What I Learned From 20 Weeks of Habit Hacking

Finding myself one-third of the way through my 2014 Habit-a-week challenge, I decided to look back and critically assess the success of my various habits. You might want to keep that link open in a new tab so that you can refer to the descriptions of each of them. This post mostly isn’t about the content of the habits, but it’ll probably be hard to read if you don’t know what I’m talking about.

  1. Lowering the Lid
  2. Straight Gait
  3. Intentional Tabbing
  4. Perspective-taking
  5. Filler Killer
  6. Befriending my Judger
  7. Pausing before responding
  8. Yes, and…
  9. Eye contact
  10. Transparency & Trust
  11. Hands Off Face
  12. Cutting Corners
  13. Pausing Distractions
  14. Pomoeditation
  15. About You
  16. Revealing Patterns
  17. TagTime
  18. Expressing Appreciation
  19. Learning & Using Names
  20. Curiosity & Model Exploration

Of the 19 habits I’ve tried so far, 7 were successes, 4 were partial successes, and 8 failed. My theory of why this happened is that the first few went well because of phenomena such as the Hawthorne Effect. Essentially, the new-ness of my challenge itself made it exciting. Also, these were habits that I’d been meaning to install for a long time, and which I was 100% on-board with thinking they made sense as default behaviours.

Then… Intentional Tabbing happened. Where the first two habits (Lowering the Lid & Straight Gait) had been easy, requiring basically just increased attention for the duration of the week… Intentional Tabbing was much harder, for several reasons, many of which apply to other failed habits. Then there were some other issues.

Reasons I failed

with how I’m addressing those reasons moving forward

Insufficient offline training

Offline training is when you practice a habit by generating triggers so that you’re prepared for when they occur and can make sure you respond with the new behaviour. I did a bit of this for Intentional Tabbing, but not nearly enough. This means that within the first day, I was just failing really hard.

From now on, I’m going to do some offline training the first day, and if it still feels hard, I’m going to do more the second day. I’m also starting to do visualization, which is like offline training but all-in-your-head.

Lack of commitment to trying

Once it wasn’t working on the first day, I basically gave up. I said something like “I guess maybe this wasn’t such a good idea… maybe I didn’t want to do this…”

What I’m going to do from now on is assess each day if I’ve kept up my habit that day, and if not, double down. If I get to the end of the week and I still feel like the habit doesn’t make sense, then I’ll ditch it. But not before. I don’t need to assume that these habits are forever if they end up not making sense, but I need to give them a fair shot for a week.

This is what I’d been intending to do in the first place, but I didn’t explicitly include an instruction to myself, “even if I have doubts, I’ll keep doing it for the whole week.” This “even if I don’t feel like it” clause is a very important component of a successful implementation intentions strategy.


This is related to the one above, but I want to underscore how insidious it can be. I think there’s a part of my brain that’s on some level addicted to my various distractiony habits. When I try to install something that has the potential to virtually eliminate those (both Intentional Tabbing and Pausing Distractions have this property) that part of my brain freaks out. It says, “What!? You can’t do this! If you do then you’ll never have any fun anymore ever!”

Now, leaving aside the fact that being productive is also fun, I think this is a legitimate concern. I think it makes sense to actually address this aversion directly, in addition to the commitment described above. This might mean something like:

  • not having to intentionally tab from 9pm to 10pm
  • not having to intentionally tab while I wear a silly hat
  • having a certain time of day or trigger (such as completing 4 pomodoros) after which I allow myself to resume my paused distractions

Vagueness & abstractness

This isn’t an issue with Intentional Tabbing—I was fairly clear with what I wanted there. Nor was it an issue with Yes, and, Eye Contact, or Hands Off Face. But with a lot of the other ones, either the trigger was hard to state explicitly, or the desired action was hard to state explicitly—or both. Which was broadly a recipe for disaster.

I don’t think that these habits would necessarily not work at all, but they’d just need more preparation, planning, and visualization-style practice, than physical behaviours like lowering the lid or eliminating filler words from my speech. So this would mean pinning down a few very specific examples of:

  • trigger
  • old response
  • new response

Classifying habits so far

The easiest habit to install

The easiest one to install was, for me, using tagti.me again. Part of what I needed to do wasn’t even so much a habit but just to get the desktop app running again. Also committing to not leaving any blank spots in my log for that first week so that I would have a sense that my data was complete.

It’s been hard to stay on top of this when I’m not in a stable routine though, because I’ll sometimes go on a walk without my phone, etc. But once I’ve got a week of perfectly-complete data, it’s a lot easier to motivate myself to fill in an entire missed day.

The biggest-impact habit

This is a hard one to name. I’ve gotten a huge amount of benefit out of Revealing Patterns. But would I recommend that to people in general? Probably not. To get to the place where I was able to do that took a lot of growth: increasing my capacity to trust the people I’m interacting with, and my ability to articulate my sense of my own patterns. And it required people I felt comfortable revealing to.

And, I think that revealing my patterns has actually achieved the underlying goals behind several of my older, less successful goals—specifically, Befriending My Judger” and Transparency & Trust. Which is to say that beyond the fact that those were quite vague, I now feel like they aren’t areas I’m lacking anymore. Three habits for the price of one!

The revealing patterns one is almost exactly what the Transparency & Trust one wanted to be, but the difference that with Revealing Patterns I actually had a concrete sense of what that would consist of and how I would do it, which I didn’t have 6 weeks prior.

The hardest habit

That would have to be Hands Off Face. Unlike most of the other ones that failed, this is one that I was actually actively trying to do for the whole week. But it was just too hard! There are so many distinct triggers that prompt face-touching that it made this generalized habit really hard. I think I might have been able to do it if I’d done a ton more of offline training or something (sprayed something smelly on my hands?) but I can’t even say that for sure.

The weirdest habit

I think that the weirdest one would be Cutting Corners. I found myself noticing a corner to cut (a typo in a personal email, for example) and feeling just like noooo, must…. fix. And I don’t even have that much in the way of perfectionistic tendencies.

What’s next?

I don’t actually know! I like to choose the habits immediately before I start them, so that they feel fresh and relevant. I have a renewed sense of commitment towards this project. I’ve had several friends tell me that this has inspired them to try microhabit hacking—including one who managed to successfully install the Intentional Tabbing habit! I’d love to hear from you in the comments if you’re doing any habit hacking 🙂 Or if you like the idea but feel like you’d need a push to get started.

If you found this thought-provoking, I invite you to subscribe:    
About Malcolm

Constantly consciously expanding the boundaries of thoughtspace and actionspace. Creator of Complice, a system for achieving your important goals.

Personal Website


Billy Graham » 3 Feb 2015 » Reply

Hi Malcom,

Thanks for posting your experiments with Habit formation. Quick question: Are you familiar with the book ‘Willpower’ by Baumeister and Tierney? It goes into the scientific study of what willpower is and how we can use it better. Some of the principles may be highly useful in your ongoing habit efforts.

Thanks, and best –

Billy G

    Malcolm » 3 Feb 2015 » Reply

    I’m familiar with a bunch of the research that has gone into Willpower, although I haven’t actually read it myself. What would you say was your biggest insight from it?

Have your say!

Have your say!


Name *

Email *