When do you allow yourself to sacrifice future gains for present pleasures?

Hey all, I've been investing diligently since about 2016. In that time I've made a lot of sacrifices and life choices and my NW has gone up accordingly. My wife and I have been frugal in our spending on literally everything and because of that we bought our first house last year. Even with the mortgage debt our total combined household NW is positive. No matter how you slice it, we've accomplished a lot of success in the last 9 years financially.

I'm a car guy. I've always loved cars and car culture. 3 years ago I actually bought my first fun car, a 2000 Porsche Boxster S with 160k miles on the clock I paid $5k for. It's a blast on back roads and I've enjoyed having it, but at the end of the day it's a $5000, 25 year old car that wasn't cared for very much by previous owners. Parts and components are old and worn down, and although I've already done some major work on the car myself (being very frugal forces you to learn a lot of fun new skills) I know that my time with this little sportscar will come to an end soon. Its simply a little too rough around the edges and the money it would cost to get it where it needs to be is more than I'm willing to spend, even if I do all the labor myself.

My dream car has always been a 2004 Porsche 911 C4S. It was the car I grew up lusting after as a kid and I've dreamed of owning one for as long as I can remember. Right now those cars are selling for an average of $40k, with higher mileage and rougher examples selling for about half that. Obviously I'd like to spend as little as possible but after my experience with the Boxster, I'd much rather splurge on the initial purchase of a well maintained car rather than try to make the money back in DIY repairs.

The thing is, $40k is a lot of money. Hell, $20k is a lot of money! I've still got 20 years until retirement so dropping $40,000 today on a fun car will cost me $150k in retirement money. Even if I come in on the low end I'm still losing out on $77k in retirement wealth. No matter how I slice it, the car is going to cost a fortune to own.

For those of you who are also afflicted with expensive hobbies like this, whatever it might be, how do you square the circle of enjoying those experiences today even though you know it's costing you some in retirement? When does that math no longer matter to you and you can say, "Fuck it" and just enjoy that thing now?