Staying on Top of Calendar Events

I’ve been participating in a Glassboard board about productivity where Eugene asked about keeping on top of calendar events. Here’s the lengthy answer Glassboard wouldn’t let me post:

This sounds like the same thing I have been through. Even though I use THE HELL out of my calendar, I get caught up in things I’m working on and then space out on the fact that I’m supposed to leave to do $THING. A good example of this is lunch time. My wife and I have lunch together most every day. But for the longest time, I would space out while working and forget to find a stopping place and leave on time. Then I would be frazzled when she reminded me over IM or SMS and I had to scramble to get there on time. This meant I was not in the best mental state when I got to lunch to fully enjoy her company. Terrible…

The first thing is to get really good at knowing how long things take. Now, I have two alarms for lunch. The first goes off 25 minutes before lunch time. When it does, I know I have 10 minutes to find a stopping place. The second one goes off 10 minutes later and that’s when I actually pack up my stuff and head to the car. This takes about 5 minutes and then it takes about 10 minutes for me to drive to lunch.

Why am I beating that scenario to death? Because it took me MONTHS to figure it out!! I’m a complete disaster. But the only way I got better at this was by paying attention and being more honest and less optimistic about how fast I can do something. “Hey, idiot, it takes you more than 10 minutes to get from sitting in a chair with your laptop open to lunch with your wife. Stop lying to yourself!” “You have never fixed any bug past a typo in less than 30 minutes!”

What does that mean to you? First, be honest with yourself about how much time you need to make those appointments happen in a sane way. Travel time between appointments. (Not just driving time. How long from sitting here to sitting there. Does it take you four minutes to get from your car to your cube? Longer? Budget the time in.) Time to gather your thoughts before and after appointments. By all means, don’t schedule meetings with no cushion between them, back-to-back phone calls, etc.

But don’t stop there. The other side of this coin is that you have to know and be honest about how long tasks take. If you finish something and look up at your clock, don’t think to yourself, “Oh, I have ten minutes. I can totally [fix that bug, reply to that email from my boss, return that phone call, google that question I had, whatever]!” Someone smart recently said that, really, assume anything you need to do will take an hour from first movement to completion. “That’s ridiculous! I’m just going to the grocery store real quick.” Oh yah? Time yourself and argue with the clock. If you find project work and client calls or ad hoc meetings are usurping your time, the time to recognize that is when someone says, “Hey, do you have a minute?” Or when the phone rings. If you answer the phone in a small interstitial chunk between appointments, don’t be surprised that you get wrapped up in that conversation and flaunt the tyranny of the calendar. Let it go to voicemail or tell the person to come back later or ask the question over email so you can give it quality time and consideration. And as I’ve heard Merlin say more than once: Not in a dick way. Let clients know that you can’t provide the highest service on an interrupt-driven basis. And be honest with yourself that you can’t do your best project work when your brain is somewhere worrying about what appointment you’re about to space and you can’t do any meaningful project work in between those calendar appointments. If you think half an hour you squeeze out between appointments to work on a project that’s ostensibly important to you is a good strategy, you’re totally fooling yourself.

If it sounds like I’m mad, it’s because I’m mad more at me than anything. I am a total dipshit about this kind of stuff. These are the lessons I have had to learn through much trial and error, so hopefully I can shed some light on things if you’re in a boat even remotely similar to mine, and it sounds to me like you are.