Based on your financial expertise, provide your response or viewpoint on the given financial question or topic. The response format is open.

How to spend more? (AKA, how to avoid being a miser)
I agree with JoeTaxpayer's answer.  The question you should be asking is not "how do I spend more" but "how do I become happier".  From what you say, it may be that you could increase your happiness simply by cutting back on these aggressive attempts to save a few bucks here and there. At the same time, if you do this, on some level your personality is probably not the type that would allow to simply "forget it".  I think many frugal people are somewhat as you describe: they don't like wasting money.  In such cases, often what matters is not so much the actual saving money as the feeling of saving money.  Therefore, I'd suggest that you take a look at which of the "money-losing" activities you mention are really worth it. The easiest ones to drop would be things like the home-improvement project, which even you acknowledge does not save you money.  If you like saving money, give yourself a pat on the back when you hire the contractor.  If you want, run the numbers so you can "prove" to yourself how much money you are saving by not doing the work. For some of the other things, it may be that spending time to save a small amount can "gamify" an everyday experience and make it more interesting.  For instance, comparing products to save a few bucks is not necessarily bad unless you actually don't like doing it.  If spending a few hours comparing two toaster ovens on Amazon or whatever makes you feel good, go for it; it's no worse than spending a few hours watching TV.  By acknowledging that you get something out of it --- the feeling of getting a bargain --- and savoring that, you can feel better about, and also potentially "get it out of your system" so that you won't feel the need to do it for every little thing.  We all have our little pet obsessions, and it's possible to acknowledge that they're irrational, while still accepting them as part of your personality, and finding a way to satisfy them in a controlled manner that doesn't stress you out too much.