The other day, my wife Aja Singer and I were having a conversation about being more intentional with our time, especially when it comes to working. We both have multiple personal and professional projects that we’re involved with, and we felt like were getting sucked into spending time on things that weren’t moving these efforts forward—everything from too many meetings, or just getting sucked into social media rabbit holes.
We looked into the concept of time blocking, which helps people spend less time switching between tasks and helps you get into extended, focused periods of “deep work”.
Most of the beginner articles felt a bit lacking for our purposes. It felt too idealistic to imagine that Tuesday mornings would be “focused project time”. That methodology failed to consider an initial time budget and also lacked the specificity we were looking for. Was that enough product time? Which projects? We sought out a different starting approach to answer these questions.
The first thing we did was to outline a kind of budget—starting with two buckets of time. The first was self-care type stuff: working out, meals, leisure reading, TV, etc. We both decided that we were going to start, as a priority, with the amount of each of those things we wanted to do.
As a caveat, we do not have kids and we’re not commuting, both of which would require lots of time adjustments. We look forward to a future where we have to take those things into consideration.
We started working through the different types of work we do in our jobs—not only based on the type of task but also on particular projects. For example, for me, I didn’t just put in “e-mail time”, I divided up the amount of time I spend responding to entrepreneur pitches in e-mail vs other types of e-mail, which I labeled “correspondence”.
I also created groupings based on the basic demands of my job. I’m active on X number of portfolio companies and meet with them at Y intervals, meaning that I should have Z portfolio company meetings per week. I baked in time to connect with my one other full-time employee as well as time for follow-ups from the portfolio company meetings I was taking.
Tallying the amount of time going into each thing was super useful, especially for Aja, because she wanted to start with a top-down view of what percent of her time she wanted to spend on her own entrepreneurial projects versus consulting for others. I wanted to keep an eye on the overall work hour tally because I definitely have a tendency to bite off more than I can chew.
What we found was that doing this exercise together created the space for really productive conversations about how we spend our time. For example, I’d never been much of a TV watcher, nor do I really ever seek to “unplug from work”. Left to my own devices, I was generally working, socializing, or working out/playing sports. There was very little “downtime”.
Aja needs downtime and we both found ourselves getting sucked into more downtime than we wanted. We’d turn on the TV during dinner, and whereas I would normally go back to work after, I felt bad that I was “abandoning her”. Similarly, if I wasn’t there, she would probably be perfectly content to read or draw—but it would have seemed awkward at 9:30PM at night when we’re on the couch watching TV to say, “Ok, I need you to go figure out something else to do with your time, because I want to read now.”
By actually counting out our TV time and deciding that it shouldn’t unintentionally be two hours a night, we opened up the time for, “What else might we like to do with this time?”
It’s important to also be really honest with yourselves about these types of questions. Sometimes, you could get overambitious and fail right out of the gate. During the pandemic, we tried both chess and puzzles. We learned very quickly that quiet concentration exercises that involve not doing a lot at any particular moment do an excellent job of putting Aja to sleep—so it wasn’t realistic to think we were going to get an hour of chess in at 9PM.
The end result was a pretty full, but not entirely so, calendar of activities:
I don’t necessarily want to go into all of the various allocations of time, but what I’m most excited about is the limitation of 15 minutes of social media time once in the morning and once later on during the day, and the limit of one TV episode at night per weeknight.
Obviously, this schedule is based on a work from home pandemic schedule that doesn’t imply much socializing—but I did consider things going back to normal when laying out where things go.
For example, I used to bounce around from portfolio company to portfolio company, bunching all my meetings together. It felt efficient, but I was actually creating a lot of commuting time in between. What I’ve done now is spread those meetings out, and followed them with things like e-mail or calls—where I can just stay put in that company’s space and continue to do work until I go home or go back to wherever I’m working at the time.
In terms of how we’re going to actually implement this into our daily lives, I’ll go deeper into this as we go along, but here’s some of the basics of where we’re starting:
1) We created new, separate (we use Google) calendars to build the template, inserting each segment into repeating blocks in perpetuity. Free/Busy didn’t matter, because the only thing that will ever go on this calendar is the template (kind of like a slide master in Powerpoint. I’m sharing this calendar with both Aja and the person who helps me schedule things.
2) I’ve been making extended use of Calendly over the past six months, and it’s been working out great. What I really like about it is how easily you can copy different views of your calendar, with varying rules for access, from a Chrome plugin and from a mobile app. I can give a founder that I want to take a meeting with a single use link to book a meeting, but I can also give one of my portfolio companies an open link to book as many meetings as they need at particular times.
What I’m going to do is to create use case links that match specific time slots—1st time pitch meeting links, longer 2nd meeting links, links to connect with other investors at certain times, or professional friends. This way, I’m not just treating everything as a call, but I’m being very specific about when and how often I want to communicate 1:1 with certain groups of people.
3) The main impediment to doing this well will be how I manage meetings and request of my time that are out of my control. I’m pretty lucky because I control most of my time. Even with the boards that I’m on, because I’m a lead investor, they are often scheduled on my side. Still, that’s not always going to be the case—so it’s important to enforce some kind of time swapping. A long, important board meeting might mean that I’m not going to watch TV later on in order to catch up with the e-mail correspondence I missed. An LP call that can only be scheduled at a certain time otherwise meant for a particular project means that project needs to go somewhere else.
It will also mean that perhaps that Calendly slot that it’s taking up also needs to be swapped. That would be a lot easier if Calendly had a free time calendar by type that could sync with a Google calendar. It doesn’t appear to—but you could hack it using the “Collective Meeting” feature, which I might try. I’d create an inverse “Calendly Time Blocking” Google Calendar that is only free when I want to be free for this kind of meeting and use it as a team member. My whole calendar would be “free” for meetings, but only when all three of us (me, the invitee, and the blocking calendar), were all free would the invitee be allowed a slot.
In this way, availability could be managed easily via the Google calendar interface as opposed to having to manage it by logging into Calendly.
I’m excited to see where all this goes and generally about being as intentional about investments of my time as I am with my LP’s capital.
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