"Making it" has nothing to do with how much money you have. It is how happy you are with your life. At retirement I went from being able to make $1000/month car payments to only half of what I had been earning. That is quite a shock. But, we were never extravagant people and we still managed to do things that made us happy. We are so diligent that we now have 5 times as much in checking each month than I had that first day of retirement.
Note to Joey... The most I have ever spent on a pair of boot in my life was $125 for a pair of Naconas.