“Asynchronous” Working

“…the mere consciousness of an engagement will sometimes worry a whole day.” — Charles Dickens

Update: This working style has been life-changing (and life-giving), especially with many work-streams from Magic Mind, to Apt AI, to 150+ startup investments, and a goal to spend 20,000 hours with our 3 daughters before they reach 10 years of age — since no matter how well one can do professionally or financially, you can never get this decade back. So as of 2023, this is my default mode of working.

Inspired by a friend, Sahil Lavingia, and his stance in 2020 to work “asynchronously” (aka, instead of having to line up “synchronous” meetings with multiple people, choose somewhat arbitrary time blocks of 30 minutes or 60 minutes, and waiting days for relevant communication to take place when calendars align), I am going to adopt an asynchronous working style in 2021.

More on his experience in his tweet thread here: https://twitter.com/shl/status/1222545212477599751

This is something that I have tried for the last 12 months, and the more that I stick to it, the more everyone I work closely with benefits — I have more time for thoughtful communication, more time for my work-streams, more bandwidth as a leader and investor for others overall.

Whether it’s running my own small team with partners around the world or investing and advising 150+ portfolio companies, colleagues and portfolio founders can get more out of me quicker by using tools like email, loom.com (perhaps my favorite productivity application in the last 5 years), text, or voice-notes for iMessage. And I am less of a burden on them when I communicate thoughtfully and comprehensively, often through a loom video than reams of text in an email, than if I fell back on old habits of saying “let’s jump on a call or find time for a meeting” that can take weeks to schedule.

This also aligns with the famous essay from Paul Graham “Maker’s Schedule, Manager’s Schedule” that he wrote in 2009 that touches on the cognitive and productivity expense of a meeting on the calendar (where you can’t do any deep work 30-45 minutes before — and takes you 20-30 minutes to get *back* into flow after a meeting).

I’ve found that this approach over the last 12 months treats every calendar like a “maker” calendar… and between the small team for Magic Mind or the founders I work with on a daily basis, I’ve realized that I am primarily working with makers that have, well, a lot of things that need to be made.

Read the (truly brilliant) essay here: http://www.paulgraham.com/makersschedule.html

I understand this is new and will seem less than ideal to some (even off-putting at times, especially to people new to the concept) — and am fully aware that, indeed, it will be less than ideal for various interactions — but I also value the freedom of an eventless calendar, the productivity and focus afforded each day with limited time, and have come to realize that these tools and this approach actually leads to higher quality communication and higher output for everyone involved (while “costing” less for everyone involved as well; 2x speed on Loom.com hours after asking a question or needing help with something is a game-changer, for example) — And all of that adds up to a very compelling equation to try this out for the next 1-2 more years.

One of my favorite Jeff Bezos quotes is “Innovators must be willing to be misunderstood,” and there is the real chance that new workflows, prioritization of certain things, experimentation, and idiosyncratic approaches will be misunderstood. But attempting to be everything to everyone is a good way to satisfy others’ desires in the short-term, and end up being nothing to anyone in the long-term. As the adage goes, if everything is a priority, nothing is.

If you’re curious, and you’re willing to be misunderstood for a short spell, try it out for your next internal meeting, sending people a loom video asking them to try out the tool for the next two weeks instead of “default meeting mindset” — and get your calendar (and sanity) back for deep work to see if you want to try it out for longer.

You can even link to this post or Sahil’s tweet thread to over-communicate why you’re choosing this route.

The truth is that we don’t fully calculate the costs of switching tasks or having days locked-in versus free to seize an opportunity that *only* becomes available at that moment, and you wish you had 3 hours to dive into that opportunity.

We also tend to stick to “how things have always been done” instead of questioning a) what is the ultimate goal of a given request to communicate #firstprinciples b) the cost of a given medium or venue chosen and c) how to utilize new technology that makes a new, optimal behavior possible.

I will still need a synchronous meeting here and there (for example, when a lot of information needs to flow back and forth between multiple people) or connecting with a new founder in person or over FaceTime (FaceTime is preferable to Zoom for the difference in latency as well as taking out the corporate context, in my opinion) — but 90% of “meetings” don’t need to be meetings. And 100% of those benefit in terms of communication shared and time saved for all involved by working asynchronously when that is possible.

From the prioritization of current work, the costs of multitasking, to the opportunity costs on your time, to getting more done in less time, to higher quality communication, to the enjoyment of waking up agenda-less that day, I have a feeling we’re at the beginning of the world waking up to both this calculation & the technology at hand that offers us a different path.