I can be pretty hard on myself. I’m always looking for ways to do more or better, to get to 100% perfection. Doing annual reviews has helped me reset my brain, to be more grateful instead of dissatisfied about the year that just passed.

This year, I started my review later than usual, in the first weekend of January. I did it with some other people who were taking the Annual Review 2020 course with Tiago Forte. The course encouraged us to reflect on the year and take a few preliminary steps before writing the review. My perfectionism and desire to capture absolutely everything got in the way of getting the review done. On top of that, I felt overwhelmed because this annual review overlapped with my quarterly review and my December monthly review.

This was something that I should have anticipated but didn’t.

In the end, I complicated a lot of things for myself, when all I had to do for my annual review was answer my usual 3 questions:

  • What went well?
  • What didn't go well?
  • What did I learn?

Well, it’s mid-February now. And while I wish I got this out earlier, better late than never. Here’s my 2019 annual review.

What Went Well?

Personal growth & development

I read James Clear’s Atomic Habits in the last few months of 2018. Thinking about habits and environment helped me start 2019 off on the right foot.

2019 was the first full year I kept a bullet journal and tracked my habits. I redesigned my digital productivity systems based on David Allen’s Getting Things Done framework and Tiago Forte’s Building a Second Brain. By the end of the year, I successfully integrated my digital productivity systems with my analog bullet journal.

One of the best things I did in 2019 was do quarterly retreats. I took a few days to a week off every 3 months to rest, reflect, and plan for the next 3 months. I eventually formalized this process into a quarterly review heading into Q4 2019.

Here are a few other notable personal growth accomplishments during the year:

  • I read 40 books with a good mix of fiction and non-fiction.
  • I took my first improv course. It was fun!
  • I started learning about design and spent dozens of hours learning Adobe Photoshop, Illustrator, and InDesign.

Family & Friends

In 2019 I learned that in order to have healthier relationships with other people, I needed to have a healthier relationship with myself first. I read six books from two authors that helped with that:

These books helped me acknowledge and accept who I am. They taught me to own my story and to present myself to other people just as I am, for better or for worse.

This year I learned that I am someone who inspires other people to be better versions of themselves. In line with this, I want friends who believe in me and inspire me to be a better version of myself. Because of this, I spent 2019 reconnecting with friends I should have valued more in the past.

For example, one of the highlights of my year was driving out to an ultimate frisbee tournament in Ottawa. I played with a friend I’d known for about a year, but never really got to know well. We ended up hitting it off that weekend. We had an amazing time exploring Byward Market after the first day of the tournament, and belting out to Taylor Swift on the car ride home.

At the same time, as I drew closer to some people, I intentionally drifted away from others. These were people who didn’t value my friendship as much as I thought they did. Part of it was my fault: I’d spent most of my life trying to please people who didn’t even like me. As comedian George Carlin said,

"We buy s**t we don't need, with money we don't have, to impress people we don't like."

I still have a long way to go in terms of being fully secure with who I am. I still find myself compromising on my standards and boundaries for people I find attractive or whom I really like. But I’m very proud of the progress I made in 2019.

Work & Finances

After reading Jim Collins’ book Great by Choice early in 2019, I spent the rest of the year applying the three qualities he outlined in the book:

  1. Fanatical discipline. A commitment to daily, consistent action, regardless of motivation levels.
  2. Empirical creativity. Risking a small amount of resources to test ideas, before committing more time and resources to a higher-risk, higher-reward endeavour.
  3. Productive paranoia. Building in financial and time buffers for my life, my projects, and business investments.

That last point - productive paranoia - was the one I struggled with the most. I’m someone who goes all out to a fault. I often end up stretching myself and my resources thin. To become more resilient, I had to learn to de-risk as much as possible.

Especially when it came to finances.

You see, not having a regular income is the bane of freelancing, consulting, and creative work. While I had a monthly income every month of 2019, not having a regular number contributed to 80% of my stress in 2019.

After a lot of reflection and honesty with myself, I decided to take on a part-time job at my church in the last quarter of 2019.

This decision didn’t come easy. Taking a job — even if it wasn’t full-time — felt like admitting defeat, that I failed somehow. But I also made an agreement with myself: I was OK working for someone else as long as I still had time to work on my own business. My decision ultimately boiled down to this:

Did I want to do entrepreneurship or did I just want the label of being an entrepreneur?

In other words, was I willing to do whatever it took to be a great entrepreneur — including taking a part-time job for a year — or did I just want to be able to say that I owned my own business?

Shoving pride aside, the answer was obvious: take the job, get myself into a healthier financial situation, use the extra time and the regular cashflow to grow the business. This turned out to be one of the best decisions I made in 2019. In the last few months of 2019, I redesigned this website, restarted my newsletter tk, retooled my note-taking systems, and learned design. All because I wasn’t spending my energy worrying whether or not I would make enough money that month.

Creative output

I want my writing to be a result of reading what interests me and discussing ideas around with other people. Taking inspiration from Austin Kleon’s book Show Your Work!, I started cultivating a scenius — an acknowledgement that “good work isn’t created in a vacuum, and that creativity is always, in some sense, a collaboration, the result of a mind connected to other minds.”

One part of cultivating this was starting my podcast. I published ten episodes as a pilot and did over two dozen interviews. While I’m naturally good at building a podcasting system and doing the interviews, I didn’t enjoy doing post-production. I’m looking to work with a podcast editor to ease this bottleneck in 2020.

As a result of all the reading, consuming, and conversing I did, I also decided to restart my weekly newsletter. I’d paused the newsletter for most of 2019 because I wasn’t sure what to do with it anymore. But in the summer, I bit the bullet, cleaned up the inactive subscribers in my list, and started from scratch.

Throughout all this, the most important thing for me was that my output had to be organic. I didn’t want to force myself to do a podcast or put out a weekly newsletter just because I saw other people doing it. I wanted to do them out of an excitement to share what I learned with the world.

And I’m proud to have done that in 2019.

Habits & routines

At first, I put my habits and routines in the “What didn’t go well” section. This is because while I’d gotten pretty good at integrating new habits into my life, there were 3 habits that eluded me:

  1. Waking up before 6:00 a.m., 5 days a week
  2. Praying and reading my Bible, 5 days a week
  3. Doing a weekly review

I couldn’t do #1 was because I went to bed around 12:00 a.m - 1 a.m. I couldn’t do my Bible reading because I wasn’t waking up early enough (#1). And for some reason, I just kept putting off my weekly review even though I knew I need it to keep my productivity systems running smoothly.

But after some thinking, I decided to add this to the “What Went Well” section instead. Looking back, I realized that 2019 wasn’t so much about how consistent I was with the habits, as much as it was …

  • Learning the skill of building habits
  • Figuring out what the right habits for me were

In terms of these two criteria, this was a win. Looking at my habit tracker in 2019, my habits looked different every month. This was because I was testing a number of different practices and routines, including The 5-Minute Journal, daily workouts, tweeting 10 times a day, and reading for 1 hour a day. While I easily stuck with each of these for at least a month, I eventually discontinued most of them. They just didn’t fit me or didn’t address the roots of my problems.

Thanks to all this testing, though, I discovered the three habits that do stick and that do address multiple areas of my life:

  1. Journaling
  2. Writing for 1 hour a day, and
  3. Mobilizing my body for at least 10 minutes a day, ideally before bed

Looking forward to focusing and going hard on these in 2020. 😎

Ultimate frisbee & fitness

Last summer I prioritized competitive ultimate frisbee over a lot of other things, including my business. No, I don’t regret spending so much time playing ultimate. In fact, my best memories this year came from ultimate:

  • Taking summer naps in the shade between games
  • Winning my first game MVP prize in my last tournament of the year
  • Long conversations with friends in car rides and parties in AirBnB’s

While I spent the year mostly injury-free, around October, I sprained my knee and had to take a few weeks off the field. I While my knee healed, I focused on strengthening my upper body and adhered to the “don’t miss two” rule to keep my momentum going.

I’d always had trouble doing pull-up’s because of my unnaturally long arms and short legs (I’m 5”7 with a 5”9 wingspan … And 5”1 legs 😂). In 3 weeks, I went from barely being able to do 1 pull up to doing 2 pull-up’s at a time. I also went from doing -40 lbs for reps for my semi-supinated grip pull-up’s to -20 lbs.

I’m very proud and happy with this progress.

What Didn't Go Well?

I had a great year in general but some things still didn’t go my way:

Freelance writing income

I expected this since I’d prioritized playing ultimate and my creative work over my business. But I also lost a couple of clients last year. One of them was because I psyched myself out and botched the job, and the other was because it was simply time to part ways.

I was secretly happy to part ways with both clients. Having more free time let me explore and learn and write for myself. And thanks to my part-time job, I still had all my basic needs covered, despite the drop in income (productive paranoia, ftw).

Church community

Despite developing many great friendships in 2019, I still felt disconnected from my church community. I just didn’t carve out enough time to spend with my church family.

In 2020 I’ll be taking more time to strengthen and develop my relationships with my church community. This means taking time to go for lunch with them, volunteering, and serving the community together.


I didn’t get sick in 2019. And while I did get stronger and improved in my skills on the field, ultimate frisbee also took a toll on my body.

As a result of playing multiple games 2-3x a week, pain and stiffness became my constant companions. After the first day of a tournament, I’d often have trouble walking because my knee would be swollen. After particularly hard weekend tournaments, I’d often have to skip out on an entire week of workouts to recover. Worse, I would barely get any work done on Mondays because I was too sore to move.

But I refuse to believe that playing through pain is normal. If I want to play at the elite level, this had to change.

In 2020, I’ll cultivate a mobilization practice and learn more about the best ways to take care of my body. I might have to miss a couple months’ worth of strength training and lose some gains. But if this means I can train and play hard for the rest of the year, it’ll be worth it.

Summary: My #1 Lesson in 2019

My biggest lesson in 2019 was that I inspire other people. While I’ve stayed away from the spotlight as much as I could — all the attention can get to my head — I’m just not meant to be a background person. I’m at my best when I write for myself and put my work out there. In fact, I realized that freelance writing was an excuse for me not to put myself out there because I was writing for other people.

This was at once a terrifying and exciting realization. Being unabashedly me has been a more terrifying experience than trying to be who other people want me to be. And while I risk other people rejecting the real me, the exhilaration of fully expressing myself, sharing that with others, and inspiring them to do the same more than makes up for it.

My Favourite Memories from 2019

Favourite Quote: “Research your own experience. Absorb what is useful. Reject what is useless. Add what is essentially your own.” — Bruce Lee

Favourite Question to Ask Myself: “What do I want to learn today?”

Favourite Podcast: Dissect (Tagline: “Long form musical analysis, broken down into short, digestible episodes.”

Favourite Song: ”There's No Way” by Lauv ft. Julia Michaels

Favourite Artist: Lauv

Favourite New Artist: Tom Misch (check out his song, “Lost in Paris”)

Craziest Day: Drove from Toronto to Guelph in the morning, then took the bus (and got stuck in it for 3 hours) back to Toronto for a close friend’s birthday dinner… Before taking the bus back to Guelph after dinner

Favourite TV Show: Abstract: The Art of Design