When Willpower and Good Intentions Fail

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Mastering Habits for Fun & Profit

The Setup

My colleague Joe gave a presentation at my employer'sinternal conference about the importance of measuring your progress towards your personal and corporate goals. He was very adamant about the importance of the OODA loop, attributing his successes to following it (whether consciously or not).

However, my own background, and anecdotesfrom others, suggest the OODA loop falls down in a very important case thatindividuals encounter every single day: when short- and long-term goals conflict. When faced with the choice of immense happiness 5 minutes from now, and possibly avoiding unhappiness 5 years from now, what's in front of you will always win.

Joe shared hisfitness story, and my own is very similar: during college I started hardcore calorie counting and monitoring my weight. I left college having lost 60lbs, reaching 163lbs - my lowest weight since middle school. It was great!But then I stopped tracking my calories/weight. I figured I knew enough to eat good portions and stay fit, and I was tired of fighting myself for every single meal.I regained all of the weight over the next couple years.

Turns out thatduring my calorie counting phase, I didn't change my unhealthy eatinghabits, I only changed how much I indulged them. I didn't give up pizza and soda and garlic bread and candy, I just limited myself to two slices and diet sodas. Consequently, when I stoppedcalorie counting, all my work was undone by eating piles of foods that fill you up quickly without giving you any worthwhile nutrients.

This incident led me to the conclusion that monitoring and measuring is only a part of success. It's crucial to know whether you're on-target towards your goals, but you'll only see lasting success when you introduce a permanent, systemic change - not merely a superficial change that's the direct result of feeling bad because of the number in your phone app.


The solution, according to what I keep reading, is to remove the need to make decisionsas often as you can; habits are key. You need to construct a system in your life where your desired outcome just falls out of your habits, without you ever having to consciously think about what you're doing, or why. That way, you're never tempted to make thewrongdecision.

The gist of habits is the Cue/Routine/Reward loop. You start with a cue (a time of day, or an event that just occurred), which triggers the habit action (eating a certain kind of food, doing a certain activity, _avoiding_a certain activity). That action leads to a specific reward, which trains your brain to keep doing the routine when encountering the cue. Positive reinforcement.

Changing cues is very difficult, but changing routines is much more feasible, as long as you understand what your reward is so you can keep getting it. Changing the routine won't work if you don't get the original reward anymore.

An example that Charles Duhigg gave was the habit of going to the corporate cafeteria andeating a cookie every day at about 2pm at work. He wanted to stop, because it was unhealthy. But why was his body doing it every day, so automatically? Did he crave the sugar rush? Was he just hungry? Did he need to stretch? Or did he like seeing his friends at the cafeteria and chatting with them?

For him to solve the problem, it was important to understand which reward was driving his behavior. Once he did that, he could replace the routine (eating a cookie) with something else that provided the same reward. If he washungry, eat a healthier snack. If he just needs a stretch, walk to somewhere besides the cafeteria.

Who You Are

One obvious objection you may raise when thinking of changing habits, is that some things are Just Who You Are. You can't stop liking that food. You can't start liking that activity. You'll never prefer salads to pizza.

Everything I read suggests that's simply not the case. In the recommended reading section, Scott Adams and Tynan both deliberately reprogrammed their tastes in food, overcoming serious lifelong cravings and habits. The trick, apparently, is something likeundergo complete withdrawal from your target food for a few months. You replace the general taste you're after (sweet, salty, etc.) with another food. Eventually, your body forgets that it ever craved the old food, and starts craving the new food. Forgoing the old food becomes easy. Scott Adams recounts never liking broccoli until deliberately cultivating a taste for it, and now he prefers it to ice cream. Tynan reports gorging on greasy foods in his youth, but now it's been out of his system for so long he finds it too disgusting to put into his mouth.

I've heard similar stories from random commenters on the Internet. So if we can reprogram desires we thought were fundamental, we can tackle any issue about ourselves that we dislike.

How? I'm still learning that myself.

Applying Habits Corporately


One example Joe gave was that in the early days of our employer, management encouraged employees to pay attention to how many transactions were run against a handful of critical software features. People got excited, and even obsessed,aboutwatching the numbers go up. To drive that obsession, management occasionally ran a contest where employees submitted predictions for what the numbers would be a few months out. The employee that came the closest, without going over, received about $100. That seriously motivated employees to pay attention to what those numbers were, and where they were going.

Joe attributed this program's positive impact on the companyto the OODA loop: getting employees to observe what direction the key business stats were headed, choose how to improve them, and do it.

While I agree that OODA made this program a success, I suggest it was the habit loop that made OODA work. The contest was a literal Skinner box - random reward for paying attention to the numbers. Without a cue-routine-reward loop, other business factors could easily overpower people's desires to monitor the transaction numbers. Employees can only become obsessive about them when they're subconsciously trained that tracking the numbers is a rewarding experience.


My previous employer, Contactology, was a bulk email sender. Think of a smaller player in the MailChimp/ConstantContact space. While working there, I learned that these companies are self-policing with regards to spam. From the outside, you wouldn't think so. You'd probably guess that they're happy to sell their 1,000,000-email-per-month plan to anyone with cash.

Turns out that email destinations (Gmail/Yahoo/Hotmail/etc.) penalize future emails from a sender if past emails were frequently marked as spam. So if Contactology sent a lot of spam, they'd find themselves unable to get_any_emails (legitimate or otherwise) into the inboxes of recipients. And that's kinda their entire business model, so it's important to get it right.

The result is these companies have a habit loop: See spammy customer -> investigate and remove -> see deliverability rates increase. The state of spam prevention inherently creates a cue/routine/reward loop that drives legitimate bulk email providers to keep spammers off their networks.


I've always been curious about what could happen if we created more systems that self-enforced desirable behavior, instead of making participants fight their natural desires. E.g., what if the government structurenaturally disincented senators from accepting large donations? Or what if it soliciting large donations naturally led to senators who were good for the people?


So yeah, that's where I am. I'm still learning to master my own habits, and to change them effectively. But everything I read indicates it's the correct approach to take. OODA driving changes to thehabit loop, and the habit loop powering OODA. One without the other will not work: habits without OODA leave you doing your existing bad things forever, while OODA without the habit loop is doomed to inaction and inattention.

Recommended Reading

  • Scott Adams,How to Fail at Everything and Still Win Big
  • The Power of Habit
  • Tynan.com-It's in there somewhere, he blogs about a lot of stuff
  • Read up on recent studies on willpower, and how it acts like a muscle - you can train it to become stronger, but using it too much too fast will drain it and leave it unable to help you at all
    • This is why habits and systems areimportant - they reduce how many things you need to save your willpower for
    • That way, rather than spending it all across 50 little things each day, you save it up for 5 big things.