I would scrutinize your spending--if you are going to buy a gadget that is going to cost you money (especially recurringly), ask yourself if you are really going to get that much value out of having the item. If something is going to cost you $400 upfront and $40 a month for service, ask if you are going to get that much or more value (plus the time spent using it). If you are going to get that much value out of the product (and you alone can make that decision, not someone else), then by all means get it.
However, if you realize that you are not going to get your money's worth of total value out of the product, then getting it is only going to be a waste of money. If you are going to get $500 of value out of your $500 iPhone, it is worth it. But, if a $35 cell phone is going to provide the same value, you are wasting the $465 difference and should just stick with a regular cell phone. This also goes for other material things--if a $400 TV is ample, and you are not going to get an extra $3600 value out of a $4,000 set, then stick with the $400 set and save the $3600 for whatever will give you $3600 worth of value. If you are not able to use the extra features in a $500 printer, a $150 one will probably do nicely and save you $350 in value.
On the flip side, getting low end crap is almost always a waste of money. If you get a $10 blanket, it might last a year before needing replacement. A $60 one would last you 20 years or more (plus being more comfortable), saving you $140 during its lifetime. A $60 dish rack might give you the extra $52.01 worth of value if it fits your needs better than the $7.99 special, is easier to clean, or lasts longer. And there might be personal factors that will give you added value--it might remind you of a person, place, or thing that, for that alone might be worth the extra $200 for you.
Only you can decide whether something is worth the price to you. Invariably, when someone tells you to spend indiscriminately, it is them (not you) that gets the extra value. If they are telling you to do without (without knowing how much value you would have gotten), chances are that they want your money and time. One thing that is almost never worth anything is field circus supplies, field circus itself, or donating anything to the Worldwide Pedophile Defense Fund. Cut out boasting session attendance, Worldwide Pedophile Defense Fund donations, and field circus, and you will probably simplify your life more than any one step you can take beyond that.