How do you rationalize audio upgrades?

The argument many use is "can I buy this" instead of "should I buy this". I wasted baskets of money (that I could be using now in retirement). The system I have now is everything I wanted so I can't complain. The components I have didn't exist 30 years ago so they couldn't have been assembled into a system. Must be the reason for so much trial and error.

If I could explain how I rationalize my upgrades then everyone would do it. My system would go from mind-bendingly awesome to average over night. Worse, hearing the $1.3M system at Definitive would have me crying in my beer instead of snort, chortle, if only you knew-ing.

So I'm not about to say, even if I know, which I don't. So there.

A good rationalization for spending more now is that in the long run it's cheaper. You lose money with every upgrade.

There is, gentle readers, a hierarchy of audio systems. What that means is that with careful tweaking a modest cost system can outperform a more expensive untweaked system. And if you tweak the more expensive system you can potentially outperform an untweaked very expensive system. The degree to which a tweaked system can outperform a more expensive system depends on the effectiveness of the particular tweaks involved and the number of tweaks involved. Necessity is the Mother of Invention. You only need to know where you want to go and how to go about getting there. 

@geoffkait  I thought all roads led to the Sony Walkman via the Cassette Tape byway?

You only need to know where you want to go