Welcome to another installment of “Monday Routines,” in which software people like you recount their Monday rituals. The goal is to peer into their day-to-day patterns and habits as they lead teams, collaborate, and deliver great software. Hopefully you’ll discover a tidbit or two to help you with your routine.
STARTING ON SUNDAY Every Sunday night before bed, I write out 3-5 big things I want to get done at work that week. Before bed every other night of the week, I write out the 1-2 things I need to accomplish the next day.
This routine has helped me sleep better because I’m not thinking about what I have to do. Once the next day’s thoughts are out, I can put them away and know they’ll be there when I get up in the morning.
CROSSFIT FOR REGULAR PEOPLE I get up at 6AM. My whole schedule is aligned around getting to the gym in the morning. It started when my wife and I first began dating. She wanted to hang out but didn’t want to wait until 8PM to eat because I was at the gym late. I finally made the grown-up decision to get up and go early. Nobody wants your time at 6AM.
We live in Coolidge Corner in Brookline, Mass. I take the T for 20 minutes to my gym in downtown Boston and then head over to Cambridge for work. I’ve been going to this gym for a while and I love it so I stick with it, even though it’s out of the way. I do “Crossfit for regular people.” I’ve worked out my entire life and was the biggest anti-Crossfit person ever, but now I love it. I don’t want to compete in anything. I just want to be in good shape, look decent shirtless, and not hurt myself. Those are my goals. I’m just always so damn sore. It’s a constant battle with soreness.
THE NOTEBOOK I try not to make my phone a big part of my morning. Having a notebook to scribble things in keeps me from pulling out my phone, trying to find an email. Now I just write things down. It’s made such a difference.
Over the last year I’ve also been trying to read more, so I aim for 10-20 minutes in the morning. I use my 20 minutes on the T to read and write my notes. Everywhere I go, I bring my Kindle and my little notebook.
STUDYING THE OLD SCHOOL I’ve recently read Ogilvy on Advertising, Scientific Advertising, and The Boron Letters. I’ve been trying to study all of the old-school great copywriters and direct marketers because those guys really had to put thought into what they were doing. They had to get people to buy based on something you had to mail back. Digging into this material has been amazing and so much fun. So those are my Monday AM books.
MEETING-FREE MORNINGS By the time I get into the office, I’ve already got a workout in and am mentally prepared for what I’m going to do that day and that week. Obviously that all changes on the fly because we’re an early-stage company. What I think is the plan can completely change by 9:30AM.
But I have this luxury: I don’t book any meetings until after lunch. Every day. Instead I reserve the time from when I arrive until lunch for the day’s Most Important Thing. I’m in marketing, so for me that’s usually writing, whether it’s copy for the website, an article, or anything like that.
Doing those bigger projects upfront always makes me feel better. It’s how I feel accomplished. So I line up a big thing for Monday morning. Then I have the rest of the week to triage the smaller stuff.
I have quick one-on-ones with the three people who report to me on Monday afternoons. That way everyone can be on the same page and have a productive week.
THE GREEKS I’ll usually grab lunch with somebody at work. David Cancel and I usually go to this little Greek place called Desfina. It’s one of the best lunch places in the area and we’ll get a Greek salad with grilled chicken. If you’ve ever seen The Wire, “The Greek” has his restaurant; that’s kind of what this place feels like.
AFTERNOON RECALIBRATION Monday afternoon I re-calibrate the rest of the week. I turn to dealing with email—which I’ll have been looking at all day, just not responding, mostly—and whatever needs my attention on Slack. I pick off some of the smaller tasks.
Then I see how much of my plan for the week still makes sense and what else I should work on.
PUTTING WORK AWAY I usually leave the office around 6:30PM. I hop back on the T and ideally get some good reading in. I try to convince myself that I’ve been on the computer for 10 hours and don’t need to be back on Slack for the 30-minute T ride, but it’s hard. By this time my wife is usually texting so we can coordinate dinner. I get home around 7:30 and try to put work away. I get Slack messages all day and night but try to just read them and jot something down in my notebook if I need to deal with it tomorrow.
DEBRIEF At bed I do a little debrief of the day since I’m super Type A and I’ll be thinking about to-dos all night if I don’t. I write down the 1-2 things I want to accomplish the next day. I look at Instagram on my phone. My wife and I read for 20 minutes or so. I’m not a big fiction reader but can’t read about marketing before bed; I don’t want to be lying awake with my mind racing with ideas for ad copy. So I’ve been reading a lot of sports books and biographies.
I try to get in bed between 9:30 and 10:30. In reality I’m not as good as I sound but I have the right system in place. That’s what keeps me going.