and operational challenges of running an online school, Ana should focus on what she does best: teach, talk to parents, and publish her best ideas.
Here, we’re stuck with a chicken-and-egg problem. We need to add a third person to the team but don’t want to hire that person until we prove the business model with sustainable revenue. In the meantime, we will continue to grow Ana’s audience by publishing YouTube videos, building email funnels, and publishing articles. Since neither of us are in a rush, we will focus on audience growth until the right person presents themselves.
By working with her, I’ve learned that teaching is a tiny sliver of running an online education business. Teachers who leave the classroom to start an online education business will focus too much on the curriculum at the expense of audience building. However, the quality of your course doesn’t matter if people don’t trust you. Thats why selling a course is so much harder than making one. Even then, good online courses are rare because running one requires such a diversity of skills, not because any one skill is so difficult.
In that way, courses are like startups. People in Silicon Valley talk about technical co-founders to complement a business-minded entrepreneur. Similarly, online courses demand a two-person partnership to cover as many parts of the skills listed below as possible.
Personal Habits
Fitness: I had planned to finish a Spartan Race Trifecta this year and maintain my gym routine, but the Coronavirus said no. Like everybody else, I’ve been working out at home. I purchased two kettlebells (20 and 40 pounds), a yoga mat, and weights (15 and 30 pounds). Bodyweight exercises aren’t nearly as enjoyable as the gym, so working out now demands an extra gear of motivation. I still work out four days per week, but my progress has slowed. The only exception is my core strength because sit-ups and flutter kicks are so easy to do at home. I don’t enjoy long-distance running (sorry, it’s not gonna happen), but I’d like to do more high intensity interval training. Fortunately, my family’s home in San Francisco is close to a collection of staircases, many of which are perfect for 45-second sprints. For the rest of the year, I plan to add sprints to my fitness regiment.
Sleep: At the beginning of the year, I set a goal to go to sleep earlier. Unfortunately, I’ve made zero progress. Most nights, I close my eyes at midnight and wake up at 8:30 am. When I was living in New York, I had the excuse of late-night socializing which kept me out until ~11 pm, but that excuse doesn’t apply in San Francisco, where I’ve spent most of the year. My nighttime rebellion, most of which is occupied by reading, may be an example of 報復性熬夜, a Chinese word which translates to “revenge to stay up late.” It describes a phenomenon where people who can’t control their daytime life delay their sleep to relish their night time freedom before bed.
Messages: From emails to texts, I’m no longer able to respond to all the messages I receive. Doing so would take away from the time I need to create the kinds of ideas which lead to all the messages in the first place. I feel guilty about my inability to respond, especially because my readers tend to be the exact kinds of people I want to surround myself with. Honest question: is there any productive person who is able to respond to all their different messages on all their different platforms? It seems impossible. I’ve given up and it riddles me with shame. Managing email is my biggest challenge, so I’m working with my assistant to create a system where she filters all my emails. That way, I can serve my students faster and devote my attention to writing.
Reduce Alcohol Consumption: My alcohol consumption is the lowest it’s been since turning 21. I’ve had less than 10 drinks since March 1st, mostly because poor sleep (measured by a 15-20 point rise in heart rate variability) and day-after-drinking sluggishness isn’t worth the fruits of red wine or the bitter deliciousness of an IPA. This year, I’ve only drank in celebratory situations and when I have, I’ve kept to one drink.
12 Favorite Problems
At the beginning of Write of Passage, we ask every student to write down the 12 questions that drive their intellectual life. They are open-ended questions specific to every individual. The exercise is inspired by Richard Feynman, a Nobel Prize-winning physicist, who once said: “You have to keep a dozen of your favorite problems constantly present in your mind, although by and large they will lay in a dormant state. Every time you hear or read a new trick or a new result, test it against each of your twelve problems to see whether it helps. Every once in a while there will be a hit, and people will say, ‘How did he do it? He must be a genius!’”
As I look forward to the rest of 2020, here are the questions that are top of mind. They occupy the horizon of my curiosities, and together, they hold the keys to my next creative breakthroughs:
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How can I run an innovative, operationally efficient company without increasing stress and sacrificing creativity?
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How can I build a ship fast, ship early culture while retaining a culture of excellence?
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How can I monetize a low-stress life where I get to explore ideas for a living?
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How can I push myself and reflect on my weaknesses without descending into self-loathing?
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How can I learn to enjoy activities as ends, not means?
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How can I communicate the benefits of writing online, and make doing so a social and collaborative experience?
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How can I find the synthesis between education and entertainment?
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How can I grow my audience while avoiding fame and maintaining privacy?
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How can I be a thriving knowledge worker without compromising my health?
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How can I make space to study religion and philosophy with the seriousness it deserves?
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How can I use the Internet to lift hundreds of people out of financial insecurity?
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How can I raise the quality of my writing while maintaining consistent output and continuing to grow my business?
Until now, I’ve spent my professional life in a state of productive wandering. I’ve hesitated to commit to any one thing, mostly because no projects had enough momentum to warrant my full attention. But Write of Passage requires it. When I started the school, I was responsible for everything that happened. Now, it can move without my push, albeit slowly.
As it gains speed, my role will shift from composer to conductor. For example, I’ve already handed over responsibility for the student experience to Will Mannon because he’s better at it than me. Meanwhile, our alumni mentors are increasingly shaping the culture by writing in the chat, posting on the forum, and leading weekly writing groups where students can talk 1-on-1. In time, Write of Passage will become the global Schelling Point for ambitious online writers.
Inside the company, I’d like to maintain our ship fast, ship often cadence without the stress it’s entailed to date. We want to create a culture of excellence and we’re not even close to taking our foot off the gas. At times, we’ll want to drive even faster. Doing so will require hard work and obsessive intensity. Sometimes, we will have to give up our nights and weekends. For now though, we need to simplify our systems and make our operations more efficient without losing our soul.
Personally, I want to spend more time in a contemplative state and surround myself with spectacular people. Those efforts begin with a commitment to long-form reading and writing, even though it comes at the cost of exponential business growth. By the end of the year, I’d like to write every day, publish another 10,000 word essay, solidify my email system in ConvertKit, create a visual brand for my online persona, officially launch my school for 9-to-11 year olds, maintain a once-per-week publishing cadence for my podcast, grow my YouTube channel to 15,000 subscribers, and my email list to 50,000.¹⁰
I have no desire to build the world’s biggest online writing school, but I want to build the best one. I don’t need a fancy house or an expensive car either. Instead, I want to surround myself with brilliant people and grow into a world-class writer, podcaster, and teacher.
To that end, I don’t want a celebrity-size audience, but I want an engaged one. With it, I’ll be able to enjoy the fruits of serendipity that can only be harvested by publishing on the Internet.
Footnotes
¹ Here’s the backstory: While watching the Coronavirus wave emerge in February, it became obvious that New York would be hit the hardest of any American city because of its density. With that in mind, I packed my bags and flew to Mexico City on March 12th. I had plans to visit Panama, but the president shut down the borders two days before my trip. After hearing the news, I planned to stay in Mexico City for two months but left when America closed the Mexican border to non-essential travel on March 22nd. Instead of flying to New York, I went to my childhood home in San Francisco where I quarantined for two months. At the end of May, I flew to Los Angeles to plan for the fifth Write of Passage cohort and then to New York where I packed my boxes and moved out of my apartment. Now, I am back in San Francisco until September 1st when I’ll move to Austin, Texas.
² Course launches force me to churn out email copy, which I don’t enjoy as much as writing essays. I prefer the slower, contemplative pace of prose. Nevertheless, I think every writer should study copywriting. However, I’m concerned that doing too much copywriting, which I do for Write of Passage, will degrade the quality of my long-form writing. It’s kind of like how many professional baseball players don’t compete in the Home Run Derby because they’re scared it’ll hurt their swing.
³ To improve, I’ve been studying writers like Eugene Wei, Scott Galloway, and David Foster Wallace, all of whom observe reality with 4K clarity.
⁴ Credit to Phil Mohun for the term.
⁵ Yeah, you liked that pun!
⁶ Intellectual curiosity and level of interest are not quantifiable, and that’s why I pursue them. Ambitious people on the Internet are under-served, in part because most of the metrics center around page views, which dilute your message in search of average people. Writing online is more productive when you aim to attract high-quality people, even if the goal is hard to measure.
⁷ Unfortunately, and this was entirely my fault, my email system didn’t allow people who were no longer interested in Write of Passage emails to opt out. I didn’t foresee how adding new tags for people who wanted to learn more about the course would make it impossible to unsubscribe from course-related information without unsubscribing from my entire email list. Luckily, the scale of the issue was small. I received a few personal emails and fixed the issue immediately.
But I’m upset with the situation. Small mistakes hurt the experience for my you, my reader, and respecting your attention is of utmost importance to me. To scale my endeavors, I’ll need an email system that supports the complexity of product launches. When I asked James Clear for advice, he responded with his typical wisdom: “There is almost always a simple solution that will get you 90% of the result you want. The extra 10% can be worthwhile, but it’s not usually worthwhile, so save the effort for the stuff that really, truly matters.” By the end of the year, I want to redesign the system to make it as simple as possible, even if it comes at the cost of performance.
⁸ Building a community is as much about repelling the wrong people as it is about attracting the right ones.
⁹ Packy McCormick, a fellow and former Write of Passage student, has seen exponential growth in his newsletter subscribers since publishing his essay on communities. Joe Wells used the momentum of his essay to start a podcast, Oshan Jarow distilled five years of experience into an essay about Universal Basic Income, Rhys Lindmark published one of the most creative essays I’ve ever seen, Jessy Lin transformed by model of artificial intelligence, and Adrienne Tran wrote about how autonomous vehicles will shape the future of commerce.
¹⁰ None of these goals exist in isolation. For example, I am not willing to grow the size of my email list if the quality of my subscriber base falls as a result.
Each week, I write two popular emails. Monday Musings is a collection of the coolest things I learn every week. Meanwhile, Friday Finds is a links-only newsletter where I only share the kinds of ideas you won’t find anywhere else.
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