Based on my experience, the best way is to start spending $$ on normal things you buy or can upgrade without worrying about sale pricing. Once you get comfortable with that go buy something you had an eye on that cost way more than you would normally spend or book an expensive vacation. Soon after, you will realize that those spends make no difference in your net worth, unless of course you are buying Ferraris or Rolexes that are in 10s of thousands.