I have a similar childhood history. One thing that works for me is comparing what the daily use cost for the thing is. Like with a laptop, it may cost $2k, and I may use it almost every day for 5 years, which comes out to a little over one dollar a day which is not too expensive. However, something like a pair of binoculars that may cost like $500, but I only use them 4 times a year for 5 years would be $25 per day that I use them even though they cost 1/4 as much as the laptop.

Also with the laptop, if you use it every day, going from a $1k laptop with a daily use cost of $0.50 a day to $1.00 a day is not a major jump in total daily cost, so going for a more expensive laptop that is going to make your daily experience better may be worth it, whereas going for binoculars that cost twice as much would cost $25 more per use, which is a much more significant dollar amount per use.

Another way to assess the laptop price it is to compare everything else that costs you $1 a day. You may even be able to cut out $1 a day from your budget. Like if you live in a cold climate, just don't warm up your car as long every day. Or buy a small size food thing instead of a large. Or skip eating out one day every two weeks.

I'm sure some folks will disagree with this though process, but it has worked for me, and has helped me assess the value of things in my life that I may not give much thought to because they are not glamorous, like a mattress.

I'm at a point in life where I've got most things that I need, so there's not a whole lot frivolous spending to for me to do. When time allows and I have some extra money, I get another flight lesson logged. And once in a while I order another batch of electronics from digikey. Beyond that I mostly put money into upgrading the hundred year old house I live in.

EDIT: And an obscene amount of PETG for 3D printing. But I feel that at this stage that's almost like groceries at this point, as most of what I print is functional/useful stuff.

I do a lot of budgeting, and I use the "pool" method.

A lot of people recommend the 50-30-20 rule: 50% of your money goes to fixed expenses, 30% goes to discretionary spending, and 20% to savings.

I tweaked that a bit and made it 60-20-20*, with the 60% being for essentials...things like clothing is included.

That 20% goes towards any guilt-free spending. I've covered everything I need, and this is money I'm allowed to spend on whatever I want...guilt-free.

EDIT: I accidentally said 60-20-30 instead of 60-20-20.

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If I need it and it's worth the price then I don't worry about spending money on it. Especially when talking about one time or long term purchases such as a laptop (which as an extremely satisfied MacBook user I highly recommend)

Subscribtion services and meals are the ones I take issue with. I dont want to pay high price for something and then have nothing to show for it. I will not pay 5 euros for a cup of coffee no matter what - it's not worth that to me. With items you technically didn't lose any value - you just traded cash for an object.

Macbooks particularly are one of the stupidest shit someone can burn money on, the extreme high price and low performance make apple computers literally the worse in the market.

For the price of a powerful computer with RTX and all, you get an useless office computer where the keyboard is even too shit to do any office work on it.

As for the actual question, I tend to spend money that I shouldn't on premium audio gear, I should feel bad about it, but I really enjoy listening to good audio and for me I feel it's worth it even if I have to postpone things that for most people are considered essential.

Also, it's very hard for me to spend money on (new) computers and camera gear. I terribly need a new computer with a good GPU for 3D modeling and a decent camera. However if I buy a new computer or camera in 10 years it will be obsolete and worth 10x less than I paid for it meanwhile stuff like audio gear or musical instruments don't become obsolete so I'm more likely to spend money on yet another paid of headphones that I don't need than saving up for a computer.