How I’m Reflecting on 2020 and Planning for 2021

[ productivity life ] · 3 min read

As I start to wind down, reflect on 2020, and plan for 2021, I thought maybe my process will be helpful for you too. So here’s how I’m doing it. (This will also be my last piece for 2020.)

Winding down 2020

My personal and work to-do list has grown; using it as a place to “park” ideas and projects is probably a bad idea. Which items are no longer relevant? Which are worth pursuing? Now’s the time to prune the list so I can focus on what’s most important.

The same applies to the dozens of saved—but unread—articles on Instapaper. Do we really need to read all of them? I’ll give myself a time-box, probably 30 minutes, to archive them in the relevant folders.

Also, the recurring obligations and meetings (this probably applies more to work). Are we still needed in them? If not, opt-out so we have more uninterrupted time for deep work.

This is like clearing our cache—it makes way for more important ideas and work.

Reflecting on 2020

To reflect, here are questions I often ask myself; I also use some of them to get feedback:

  • What have I done well, and should do more of?
  • Conversely, what should I do less of, or stop doing?
  • Did I learn and grow as much as I wanted to?
  • How has my thinking, and plans for the next 5 - 10 years, changed?

The sole habit I tried to build in 2020 was writing more. The intent was to learn via writing, share my knowledge, and answer questions I frequently get. Along the way, I provided a way to get email updates (i.e., email list) and shared my writing on Twitter and LinkedIn. Some questions I have:

  • Writing: How much have I written? What are the main topics? What resonated with people? What were my personal favorites?
  • My site: How has traffic grown? What are the top pages, sources, geography?
  • Email list: How has it grown? Which emails did people open more? Which sign-up channel was effective?
  • Social: How has my Twitter audience grown? How does Twitter & LinkedIn respond differently to the same content? (Know how to track LinkedIn audience growth? Please teach me 😊)

What else would you like to know? Tweet me or post in the comments below!

At the start of 2020, I joined Amazon as an Applied Scientist. It’s a great opportunity to build and ship machine learning systems to millions of customers worldwide. Lots of learning and growth. My team’s mission (helping users read more) also aligns with my values. Some questions to think about:

  • What projects did I ship? Which did customers like and were successful?
  • Conversely, what didn’t work with customers and what did we learn?
  • What capabilities have I contributed to the team?
  • What should I do more, less, and stop doing? (Ask the team for feedback)

If you’re looking for more year-end reflection questions, here’s 50.

Planning for 2021

To plan for 2021, I adopt the Working Backwards approach. What do I want to be at the end of 2021? How would I have grown? What will I have achieved? How will life be different? One thing’s for sure—I want to build on my writing habit and continue thinking and learning in public to help others.

Specific to work, here’s my step-by-step:

  • Go through my team’s plan for 2021 (OP-1)
  • What are the 3 - 5 big items I can contribute to?
  • Break each item into smaller chunks and prioritize
  • Align with my manager
  • Define my OKRs

The question I ask myself every year

And finally, here’s my favorite question that puts everything in perspective:

“If I’m told that I only have three years to live, what would I do differently?”

What’s your year-end ritual like? Tweet me or share in the comments below!


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