Start With a Full Calendar

I just love an empty calendar. It promises something valuable and rare: Time. Time to think, to work, to do whatever the hell you want.

But for most people, empty calendars aren’t realistic. And that includes me.

My calendar often looks like a minefield. A 15-minute “quick chat” explodes, destroying Tuesday afternoon. I agree to present at a local conference at 11 a.m. on Thursday — hey, at least I’ll have the afternoon free — but forget that public speaking sucks up all my energy. Our regular team meeting is every Monday, which means that all I’m doing every Monday is attending our regular team meeting.

I enjoyed a meeting-free stretch last year while we wrote Sprint, but that’s not normal. No… most weeks I have to fight and scrape and resort to dorky tricks to regain control of my time.

My favorite trick is to Start With a Full Calendar. Fill your calendar with activities that matter to you, before others can fill it for you.

I learned this trick from Graham Jenkin, the COO at AngelList.

In 2007 and 2008, Graham was my boss at Google. He managed something like twenty people, and he gave each of us personal attention and true support. I learned a lot from Graham in those years.

But Graham wasn’t just a great manager. He also led the redesign of AdWords, Google’s flagship advertising product. While managing us, he was designing user interfaces, testing with customers, reviewing specifications, and negotiating with engineering. I often wondered where he found the time, but assumed he was just really busy. I was wrong.

One day I was trying to schedule a meeting with Graham, so I clicked on his name in Google Calendar and overlaid his schedule on mine.

It was the typical calendar of a corporate manager. Each day was packed with meetings: short events with names like “Graham Alex 1:1” and “Sync on AW3”; longer stretches for “Ads Product Review” or “Promotion Committee”; and the occasional multi-day block for “Managers Offsite” or even “Vacation.”

But there was something unusual about Graham’s calendar.

A solid block of color across the top of the screen caught my attention. From 7–11 a.m. each day, Graham had scheduled time with himself. It was labeled“Do not schedule / Morning routine.”

I asked him about it.

“That’s my time. I wake up early, get to the office early, hit the gym, grab breakfast, then work for a couple hours before my meetings begin,” Graham said.

“Don’t people schedule over it?” I asked.

“Sometimes they try, but I just tell them I’ve already got plans.”

(Update: Joe Tullio found a 2010 blog post where Graham describes his calendar in a lot more detail.)

Ten years later, I still use Graham’s trick.

In fact, I copied his “morning routine” bit almost word-for-word. Every day, I wake up early (5:30 or 5:45 a.m.) to exercise and write for two hours.

When I’m working on a big project, I schedule time with myself. Time for writing, editing, research, and the occasional bout of web development (although I haven’t updated my coding skills since Graham was my manager).

Sprints give teams an excuse to schedule time together. It’s not a meeting, per se, or an offsite (although you will bond with your colleagues). But it’s the same idea: fill your calendar with important teamwork before others can fill it for you.

I picked up a few tips along the way:

• Play offense, not defense. Don’t fill your calendar with “do not schedule” blocks just because it’s empty. Be strategic and purposeful with your time — schedule important projects and activities that you want to make time for.
• Don’t be greedy. Resist the urge to gobble up every scrap of unscheduled time. It’s good to leave space for opportunities, and your team will appreciate your availability.
• Be serious. When you schedule time for something important, be serious about protecting it. Learn from Graham and tell people you already have plans.

I’d love to be like Jason Fried, the CEO of Basecamp, whose calendar is as empty and still as a country pond at sunrise. (Seriously, I feel more calm just looking at it.)

And having glimpsed the power and beauty of an empty calendar in my own life, I’m searching for a way to re-create those circumstances.

But until then, I’ll just have to keep a full calendar.