writing annual letters

01.31.22

published looking back in time while near the beach in lanikai reflecting on january memo for coaching on annual letter writing.


while most people look for gifts, relaxation time, or celebration experiences at the end of the year, i look for thoughtful annual letters.

what is an annual letter?

smart people find a time to reflect each year, whether it's chronological with the new year or subjective milestones like a birthday.

ambitious people publish and share their reflection with the world in terms of what they learned looking backwards as well as what they will build ahead.

this is a playbook of some of my favorite examples of annual letters.

why are they important?

pain + reflection = progress

- from ray dalio

  1. reflection builds understanding. i find writing it down helps sharpen my thinking.
  2. clarify what's next from understanding what has worked, hasn't worked, as well as new things to focus on.
  3. sharing one's journey creates serendipity, especially in the great online game.

more here in this twitter thread →

3 recent examples from founders and investors

1. noubar afeyan, flagship pioneering founder + ceo, on intersection of biotech and machine learning:

one aspect of this powerful convergence that particularly excites me is the ability to  harness machine learning to computationally generate new scientific hypotheses that can then be explored and tested. ai and ml tools also enable what I think of as disease time travel. What do I mean by that? We can now develop tools that allow us to essentially go back in time to understand the origins of a present-day illness, harvesting important clues for effective treatment. Similarly, we can use biological datasets to travel forward and predict the future

read more in 2022 annual letter | flagship pioneering →

2. mark suzman, ceo of bill & melinda gates foundation, on sustainable impact:

we often let our enthusiasm about a potential breakthrough innovation blind us to the reality of the complex set of relationships needed to achieve and sustain implementation and impact, including the vital role of government and community engagement at every level. Even with our work in the United States, we quickly ran into setbacks after our first major education effort to build smaller schools did not show the results initial pilots had promised.

read more in 2022 gates foundation annual letter →

3. jeff bezos, former ceo + founder of amazon, on creating > consuming:

if you want to be successful in business (in life, actually), you have to create more than you consume. your goal should be to create value for everyone you interact with. any business that doesn't create value for those it touches, even if it appears successful on the surface, isn't long for this world. it's on the way out.

read more in his 2020 final letter to shareholders here →

4 examples from tks activates

my previous annual letters

write one

some tips

  1. schedule time with yourself to complete it and add it to your calendar. know it will most likely take multiple sittings and a few hours. treat it like a coffee date with yourself by having it in your calendar and include a beverage of choice to meet you. the ☕ will increase enjoyment and the 📆 invite will increase the probability of it happening.
  2. check out different examples to see what format you like. and replicate it. no need to reinvent the wheel. for example, james clear writes simply and clearly (get it 😉?) in his 3-2-1 newsletter.
  3. do what makes sense for you. whether it's a quick video update or a twitter storm, there is no need to make the letter one way or another. the medium itself is open to the message you want to share.

more resources


if you liked this, have feedback, or more resources to share, send me a note on twitter.


made with 🖤 in sf.