Not to be totally stereotypical, but I come from a family that didn't buy retail. I'm mostly cured of that, and especially in the following areas, where I am unabashedly profligate.
  1. Babysitting/childcare.
    Always worth it to have time.
  2. Good food.
    Sometimes I spend on this to a ridiculous degree, I admit.
  3. Medium-nice clothes.
    Never used to, but now that I do (and doing a lot of my shopping in Paris helps), I'm a lot happier when I get dressed.
  4. Supporting/buying creative projects made by people I like/admire.
    Whether or not I enjoy the final product.
  5. Monthly or weekly unlimited subway passes when I'm in NYC or Paris.
    Without calculating/caring whether it's really worth it given how much I'll be traveling.
  6. Medical care.
    Duh. Priorities.
  7. Indie computer games.
    Such small amounts of money bring me so much mental relief.
  8. Snow removal service in winter.
    Thank god for the Connecticut Commercial Maintenance Co.
  9. Spotify Premium.
    I'm not that into music, so it's all I need.
  10. Pour-over and cold brew coffee.
    I came to coffee late in life (after kid #2) and started with very good stuff.
  11. Expensive elaborate Lego sets for my 5-year-old.
    Worth it on many levels.
  12. Maybe my next list should be stuff I always do resent spending money on, at least a little?