It appears that you are satisfied with yourself, and are enjoying your life, but you don't enjoy the things that you own. I would think that if a thing enriches your life that you would be enjoying it. But, that's just my opinion.
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The message I took away from Rogue's original post has nothing to do whether he is happy with his current stature in life. It's just Rogue's way of initiating conversation, which appears he has succeeded at.
I am one of the fortunate people who can afford three vehicles. I'm not frugal to the point I drive a 75' Nova and live in a hut. But I have thought about that; I have no right to be jealous. I have some fine toys and I should be grateful. I need to keep that in mind the next time a Lexus parks next to me.
If you don't live below your means, eventually you'll end up living below a bridge..... :(...... Jim
Early on I subscribed to Dave Ramsey's method of getting debt free. I found being in debt very stressful, based on the instability in the job market and world financial situation. Mr. Ramsey wrote a profound book, and using his methodology (even before his method was named) I paid off everything I own. Now I pay cash for what I can afford, and I do enjoy a new toy every now and again. Just remember, we're all going to bite it one day, and we don't want to make Uncle Sugar fat. Boomers are going away fast. My though is, as long as your family is secured now and in the future, everybody is fed and housed, why not? If it's within the budget, I say go for it.
I have a 2005 Nissan Maxima with 115,000 miles on it. It still runs good and does what I need it to. But, the paint on it has deteriorated and it needs a paint job, but they are expensive. A good paint job will cost as much, if not double, what the car would be worth after painting, so I keep putting it off. So why not buy a newer car? I'd like to but the way I view it, my choice is do I want to drive really nice car today, or buy groceries ten years from now! One's current level of spending often reflects their expectation for the future. I like the sign, "I'm spending my children's inheritance." But I sure hope the inheritance I leave them is not a negative bank account!
I live happy with the thought my wife & i have achieved our savings goal and when retirement comes we will have more time & money to play.
Riding & overseas travel are what we want in retirement without worrying about how we will pay for it.