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I think a good balance between Type I fun and Type II fun is where its at. Type II fun really tickles the curious part of us and provides a healthy does of challenge and growth(hopefully). Type III fun is great until you're in a stretcher on the way to the hospital and no one knows if you're going to make it, at which point it ceases to be any type of fun.
This is a long time favorite post of mine. Kelly Cordes is rad.

As alluded to at the end of this, the real bastard about the fun scale is that if you live in type II fun long enough, the things you do for type II fun become type I fun.

... and that's how people wind up thinking ultras are a great idea, kids!

Agreed. I started backpacking with my brother a few years ago and it was miserable the first few times because there were so many things that we were anxious about, we bad with, or just didn't know to do. For example, we bought heavy waterproof gear and learned quickly there is no avoiding getting wet, so might as well trade in the waterproofing for fast-drying. Now we can open up a little and have a little fun in the rain. Same with coffee. We used to lug gear around to make piping hot coffee, now we heat up a little water and mix in a little instant and we get 75% of the benefit with very little overhead.
Well see you were just optimizing for the wrong things. You thought avoiding wet was the thing to optimize for, but now, with experience, you find other things are more important to you and you aim at optimizing those. What things are wrong and right vary by person and by purpose (and probably by time, too).
Where do you bucket: "wow this is so miserable, lol, this is great" while doing the thing?

I wrote out and deleted a comment about this being a subset of Type II but maybe it's just a damaged person's Type I...

that sounds like just the normal fact that i summarize as "the first half-mile always sucks", which appears to be true for any sort of fun.
My body being in pain and my brain enjoying working the body are not at odds with each other.

In my experience trying to become an ultra runner, its not that I enjoy the pain. I enjoy the workout. I enjoy the run while my body is in pain, not that I enjoy the pain itself.

When I tell people I swim, they're always like, "Oh wow! That is so good for you." But they don't understand, I'm not fast or a strong swimmer or anything. It's cold, I struggle with my form, I'm slow, I can't kick turn, I'm constantly gasping for breath. Swimming is getting in the pool and convincing my lizard brain that I'm drowning for an hour. But when I get out the endorphins are fantastic, like every cell of my body is so relieved to be alive.

At same time, the struggle to overcome that lizard brain response to hard physical work is itself enjoyable in a way. It wasn't when I started working out but after years it has become an acquired taste. If you'll forgive a little hyperbole, it's the moment when I look my own mortality in eye and say, "you might win eventually, but not today."

This misses one type of fun, Type 4 Fun:

When something is fun in the moment, but in retrospect was not fun at all and was awful. The most obvious example is drinking too much on a night out, or binge eating.

> The most obvious example is drinking too much on a night out

I've found interesting (russian meds) and creative (supplements like NAC) solutions to that problem on reddit.

Even funnier: they seem to actually work! No headache the next day!

I'm not only talking about the hangover (But you've inspired me to look into MAC), I'm talking about the things you do when too drunk at a bar. Acting like a fool and being embarrassed about it, spending a lot of money on drinks only to not even remember the next day.. things like that.

Going out to a bar and having the right amount of drinks can definitely be Type 1 fun, but when you pass a certain threshold of drinks it slides to Type 4

Then a few years later you joke about it with your friends and it becomes Type 5 fun :)
Interesting, I've never heard Type IV before. I've always heard the more succinct definition: Type I -- fun now, fun later, Type II -- not fun now, fun later, Type III -- not fun now, not fun ever. But now that you mention it, the fun classification is obviously just a 2x2 truth table:

                         fun now?
               +------------+------------+
               |     Y      |      N     |
         +-----+------------+------------+
    fun  |  Y  |   Type I   |  Type II   |
         |-----+------------+------------+
  later? |  N  |  Type IV   |  Type III  |
         +-----+------------+------------+
Clearly, we have to switch the Y/N, both in rows and columns, then start our numbering scheme a bit earlier.

Type Null fun is not fun: not now, not later. This puts something as being fun now and later at Type III, which sounds just like a lot of fun, and so it is; Type I and II Funs would be mixed bags. You could even say that Type I + Type II = Type III.

One of my favourite examples of type III fun: The Apollo 13 mission. It's just so ludicrous, and it embodies the "not fun in the moment and let's not do that again" sentiment.
My friends and I used to dare each other to run around the house barefoot in the snow. By the time I was half-way, my feet hurt so bad I could barely walk, but it didn't matter, because I saw my friend who was running faster than I had ever seen before, that I could barely stand up due to laughter.
As a climber, I found this example of type III fun hilarious:

> Offwidths

For those not familiar, they involve shoving part of your body into a crack and trying to wriggle your way up. The shoulder/knee jammed in may keep you from falling out while also introducing a significant chance of getting stuck and needing rescue. Meanwhile the majority of your weight outside the crack creates an uncomfortable/painful torque.

And yet, there are people who actually enjoy offwidth climbing. Personally I've enjoyed the challenge, but the ones I've climbed has led to days of pain afterwards. There's still an allure to attempting them though.

I've had jobs that were type II. Generally anything in the entertainment industry, and most specifically being a roadie. There were moment of type I, but a huge amount of the time it was an exhausting, boring, grind, with #$@$@ tour managers and others. Mostly hated it at the time, but two weeks after getting back I'd be hustling for the next tour. Perverse!
Type 2 fun is a perfect example of the fading effect cognitive bias.

Fading effect bias interestingly causes the emotion associated with negative event memories to generally fade faster than the emotion associated with positive event memories.