100 days of exercise, journaling, and habit-forming or: How I spent my 3-month vacation from work

Photo by Nik

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.

Daily Colour Schemes

An oddly satisfying habit I've picked up this summer: making a colour scheme every day with the Adobe Capture app. You can check out the colour schemes I've made at color.adobe.com.

The Highest Form of Disagreement

The Atlantic has a good read on being charitable with the people we disagree with. In a nutshell, leaving behind the straw man and weak man versions of an argument we often construct. Instead, building up a steel man version of that argument. 

It reminds me of investor Charlie Munger’s advice on “having an opinion.”

I’m not entitled to have an opinion unless I can state the arguments against my position better than the people who are in opposition. I think that I am qualified to speak only when I’ve reached that state.

—   Charlie Munger

It’s good advice.

What I learned about building habits from 30 days of exercise

As of this morning, I’ve done some sort of bodyweight exercise for 30 days straight. It’s been mostly push-ups, with some chin-up training, dips, and squats, mixing it up with lighter and heavier days so I don’t over exert myself.



I use the Todoist app to remind myself to do this (and some other fundamental things) every morning. It’s one of a very limited set of Q2 activities I have set as a top priority. After I check off the activity in Todoist I then mark the chain in a calendar using a “chain” app. There’s tons of these. I like the Your Chain! app and that’s where I grabbed the screenshot above.

What have I learned? Probably the first thing to note is that this milestone of 30 straight days of exercise — one I haven’t hit before — is the result of literal decades of failure to do something like this. So, I haven’t actually learned anything in 30 days. It’s been more like, I’ve learned a lot of things just by living, trying, failing, and trying again.

Which brings me to the second thing I’ve learned from trying to build good habits, something that seems really obvious but I don’t think it really sinks home until you face it: you can always try again. Miss a day? A week? A year? A decade? You can just try again.

When you’re trying again, start small. Like, really small. My 30 days of exercise was preceded by another month of haphazard exercise but I started small. With one push-up a day. The next day I took it to two push-ups. And so on. I knew I could do more than that but I also know that I have a tendency to want to ramp up too quickly, get hurt or discouraged, and then stop. So I started small. I missed a few days and then came back to it.

And I was lucky enough to remember why I started. Remember why you started is one of the little inspirational sayings that’ll pop up in the Your Chain! app as you progress. I’ve tried to recall it when I’m tired or rushed with other habits I’m trying to build and it’s helped me press on.

Lastly, I’ve learned that everyone is different. You have to figure out what works for you. What worked for other people in building habits hasn’t always worked for me. And what works for me might or might not work for you. One book that really takes this idea to heart is Gretchen Rubin’s Better Than Before: Mastering the Habits of Our Everyday Lives. I recommend checking it out. Also good but, in my opinion, more entertaining than informative, is The Power of Habit: Why We Do What We Do in Life and Business by Charles DuhiggRubin has read The Power of Habit so if you read Better Than Before you get the best of Duhigg’s book too. 

Good luck with whatever you’re trying to do. 🙂


The Checklist Manifesto

I’ve been catching up with Shane Parrish’s Knowledge Project Podcast recently. It’s really good. I was happy to hear his guest for February’s edition, Naval Ravikant, mention The Checklist Manifesto as an example of book with a great idea that should have been just a blog post. Why? Because it already is a blog post. Or, well, a magazine article, at least.

Check out the excellent New Yorker article that pre-dates the book: The Checklist.  I assume it was the base for the book. The gist is that checklists save lives, most dramatically with people like your doctor or nurse, and could have an impact in your own life.

In December, 2006, the Keystone Initiative published its findings in a landmark article in The New England Journal of Medicine. Within the first three months of [rolling out checklists to combat their higher than national average I.C.U. infection rates], the infection rate in Michigan’s I.C.U.s decreased by sixty-six per cent. The typical I.C.U.—including the ones at Sinai-Grace Hospital—cut its quarterly infection rate to zero. Michigan’s infection rates fell so low that its average I.C.U. outperformed ninety per cent of I.C.U.s nationwide. In the Keystone Initiative’s first eighteen months, the hospitals saved an estimated hundred and seventy-five million dollars in costs and more than fifteen hundred lives. The successes have been sustained for almost four years—all because of a stupid little checklist.

The “Golden Age” Fallacy

This is an easy fallacy to find oneself falling into: looking at the evils or wrongs of the day and thinking to yourself, “things are getting worse! It used to be better!” I think it’s especially easy to fall into if you’re a parent, or if you follow politics, or you follow the news in general, or, well, if you’re human. RationalWiki has a good explanation of it in their Good old days entry. Remember the good ol’ days? Then there’s a good chance you could be making this mistake.

“Good old days” is a term that is often used in when engaging in nostalgia, remembering only the positive aspects of times past while sweeping concomitant negatives under the rug. It has also been called the Golden Age Fallacy.

It is important to note a distinction between this fallacy and legitimate comparisons: not every positive appraisal of the past is wrongheaded, because the world really has changed. It’s just that it’s also always been complex and uneven, and no period or people have ever had a monopoly on virtue.

The empathy of Sherlock Holmes?

This older article in Aeon looks at the science of empathy with Sherlock Holmes as a guide.

The ability to see the world from another set of eyes, to experience things vicariously, at multiple levels, is training ground for such feats of imagination and reason that allow a Holmes to solve almost any crime, an Einstein to imagine a reality unlike any that we’ve experienced before (in keeping with laws unlike any we’ve come up with before), and a Picasso to make art that differs from any prior conception of what art can be.

To empathize well can be powerful stuff.

Bob Dylan’s 2016 Nobel Prize Lecture

This lecture starts out a little stiff but it takes off when Dylan begins to share his understanding of three “grammar school” texts — Moby Dick, All Quiet on the Western Front, and The Odyssey — that have influenced his work. His voice becomes almost sing song at times. A few phrases and words from his own work pop up. His rambling scattershot intertwining of his personality with this great tradition becomes like its own example of how he might see himself as an artist. Like I said, it starts out stiff but really takes off — if you’re a Dylan fan. Worth a listen.

Marcella Hazan’s The Essentials of Classic Italian Cooking

I’ve made three recipes from here so far and they’ve all been amazing. I wish I’d bought my copy new instead of used — this copy is kind of dingy — but at the same time I like that I have a battle tested edition. Looking forward to putting it to further tests.

The science of compassion

Here’s an article from 2012 in the New York Times on how compassion affects our behavior and what behaviors might make us more compassionate: Compassion Made Easy. It’s a quick read with a small trick at the end that could make you more compassionate.