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It's not necessarily the "spending money" part, it's the wasted time and foregone opportunities. I'm still pretty young, but I can't get back wasting my early 20s on computer games and older women. Once the time is gone, it is gone forever.
If those are things you really enjoyed, maybe it's not really wasted. After all, it brought you joy (which I think it must have, since you are still doing the same thing. Spending all day on city-data talking to retired people isn't that much different from spending all day on computer games and older women.) Computer time and spending time with older people make you happy, that's not such a bad thing.
Say you were one of the lucky ones. You avoided the three big ones, Illness, Divorce, and Unemployment. Invested wisely, lived frugally, and all your close relatives and friends are doing well enough never to ask for a handout.
But now you find yourself on a big wad of cash that's waiting to be spent but not enough time to spend it or your body is too worn and beat up to enjoy travel and other hobbies.
Anyone regret being too thrifty in your younger years? Of course hindsight is 20/20.
Why would people regret having a wad of cash saved and invested?
I honesty think I had the right balance. For a time I was making pretty good money, this allowed us to do things like take trips to Alaska or the Caribbean. But even then we stayed at inexpensive motels and were careful to save on meals etc. We lived a good life while still being responsible.
Nobody is saying you shouldn't save. But the question seems to be did you save to the point where you denied yourself lots of things you really wanted and now once retired feel let down somehow. That you really didn't need to deprive yourself so much THEN to be happy and secure NOW.
Lots of people never get to the point where they enjoy their retirement because they can't get out of "scrimp and save" mode - those are the people I feel sorry for and exactly what I don't want to be. Saving for no purpose seems very sad and empty.
I can’t spend my money now, we’ll not fast enough. When I was younger, that’s a different story.
I have a credit card to open to get reward points and I’m still waiting closer to the must open date before I apply. I do have a trip coming up that will fill the minimum of requirement. Other than that I can’t think of anything to spend. I wonder if we get more sensible as we get older or what. I don’t even eating out as much, different from just 6 months ago where we at least dine out twice a week. And they are not for money reason.
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