I've been pretty careful with my spending most of my life, but I'm now getting to a point where I'm letting myself relax a little about it. I've been ramping up my restaurant spend, but after a few months of this I'm coming to the conclusion that I usually prefer the $50/person restaurants over the $300/person places. I'm going to be doing some luxury travel and I expect that will be a more regular thing. (Though, similar to restaurants, I may wind up staying at cheaper hotels, not necessarily to save money per se, but because I'm not as interested in the all-inclusive resort type of experience. We shall see.)
Some things most people wouldn't even consider lifestyle creep that I've been doing recently are having a housekeeper come by every other week and working out with a personal trainer 2x/week to get myself into better shape. No regrets about either one of those, though I still hate going to the gym. We also invested in other timesaving services like landscapers who come by to do the weeding and pruning, an irrigation system to water the lawn, etc.
What are some ways you've let yourself spend more that you felt improved your life?