The 8-Week Habit Challenge

I have the self-control of a tiger at a bunny convention.

I try to pretend otherwise, and in some instances manage to succeed, but the fact remains: I don’t spend nearly enough of my time and energy on the areas of my life that I deem important.

The time has come for a change. And I need your help.

Rather than try and magically increase my self-control, I will be trying to take willpower out of the picture entirely by instilling within myself a series of productive habits. Research has shown that the best way to successfully train a new habit is to use either external incentives (e.g. financial) or social accountability. I plan on using both.

Keystone Habits

There once was a fat man named Melvin. For years, Melvin had tried everything he could think of to lose weight. His friends watched as he cycled through fad diet after fad diet—vegetarian, pescetarian, Dukan, Atkins, Flintstones, Crazy Chicken—he would stick with one for a few weeks, lose a few pounds, get tired of it, and gain all the weight back. Every New Year’s he would sign up for a gym membership, always on the lookout for that extra perk that might successfully keep him coming back. But no matter how excellent the towel-service, by mid-February Melvin was nowhere to be seen.

One day Melvin decided to try something different: he would start keeping a food journal. Rather than specifically restricting what he ate, he would eat whatever he wanted but make sure to write it down. Each night, he would read over his food intake for the day.

Soon something magical began to happen: Melvin began to lose weight.

Instead of being restricted by some externally imposed, arbitrary set of rules, Melvin was now thinking for himself. Each time he was about to reach for a snack, or order that extra Diet Coke with his meal, he thought about having to write it down and was able to stop himself. The constant health-awareness even began to extend itself to his fitness activities. The small decisions like taking the stairs instead of the elevator began to add up.

For Melvin, this food journaling turned out to be what is known as a keystone habit. A single important habit from which a cascade of others easily follow. Identifying these types of habits is one of the most important parts of making major life changes.

My 3 stickK’ing Keystones

In my article about habit formation I mentioned two apps that I found to be quite useful: and stickK. The former is great for easy check-ins with large numbers of habits or for hiring a coach, and the latter allows for more social interaction via Referees and Supporters as well as the capability to add in a financial incentive. I have decided to use both—stickK for my keystone habits and for the rest.

Soon I’ll write a post talking about my overall self-improvement plan and all of the habits that will entail, but right now I want to limit the focus to three (hopefully) keystone habits:

  1. Meditate 10 minutes per day — I’ve been listening to The Tim Ferris Show for quite a while now, where he interviews the world’s top performers (CEO’s, pro athletes, best selling authors, etc). One of the most common similarities that these people have across the board is a regular meditation practice. Meditation is something that I’ve been doing off and on for a while now, but everything I’ve read about it states that after the first 10-15 days of constant practice there is a qualitative change that has far-reaching effects. I have yet to reach that point, but I plan on doing so by two weeks from today.
  2. Work 1 hour before noon — Once I’m in the groove, I can go on working for hours. It’s getting started that I have serious problems with. I know that a single hour doesn’t sound like much, but the point here is consistency + achievability. This habit is designed to get the ball rolling each day.
  3. Blog 3 times per week — And now we get to the whole point of this post: external culpability. I will be blogging primarily about my various adventures on the quest for self improvement, shorter pieces about things that I have learned and find fascinating, and occasionally some bits about my musings on life. By sharing it with all of you I hope to be able to both organize my thoughts better and to force myself to apply everything I learn to my daily life (and help you all do the same).

My Challenge to You

I have signed each of these habits up on stickK, complete with a $5/week penalty that gets donated to an anti-charity if I don’t check in. As of right now I have $200 on the line—the problem is that money by itself has never been much of a motivator for me.

Instead, I want motivation through social pressure and group-accountability.

Do you have some aspect of your life that you’ve been meaning to work on? Something you keep trying to change but haven’t quite managed to do so?

Now’s your chance.

Sign up for, make at least one commitment (it’s best not to try too many at once), and add me as a friend. You can use the above three links to join as a supporter for my habits, and I will do the same for yours. If you want I can even be your referee. To increase your number of supporters, comment on this post with your username / link and everyone else can join you as well.

Each week you will be required to check in and report on your progress (or miss it and get fined).

Who’s with me?

Traveling Alone: The Crazy Stranger Challenge

Monkey Me
Making friends is easy!

Traveling alone is awesome.

Traveling alone sucks.

I plan on writing a more detailed overview of my experiences as a solo traveler when I finish my trip, but for now I wanted to share a quick thought that I had today and then to ask you all for some help.

Feel free to read the background thoughts or just skip to the bottom for the challenge.

Approach Anxiety

We’ve all been in situation where, for whatever reason, we want to talk to a stranger. They could be some attractive member of the opposite sex, a celebrity you see on the street, or just someone who you find interesting for whatever reason.

We want to go over and talk to them, but it’s difficult.

The degree to which this is the case varies based on the person- e.g. introverts might have a harder time with it than extroverts (although that’s a totally different can of worms that I won’t get into right now- shyness and introversion have been shown to be fairly disparate), but almost everyone has this feeling to some extent.

But what is this feeling exactly? Why is the simple act of talking to someone difficult? Isn’t it something we do every day?

I would posit that this anxiety is really just the fear of being judged. We want to go over and talk to them, but what will they think of us? Will they think it’s strange? Will they think I’M strange?

There are three main workarounds that I have found for this problem.

  1. The hard way: change yourself. Keep telling yourself (perhaps in the 3rd person) that the world won’t end if you go and talk to someone, and maybe you’ll start to believe it. Or at least you will after enough practice. I’ve been working on this for years but still have a ways to go.
  2. The easy way #1: do something to artificially ensure that they won’t think you strange.
  3. The easy way #2: do something to yourself to artificially ensure that you won’t care if/when they do.

The latter two are the ones that I want to focus on right now.

The second can be accomplished by putting yourself in situations where starting a conversation would seem totally normal. This is how something like speed-dating works: they are able to mostly eliminate approach anxiety by imposing a setting where you are required to talk to someone, so at least the act of you starting a conversation won’t be judged (what you say is of course a different matter).

One way that I have found this method be applicable while traveling is in the difference between meeting someone during the day vs at night.

If I happen to be staying one bed over from someone at a hostel or sitting next to them on a bus, it’s quite natural to start up a conversation. Hostels tend to be very friendly environments where everyone is open to meeting people. If I have to sit next to someone for an extended ride then saying a few initial words is just polite.

Now fast-forward a few hours. I’m now at a bar by myself. Like a creeper™. Suddenly that same girl who would have been totally friendly when chatting back at the hostel will think I’m weird if I just come over and just start talking to her at her table (or at least my instinct is to assume that to be the case).

Thankfully I’ve so far been able to avoid the above situation by just making friends during the day or arranging to meet people at night, but not every day can be a winner.

This brings me to Method #3.

The easiest example of this method the Costume Phenomena. Put yourself into a crazy enough outfit and suddenly it’s not you that they’re judging anymore.

Everyone wants to talk to a gorilla:


Even for less full-coverage costumes where your face is visible, you can still effectively hide behind the alternate persona.

But while this method is loads of fun, it’s hard to really apply in too many different situations.

Instead, a lesser version of this method involves changing not other people’s perspective of you, but your own perspective of the interaction. When someone dares you to go and high-five a stranger, you may feel a bit nervous, but it’s not too bad because at least YOU know why you’re approaching them. It’s someone else’s fault. Any judgement should really apply to them.

This finally leads me to the real point of this post.

The Stranger Challenge

I’ve started to play little games with myself both to give me an added kick to go meet people and just to make the interactions more hilarious.

Last week I played the accent game for a few days. One night I successfully convinced two Irish girls that I grew up in Dublin, but they were able to guess that something was off and that really I also had one parent who was British. The next day I kept it up and thoroughly confused a newlywed couple at Chabbad visiting from Canada.

I have plenty more ideas for things to do that are successively more crazy, but I think it would be way more fun if the challenges were actually externally imposed. I am therefore throwing down the gauntlet to all of you: post a comment(s) with some type of challenge for me to do involving strangers, and up/downvote other peoples’ suggestions. I’ll see how many of them I can manage to do over the next week.

Let the craziness commence!