There’s an interesting article in WSJ on how people have been conscientious and frugal their entire life saving for their retirement but this frugality prevents them from spending in retirement and threatens to keep people who have enough money to enjoy life from spending that money.
https://www.wsj.com/articles/the-mental-mistakes-we-make-with-retirement-spending-1492999921
We are not officially retired (i.e., I’ve been a SAHD without an externally funded paycheck; DW still works). We have saved multiples of what we need.
Our last vacation, in Grand Cayman, is where I finally broke through. We like strong coffee. We opted not to drink the okay coffee, but weaker than we like, at breakfast, and had multiple double espressos instead. I found myself counting the espressos, like watching a taxi meter, until I thought: WTH! We are going back in a few weeks, and I will enjoy every espresso!
Yesterday was my last day of work. I am 59 and officially retired. And here I am on CC. I think I need a better plan. 
@ChoatieMom --Congrats on your retirement and I got a laugh out of your post!
@IxnayBob, if you are anywhere near Tukka (restaurant), I highly recommend it. GC is one of our happy places.
I totally get counting the coffees (and drinks). But we, like you, have started to say what the heck. We do tend to stay in places that have at least partial kitchens, and eat some meals in, but we find a balance.
Congrats, @ChoatieMom!
Great article, @cbreeze. Thanks for sharing. I found a lot of relevance in it. Especially since we still have some college tuition bills, I struggle with what is prudent and what might be too frugal. I guess this tendency to save is what got us all to the place where we are having these discussions and have some savings to discuss. Not a bad thing overall. I try to think of what brings me happiness - travel, time with family, experiences, time to relax - and things I don’t really care about - consumer goods, impressing others. Our plan as well is to use some of our savings to make our kids lives easier at different points in their life through paying for vacations, helping with down payments, etc. We also fund Roths for them every year.
@planner03 Have you thought about what makes you happy when it comes to spending? Are there ways you could help out the kids now instead of just bequeathing your wealth to them? (I like how your user name has planner in it. )
@1214mom, we are staying at the Kimpton, all the way on the opposite end of the island. If we rent a car to explore, I’ll keep Tukka in mind. We’ve only had one meh dining experience on GC (Morgan’s), the others were noteworthy. If it weren’t for the large dog restriction, . . .
What I most regret is cashing in vacation instead of taking it. Over the years, due to numerous job changes, I’ve probably cashed in 3 or 4 months of accumulated vacation, and started new jobs right away instead of taking the time off.
I’m somewhat allergic to spending, But DW is helping me with that… the purse-strings are loosening. 
We’ve taken 3 pretty nice (i.e. expensive) vacations abroad in the last 5 years, did a big landscaping project which wasn’t really necessary but looks really nice, I bought myself a really nice musical instrument a few years ago. Last car I got I splurged on the heated leather seats and fancy stereo.
It certainly helps that we are done with college and the kids are launched.
There were times we let money drive certain choices, like where we went on family vacations and what-not, and in retrospect we could have afforded to spend the money. Probably the single biggest money-driven decision we made was to not be full-pay at private colleges. Both kids went to public universities (and were successful and had a great time, etc), and that decision probably saved me and them close to $300,000. Looking at where we are now, we could have swung it (or the kids could have a lot of debt), although we didn’t know that at the time. So I have no real regrets about that one.
@IxnayBob Are you still considering buying a home there?
@ChoatieMom - congrats. I am very jealous. B-)
@ChoatieMom , congratulations!
I can’t retire until I’m eligible for retiree medical benefits, which happens to be the same year retired Husband qualifies for Medicare, so our insurance premiums will go down. He has too many health issues to count on ACA remaining available and still sleep at night. (Not meaning to get political here).
Sort of. At least two things are contra: their large dog ban and wondering when they’ll be under water. Literally, not financially.
It has a lot to commend it though.
What’s the rationale behind the dog ban? Just curious.
@doschicos , they say they don’t want any breeds that were used in dog fighting. I get the other restrictions (e.g., the island is rabies free, and they want to keep it that way). I can also see restrictions on loose dogs, since there are loads of chickens on the islands that roam all over the place. I guess the common theme in the below list is large and capable of causing damage. For me, I’d be more scared of our Yorkie than our Pit Mix 
I guess I can understand the concerns, as unpopular as that opinion might be among fans of the breeds posted above. I haven’t been to the Cayman Islands but many Caribbean islands constantly fight a wild/street dog problem. Of the islands I am more familiar with, island dogs tend to be a pretty laid back, happy bunch (kind of like the human inhabitants ). Imbuing more aggressive traits into that mix might not be pleasant. I noticed Bermuda has a similar policy.
I am happy we were frugal when the kids were little and I don’t regret it one bit. We enjoyed our frugal vacations and the adventure of sleeping in tents and camping and staying with relatives. I won’t regret we didn’t spend more money, because I don’t believe it would have been more enjoyable just becuase it was more expensive. No regrets. I am thankful that, as I worked in the school system until the kids were off at college, I had all vacations off with them, and that allowed us the greatest gift of all - time to just hang out and be together in a leisurely fashion…
I just don’t agree with the premise that the more expensive event, food, vacation, wine, have you, is necessarily better.
“@colorado_mom, what would the advantage be of taking Social Security early in relation to not having pre-65 medical insurance?” - That is when we will be paying $2000 (?) per month for medical insurance… ie higher expenses than today. DH leans toward letting investments grow during that time. We won’t do closer analysis of the situation until it get closer - too many changeable factors.
Ouch. Got it. It’s too bad that the age for Medicare enrollment isn’t lower.
@ChoatieMom - Happy Retirement Day to you! We’ll want reports down the road. For now, just enjoy sleeping in!
Per “in retrospect” spending thoughts, hindsight is 20/20. I think for the most part we made the best choices with the info at hand. (In some cases job situation held better than hoped. Prior to that, we had job woes… but survived them fine because we always spent below our means). In my mind, the main thing is we got both kiddos through college with almost no debt. Since jobs are still holding, we try to do nicer things even if they won’t be affordable later. We just rented a a with the kids in Cape Cod near relatives (on July 4th week - gasp).
I was a little surprised at some of these rankings. Affordability and quality of health care do not seem to appear together.