As 2019 comes to a close, it only makes sense to reflect back on how things went. I’ve been doing this exercise for a few years now informally, but this is my first time publishing it! I’ll follow the format of asking myself:

  • What went well this year?
  • What didn’t go well this year?
  • What did I learn?

These questions should provide solid coverage on this past year. They will also help me decide what tweaks I want to make for 2020. Before we dive in, here's the "brochure version" of my past year.

What went well this year?

🌀 Starting a new chapter

I started my first full-time job at Squarespace and moved to New York City! Over the nearly 10 months since I started, I've learned a ton working with a team of super smart data people. A few takeaways that stand out to me: how to drive impact in organizations, working with data infrastructure, and thinking about product and growth in strategic ways.

Outside of work, moving is never easy, but I've fallen in love with the energy that comes with NYC. There were definitely challenges coming out here with few connections, but I'm super happy with things now. I could see myself in the city in some form for years to come.

🎒 Backpacking around Europe

I spent the first 3 months of 2019 backpacking around Europe, most of it solo. This was a transformative experience, and I’ve written about it in the past, but I’m all in on long-term travel. I’ve never been so uncomfortable, challenged, and energized before. I’m itching to get back out there sometime in 2020.

📊 Teaching at DataCamp

While I was traveling, I worked remotely with the team at DataCamp to design and ship an online course called Practicing Statistics Interview Questions in Python. This was my first time doing something like this, and I enjoyed it.

This was also my first formal exposure to remote work. While it was part-time, I think I better understand the hype now. Briefly living the "digital nomad" life turned out to be pretty sweet. I want to do this again at some point.

More unexpectedly, I learned the power of recording my voice. I realized that I spoke more confidently and operated differently in the days after I recorded audio for the course. I've put a bookmark in this for now, but I want to revisit audio at some point in the future. Who knows, maybe I'll jump on the podcast bandwagon.

📚 Reading

I read 24 non-technical books this year, which is the most that I’ve ever read! Here’s the full list in reverse chronological order. Some notable ones were The Way to Love, Poor Charlie's Almanack, and The Mom Test. I couldn't recommend these enough.

  1. Atomic Habits: An Easy & Proven Way to Build Good Habits
  2. Never Split the Difference: Negotiating As If Your Life Depended On It
  3. Poor Charlie's Almanack: The Wit and Wisdom of Charlie Munger
  4. The Art of Learning: An Inner Journey to Optimal Performance
  5. The Lean Startup: How Today's Entrepreneurs Use Continuous Innovation
  6. Superforecasting: The Art and Science of Prediction
  7. The Mom Test: How to Talk to Customers
  8. Zero to One: Notes on Startups
  9. Think and Grow Rich
  10. The Lessons of History
  11. The Magic of Thinking Big
  12. The Dip: A Little Book That Teaches You When to Quit
  13. Astroball: The New Way to Win It All
  14. Waking Up: A Guide to Spirituality Without Religion
  15. Influence: The Psychology of Persuasion
  16. Keep Going: 10 Ways to Stay Creative in Good Times and Bad
  17. Blue Ocean Strategy: How to Create Uncontested Market Space
  18. The Way to Love: Meditations for Life
  19. Drive: The Surprising Truth About What Motivates Us
  20. The Little Book of Common Sense Investing
  21. Principles: Life and Work
  22. Valley of Genius: The Uncensored History of Silicon Valley
  23. Hooked: How to Build Habit-Forming Products
  24. Levels of the Game

📝 Writing

While I didn’t write as consistently as I would have liked (more on this later), I did ship at a decent pace for the first half of this year. Overall, 18 blog posts isn’t too bad here! The full list is as follows:

  1. 23 Principles for 23 Years
  2. Learning in Ways That Don’t Scale
  3. Practical Psychology for Data Scientists
  4. The Twitter Experiment
  5. One Perfect Mattress for Everyone: 6 Lessons form Casper’s Success
  6. Why I Quit the Medium Partner Program
  7. Data Scientists Are Thinkers
  8. 10 Reads for Data Scientists Getting Started with Business Models
  9. The Single-Player Mindset
  10. What Should Onboarding Look Like for Data Scientists?
  11. What I’ve Been Reading Lately
  12. Compilation of Advice for New and Aspiring Data Scientists
  13. I Backpacked Solo Across Europe for 3 Months
  14. MVA: Minimum Viable Analysis
  15. 13 Essential Newsletters for Data Scientists: Remastered
  16. Reasons Don’t Matter: A Lesson from Steve Jobs
  17. Your Goals Won’t Motivate You
  18. How to Think About Travel

What didn't go well this year?

💻 Front end development

I spent a lot of my free time during the back end of 2019 working on teaching myself front end development. I want to be able to build and ship my own products. I studied CS in school and I spend plenty of time programming as a data scientist, but development was an area that I was unpracticed in.

It wasn’t smooth sailing. I went through lots of books, lots of courses, and a few projects, but I'm still not where I wanted to be over 6 months since kicking off this learning initiative.

In hindsight, I spent too long developing my mental model for development. I spent hours and hours reading about Javascript and watching other people code. I didn’t dive into building things myself early enough. Moving forward, I’ll emphasize getting my hands dirty, even if it might be uncomfortable. Building out my website with Gatsby, React, and Node.js, was a good start to this.

🔥 Routine

While traveling, it was extremely difficult to get into a routine. When I moved into my first apartment, it was still hard to get back into the swing of things. Even now that I’m in my next apartment, which I’ll be in for a while, it hasn’t been as automatic as in the past. I’m getting there, but I want to be much more consistent about waking up early, meditating, journaling, and then getting to the gym before I start my day.

📝 Writing

I touched on this a little already, but I fell off the writing train pretty hard about halfway through 2019. One missed day turned into a month turned into 6 months. Once this happened, the mindset of "When I do X, then I'll get back to writing" wasn't helpful either.

Going into 2020, I’m making writing part of my routine and I’m going to ship much more frequently. Stay tuned for more here and subscribe to get updates on my progress weekly.

🤔 Ideas

I’ve been good about writing down my ideas in Evernote the last 3 years or so. I struggled with this in 2019. This was mostly the product of me changing my note taking style.

This change involved me going back through previous ideas and breaking them up, expanding on them, and putting them into their own "notes." This should prove helpful in the future, but it was a grind to work through all that technical debt from past years. Luckily, everything is where I want it to be now. It's just a matter of rebuilding the habit.

What did I learn this year?

📆 Going beyond goals

It’s difficult when you don’t have a seemingly predetermined path laid out for you like you often do going through university. Ambiguity is the name of the game now, and it's a scary thing. You have to be very intentional about what you want and you have to take initiative in order to make it happen.

🗣 The importance of focus

I took on a lot of side projects that I didn’t end up loving this year. They have their benefits and I would likely do them again, but there were points in all of them where I didn’t feel like they were the best uses of my time. I need to focus more on the work that matters in 2020.

🧳 How to work in an organization

This is harder to quantify, but I feel like I’ve gotten really comfortable operating in a team and manufacturing impact with my projects in an organization. I was close before, but it’s really clicked for me this past year that great work != great impact. There's more nuance to producing work that matters.

🎒 The power of long-term travel

I had heard about the benefits of solo travel. I wanted to see what all the hype was about, and it really did live up to my expectations. Being able to wander around and explore, to do whatever you please and not make any compromises — it’s pretty awesome stuff.

Plans for 2020

👨🏼‍💻 Learning by doing

This is a continuation and correction of my previous plans to teach myself how to develop products. I got too caught up in learning foundational concepts and didn't get my hands dirty enough in 2019. I'm going to learn by doing in 2020.

👋🏼 Talking to people that I admire

I want to take advantage of being in the city. I'm surrounded by people that I admire and I have a lot to learn. I want to have more long-form conversations with smart people.

📝 Writing consistently

I’m carving out time to write every morning. This is going to be a big one for me, my thinking, and my happiness. I know that is the thing that moves the needle on everything else.

I've got grand ambitions for 2020 and it should be a great one. Niklas Goeke talks about how themes can be more useful than goals in many situations. I tend to agree with this. My theme for 2020 is "Reach."

I want to take the foundation I've built and take things a step further. I want to reach for more impact and opportunities that feel uncomfortable or far away. I know that they are closer than they seem. I just need to reach for them.

Good luck to all of you on a new year and if you're like me and can't get enough of these yearly reviews, then check out Anne-Laure Le Cunff's Annual Review spreadsheet with dozens of them!

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