Side Quests




Life ever feel like the worst video game main questline you’ve ever played? Wake up, scroll, work, scroll, work some more, get a little drunk, sleep like shit, repeat. Your life may not look exactly like what I described, and hopefully it does not, but I’m sure you can relate. Sometimes it feels like there’s one linear quest that you are on until you die.

But as anyone who has played video games knows, very often the happiest moments happen when you abandon the main quest for a while and embark on a bunch of 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 crushingly urgent until you put some distance between you and it.

Below is a running list of some side quests I’ve embarked on in life. If you make a similar list, which I’d encourage you to, I’d love to read it. Send it to me if you know me. If you don’t, share it with your friends.

Criteria: 1) The thing isn’t in the ‘main questline’ of my life, like paid work or relationships or moving to a new city, 2) it was a one-off event, not something that happens routinely, and 3) it feels unique and memorable to me in some way. They are in reverse chronological order.

  • Spent a few months learning about coffee. Now make better filter coffee / french press than I can buy in most coffee shops. And I’m writing an essay on coffee, which I’ll publish soon.
  • Made a recommendation engine that asks you a series of questions and then tells you where you should visit in Europe.
  • Walked from the southernmost point of my city to the northernmost point (~25 miles) without using a map.
  • Hiked/ran 100 miles in 3 days in the Sierra Nevada mountains, near Granada.
  • Abandoned my hostel in Switzerland because hostels kind of suck. Didn’t know what to do, so took a train to a town nearby. Wandered past a bunch of full hotels until I got to the very end. Found what became my favorite hotel in the world. Stayed there for the night.
  • Made a bet to write a book within 3 months or lose $100. Wrote a ~40,000 word novella, which I finished drafting on the night the bet ended.
  • Arrived by ferry to a quiet Croatian island. Didn’t have plans. Rented a bike and went from beach to beach on a hot day, swimming in the cool ocean and then biking and then swimming again.
  • One morning on the coast of Croatia, noticed a castle really far away on a hill. It looked cool. I spent the next 6 hours walking there. It was very cool.
  • Showed up with a friend in Andorra with limited winter clothing, no snowboarding equipment, and no idea of how to get to the resort. Were on the slopes 12 hours later.
  • Went to El Chaltén with no plans and no sleeping bag. One day I hiked up to the Paso del Cuadrado. The next morning, I got up and summited one of the peaks near my campsite by the lake, then slid down on the snow. 
  • Decided, with the boys at 2AM, that it would be a good idea to go explore some caves. Spent a few hours climbing through the most claustrophobic spaces I have ever experienced. Ended up in an ampitheater-sized cavern, just the three of us. The three of us and lots of bats.
  • Rented an inflatable raft on the Henry’s Fork of the Snake in Idaho so we could float the river and fish. None of us knew how to row. Almost lost the boat once, almost flipped the boat ~50 times.
  • Went on a road trip across the western United States with no plans and no idea where to sleep. Ended up spending lots of time in Idaho and Montana and Wyoming, sleeping in the wilderness, and showering at Planet Fitness.
  • Started a piano YouTube channel where I wrote covers and learned Adobe After Effects. Got a few million views, which was cool.
  • Learned guitar, starting with a song by Alabama and then progressing to all the other songs I liked.
  • Ran a fly fishing YouTube channel with some friends. Got recognized on the river, and off of it, more than a few times. Kind of fun.
  • Ran a travel website.
  • Ran an online fly fishing magazine.
  • Ran a weekly fly fishing report website.
  • Ran a site about Apple tech news.
  • Ran a column where I prompted my grandparents to write essays about their childhood.
  • Ran a weather blog.

I’ll keep adding to this list as I think of more. What you see above is half an hour of thinking and typing. For more side quest inspiration, the GeoWizard channel on YouTube is a good one. Jet Lag: The Game is good, too.