This past year, I found myself sneaking into a freight train yard with a libertarian one morning at sunrise. I also found myself camped on impossibly remote alpine peaks scattered across British Columbia and Alaska that were so beautiful they would each have a national park dedicated to them in the continental US. I dealt head-on with the type of bureaucracy that I otherwise habitually avoid. I spent a long month taking care of dogs. I consumed enough psilocybin in one dose to know that I don't need to take any more. I waded into the strange and occasionally shady world of totaled vehicle auctions, and bought a wrecked Tesla from a car graveyard in Cleveland that ended up almost burning down my friend's garage.

These are all things that I almost certainly wouldn't have done by default. Some of them I really actively didn't want to do. But I found myself doing these things because at the end of the 2022, I had six friends staying with me from out of town. On the last day of the year, we started considering the year to come — but instead of going through the usual motions of making New Year's resolutions for ourselves, we decided to make resolutions for each other.

We wrote our names on a wall, spent the day brainstorming, did some group decision making, and by January 1 each person had six “challenges” they had to complete in 2023. It's sort of like having six “new year's resolutions,” but defined by your friends, without you having any input into what the resolutions might be.

Completion was mandatory: we decided that anyone who — for whatever reason — failed to complete their challenges, would lose a pinky finger (we're extreme, I know).

I can understand why someone might consider this to be — at first glance — insane. It is, at the very least, a pretty big dice roll. Turning your resolutions over to your friends might have unpredictable outcomes, but friends can have a uniquely insightful perspective, as well as a kind of permission to challenge you in ways that you might not give yourself. And while the resolutions you make for yourself might quickly be forgotten or fade in significance, the resolutions a group makes for each-other can have an enduring liveness of their own.

After a year of challenges, everyone from the first year is signed up for a second round in 2024, and our numbers have grown from seven to ten. I think it has been a ritual worth doing.

The challenges for everyone have mostly fallen into a few broad categories:

1. Something a friend would probably love to do, but they likely wouldn't make the time to do it without a deadline or some group accountability (ex: “make and screen a 5 minute stop motion animation video”).
2. Something a friend would do amazingly, but would probably never even consider for themselves (ex: “write a religious text.”)
3. Something a friend probably wouldn't choose to do, but the rest of their friends feel would be valuable for pushing them out of their comfort zone (ex: “perform a 5 minute stand up comedy set at an open mic”). This has been, I have to say, a somewhat popular category. However, the symmetrical nature of these challenges is important. The people you're pushing out of their comfort zones might choose to respond in kind.
4. Something someone actually needs to do but has been neglecting (ex: “get your drivers license”).
5. And a cross cutting category: something, regardless of the above, everyone else will enjoy the fruits of (ex: “write and record a love song”).

My challenges for 2023 were:

1. Take a libertarian on a train hopping trip.
2. Renew my driver's license.
3. Take a heroic dose (>=5g) of psilocybin.
4. Fly a helicopter from Southern California to Alaska
5. Convert my internal combustion engine car to an electric car.
6. Foster a dog for one month.

Some of these I never understood the underlying motivation for, and still don't. However, even without precise insight into my friends' inscrutable wisdom, it was — at the very least — a more interesting year than it likely would have been otherwise.

I recommend doing this with your friends. It doesn't even have to be on NYE. Here's a recipe:

1. Get people together, preferably in a place where you can all stay overnight.
2. Put a row of post-it notes on a large wall: one post-it for each person with their name on it.
3. As the gathering progresses, everyone can write ideas for challenges on post-its and stick them on the wall under the column of the appropriate person. This doesn't have to be super focused time, and can progress while people are doing other things together.
4. Towards the end of the gathering, get everyone together in a focused way and “sort” the challenges in each person's column through voting, consensus, or whatever mechanism you choose. The top N for each person are their challenges for the year.
5. Define some stakes, and possibly some rewards. You don't have to be as insane as us, but there should probably be some considerably motivating factors at play.
6. Set the date for when you will reconvene, and start a group chat to keep everyone updated in the mean time.

If you're enough of a maniac to try this, let me know how it goes for you!