Right now, in your situation, would you rather have a coffee or a haircut?
Would you rather have 2 coffees or 1 haircut?
And so on. There are plenty of exercises to determine how you (personally) value things, and also the shape of your utility curve. That was one of the most interesting classes I ever took: decision and utility theories.
A lot of the work was understanding the impact of different personal (or institutional) utility curves, how to determine your own and how to maximise you return not in absolute terms, but in relative terms using your utility curve.
When you take in account non-linearity of utility curves, lotteries make sense, for example, since for most people the utility of $1 is far less than 1 millionth of the utility of a million dollars.
The same with insurance. Insurance always has a negative expected value in absolute terms, but when you take in account that U(-$1) << U(-$1M)/1M, they make sense, since your utility-adjusted expected return is positive. That's also why your insurance should always have the maximum possible deductible.
Insurance works because companies and people have different utility curves.