A new calendar approach for 2017

Four weeks ago, I revamped my whole approach to using a calendar.

After seeing it mentioned on Twitter from a few people, I purchased Jocelyn K. Glei’s Unsubscribe and devoured it on a long flight. Inspired by the ideas from this book and other sources, I started to redo my calendar and rethink my entire approach to working.

First up: email

I have 6 email accounts, and some back-of-the-napkin math tells me I get about 220 emails on weekdays (not including spam). That’s 83% more than the average 121 emails per day most people get as reported by technology market research firm Radicati (PDF, 600KB). That’s probably not as much email as some of you reading this might get, but it’s certainly enough to overwhelm me.

A quick look through my Harvest data tells me that I worked 868 hours in 2016, 135 of which went to non-project-related email — just over 15%. (For the curious, that roughs out to processing about 366 emails/hour, though that includes a hefty bit of automation like Gmail rules for auto-archiving and services like Unroll.me). Although I wish otherwise, I don’t really see a way to run my business without email — hence the significant portion of my workload — so I’m always open to better ways to manage this volume.

One of my favorite things about Unsubscribe is that it doesn’t jump right into the tactical. Instead, Jocelyn starts by tackling what she calls the “neuroscience and cultural baggage that shape our conflicted feelings about email.” For me, it helps to understand why an approach might work before attempting to implement it. This passage really spoke to me:

Once you start thinking of the irksome email requests you get as someone just throwing spaghetti at the wall and thinking, “Who knows what they’ll say? I’ll just give it a shot!,” it really takes the pressure off. You no longer assume they’re expecting you to say yes, and it becomes much easier to say no (p. 36).

In other words, Jocelyn is giving me permission to not have to answer every email. This is much more in line with an approach I’ve been adopting in other areas of my life and work: accepting the firehose.

Accepting the firehose

I used to love RSS. It was the main way I kept up-to-date with all the things going on in the industry. But, as information increased, my RSS feeds quickly got to the point where I could no longer keep up, and it was stressing me out to feel like I was on top of it.

Along came Shaun Inman’s Fever. It was a different kind of RSS reader, in that it surfaced information according to its traction rather than its chronology. That became a crucial philosophy in how I felt I could manage the firehouse of increasing info: the important stuff would rise to the top, so I could worry less about the stuff that didn’t. I was then free to add as many feeds as I wanted, as I figured the good stuff would make its way to me, not the other way around. My strategy with Twitter was similar: where I used to keep the number of accounts I followed to a minimum so that I could keep up, I now follow whomever I want and figure the good stuff will make its way to me. Unlike many, I highly value all the different flavors of “what you missed” functionality that social networks are starting to build in.

But this approach never made its way to my email. For a few years, I’ve been an Inbox Zero kinda guy. Never really achieving it for long, my unified inbox has hovered at about 50 messages for the last six months. With Unsubscribe’s “you don’t owe anyone anything” reminder, I think I’m ready to accept the email firehose. That means I’m making peace with the idea that I have more email than I can get to, and not all of it deserves my attention. I’ve written about priorities before; now it’s time for some dogfooding as it relates to managing email. (Ironically, letting go of the Inbox Zero mentality has gotten me closer to Inbox Zero than I’ve been in a long while.)

Calendar half-full

Some of the first things I work on with my apprentices are evaluating useful approaches to time management. For some of them, it’s the first time they’ve ever relied on a calendar to help them structure their days. Where do you start with a blank slate?

My most frequently recommended piece of reading is Jessica Hische’s Productivity Quest: Ultra-Schedule, specifically step 5. I love the idea that she starts every week with a full calendar, as opposed to an empty calendar that needs filling. I’ve always defaulted to the idea that my main work would fit in the empty slots, after everything else has been scheduled. (Just writing that out makes me realize now how silly that was.) Instead, I very much recognize the value in having the most important things scheduled. Eileen Webb touches on this idea too in her post, “Productivity in Terrible Times.”

So I set out to block out a boilerplate calendar for each day that could be filled-in with further details as I got to them. This is what that boilerplate looks like:

In Unsubscribe, Jocelyn suggests starting every morning with what she calls meaningful work, which she defines as “work that contributes to your legacy, helps you advance your career, expands your skill set, etc.… When you finish such work, you have the satisfying feeling of time well spent and a job well done.” This work should happen before doing any other work, especially checking email. She reasons that, by doing meaningful work for the first 60–90 minutes of your day, no matter what happens later that day, you will have advanced your personal mission.

This reminds me of the talk, “Begin With the End in Mind” by Ryan Carson at the 2016 99u conference. Ryan’s thesis is that accomplishing what matters to you is much more attainable when you schedule time on your calendar to make it happen.

After some reflection, I’ve narrowed my current personal mission to this: connecting people to opportunities they might not have on their own. I’ve identified four goals I’d like to accomplish over the next quarter that advance my personal mission, and have post-its on my desk that remind me of these goals constantly. In no particular order:

  1. Launch a new SuperFriendly site that shows how we’ve connected clients to new opportunities in their businesses.
  2. Launch a new personal website that better shows agency owners and product teams and how I can coach and mentor them to get better work and/or get better at it.
  3. Move SuperBooked into public beta so that freelancers and agency owners can more effectively find and share work.
  4. Release the podcast I’ve been working on about apprenticeships, mentorship, learning, and teaching in the workplace.

(I have some more specific OKRs — Objectives & Key Results — for each of these, but that’s a post for another time.)

I’ve been an early riser for the last 7 years; I’m generally up at 5am most weekdays. My workday starts at 5:30am, and I spend the first hour dedicated to one of these four things. Which one I work on is determined by which one I’m most excited about that morning.

Daily Work slots

I scheduled time for daily work. Having scheduled time for work is pretty new for me, but I immediately love it. Knowing that I’m guaranteed 3½ hours every day during work hours to do my work reduces a lot of my anxiety about the whens and hows of getting things done.

Call slots

I scheduled call slots. I’m on the phone (hangouts and Skype included) a lot. Between work reviews, team meetings, new business, and just liking to talk to people, I think this was the biggest detriment to my productivity. I’d randomly schedule calls whenever the other party was available, cutting short my own momentum in getting work done.

Looking back at the last few months, I averaged just over 6 scheduled calls/week, and I know there were a handful of unscheduled calls each week too. Having 10 slots for calls gives me the stability of knowing my momentum won’t be disrupted. A big part of productivity is prioritizing, and scheduled call slots let me prioritize my work while giving me a rationale for why I won’t do a call at 2pm. I’m working my way up to the Warren Buffet-style one-day-advance method, but for now, this works great for me.

Email checking slots

Per Unsubscribe’s recommendation, I have a morning and afternoon slot for checking email, Twitter, Slack, and even sorting through snail mail. These slots are the only times that these apps are open; otherwise, they’re closed. One small suggestion the book makes is to move to a different physical location during these times to mentally establish switching gears. I have yet to put this into practice but will be trying to soon. I’ll likely do something like making my iMac or Surface Book my work machine and then only checking and responding to email on my laptop or iPad so that I get the full experience of context switching.

Unsubscribe also makes many specific suggestions that I won’t mention here on how to make the most of these times, so go buy it if you’re curious.

Setting up tomorrow slots

The last slot of the day is devoted to filling in tomorrow’s tasks. All the slots in green and/or with brackets around the title indicate slots that need more specificity. At the end of each day, I’ll change a general “[Daily Work]” slot to something more specific like “Comps for [Client],” “Write proposal for [Client],” “[Client naming exercise] ” etc. Green means it needs to be scheduled; once it’s filled-in, it changes to orange. If a call slot hasn’t been booked by the end of the previous day, it turns into a “Daily Work” slot.

What’s next

The last four weeks of trying this — holiday break notwithstanding — has moved my work-to-email ratio from something like 50/50 to more like 60/40. A tiny improvement, but I think it’s headed in the right direction. Also, while the statistical significance is small, the addition of meaningful mornings makes me feel much more accomplished every day, and that’s a big deal for me.

As I try this out more, there are a few reminders I’ll need to keep top-of-mind and missing things I’ll be looking to integrate:

  • Flexibility. Even though the rigidity of this schedule is its strength, I know I’ll need to be flexible about how it bends. I’ll try not to break work momentum with more calls, but I’ll also be open to transforming a call slot into an email slot if the day calls for it. I’ve also noticed that having time blocks set up allow me to switch things, so some days have me eating an earlier lunch to accommodate a noon-time call or later lunch if I have some morning momentum and want to keep working through. I also allow myself to work longer on busier days and try to turn in early on others.
  • Family time. Weekends and everything after 6pm on weekdays is family time, and I don’t check email at all during these times. I haven’t specifically put these times on my calendar, mostly because I’m not around a calendar to need to know what to do, but I also realize how that conflicts with the “schedule it if it’s important” theory. Ok, I just put it on the calendar this very second, so I’ll see how that goes.
  • Exercise. There’s nothing here about exercise, and honestly, I’m struggling to figure out where it can fit. I know it’s important, but I just don’t like early morning or late evening workouts and finding time during the day feels really disruptive. I’ve joined a sort-of dad’s pick-up basketball league where we play just about every Friday night from 11pm to about 2am, and my wife and I will usually do a few hours of racquetball every Sunday, so exercise isn’t completely absent from the routine. Still though, I’d like to integrate it more into work days. I think I’ll have to simply decide it’s a priority and sacrifice other things for it.
  • Better mornings and nights. I’ve recently discovered the writings of organizational psychologist Benjamin P. Hardy, who has a lot of good to say about what makes for great mornings and great nights, among other things. His advice works in recommendations about diet, sleep, screen time, prayer, showers, reading, journaling and more… all things I’d like to be more intentional about in my daily life.

As always, it’s a grand experiment. I’ve set all of these calendar slots to expire on March 31, 2017, so it’ll be a full quarter of giving this a shot. Follow me at @danmall on Twitter to see if I stick with it!

Special thanks to Emily Mall for reviewing this piece.

Originally published at superyesmore.com.



Founder & Director at @superfriendlyco. Enthralled husband and dad. Co-founder @typedia and @bizologyshow. Formerly at @bigspaceship, @happycog, and @four24.

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Dan Mall

Founder & Director at @superfriendlyco. Enthralled husband and dad. Co-founder @typedia and @bizologyshow. Formerly at @bigspaceship, @happycog, and @four24.