Annual Review: 2019

The New Year is a time to stop and slow down. It’s a time to reflect on the previous year and plan for the upcoming one. Every holiday season, I reserve time to conduct an Annual Review.

We spend most of our lives in the trenches. We’re heads-down, focused on the people we love, the commitments we’ve made, and the work we’re responsible for. But once a year, we get a chance to reflect. I write about where I’ve been, where I’m at, and where I want to go. I approach this process with an attitude of loving criticism. That way, I can balance the frustration required to improve with the satisfaction of meeting my goals required to keep my energy high.

In the spirit of writing online, I want to share my experiences and publicly commit to my goals for the new year. This Annual Review is focused on four sections: (1) a review of my 2019 goals, (2) things to celebrate, , (3) things to improve, and (4) goals for 2020.

1. My 2019 Goals

Help 1,000 People Start Writing: My Twitter audience roared with excitement when I announced my vision to help 1,000 people write in 2019.  The idea for a course hadn’t entered my mind when I wrote the Tweet, and I don’t know if I’ve succeeded or not. I receive messages every week from people who write because of my encouragement, but I only taught ~450 people in Write of Passage this year. I could have taught 1,000 readers by lowering the price. But after making dramatic improvements to the course, we raised prices instead, which attracted an even more committed group of students.

Grade: B+

Publish Five Long Essays: At the beginning of the year, I had never published a proper long-form essay. I’ve always struggled to organize my ideas. Friends who edited my essays overwhelmingly told me that my ideas seemed disjointed. This year, I changed that. What the Hell is Going On was born out of a conversation at the Thanksgiving table, where I felt like all the grownups operated with an outdated model of the world. To date, it’s the toughest essay I’ve ever written. I followed it up with three other-long form essays: The Ultimate Guide to Writing Online, Peter Thiel’s Religion, and Why Did the Boeing 737 Max Crash? The Boeing essay was particularly well-written not because I improved my writing, but because I hired a professional editor to help me with it. We now work on every essay together.

Nevertheless, I’m going to fall short of my goal to publish five long-form essays. The fault is mine. I abandoned my daily writing habit from mid-September to mid-November. By doing so, I disappointed myself. For those two months, I over-committed myself, turned my attention to the operations side of Write of Passage, and woke up too late to write while the world was quiet. I’ve published four essays but still struggle with organization. I’ve re-organized my 25,000- word news essay four times. I’ve hired a writing coach to help me structure my ideas in conversation before I devote the time to writing them. Long-form essays may be out of fashion, but they attract kind, loyal, and intelligent readers.

Grade: A-

Naked Brands Book: Naked Brands was the first viral article I ever wrote. At the beginning of the year, it was the idea I was most known for. To research a potential book, I launched a Naked Brands Interview Series, but it never took off, in part because I lost enthusiasm for the idea. Furthermore, the success of Write of Passage pushed me to drop the Naked Brands idea and pivot towards online writing, where I can help many more people.

Grade: N/A

25,000 Email Subscribers: I don’t know if I underestimated the difficulty of reaching this goal or if I didn’t work hard enough to do it. As I write this, I have 15,300 email subscribers. To be fair, I started the year using a bare-bones email service provider and knew almost nothing about email marketing. Switching to ConvertKit was a smart first step, but I didn’t get into the mechanics of email subscriptions until November when I signed up for Brennan Dunn’s Mastering ConvertKit course. I didn’t even make my first lead magnet until December. Even though the quality of my emails improved, I didn’t do the necessary work to grow my list.

Grade: C

50,000 Website Visitors Per Month: Nailed it. And I exceeded my goal. My goal was to increase the number of page views on my website without reducing the quality of my writing, and I think I succeeded. Nevertheless, my goals changed throughout 2019. At the beginning of the year, I mostly cared about having a large audience. But now, I care much more about attracting the right people. I measure the success of my posts by the quality of students in Write of Passage and the number of interesting emails I receive.

Grade: A+

2. Things to Celebrate

Write of Passage: I still can’t believe the success of Write of Passage in 2019. I teamed up with Tiago Forte at the beginning of the year, and we decided to meet in Mexico City to structure the course and film the modules with a film crew from Los Angeles. The first two cohorts were a good start — we had enthusiastic students and thoughtful discussions. But as with any new venture, parts of the course were shaky and incomplete. However, after the second cohort, an alumnus named Will Mannon called me with a list of suggestions for how to improve the course. Instead of implementing them myself, I hired him to do it. By obsessing over the student experience, he made dramatic improvements to the course. In fact, his work was so good that I hired him full-time.

The third cohort featured 200 students from 28 countries, including Panama, Nigeria, and Indonesia. In just 10 months of working on Write of Passage, I’ve taught almost 500 writing students and built a global community of online writers.

Of all the messages from students, this one is my favorite:

Write of Passage might prove one of the best career decisions I’ve ever made. Six weeks ago, I began Write of Passage with vague notions of what I wanted to accomplish. Today I emerge with a razor-sharp niche, weekly newsletter and a strategy to succeed. I feel like I’ve undergone a creative exorcism and been plunged into an ice-cold bath, but it’s amazing.”

Making  Write of Passage  with Tiago Forte

Making Write of Passage with Tiago Forte

My Partnership With Tiago Forte: You won’t find a better person than Tiago. The working partnership I developed with Tiago Forte was the highlight of the year. We met on Twitter in March 2017, when I asked to record a podcast with him. Our conversation continued for more than an hour after the recording ended, and Tiago invited me to participate in the next cohort of his Building a Second Brain course that August. I enjoyed the course so much that I became a New York City ambassador and hosted local meet-ups for alumni. As our relationship improved, we sensed an opportunity to create a writing-focused course together, and we actually did it. We told our story on one of the most popular episodes of my podcast in 2019.

Me and Tiago in New York City

Me and Tiago in New York City

Writing: In 2019, I focused on publishing in-depth essays on my website and writing weekly messages in my email newsletters. I successfully did both. Two essays, What the Hell is Going On and Peter Thiel’s Religion were particularly popular. Combined, they hold more than 30,000 words and have received more than 200,000 page views. Beyond those long-form essays, my most popular articles of the year were Learn Like an Athlete, Why Did the Boeing 737 Max Crash, and The Ultimate Guide to Online Writing

Some other statistics:

  • 13 Friday Finds newsletters

  • 29 new articles

  • 52 Monday Musings newsletters

  • 533,000 unique visitors

  • 1 million page views

IMG_0913 2.jpg

Friendship: I’ll remember 2019 as the year of tremendous friendships. My first few years in New York were surprisingly lonely. Even if the city is full of people, it lacks community. Most people build friendships at work or in their co-working space, but I’ve worked at home for the past couple of years.

I’ve also tried to surround myself with kind and intellectually curious people who enjoy long conversations about provocative ideas. A few friends had a particularly impactful impact on my life. This list is by no means exhaustive, but a few people have blown me away with more love than I deserve.

I saw Lyn more than times than any other person this year. Together, we conducted weekly Bible studies, attended Tim Keller’s excellent eight-part Questioning Christianity series, and co-hosted a weekly Questioning Christianity group. Even though she’s a couple of decades older than me, I’ve developed a trusted relationship with her and her family. From a friendship perspective, this was the best surprise of the year.

I’ve learned that close friendships are built by spending multiple days at a time with people. This year, I shared an apartment with Alex Hardy, worked with Sid Jha, spent two days with Brent Beshore in Missouri, five days in Mexico City with Will Mannon, five days in Michigan with Kevin, six days in Toronto, Chicago, and Los Angeles with Nik Sharma, seven days with Eric Jorgenson in Missouri and Michigan, eight days with Zander Nethercutt in Michigan and Missouri, and 10 days with Brendan and Yassine in Morocco. Beyond that, I built tremendous friendships with Adil Majid, Cameron Porter, and Jeremy Giffon — all of whom I see on a near-weekly basis.


Christianity:  I explored Christianity than any other subject. In addition to the aforementioned discussion groups, I wrote a 15,000-word essay, inspired by the work of Renée Girard, about Peter Thiel’s Christian influences. Even when we write about others, we write about ourselves. Through this essay, I developed an appreciation for religion and grappled with my own relationship to faith.

Travel: My 2019 travels were mostly constrained to North America. The year began with a four-day work trip to Toronto, where I recorded podcasts with Andrew D’Souza and Alex Danco. Then, I traveled to Chicago for podcast interviews with Nick Kokonas and Jason Fried. During the summer, I visited Los Angeles, where I recorded podcasts with Mason Hartman and Jeff Morris Jr. Instead of spending time in Santa Monica as I usually do, I spent most of my time in Burbank and West Hollywood.

Right around that time, I saw a Tweet showing that Michigan used to have five of the 10 wealthiest cities in America but now has zero. Sensing a fascinating sociological shift, I made plans to see the entire state of Michigan. During an 18-day stint, I visited almost every major city in the state, including Traverse City, Grand Rapids, Lansing, Ann Arbor, and Detroit. The Ford Factory in Dearborn, Michigan was the highlight of the trip, along with back-to-back days at Arcadia Bluffs — one of the prettiest golf courses I’ve ever played. Finally, I’m writing this annual review from Mexico City during my second Mexico trip this year. In February, Tiago Forte and I flew down a Hollywood film crew for 10 days while we recorded the lecture videos for Write of Passage. I’m back now for 2020 planning for Write of Passage and my Annual Review Workshop with Tiago.

Speaking with Morgan Housel, Jim O’Shuaghnessy, Christie Hamilton, and Eric Balchunas at Bloomberg in Washington D.C

Speaking with Morgan Housel, Jim O’Shuaghnessy, Christie Hamilton, and Eric Balchunas at Bloomberg in Washington D.C

3. Things to Improve

Home-work balance: I moved to a bigger apartment in Williamsburg, so I could upgrade my home office. On the positive side, the apartment is a major improvement and the location is exceptional. But I still work from a desk in my room. Since my computer is so close to my bed, I’m unable to calm down at night and rarely close my eyes before 1 a.m. Beyond that, I’d like to record more videos, but my room doesn’t have enough space to do this. So I’d like to find a dedicated workspace next year where I can film videos, record podcasts, and find a flow state while writing. To be honest, I can’t tell if a work-reserved space is a frivolous luxury or a major productivity and happiness boost.

Delegating Operations: Online course instructors are part marketers, part educators, and part operators. I enjoy marketing and teaching the most, but as the course has grown, I’ve had to devote more energy to operations. In an ideal world, I’d devote all my waking time to learning, creating, and building relationships. But in the past few months, I’ve devoted too many hours to nitty-gritty operations where I don’t perform well because I’ve never been detail-oriented. The more I can delegate operational tasks to people who are more competent than me, the better. I’ve already made some improvements. I hired an editor to improve my writing, a personal assistant to take care of basic tasks, and a full-time course manager to manage operations and improve the Write of Passage student experience.

Time for Writing: Writing is the most productive thing I do. Publishing articles improves my thinking, grows my business, and attracts incredible people into my life who I’d never meet otherwise. But it’s a time and energy-demanding activity. And since my writing often falls into the “important, not urgent” category, I tend to neglect it. This year, I made a goal of writing for 90 minutes per day. But on most days, I wasn’t able to for the reasons mentioned earlier. Now I’ve found relevant solutions. And to improve the quality of my output and the quantity of my essays, I plan to make changes for 2020. First, I’m going to raise my daily writing goal from 90 minutes to 120 minutes per day. To do that, I’m committing to a dedicated writing time from 9:30-11:30 a.m. every day. And finally, I’m going to track my daily progress with this daily writing tracker, which you can download here.

The Podcast: 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’ll describe each challenge in turn. I record most of my conversations in Manhattan. I have to lug all my equipment around the city for each episode, which is unenjoyable and stressful because I don’t want somebody to steal it. Fortunately, I found a recording studio in Manhattan that I plan to use next year.

For years, the podcast was a standard interview show. But now, it feels repetitive and too much like the others. I’m blown away by the quality of Eric Weinstein’s conversations on The Portal and hope to emulate some of his conversational tactics next year. Additionally, the podcast didn’t grow much this year, and I don’t know why. Next year, I’ll aim to grow the show by spicing up the conversations, promoting it more on email and Twitter, and appearing more on other podcasts where I can mention my own. Nevertheless, I’m still frustrated because I still feel like I’m missing some low-hanging marketing fruit.

on’t think I’ve ever met somebody as inspiring as  Eric Weinstein . I haven’t been the same since our conversation — and all for the better. What an exceptional person.

I don’t think I’ve ever met somebody as inspiring as Eric Weinstein. I haven’t been the same since our conversation — and all for the better. What an exceptional person.

Email Growth: Email is the bread-and-butter of my business. I didn’t miss a single Monday Musings or Friday Finds. I overvalued the benefits of social media followers and under-valued email. The good news is I switched from Substack to a more advanced email service provider called ConvertKit. (To my embarrassment, I accidentally sent an email to my entire list during my first week on the platform.) By switching to ConvertKit, I’ve segmented my list into specific audiences and send them emails based on their interests. Unfortunately, my list didn’t grow as fast as I would have liked. It’s 100% my fault. I didn’t dedicate the time or attention to growing my list. I also didn’t publish frequently enough or create lead magnets for the website. Email list growth should have been a bigger priority. Next year, I plan to work with an email consultant to grow my list and create a better experience for my readers.

4. Goals for 2020

Setting goals is a delicate balance. I want my life to be productive but surprising. At the New Year, I set bold, big-picture goals at the outer edge of my capabilities. That way, once I’ve defined my general orientation, I can work small and iteratively throughout the year. If my goals are too loose, I won’t achieve them. But if they’re too concrete, I’ll give up serendipity and lose the flexibility to change direction as I learn.

I am emotionally driven to my core. I relish the surprising messiness of everyday life and the ability to pivot fast when new information comes to light. In the past, whenever I’ve tried to be too rational, I’ve rebelled against myself.

Until I worked with Tiago Forte, I didn’t know how to properly set long-term goals. He taught me to commit to focusing on the ends, not the means of achieving goals.

Until I worked with Tiago Forte, nobody taught me how to properly set long term goals. He taught me to commit to focus on the ends, not the means; to walk towards predetermined end states without becoming attached to the process of achieving them.

At a more concrete level, goals should be explicit and easy to evaluate. Every goal should be clear and concrete enough to evaluate with a “Yes, I achieved it” or “No, I didn’t” by a specific end- date.

Every goal should serve me, my family, and my students. And since I’m a creator, they should all create new knowledge. Earlier this year, I turned down an opportunity to co-found a company. The founder wanted to stay in stealth mode, so I wouldn’t have been able to write about it (which can create knowledge). The company is thriving, but I don’t regret my decision. The more I can share what I learn through writing, the better.

I use emotional cues and consider the potential end results to drive my goal-making process. Every goal should be so ambitious that I can’t even sit down while thinking about it. The soup of nervous energy should come from a stew of nervousness, excitement, and grandeur. A goal isn’t grand enough unless it makes me say: “I can’t believe I’m actually going to do this.”

Life will always be more interesting than anything I can imagine, provided I keep my heart open to the sweet song of serendipity.

Hassan II Mosque in Casablanca, Morocco

Hassan II Mosque in Casablanca, Morocco

What I Plan to Achieve

Enroll 800 Write of Passage Students: I’ve never believed more in the benefits of writing online. And the student experience is better when the course size grows, provided that everybody who attends is curious and committed. Write of Passage will be offered in three separate cohorts in 2020, so on average, each cohort should have almost 300 students. Achieving this goal will require a tremendous marketing effort, with a particular focus on mastering launches. To achieve this goal, I plan to refine my launch checklist, add a host of digital workshops, and work with coaches who can teach me best practices.

60% Write of Passage Completion Rate: Write of Passage won’t improve the world unless we increase completion rates in addition to growing the size of the cohorts. Online courses are famous for terrible completion rates, but we plan to transcend those norms. First, we’ll increase alumni engagement. Then, we’ll add small writing groups and foster student-to-student friendships. By being more engaged with one another, more students will complete the course.

Additionally, the more feedback we can receive from students, the better. We plan to increase student feedback through email, Zoom breakout rooms, and one-on-one phone conversations.

120,000 Words on My Website: The Internet rewards people who are prolific. If I write 120,000 words, it’ll be equivalent to two average-length books. I’ll keep the word-count strict, so I can freely navigate between short and long-form essays. Up to a certain point, quality and quantity aren’t at odds with each other, so the more I publish, the faster my writing improves. I’d like to publish more, but must cater to the demands of running an education business.

200,000 Page Views and a 10-Minute Average Reading Time on Secret Essay: This is the coolest and most ambitious essay I’ve ever worked on. Inspired by Tim Urban’s series about Elon Musk, I plan to publish an alternative-style biographical essay on a public figure I admire in 2020. The goal of 200,000 page-views will force me to clarify this person’s ideas, while an average reading time of 10 minutes will encourage depth and rigor in my research process.

50 Days of 1-on-1 Time with Friends and Family: Nothing makes me happier than long conversations with wonderful people. Over the past three years, I’ve prioritized meeting new friends. By almost all accounts, I’ve succeeded at meeting new people. But during those years, I spent more time meeting new people than deepening relationships with the people I already knew. It’s time to change that. For the first time in my life, my desire to meet new people has fallen. I want to build relationships with the people I already know instead. I want to write with them, eat with them, and travel with them. I want to spend long hours with my closest friends, and see them for days at a time. In 2020, I plan to spend 50 days in quality one-on-one time staying with close friends or family members.

Visit Three New States and Three New Countries: The best way to achieve multiple ambitious goals is to combine them. Next year, I hope to spend more time on the road with a different friend every trip. In America, I’d like to visit Alaska, Maine, and Massachusetts. People rave about the beauty of Alaska and Maine, but I’ve been to neither. And in Massachusetts, I’d like to visit Boston, Nantucket and Martha’s Vineyard. Abroad, I’d like to travel to India, Japan, and Singapore. The center of economic gravity is moving to East Asia, so I’d like to study their cultures and governance systems. If I could add two countries to this list, I’d add China and Taiwan.

I’m proactive about traveling domestically and reactive about traveling abroad. Traveling across America is easy because the culture is so familiar to me. But the quality of trips abroad are determined by the people I travel with. For example, my trip to Morocco was a success because my friend Yassine speaks fluent French and Arabic and frequently hosted road trips across the country when he was younger. Thus, he planned the entire trip and hosted us at his childhood home in Casablanca. If a similar opportunity presents itself, I’ll jump on it.

50,000 Email Subscribers + 50% Open Rate: As I mentioned before, the strength of my email list strongly correlates to the success of my business. In addition to feeling comfortable on ConvertKit, I finally understand how to create lead magnets, segment readers, and produce high-quality emails every week. Fifty percent of subscribers open Monday Musings every week, while Friday Finds’ open rate is usually north of 70%. But now, it’s time to focus on list growth. As I write this, Monday Musings reaches 13,500 subscribers. But by the end of the year, I want to grow that number to 50,000. I’ll start by creating lead magnets for all the most popular articles on my website. Then, I’ll hire a coach to inform the execution process. And if I have the resources, I’ll build a referral program inspired by Morning Brew.

Helping the butcher in a Moroccan market

Helping the butcher in a Moroccan market

Beyond these concrete goals, I’d like to improve upon a number of habits:

  • Go to sleep earlier: I work at home alone during the day, so all my socializing happens after work. I don’t usually meet friends until 7 p.m., which means I don’t usually come home until 10 p.m. Moreover, even without coffee, I have too much energy to read during the day, so late nights are reserved for reading. As a result, I don’t usually close my eyes until 1 a.m, which means I don’t wake up until 9 a.m. Ideally, I’d be in bed by 10 p.m. and up at 6:30 a.m. But given the realities of my life in New York, an earlier sleep schedule may not be possible or desirable.

  • No caffeine after 1pm: I have an irrational joy for the froth of a flower-topped latte. On most days, I don’t leave my house until 2 p.m., so when I treat myself, I tend to stay up later than I’d like. But avoiding caffeine (even decaf) is a smart sacrifice to make. In the new year, I’ll replace caffeine with tea in the afternoons.

  • Finish a Spartan Race Trifecta: I enjoy the challenge of weight-lighting but panic at the huff-and-puff of cardio. But before my first Spartan Race in November, my fear of failure overwhelmed my hatred of cardio, and I changed my fitness habits. In order to complete a Spartan Race Trifecta this year, I’ll have to ramp up my cardio.

  • Reduce alcohol consumption: As a society, we should drink much less alcohol. New York has a heavy drinking culture, especially among people in their 20s. I drank a lot when I first moved to the city, but I’ve since slowed down. My moment of introspection came on July 3 2018, when I had way, way, way too many drinks at a party. Since then, I’ve only had one hangover. I’ve also started sleep tracking and have since seen that my sleep quality goes down after only one drink. My resting heart rises and my REM sleep disappears. In 2020, I’ll reduce my alcohol consumption by drinking tea and seltzer water instead of beer and cocktails.

  • Two hours of writing per day: Writing is the most productive activity in my life. Through it, I improve my thinking, grow my business, and attract quality people into my life. Ironically, I don’t like writing. It’s never come easy to me, but that’s exactly why I’m able to teach it. In the past year, too much of the energy I would have spent writing went to operations for Write of Passage. But now that I’ve hired an excellent director of student operations, I want my time back. In 2019, I had a goal of writing for 90 minutes per day. But next year, I plan to raise write for 120 minutes — two hours per day.



Best Surprise: The Beauty of Northern Michigan

Best Meal: Chicken and Waffles with Sid at Roister

Coolest New Experience: Speaking at Bloomberg in Washington D.C

Favorite Weekend: A conference in Sea Ranch, California

Favorite First Meeting: Austin Rief

Favorite New City: Detroit

Favorite Sports Moment: Tiger Woods winning the Masters

Favorite New Golf Course: Arcadia Bluffs (Bluffs Course)

Favorite Work of Art: The Diego Rivera Murals in Detroit

Favorite Tour: The Ford Factory in Dearborn, Michigan

Favorite Day: Zander’s birthday at Arcadia Bluffs

Most Intense Week: Creating Write of Passage

Favorite Travel Experience: God’s Bridge hike in Morocco

Favorite Artist: Above & Beyond

Favorite Song: Lonely by Illenium

Favorite Songs: Spotify playlist of my favorite songs of 2019

Favorite Concert: Illenium at Madison Square Garden

Favorite Quote: “When is the last time you had a great conversation? A conversation that wasn’t just two intersecting monologues, which is what passes for conversation a lot in this culture? But when you last had a great conversation, in which you overheard yourself saying things you never knew you knew, that you heard yourself receiving from somebody words that absolutely found places within you that you thought you had lost, and a sense of an event of a conversation that brought the two of you onto a different plane, and then, fourthly, a conversation that continued to sing afterwards for weeks in your mind? And I’ve had some of them recently, and it’s just absolutely amazing. They’re like, as we would say at home, they are food and drink for the soul.” — John O’Donohue

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