Ian Daniel Stewart

Many of my friends and family know this already but for the past three months I’ve been on vacation from work. Everyone that works at Automattic (What’s that? You’ve probably heard of our biggest project, WordPress.com) can take a 2-3 month vacation, or sabbatical, every five years. That’s a lot of time to take off work! I haven’t had that much time off since I was four or five. “What are you going to do with all that time off?” One thing you could do with some time off like that is try and make some changes in how you live your life. One of the best ways to do that is through habit-forming.

You’re probably most familiar with how important habits are in their bad form. The things we all do that we can’t help doing. Things like procrastinating or always interrupting people or even addictions like gambling. A good habit being something like always saying “please” and “thank you” or exercising. Both types compound. The bad ones are easy to form and are destructive, eating away at every part of your life to some degree more or less. The good ones are hard to form and improve every part of your life.  Some habits are foundational, or keystone, habits. These have the greatest chance to compound and have the greatest reach into every part of your life. Procrastination is a good example of a negative keystone habit. Exercise is commonly cited as a positive keystone habit. (For a good introduction I recommend The Power of Habit and Better Than Before.)

So with all this time off I figured, “what the heck, I’m going to try and build as many positive habits as I can and see if I can reshape my life in a really rewarding way.” Or something like that.

First, I’ll get some math out of the way for the careful reader who has noted that 100 days is more days than there are in three months. I started this project before my 3-month vacation. This was probably the smartest thing I did and is the biggest “secret” for building good habits: you can start anytime. I started with one push-up one day in May. I didn’t wait for a special event like a holiday or the start of the week or the right time. I just started doing a small thing where I wasn’t doing something before. I also learned this from my colleague Lance when he told me, after finishing his sabbatical, that he started doing things he could have started doing at anytime. He didn’t need to wait.

To start things off, I spent some time thinking about where I wanted to be 1, 5, and 10 years from now. Conversely, and just as important, I spent some time thinking about where I didn’t want to be. I wanted to figure what activities were going to get me to where I wanted to be and keep away from where I didn’t want to be. This wasn’t really elaborate. I just wrote some rough notes down in the spirit of “something is better than nothing.” I also looked at various people I know and picked out qualities I admire in them. (Attention everyone I know: you’re all doing something I admire.)

With this list of activities and qualities in hand I tried to pull out some key daily activities and processes that were good in themselves and were likely to reach out and improve other things. What are the keystone habits I think I need to live a good life that is always getting better, however I believe that should be defined? (As opposed to always getting worse or even stuck in neutral.)

Exercise is one keystone habit for me. I’ve written before about achieving 30 days of regular exercise. As of yesterday I’ve hit a 100 day streak of daily exercise and I’m hopeful that I’ve baked that habit in. I realized just this morning I can no longer joke about being a person who doesn’t exercise.

Here’s one cool result: on June 19 I put together a chin-up bar in my basement and did exactly 0 chin-ups. That was my best effort: nothing. Zero chin-ups. I couldn’t even lift myself up. A month later on July 19 I did 1 full chin-up around 10:45 in the morning. After lunch that day I was able to do two if you count craning your neck to get your chin to touch the bar. About an hour and a half later I was able to squeeze the bar as hard as I could and pulled out two chin-ups. A month after that on August 19 I was able to do 4 chin-ups. Here’s what I wrote in my Journal that morning.

4 chin-ups! Today was the day!!

And then a few hours later:

Knocked out two more chin-ups for good measure!

I’m able to share those anecdotes because of the other keystone habit I’ve been working on: Journaling. I write in a digital Journal everyday, throughout the whole day (That’s how I know the time of day I’m writing, via a timestamp) but usually just in the morning to record my exercise progress and then later on in the evening.

What else do I write about? I use Todoist to deliver a custom set of daily, weekly, and monthly questions to me. These are journal prompts and challenges, in the form of questions, that I’ve pulled from various sources but primarily from thinking errors defined in Cognitive Behavioural Therapy, common mental models and human biases, common logical fallacies, and Richard Wiseman’s Emergency Happiness Diary. (Who couldn’t stand to be a bit happier more regularly?)

My idea here was to do something like mental exercise. “If I can exercise my body to improve my physical health, why can’t I do the same thing to improve my mental health?” I figured it would look like this: spend some time every day trying to figure out all the different ways your bad habits, instincts, and too-quick-for-some-situation System 1 Thinking got you into some sort of trouble recently. Thus the journal driven by a custom series of journal prompts.

Basically, I’m trying to figure out where I was systematically stupid every day so I’m less stupid more often.

Some time in early June, after I’d figured out that writing in a journal was likely going to be a keystone habit for me, a friend on Facebook shared an article about rope-free climber Alex Honnold. In about four hours on June 3, 2017 he climbed the 3,000 feet of El Capitan without any ropes or safety gear. “What may be the greatest feat of pure rock climbing in the history of the sport” and “the ‘moon landing’ of free soloing.”

How’d he do it? Well, he trained. A lot. And he also kept a journal.

Some of his poise can be attributed to his detailed preparation. He is obsessive about his training, which includes hour-long sessions every other day hanging by his fingertips and doing one- and two-armed pullups on a specially-made apparatus that he bolted into the doorway of his van. He also spends hours perfecting, rehearsing, and memorizing exact sequences of hand and foot placements for every key pitch. He is an inveterate note-taker, logging his workouts and evaluating his performance on every climb in a detailed journal.

I started to wonder what could happen if someone prepared for the ups and downs of life like Alex Honnold prepared for his dangerous climbs. I was already logging my exercise and using that to make progress and adjust goals. And in a way I was logging my efforts to think and act more correctly. Could I review that? The answer was, “probably,” so I made up a daily, weekly, and monthly form and started reviewing my progress in my journal.

Yes, I’ve been filling out a regular self-review form on my summer vacation.

It’s probably unusual but I think that activity in itself is a keystone habit. It’s helped me refine my personal goals on the fly and add continually, to an ever-growing list of daily, weekly, and monthly habits. Habits I’ve been sticking to!

An example: It’s where my recent habit of collecting colour schemes came from. One day while examining some stress I have around my abilities as a designer I started thinking about what parts of that role I felt weak in. One of those weaknesses (there are a whole bunch) is that I’ve always felt I was lacking in my use of colour to create a harmonious design. During my weekly review I literally ask myself if there are any cool ideas or hacks I could implement to correct some of the issues that popped up during the week. One Friday (the day I do my review, on a natural end of the “working” part of the week for me) I realized I could start making daily colour schemes to try and correct this. It’s a small easy to accomplish habit and it’s fun. Better yet, I’ve created 63 colour schemes and now find myself thinking about the use of colour more as I go about my day. That one example may not be a lot but — and I think this is really important — it’s better than nothing. Nothing was literally what I was doing before to improve that.

So, that’s it. I’ve done a whole bunch of other things over the summer too like go on family vacations, read, and just plain take it easy. But I’ve also tried to build up some keystone habits and I’m glad I did. Give it a shot, maybe with something small. You might be surprised at what you could get up to in a 100 days.