When I was a kid, I didn't work. I got a tiny allowance ($5 per week, or maybe per month), and every now and then I'd age or undergo a holiday, so friendly relatives would send me money. But the only things I wanted to buy were desktop computer parts and video games, and I easily saved enough money for those. Parents took care of everything else–thanks parents!
Later, I was a college student. Sometimes I wanted to buy Chinese food, but that's about it; I still had roughly no spending. (Apart from how expensive school was, but again, I mooched from parents and scholarships–thanks parents!). Still, I felt like I should earn money, so first I worked as a dishwasher for around $8 an hour, and then as an inept ResEd student web developer for maybe $9.50 an hour. Suddenly the savings I had slowly built from that $5 per week allowance seemed meaningless.
Still feeling like I should be doing something career-related, I nepotised into a co-op preprofessional software engineer summer job at IBM. (Thanks Dad!) That was $20 an hour, full-time, with overtime even! After a few months of that, I came back to that student web developer job and realized I didn't care about it at all–I'd written more than my share of abominable Perl forms, and with $13,000 in my bank account, why would I want to get paid $9.50 an hour to write more of them when I had better things to do? I helped them hire a younger minion and lounged around on my coins. The money I had made from the web developer job also never mattered.
After college, George, Scott, and I started Skritter, and apart from rent ($300/mo) and food ($6/day), I had a few other small expenses (lasers, bowie knives, whips, etc.), but really, life was cheap. Skritter survived at first off of the entrepreneurship grant our school gave us (more mooching). I was finally glad I had made some money at IBM, because those savings kept me out of debt until Skritter could slowly become profitable. I could also calculate utility and buy a few things, like a sick office chair and some large computer monitors–they were like like three cents per hour of use!
Across several years of working on Skritter and moves to Costa Rica, Pittsburgh, and Sunnyvale, revenues grew, but my spending habits didn't change–I was still living like a kid who occasionally needed to eat something or upgrade his computer. If I had to buy something, I'd buy the cheap thing—I mean, you gotta save money, right?
Except I now knew third-hand from George's economics classes that there's this thing called consumption smoothing. If you can predict your future income, and if you aren't liquidity constrained, then you might adjust your current spending so that you can have a constant standard of living. (I have no idea why you'd want a constant standard of living, but you could also target a gradually rising standard of living and maximize your enjoyment despite hedonic adaptation.)
Now those are usually two too-big ifs, but in my case, it was easy to see that I was going to make more money later (even if I didn't work–yay recurring revenue), and I had more savings than I knew what to do with. I also realized that if I'd been thinking like this when I was younger, I could have enjoyed some of the money I'd worked so inefficiently to stockpile before my increased income devalued my efforts.
So I said, hey, I know what to do–I'll spend more money! If there's a cheap thing and an expensive thing, I'll buy the expensive thing, because I don't want to spend time comparison shopping, and the expensive thing is probably better (healthier, lasts longer, faster, weighs more, whatever). Free app? No thanks, I'll take the paid app on principle. If there's an opportunity to trade money for time, I'll do it! I'll just establish an hourly rate for myself and quickly calculate whether I should take the bus or an Uber, clean my place or get a Homejoy, go grocery shopping or get Safeway.com, do my taxes or hire an accountant, live far away or in the heart of things, and so on.
At first, it didn't work, because most of my decisions I made by habit, not by calculation, and thus I fell back into the habit of not spending money (even though I was desperate for more time to spend on startups and relationships and personal growth). I would have to really think about it to justify spending, and the point isn't to spend time thinking about it, but to just do it and save my time.
Then I went to a CFAR workshop and got the idea to perform a ritual to help me recalibrate my spending. Rituals can often tap into something a little deeper to help one change one's habits and thought patterns. So I came up with one to solve this problem.
I may or may not have gone into the yard, made a fire, and slowly fed $100 into the flames while concentrating on how money is useless if you don't use it.
This worked. I immediately got much better at trading money for time, at consumption-smoothing when it makes sense, and about not irrationally overvaluing money. I shot up to new levels of productivity, bought better possessions which I have been much appreciating, and worried less than ever about money–while still increasing my savings, since for me, it's not these little things that affect my wealth, but the efficiency of my startups. Not that my current savings really matter, either, beyond having a buffer–I can still predict that my future income will dwarf any current optimizations of my savings.
Of course, a lot of the consumption smoothing behaviors and specific examples of recalibrated spending are situation-specific, so don't take any of that as general advice. But you might want to come up with your own hourly rate and think about whether it really ever makes sense for you to prefer free apps, not buy books, comparison shop on small purchases, and things like this. I can guarantee that if you haven't consciously calibrated all your spending, then some of it is miscalibrated. (Worst example I've heard: immigrant graduate student still cleaning dishes with own spit to save water, to horror of American roommates.)