I don’t know if it’s guilt or apprehension, but I do feel weird spending money especially on myself.

As an example, I bought myself a nice watch. By any objective measure, I can afford it. The kids are still going to college, the bills are still going to get paid, we’re still going to be able to put gas in the cars, etc. Plus, it was preowned and I’d get most of what paid back of I sold it. The reality is buying the watch has a negligible effect on our finances, but I don’t feel that way. Instead, I feel like the world is going to collapse. OK, maybe not that badly and at least I’ll know what time the world collapsed.

Guilty to a degree.
The wife and I have very well paying careers, and we are classic dinks ( double income no kids)
About 8 years ago we move across country for a lot of reasons, but a big one was in a span of about 2 years went to 8 funerals all of people under 55. A number of them were military guys I served with, all sorts of causes( sudden cardiac death, rapidly progressive Lou Gehrig disease,brain tumor, leukemia, etc) my wife and I had a deep conversation - all these guys probably had dreams or ideas - when I turn 60 I am buying or doing that, when I retire I will go to x, etc
We decided if we wanted to do something go somewhere or buy something to go ahead and do it.
While I don’t hesitate to let my wife spend money, or spend on everyday stuff ( I know lots here would call guns and associated items everyday stuff) I still hold back on gun related purchases.
Don’t know why. But will only buy a new gun once I sell another, or get unexpected cash. ( work bonus, overtime, win a raffle etc)
A couple years ago I sold enough guns and related stuff to put together a 3 thousand dollar rifle, and didn’t feel guilty about i5 at all, but would have if I just gone out and bought it

No.

The older you get, the less guilty you feel.

I grew up poor and struggled for the first 9 years with my wife. I do well now and plan on spending or giving away all I've made before I die. I told my child that all our possessions will be handed down but don't expect to get to spend what my wife and I struggled most of our early lives to accumulate. No I don't feel a bit guilty.

You have to ask yourself, "what are you working FOR". What are you saving every penny FOR? What happens if you don't make it that far?

Personally I think a good phylosophy is to save 20% of your income for the future, and play with the rest. BUT this also means no or minimal debt. My dad passed away at 56 years old. That changes things and viewpoints.