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The Friends Game: A System For Thriving As An Introvert

I’m an extremely introverted person. Left to my own devices, I prefer to spend most of my time alone, working on things I find interesting or important.

That doesn’t mean I don’t enjoy having a tapestry of friends or going out to busy places. These are things I like to do every so often. I even like organizing big parties on the rare occasions I can muster the energy for it.

But being an outgoing socialite is not my natural state. Nine times out of ten, if you ask me what I’d like to do, my answer will be to stay home and play a game. Or maybe go out for a quiet cup of tea with one or two friends.

My natural, happy state is to keep to myself. I have a rich and very rewarding inner-life. I can sit alone and just think about stuff for hours.

  • Why is the sky blue? Let’s look it up on Wikipedia!
  • How many different types of plants can I name in 10 minutes?
  • What can I do to improve my solo workout routine? Let’s learn about how muscles work…

Truly random things. And that makes me happy!

Yet, I realize part of becoming the smartest Riskologist I can is to make an effort to foster relationships. The more great people I have in my corner, the more inspired I am in my work. The more driven I am to improve myself. And the more resources I have to solve difficult problems or do big things I couldn’t do on my own.

But this does not come naturally for me.

A while ago, I decided to try an experiment by creating a simple system that would help me keep up with my friends by giving me a template to work from.

I resisted the idea for a long time because—like a true introvert—I tend to despise anything that even begins to resemble an unnatural approach to relationships. Setting a calendar reminder to “call Nana” would make me feel like a failure. Like I needed some crutch to do something that should just come naturally.

But this was a limiting belief. And I realized just how limiting it was when I gave in just a bit and allowed myself to test a system that helped me connect with my friends and relatives more regularly.

I’ve had better relationships with friends this year than I’ve had my entire adult life. I’m happier and healthier. And now I love my little system. I call it “The Friends Game.”

Here’s how it works. I hope you find it useful.

The Friends Game: A System For Managing Your Introversion

Earlier this year, I showed how anyone can use a service called Trello to manage the risky projects in their life. It’s my preferred to do list app (and I love to to do lists).

Because Trello is so flexible, I found a way to use it not just to aid me in keeping in touch with friends, but to gamify the process so it’s fun and motivating to keep up with.

Here’s how I do it. You can easily create a system that works just the same.

First, Create A New Trello Board

Trello lets you set up an infinite number of “boards” which, for most people, are synonymous with “projects.”

Give your board a fun name—something that’ll actually make you want to look at it. Sounds silly, but this is a real psychological hack I use to keep myself interested in things. If you’re not having fun, you’re not going to keep using it.


Set Up Your Board For A Monthly Check In

When you start a new board, it’s automatically populated with three lists: To Do, Doing, and Done. Go ahead and delete/archive these. We’re not going to use them.

Next, set up 12 new lists, and name each one by month.


Set Up Your List Of Friends

Finally, add a card to January (or whatever month you’re starting in) for each person you want to keep in touch with.


Now, It’s Time To Play The Friends Game…

Now, the fun starts. Your list is set up, and the goal is to see how many people you can advance, each month, into the current month.

When you get in touch with someone from your list, move them into the current month.

As an added reminder to myself, I like to leave a little note on the person’s card each time I have a great conversation with them.


By the end of the year, you have a nice little record of all the important stuff that’s happened to each person over the last 12 months. Maybe send them a Christmas card telling them how proud you are of everything they accomplished?

In a perfect world, you’d move everyone into the current month every single month. But let’s be realistic. You and me? We’re introverts. And we ain’t perfect. So, after a few months, our list starts to look more like this:


Without this system, we either don’t think about the people we haven’t connected with in awhile at all, or we think about it, feel guilty, and tell ourselves, “It’s been so long. I can’t email them now; it would seem weird.”

The result is the same: our friend drifts further and further away.

But thanks to the game aspect of this system, it’s a lot easier to tell yourself, “No! I have to move them out of February and into May!”

Introverts: You Need A System

When you’re incredibly introverted like I am, keeping in touch with good people you want relationships with does not come naturally.

But that’s okay; there’s nothing wrong with you. You’re amazing for a lot of other reasons.

And if you want to be amazing at building relationships too, you can be. You just need a system that’s fun and easy to follow. Whether you use the one I just described or create your own, here’s to building meaningful relationships with more amazing people.

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