I grew up on the edge of poor and had a lot of low-paying jobs before my fortunes improved and got lucky with my investments. So I've always watched every penny and tried to get the best deal on everything from cars to homes to .. pussy.
Now, as a septugenarian, I realize I have the assets to live a pretty good lifestyle for the decade or so I expect to have decent health. This gives me a lot of options for sugar, which is my preferred (and most expensive) hobby. I'm shifting my mindset more to be more "generous."  
This attitude is paying off and I have at least a couple of hot ones in the fire, though I still have certain reflexes and reactions, and can't bring myself to spend 1k for an SB PPM.
I don't want to die with zero.. I still want to leave something significant to my kids. But it is a strange feeling to think about spending down the nest egg instead of building it up.
I suspect some of you are in a similar position. Interested to hear your thoughts.

When I fully retired at the age of 59, I flipped all of my stocks and 401k's to a financial manager.  At the time we developed a set of objectives for how to live my remaining years.  

 
Primary Objective: Make sure I have at least $1 in the bank when I die. I don't want to leave the world with any debts to be passed to my heirs.  

 
Stretch Objective:  Leave a substantial estate to my heirs. Substantial meaning they can maintain or even improve their standard of living after I am gone.  

 
Dream Objective:  Leave more than I started with to my heirs.  Meaning I achieved substantial grown in my net worth from my retirement start until my demise.  

 
All of these were based on a set standard of living that was comfortable to me and allowed me to enjoy the hedonistic pleasures I want along the way. Those pleasures include international travel, upscale culture, food and beverage experiences, and of course great pussy.  

 
My family wasn't necessarily poor, more like middle class in the 60s through the 80's. But after that as I entered adulthood, I found myself on the low-income side and had to learn hard lessons about money and credit management.  I narrowly avoided bankruptcy a few times (while my sibling, sadly, did not). But I eventually found a career path that enabled me to earn a higher level of income. With the hard-learned lessons of my 20's I was able to leverage that income and accumulate a modest amount of net worth.  But those learnings persist: Live beneath your means, only use debt sparingly and wisely, set a budget and stick with it, save and invest always.  

 
Now I am on track to hit my stretch objective.  That means I can continue to pay for my hedonistic indulgences in addition to living at the comfort level I want.  I too can't bring myself to spend $1k for an SB PPM, other than a few bucket list experiences. Fortunately, I've been able to live in the sugar bowl offering allowances between $300-$500 ppm and having BCD's at least once a week (which is suitable for my libido).  

 
I still must manage my money, budget, and debt carefully. It would be far too easy (and a really bad idea) to just spend without a care.   But I'm in a good place and think I can maintain it for as long as needed and while I still want to have sex with hot 20-something babes.  

 
Life is good

 
The Cat

END OF MESSAGE

I'm re-reading Alexander Green 's excellent book: The American Dream. Why it';s still alive and how to achieve it. Chapter 19 directly addresses the dilemma you are describing:  We've spent our lives doing the right things: working, saving, and investing, and always living below our means.  Now that we've achieved financial freedom it feels wrong to spend money frivolously.  But I am realizing that at the rate I'm going, I will leave a considerable fortune behind, which is dumb! So I'm finding it easier to spend $ on the things that matter to me, esp sugar dating.  Look at one of the online calculators like this Savings Distribution Calculator
https://www.dinkytown.net/java/savings-distribution-calculator.html
Enter your net worth, your rate of return, and your years remaining, and your monthly spending.  You might be surprised to see that you are still gaining wealth every year, NOT spending down the nest egg.

I have not completed;y stopped working yet but I am dramatically reducing my workload and probably will stop in the next year or two. So Mouche I have spent quite some time figuring out how to make retirement happen where I can be happy and not especially stressing about money. One principle I learned from the land gentry is "never touch principal". With that in mind you will never run out of money and will be able to leave it to heirs. So my main goal was figuring out how to meet my needs (including sugaring) living off interest/dividends. In addition I have to be mindful of the devastating effects that inflation has on savings. I am hoping that I'll live another 20 years at least. Even at 3% per annum inflation really cuts into your savings. (Which also means that SBs will need more $ in the future to offset their inflation.) So I had to factor that in. I now have a plan which means I will never spend down my nest egg.

Yes. What got me started on this was a couple of articles suggesting people are underspending in retirement and losing in quality of life.  
Since I've traveled a fair amount already I think the logical place to make up the gap is .. you know what!
And yes we'll probably keep earning from compounding. It's just hard to break that mindset.

Some use 2% and some use 4-6 %.  Its easy to figure and history is very solid on the the 3% rule that you wont die broke.
If you have a million in the bank and conservative investments you can pull out 30 k per year. I cant live on that and need at least 100 K  per year with no debt. That puts the minimum at at 4 million to retire and it dam sure would not hurt to go higher. Like the poster "Scaramouche "  I think about this all the time. Most savers struggle with spending retirement funds like myself. I am on the same page as Scaramouche  and would love to hear about how others view this subject ?      

I don't use a percentage rule.  I just spend as I see fit, without compromising or overspending.  My most important tool is calculating my net worth every year in January.  So far, for the 12 years I've been retired, my net worth each year has gone up, even though I'm spending more!  So, no worries.  And I know I can spend even more if I want to.

Like Sweetman, I don't follow rigid formulas. But I do pay attention to these guidelines, so digging into the details:

The 4% rule (or variations of it) is designed for a 30-year time frame, roughly 65-95 even though most people don't live that long. Social security assumes the average guy who hits 65 will live to 83. It also doesn't assume other income. My social security covers my essentials, so my nest egg is purely fun money, and I conceivably might have some other gigs.

If you've hit 70, this time frame shrinks to 20-25 years, giving more latitude. And thinking about sugaring.. Sweetman is an inspiration to us all but I would feel exceptionally lucky to be able to keep doing this at 80 and above, so take that spending plan down to 10 years.

If I'm a hunchbacked, shriveled up 85-year-old.. I WILL pay for the 1K SB and probably could only do it once a month... if any ladies are reading this, you need to wait a decade or more!

If I'm 90... I think I've solved the mystery of the 1K platonic SB!

My long term plan is to have a young wife to care for me in old age.  So, I need to leave her and my kids something.  I'm still working though.  I may sell my practice and fully retire some day.  I don't see me doing nothing all day anytime soon.

Here’s a subject we should all comment on. My income and net worth has surpassed all my dreams. That said, I still can’t go over 300 for pussy. The few times I have I found it no more satisfying than the ladies I meet on my budget. Also, when I see how hard others work for 300 after tax dollars, I just can’t justify it.  I have no problem telling them they are out of my range and the bullshit that I’m living on a fixed income. We part on friendly terms.  I recently found a super keeper, and it just reinforces my discipline.

My kids could care less, but I feel better about things.

As we age the biggest threat to any of us is a major market decline ( that we are due for, last one being in 2007-08 ) a major health issue or possibly a real multi country war. We have all been through market declines. Losing 40% or more of your stock assets will get your attention, even worse if it takes 10,15 or 20 years to recover. At 50 years old  we had time to recover not so much today. A major health issue is probably the biggest threat. I know a US Trustee in the bankruptcy court and he said all he does every day is deal with people who had good lives but lost everything to a health issue costing 100-300 K per year and ran out of money . Most made the mistake of going with the Medicare advantage plans. Regular Medicare may cost you a few hundred per month but your Dr. calls the shots and its almost unlimited coverage. If a large War breaks out we will probably have a lot more problems  other than pussy and money. Lol