Setting up a system

Like most people, I have struggled over the years to comes up with a organizational/productivity system that works for me.  Disclaimer: I do not yet have it down perfectly, and am not claiming guru status.  But I do have a few things that have worked pretty well, and I have noticed some things that others do that seem to work, so I will share those here.

I have a somewhat elaborate system which I will explain below, but at the end of the day it all boils down to a single strategy: getting things into my calendar.  The other main thing I try to solve for is simply not forgetting things.  I live in a constant stream of emails and meetings, and it’s easy to forget something important.  So a goal here is to help ensure that I don’t forget things and ultimately, that I’m focused on the most important thing most of the time.

I live by the calendar and generally obey it.  This is a trick I learned from Fred, who doesn’t use any productivity system except for brute force email and calendaring everything.  Getting something into my calendar is the most sure-fire way that it will get done — having a date and time attached to something gives it a lot more weight than a wishy-washy entry on a list of to-dos or “priorities”.

Working backwards from the calendar as ultimate do-place, I have a few tricks for capturing and prioritizing, loosely based on the “Getting Things Done” theory of capture/clarify/organize/etc.   As much as possible, I try to get big things out of my Inbox and into a place where I can see and organize.  For this I use Trello.  I have a board I use every day that looks like this:

From right to left:

The main show here is the “priorities” list, where I try to pluck out the important big things on my plate — this helps me make sure I am not forgetting something.  Roughly daily, I review this list, sort it, and make sure things are in my calendar to do.

Another list in my Trello is “meetings”.  I use this list to capture high-level takeaways from meetings.  I am a big believer in the concept of the “commonplace book” and the value of taking notes and reviewing them over time.  For me this step is more about just general processing rather than to-dos, though there is a to-do component.  I take meeting notes by hand in a small notebook (currently a moleskine but in the old days I used a spiral bound), and always mark follow-ups with a “F/U” with a circle around it — this is a trick I learned from Phil Myrick back when I worked at PPS.  As a way of processing the meeting notes, I make a card in trello for each meeting and add the follow-ups as checklist items (Dani has a system similar to this, using Notion, and I’m always impressed with how well it seems to help her process meetings).  For little things, I just do them right away, for bigger ones, I prioritize and calendar them.

On the left is the “Inbound” list.  I use this to capture fleeting thoughts, ideas and notes.  Things get on this list in two ways: 1) via Wunderlist, which I mainly use by phone — I have found this to be the easiest and quickest way for me to jot something down on the go.  I use Zapier to move things from my main list in Wunderlist into “inbound” on Trello.  2) I use Trello’s built-in email-to-board feature to get larger items out of my inbox and into Trello.   Again, the goal here is just to capture so I can process/prioritize later.

Another input into this system is my other notebook, the Ink+Volt Planner. I am on my third year of using this wonderful tool: it’s a structured goal and priorities setting notebook that helps you create and reach yearly, monthly and weekly goals.   I find that the Ink+Volt, like meditation, helps me cut through the noise and see what’s important more clearly.  I do a planner session every week (it’s in the calendar), and use that to inform all of the above.

Having now written all of this, it seems pretty clear that this is a lot of work, and may be excessively complex.  My wife would probably describe this as “planning to plan”, and just an elaborate mechanism for avoiding doing the actual stuff, or something like that.   That may indeed be so, and I often think about Fred’s simple strategy of blast relentlessly through email and calendar everything.  It is impressive and seems to work.  Mostly, I use this system so that I am not just at the whims of my inbox.

For sure, my biggest weakness is email, which I still struggle with.  Albert has a system here, which seems to work for him, which is: using a set of predefined gmail filters, clear the inbox daily.  Not the entire inbox, but a few filtered versions (family, USV team, his portfolio companies).  I’m not there yet.

So, there you have it.  That’s my system. It’s a work in progress.  What’s yours?