Just being pedantic here, but: if we take your approach to the extreme, we would only ever pick the one thing that maximizes joy. Eg say one week trips above are the coolest thing you can think of. then you'd compare any potential purchase against it, and it would fall short. So you'd end upmnever buying anything (except tickets for one week trips). Don't get me wrong, your strategy sounds sound, I'm just saying that it's too greedy of an algorithm to apply it thoroughly. A slightly improved strategy would be to instead think of marginal prices: how much would I be willing to pay for X, instead of another piece of Y. Ie, if you already had 10 one week trips this year, you'd not be willing to spend as much for #11 than you'd be willing to spend to go from from 0 to 1 trips or 1 to 2
> then you'd compare any potential purchase against it, and it would fall short. So you'd end up never buying anything (except tickets for one week trips)
I think there's a number of folks out there who do this all the time, except it's not trips. It's saving for retirement in general.
If all you do is compare every outgoing dollar to "but if I invested this instead, then over X years it would have compounded to $X" you never buy anything non-essential because spending $400 today really means $1,787 in 30 years at 5% (of which $1,387 is interest), so now you need to ask yourself if future self is happy about that decision.
This becomes more important with larger purchases, a $30,000 car is really $134,032 after 30 years at 5%. Now this becomes a question of "is this 30k car worth trading 1 year of my life while working?" because it kind of is, especially if you factor in income tax on a pretty normal software developer's salary.
