My 2022 Mid-Year Review

Written on July 1st, 2022

This memo will summarize where I’ve been in 2022, and where I’m headed. 

At the start of the year, I identified five areas of focus for 2022:

  • Write of Passage 

  • Reading 

  • Writing

  • Chinese

  • Friends and family 

I’ll take each area in turn: what went well, what can be improved, and where I’m heading next. 

Write of Passage

It’s been a whirlwind six months for our business. In January David and I hired Michael Dean as our fourth employee (myself, David, and Becca, David’s producer, being the other three). We held a team retreat in Sedona, Arizona the first week of January to outline our plans for the year. Our big goal: build a Write of Passage media company to help draw attention to our flagship Write of Passage cohort, thereby increasing revenue, while also highlighting our best students’ writing. We hired Michael as Director of Content to pioneer this effort and work with top Write of Passage students 1:1 to develop the best essays of their lives. 

We ran the 8th cohort of Write of Passage from March 2nd - April 6th. The cohort was a massive success, with roughly 300 students participating (200 new, 100 returning) and a slew of new improvements. We ran our strongest-ever Alumni Mentor program, David and I made curriculum improvements, we added a secondary social hub for real-time video and text chat (Geneva), we shifted all course materials away from Teachable onto our Circle community, we created a refreshed “Build Week” schedule to help onramp students into the course, and we had a big team of Editors guarantee that every student article received high-quality writing feedback. 

After 18 months of stellar work, our Write of Passage producer, Becca Olason, left the company for a rare-in-a-lifetime chance to travel Europe for six months with her partner. We miss Becca’s rare mix of attention-to-detail and perennially upbeat attitude. As Becca transitioned out of the company, we hired Dan Sleeman to work as Director of Course Operations. Under our shared cost partnership with Forte Labs, Monica Rysavy helped us run operations for Cohort 8. Monica passed the baton to Dan in March and April, and Dan joined the team as our fourth full-time employee. He brings a rare depth of skills in education and no-code tools that has helped him grow into an indispensable team member. 

Soon after Cohort 8 ended, we hired two new team members – all-star WOP mentors Simone Silverstein and Tommy Lee joined the team full-time as Video Producer and Creative Director, respectively. Their first day coincided with our biggest-ever team retreat. We spent a week in the sunny Bahamas planning our two newest products: Write of Passage Liftoff (for high schoolers), and Write of Passage Business (for teams / companies). These are exciting new product lines that I’ll have plenty more to say about in the coming months. 

My role has shifted from jack-of-all-trades Course Director to my new official title of “co-founder and Chief Product Officer”. Fancy title aside, I’m laser-focused on hiring a team of skilled teams to develop our two new product lines, while ensuring all three of our products (Write of Passage flagship, Write of Passage Liftoff, Write of Passage Business) maintain our exceptional quality standards and the singular, je ne sais quoi Write of Passage vibe that students have come to expect from our programs. My job is simple: build and deliver the best educational experiences on the Internet for high school writing and business writing. Unlike with past cohorts of Write of Passage, however, I’ll have teams of several employees to help us build on each front. I’m already working with two of our top Write of Passage alums, who happen to be high school students, on developing a high school-oriented curriculum for Liftoff. 

I’m thrilled to take on my new responsibilities, which includes direct reports, hiring, and leadership huddles with David and our excellent new COO, Chris Monk. Chris joins us after nine years building the education company Decoded. I’m also excited to be working with Matt Tillotson, another all-star WOP Mentor who joins us as Director of Customer Success. Matt will be hiring and running our Cohort 9 mentor program, plus our other part-time teams for the WOP cohort (Editors, Ambassadors). These programs have a major impact on the quality of the Write of Passage student experience. Matt will also help shape our Write of Passage student experience, and he’s currently helping us build a robust hiring system. 

I’m proud of the work I’ve done on Write of Passage during the first half of the year. These include: 

  • Running a successful Cohort 8

  • Hiring five new employees (which took dozens of hours of interviews)

  • Creating the vision for two new product lines 

  • Starting to create these new product lines

My Work Habits 

Working with a team feels a lot different than running Write of Passage only with David and Becca. We’ve graduated from Google Chat to Slack. We’re implementing an org chart, performance reviews, and two-week work sprints. We track all project lists in Monday.com. Adding these new systems is a relief – David and I are both right-brained creatives, and scheduling and planning doesn’t come naturally to us. In the past, we would meet for planning sessions between cohorts and write up hundreds of sticky notes of new ideas for the course. Generating ideas was never a problem, but implementing these changes tended to happen in intense bursts in the few weeks before a cohort started. Our new systematic approach to project execution helps to spread the work out evenly through the WOP “offseason”. 

I’ve identified three ways I can improve in the second half of 2022: 

Work faster

Sam Altman and Tyler Cowen often tout the importance of working quickly. Successful people move fast. They respond to emails promptly, they finish their work ahead of deadlines. They act decisively and course-correct quickly in the face of new information.
I began working on Write of Passage in October 2019. Generally speaking, I’ve learned to move fast. In less than three years, between Write of Passage and Building a Second Brain I’ve built and delivered ten cohorts to more than 2500 students. For many of those cohorts I was the only full-time employee working on the student experience. Between emails and internal memos I’ve written hundreds of thousands of words. I’ve replied to over 10,000 student emails. We wouldn’t have made it this far if I didn’t move fast. 

That said, I can get better. At times I’ve felt fatigue from sprinting so hard over the past two-plus years. In recent months, I noticed places I can move faster, whether that’s my message response time or completing projects ahead-of-schedule. My commitment for the second half of 2022 is to move even faster in all areas of our business. We won’t build phenomenal products moving slowly. 

Be more focused

Focus is IQ for the 21st century. When I sit down and focus, I can crank out work (for instance, in less than 45 minutes I’ve written 1200 words of this memo). That said, my focus varies too much day-to-day. Some days I wake up at 6am and plunge into Deep Work with blistering focus. Nothing can stop my momentum. Other days, petty tasks in email or Slack drag me into distraction. Twitter tugs at my attention while the sun is still coming up. My attention flits between writing, email, and petty Internet distractions.

To improve my focus in the second half of 2022, I’m adopting a new rule: no Twitter or YouTube before 5:00pm. I’ve limited my time spent on Twitter this year – it’s a much smaller part of my life – but lately I’ve been pulled back into recent spirals in politics and the culture wars. YouTube has also slowly crept back into my life. That algorithm knows me spooky well. My new rule will free my work hours from my two biggest sources of Internet distraction. 

Learn proactively

Reading Talent by Tyler Cowen and Daniel Gross highlighted a major area for improvement: What am I practicing at work similar to how a pianist practices scales? To develop a strong answer to this question, I’m going to create a flywheel of learning around my work:

  • Consume high-quality information about product building, business, and learning design (articles, books, videos, podcasts, Reddit threads)

  • Write internal memos summarizing what I’ve learned

  • Share the best ideas I learn in-public 

It’s not enough to work hard. I need to spend additional time outside of official work activities making myself a better thinker in product building, learning design, and business-building. What new mental frameworks will I uncover and adopt in the coming months? Keep following my writing to find out. 

Reading 

I’ve spent thousands of hours reading since I graduated college (as my vanity book list and apartment decor will attest). Were money no object, I’m confident I could fill a happy life simply reading great books. That said, I’ve read less in the first six months of 2022 than at any point in the past six years. The only books I read: 

  • The Moon and Sixpence (W.S. Maugham)

  • Irrational Man (William Barrett)

  • Niels Lyhne (Jens Peter Jacobsen)

  • Nietzsche (Stefan Zweig)

  • The Myth of Sisyphus (Albert Camus)

  • Talent (Tyler Cowen, Daniel Gross)

I’ve also read parts of other books, including Emily Dickinson, Fernando Pessoa, Michel de Montaigne, George Eliot, Nietzsche, Emerson, and John O’Donohue.

Compared to how much I’ve read in the past, my list of books feels thin. And that’s okay. In past years I’ve sometimes read too much. I want to be focused on creating, not just consuming. Most of my reading time has been converted into Chinese studying time, as you’ll read below. 

Going forward, I have a few tweaks to my reading system:

Read high-quality articles

Recently I found an article titled Crony Beliefs by Kevin Simler. A quick skim made it clear: I want to read more of this type of article. It’s a 5,000 word exploration of a hyper-relevant topic. I’ll walk away with a new mental model for receiving the world. A worthy investment! 

Often the best ideas are found in high-quality articles rather than books. I used to devour sources like Ribbonfarm, Tim Urban, David Cain, and Zat Rana. But I’ve fallen out of the habit of reading high-quality online articles. I’ll resume this process for the rest of 2022. My focus will be on articles related to my work, or new mental models for seeing the world. 

Review past books

What I’m doing with what I’ve read matters more than the total number of books I’ve read. I’ll spend the rest of 2022 reviewing books I’ve read – using Readwise to scan my favorite sections into Evernote for review. I’ll use these notes to fuel my future writing. I have a glut of books I’ve read but haven’t processed or written about. I won’t be able to review every book I’ve read in the next six months, but with focused attention, I can put a sizeable dent in my “to be reviewed” stack. 

Writing

Time to face the brutal truth: I haven’t written in public nearly as much as I would have hoped over the past six months. In fact, I’ve only published six articles on my website this year. This Mid-Year Review counts as my seventh. As former Redskins coach Steve Spurrier once said: “Not very good!” 

Before I mentally flog myself too much, a few thoughts: first, I’ve written tens of thousands of words for work this year. No, this writing doesn’t count as “writing in public”. But I’ve kept my writing skills sharp, even if I’m not sharing much of it publicly. Second, I have shared nearly 500 pieces of content in Chinese in 2022 (see next section). So while I haven’t shared nearly as much writing in public as I would’ve liked, I have been creating in public, albeit in a different domain. 

I write in two different modes: Artist Mode and Business Mode. My articles on my site are Artist Mode: I write lyrically and stylistically, some have said poetically. I’m proud of my best work. I love writing as an art, but it’s slow. I’ll spend 30 minutes crafting the perfect rhythm and cadence of my opening paragraph. The sentences don’t sing by accident. 

Meanwhile, this memo is written in business mode. It’s the casual, approachable tone I use in all of my internal memos. My Business Mode writing is imperfect but blazing-fast (I’ve now written 2,000 words here in under 90 minutes). My goal for the rest of 2022: write way more in public using Business Mode, with the occasional Artist Mode piece sprinkled in. I’ll focus my writing on the following topics: 

  • Writing about learning (sharing what I learn about about product building, business strategy, and learning design)

  • Writing about Write of Passage (updates on what we’re doing as a business)

  • Weekly writing about Chinese (I’ll create a Substack or Ghost account to share weekly updates on my Chinese learning process)

  • Long-form articles (I’d like to write three long-form articles in the next three months: What Existentialism Makes Me Feel, Chasing Chinese: My Chinese Learning Journey, and the Creative Cosmos)

  • Book Twitter threads (summaries of favorite books I’ve read, presented in an *original* manner)

How much will I write in the second half of 2022? Follow my website or Twitter to find out. Or just check in at my Annual Review article. 

One thing I won’t be doing, for now: focusing on building a Twitter audience. I have just over 4,000 Twitter followers, based on past Tweets about books and course-building. More and more people these days are writing high-value threads with catchy headlines to grab followers. Why haven’t I joined the Great Thread Game? Three reasons:

  1. I want to spend way, way less time on Twitter (I’m easily addicted to doom-scrolling, so I’ve made a focused effort to stay off the platform in 2022).

  2. There’s no value in winning games that don’t matter to you. I have enough credibility on Twitter to message people if I ever need a connection. I don’t have any short or medium-term business goals tied to building a Twitter audience, so I haven’t felt a desire to spend hours crafting threads to build an audience.

  3. Time spent on Twitter takes away time spent on work or Chinese. And I’d much rather play the Infinite Chinese Game than the Great Thread Game. 

Maybe I’ll join in the Great Thread Game someday. For now, I plan to use Twitter to share my article writing, book reviews, and not much else.