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A challenge to step out of your comfort zone once per day for a year

Darko Savic
Darko Savic Aug 07, 2021
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A year-long community-based challenge where once per day everyone does something that is outside of their zone of comfort and then reports back to the community for accountability.

Why do this?
  • To open yourself up to new opportunities.
  • To discover new passions, interests, and people.
  • To test yourself and recalibrate your sense of self-worth.
  • It's like speed dating potential changes in your life.
  • To build up more discipline to do hard things.
  • What doesn't kill you makes you stronger.
  • It feels fun (when it's over).
It should be something that feels psychologically uncomfortable but is otherwise beneficial or at least not harmful.

A few examples:
  • public speaking
  • walking up to people you don't know and getting a conversation going
  • cold showers
  • waking up early
  • giving someone critical feedback
  • no phone for a day
  • embarassing yourself in front of others
  • and so on...
Every day, people have to report back to the community and describe what they did, how it went, how it made them feel, and why they consider it to be outside of their comfort zone. I imagine the reports like tweets. They should be brief. Maybe a maximum of 1000 characters with the ability to nest multiples in a thread if someone wants to write a longer story. Community members can like and comment.

A dedicated platform

While this could be done by a bunch of friends via any group messenger app, slack, etc. Ideally, though there would be a platform specifically designed for the purpose. People would sign up and join cohort accountability groups of about 30 individuals. The plaform would neatly organize the submissions by day and keep a scoreboard of people that successfully completed or missed some days.

Those that missed up to 5 days could be given the opportunity to catch up for the missing days or drop out of the group. People that dropped out could sign up for another round with a new group.

If too many people in some group dropped out, the group could ask to merge with another group.

Catalogue of uncomfortable things to do

As the platform grows, it should assemble a catalogue of uncomfortable things to do. When people run out of ideas, they could try some of the things others have been struggling with. The catalogue can be categorized by various criteria so that people can zoom in on their fears.
Creative contributions

I did this for a month and have some remarks/suggestions

Povilas S
Povilas S Aug 15, 2021
It's a great idea and initiative to build such a platform/community. I think the platform should have options to do the same challenge but in different time periods (from one day to one year, maybe a day, a week, a month, and a year or other options). The people would be grouped according to the time period they chose for the challenge (they could additionally be grouped by their location and other factors).

Completing shorter periods would give you points and help prepare for the longest challenge period or alternatively you could initially start with the year one if you felt like it. You could repeat short challenge periods as many times as you wish, so for example, whenever you felt like doing a challenge tomorrow, you could "sign up" to a day-challenge group.

But having done this for a month I could say that the most complicated part is perhaps not even the challenges themselves, but the part where you have to come up with something new for each day and find time to execute it amongst your daily schedule. It becomes a job upon itself.

A big part of the complication is that you start doubting which thing would count as something out of your comfort zone and which not, to be sure, the challenge has to be really intense and preferably something you've never done before, it's easy to think about big things that would count (like a parachute jump) that feel truly challenging, but the thing is that big things usually require big resources and plenty of time. To put a truly big challenge into each day is infeasible if you have other things to do.

So you're inevitably left (if not initially then after some time of doing this for sure) with small to medium challenges and have to juggle around with those to find something challenging enough and not too time-consuming. Then additionally even if you find one of those, in practice it might not work out - e.g. you might not manage to get the conversation going with few strangers in a row - will you continue then until you do (could potentially take the whole day) or will you count the challenge as completed because you've tried enough? Completing one challenge will eliminate possibilities for doing similar ones because you won't feel like you're doing something considerably more challenging (e.g. talking to a stranger after embarrassing yourself in public might not seem so challenging anymore and vice versa). All similar complications add up to make the process more difficult as you continue.

The catalog of uncomfortable things to do would therefore be immensely helpful, but for me, it seems the best to do such a sequence of daily challenges when you have free time and can dedicate all of it just for that purpose, it would be like a game or/and a job. People having a gap year and some spare money could take the most of this. Maybe an AI-powered app, similar to this one could help people find the right challenges according to their unique situations/routines/finances, etc. so that the planning part wouldn't get in the way.
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General comments

Darko Savic
Darko Savic2 years ago
“Do something everyday that you don't want to do; this is the golden rule for acquiring the habit of doing your duty without pain.” - Mark Twain
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