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Do More Side Quests 


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One weird fact about our world is that there is a whole genre of video games in which you simply follow monotonous routines for hours on end. Literally, work simulators. You drive a truck, or drive a tractor, or drive a taxi, or work a desk job, or work at an immigration border. Wake up, do the same thing over and over again, repeat. The days blend into weeks blend into months, and then you’ve beat the game. And you move onto the next one.

Life feels like that sometimes too: routine, monotony, a linear questline to the finish.

But when the game of life finishes there are no other games to play, no catalog of fake job simulators for you to choose from. It’s done. And so if we are going to compare life to a video game, it should hopefully be the best one you’ve ever played.

There is some exciting upside here. Unlike most video games, the world that surrounds your life is extremely malleable. More so than you think. You can go read all the complicated essays about agency and taking your life into your own hands, but their core point is simple: just do things. Creative, ambitious, difficult, fulfilling ones. One of the best ways to do this — and to make your life more enjoyable and fulfilling — is to do what we’re going to call side quests.

The rest of this essay is about defining side quests, then helping you brainstorm some of your own. Some examples of what we mean by side quests (which are different from hobbies):

  • Host an Olympic games for you and your friends.
  • Move to a beach for a month.
  • Build the crazy website and/or tool you want. If you can’t code, learn (and use AI).
  • Walk across your city’s entire metro area without a map. 

Why side quests? Anyone who’s played video games knows that very often the best parts happen when you abandon the main quest and go on adventures. This is true in real life too, and you probably have more room for side quests than you think. The main questline always feels so urgent until you put some distance between you and it. So here are some thoughts on departing from the main questline for a while.

Why side quests are not hobbies


An essay like this runs the risk of being obvious; of making something simple more complicated. You already do non-work things that you enjoy, so aren’t you already doing side quests? The answer is maybe not — and the criteria below explain why.

A good side quest is all of the following:

  • Sufficiently ambitious and/or hard
  • Memorable
  • Something that can be done alongside your normal life
  • Complete-able or done over a fixed period of time
  • Bonus points for the side quest being kind of insane

These criteria are important because they distinguish side quests from your hobbies. It’s great if you really like fishing or going to the movies or spending time with your friends, but those are not side quests — they are hobbies. In the same way, a standard vacation is not a side quest either. A side quest may lead you to discover a hobby or it may be the reason you book a trip, but these things are not side quests on their own.

Look at it with this lens, and our best guess is that not that many people are really doing side quests. If you want to do some, look at the criteria above and think. Or look at the list below for inspiration.

A few examples of good side quests


The hardest part about side quests is legitimizing them in your own mind — being okay with spending a bunch of time on things that are not directly related to you making money, or getting into a relationship, or somehow furthering your life’s main questline.

  • Write a book in 3 months. Or 2, or 1.
  • Travel somewhere new. Find something cool-looking in the distance. Walk there.
  • Start a blog for at least 90 days. Publish 1,000 words a day.
  • Book a trip without making any plans in advance. See what happens.
  • Go a whole week without telling people what you’ve done.
  • Run a marathon. Never really run? Run a half marathon. Then a marathon.
  • Race rickshaws across Sri Lanka (or similar).
  • Make plans for a trip, then ditch them and do something else.
  • Hike a very tall mountain.
  • Try talking to strangers for a month. See what it’s like.
  • Wear brighter colors. Or wear all black.
  • Master cooking caramelized onions.
  • Record a video of you and your family (or use Legacy).
  • Get outrageously good at something, like typing or backgammon.

This essay exists because, a few months ago, we wrote down our own favorite side quests that we have done so far in life. It’s a fun exercise all on its own: if you’ve done a lot you can look back on all the memories you’ve made, and if you find yourself struggling to think of items for the list then it’s a good sign to get out there and start doing things.

After writing our own lists we thought it would be fun to write about the concept in general, and to encourage you to make your own list. Start by writing what you’ve done so far, then brainstorm for the future. And have fun playing the game of life.

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