“Asynchronous” Working In 2021

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

Inspired by a friend, Sahil Lavingia, and his stance over the last year 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.

This is something that I have tried for the last 6 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 55 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.”

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 6 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 Paul Graham’s brilliant essay here: Maker’s Schedule, Manager’s Schedule

”A single meeting can blow a whole afternoon, by breaking it into two pieces each too small to do anything hard in. Plus you have to remember to go to the meeting.”

I understand this is in contrast to many norms and will seem less than ideal to certain people (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, and have come to realize that these tools and this approach actually leads to higher quality communication and higher output for everyone involved over time (while “costing” less for everyone involved as well; 2x speed on Loom.com is a game-changer, for example) — And all of that adds up to a very compelling equation to try this out for the calendar year of 2021.

If you’re curious, try it out for your next meeting, sending people a loom video asking them to try out the tool instead of finding time on your calendar, and get your calendar (and sanity) back. You can even link to this post and 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. We also tend to stick to “how things have always been done” instead of questioning and utilizing technology that makes a new 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 enjoy a coffee meeting with a friend, or connecting with a new founder in person or over FaceTime (preferable to Zoom for the difference in latency) — 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.

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 and the technology at hand that offers us a different path.


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