Why I Stopped Letting My Calendar Run My Life

Anatomy of a failed productivity experiment

I used to play my calendar like a game of Tetris. I would stack obligation after obligation for every minute of my waking life. Go to the gym, then work on this, then meet with that person, then meet my friend and so on.

My thinking was, if it’s in my calendar, I’ll do it. However, there were two major flaws in my strategy. First off, it usually didn’t work. I would often not do what my calendar told me I was supposed to be doing. This contributed to feeling like a failure on an almost daily basis, which only further hurt my productivity. Secondly, doing things simply because they were in my calendar was actually hurting my total output.

In this article, I share why I stopped using my calendar to manage all my time and what I do now to make sure I’m executing on the highest impact activities.

Do the right things

At one point in my calendar stacking phase, I had blocked off thirty minutes every morning to go on Twitter to network with people in my industry. I needed to put that in my calendar because I wouldn’t have done it otherwise. But the reason why I wouldn’t have done it was because it wasn’t the best use of my time. There were higher ROI activities that I should have been doing instead of browsing Twitter.

My calendar became a laundry list nice-to-dos rather than best-to-dos. My best-to-dos get done because there is a clear incentive for doing so. I don’t need my calendar to remind me to do important things like my job, writing, spending time with my girlfriend or exercising.

I started to recognize that the need to put something in my calendar in order to do it was actually an indication that it wasn’t very important. Spending more time networking on Twitter would have been nice, but things like exercising, doing my job, reading and writing were far more important.

Seize new opportunities

As the rate of innovation increases, the best strategy today can become counterproductive tomorrow. In this fast moving world, new opportunities can present themselves without prior notice. I make sure I have time in my schedule to seize these opportunities.

About a year ago, after I had kicked my calendar addiction, Amazon’s self-publishing team called me on a Tuesday afternoon and asked me to do a video shoot with one of my favorite writers, James Altucher, on Wednesday morning. I said “yes”, enthusiastically. This turned about to be an incredible opportunity for me to meet James and people at Amazon. Had I been glued to my calendar, I could not have seized this opportunity.

I also value having unstructured time for trying new things. Some of the things in my life that I’m most proud of have come as a result of experimentation. Writing started off as an experiment. I wrote a couple blog posts on a wim without any goal or expected outcome other than the experience itself. Giving myself this space to explore has lead me to making thousands of dollars per month from my writing.

Energy management

Time of day is a fairly useless criteria for determining what to work on. Simply because the clock says 9AM and your calendar says to do X at 9AM does not necessarily mean it’s best to do X. We all have deadlines, of course, however, by my matching my work to my headspace, I’ve increased my productivity over the long-term.

When I was scheduling every second of my day, I would find myself “in the zone” on something like writing, until I would get a notification on my phone that I needed to switch tasks. Because I was feeling energized, motivated, focused and creative, I was getting great work done, but my calendar told me to switch to something that required a different headspace, such as emails.

I know it may seem like certain things need to get done at a certain time. However, after experiencing periods where it seemed like I was scrambling to meet deadlines all day everyday, I now recognize that it’s often because I’ve either overcommitted myself or am not effectively managing my work (or both). Blocking off stuff in my calendar was just a band aid that didn’t address the underlying root cause.

Building a stronger system

Letting my calendar be my master put me on auto-pilot. Not needing to make decisions about what to work on can be great for some things in some situations. However, deciding what to do with your time is one of the most important decisions someone can make. Therefore, I prefer to make conscious choices about the best way to spend my time at any given moment.

Breaking my calendar stacking habit has also given me more discipline in what I committee myself to and made me more conscious of how I’m managing my system as a whole. Instead of adding band-aids that can help me eek out an extra ounce of productivity in the short term, I’m creating a system where I can stay productive for decades on end.