Has anyone based discretionary spending on investment outcomes?

I’ve always had a harder time spending for fun because there’s always that voice saying you should invest. So I’d like to tie some of that spending specifically travel to investment outcomes just thinking through how to structure it.

Was thinking of placing my budgeted amount for travel in a separate investment account maybe a year out from having to plan the trip. If it goes well I get to enjoy a better trip if I go bust no trip for me. Now in reality I’d have a stopping point and if the account draws down to my minimum I’d take the money out and deal with a less than luxurious trip which I’m okay with. I’ve also kicked around the idea of a separate account but a large sum and then any amount it generates either from dividends or selling options would be “trip money”.

Open to other ideas.



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