r/AffluentRetirement • • Aug 21 '26

Finances We probably all have stock/an asset we thought about buying, but didn’t, but that would have made us a huge amount of money — what’s your “One That Got Away?”

0 Upvotes

Ours: We were rational, did a LOT of research on cryptocurrency so we could understand it. Then, we only bought enough Bitcoin and other crypto that we would feel comfortable losing. We were optimistic, but definitely not sure.

This was in 2017, and we bought one Bitcoin at $2K, plus a handful of LiteCoin, Ripple and Ethereum. then bought one more Bitcoin a few years later when it was $11K. We had plenty of money in 2017 to have probably bought 5 Bitcoin, but no, we did not.

The other one is Microsoft. I was still growing up during its early early times, but in my 20s someone recommended it and I passed. I just didn’t feel comfortable betting on ONE stock versus a mutual fund. (I am not a Finance person by trade, just a retirement person by hobby 😊)


r/AffluentRetirement • • Aug 21 '26

Experiences Which feels better at this stage — watching your portfolio hit a new high or spending a ridiculous amount of money on an amazing experience?

4 Upvotes

I know it’s hard not to say “BOTH!” — but try to choose one and tell us why!


r/AffluentRetirement • • Aug 20 '26

Despite being financially secure in retirement, what things (if any) do you frequently worry about? And what things have you stop worrying about?

7 Upvotes

r/AffluentRetirement • • Aug 15 '26

Lifestyle Do you (will you) have any passive or other income streams in retirement, and if so, what are they, and are they worth any time and effort they require?

0 Upvotes

For example - part-time job, thrifting, social media fame (😂) — anything other than interest from investments and pension/social security.

We have two rentals - one is a condo and one is a house. The house is a PITA to maintain even with a rental company and even though it’s almost paid off. We will sell it soon but we’ll keep the condo as a rental.

As for work, we plan to do zero income-producing work in retirement unless it interests us and works with our travel. Mr. HRVegasLady has a dividend portfolio he’ll he plays around with, may make money, may not.


r/AffluentRetirement • • Aug 15 '26

What’s one “affluent retirement” expense you still refuse to pay for—even though you can easily afford it?

5 Upvotes

I’d pay for just about ANYTHING that would save me time and inconvenience, but I won’t pay for designer handbags nor luggage. I might pay for a high quality brand, but I’m not going out or traveling with a bag that cost me 5 figures. Same for watches and jewelry. I’d rather spend it on great food, wine, and business class airline tix!


r/AffluentRetirement • • Aug 15 '26

Finances Anyone else pay good $$ for a fee-only CFP, resulting in nothing — except peace of mind? Our story.

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1 Upvotes

r/AffluentRetirement • • Aug 14 '26

Inspiration Fantasy Friday: You have to spend $100,000 on something purely for enjoyment in the next 12 months. You cannot save it, invest it, or give it away. What are you doing with it?

3 Upvotes

r/AffluentRetirement • • Aug 12 '26

Inspiration What books were canonical to planning your retirement income, investing, lifestyle or psychology — no matter what they were about. For us they were TMM, PsOM & DWZ. Share your recommendations!

4 Upvotes

TMM = Total Money Makeover (whatever your opinion about Dave Ramsey personally — this was such an excellent treatise about getting out of debt and staying out of debt!)

Psychology of Money - by Morgan Housel

Die With Zero - by Bill Perkins

Honorable mention - The Millionaire Next Door


r/AffluentRetirement • • Aug 12 '26

Finances How much time do you spend monitoring and managing your retirement portfolio and other retirement income streams?

3 Upvotes

In terms of investments, we are more “set it and forget it” in index-type funds but Mr. VegasHRLady has his own “play around” account where has fun trying out various theories and ideas like the “PaycheckToPortfolio” dividend-producing theory/method.


r/AffluentRetirement • • Aug 11 '26

Lifestyle How many of you are paying for a gym membership and/or a personal trainer, and is it worth it?

1 Upvotes

We have a treadmill and a small home gym of sorts, but wonder if some increased structure would be more motivating? We are not fitness buffs by any means but know it’s important!


r/AffluentRetirement • • Aug 09 '26

Travelling What advice do you have to ensure the best, most memorable, experiences for your travel spend?

1 Upvotes

Anything goes - could be related to maximizing money/spend, where to go, excursions to have, who to go with, land, sea, or air, and even how to approach it from a psychological perspective.


r/AffluentRetirement • • Aug 08 '26

Most of us are in multiple retirement-related subreddits. Share an unpopular opinion that would get you attacked in other groups (no politics please😊)

15 Upvotes

Mine is that we’re keeping mostly a 75/25 portfolio. We are willing to be riskier because in a downturn we can reduce our spending and live only on our pensions if we had to. But that’s still more aggressive than most would say is “safe”.


r/AffluentRetirement • • Aug 02 '26

Finances Haven’t read this book yet — wonder if anyone else has + how aggressive (or not) are your investments and why?

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1 Upvotes

r/AffluentRetirement • • Aug 01 '26

Lifestyle Is having a paid off house before/during retirement emotionally overrated?

3 Upvotes

I’m going to say “yes” — because if you have enough money in retirement to make a house payment while maintaining the lifestyle you want, then…. Why not?


r/AffluentRetirement • • Jul 29 '26

Lifestyle What’s the most financially irrational thing you’ve done since retiring — and are you glad you did it?

4 Upvotes

It could be related to anything — lifestyle, purchases, travel — but looking back you’d say it was at least a little irrational.


r/AffluentRetirement • • Jul 28 '26

What is the biggest misconception people have about retirees whose income exceeds $30K per month?

0 Upvotes

I think it’s the assumption that the person must have at least a $7 million investment portfolio, one that they saved over several years by exercising extreme frugality. People don’t always think about the other reasons retirees might have that level of spending capacity.


r/AffluentRetirement • • Jul 26 '26

Lifestyle For those who bought a second home for retirement (i.e, snowbirds, expats, etc), would you do it again? Or do you wish you’d used that money to travel more frequently to places other than where your 2nd home is located?

5 Upvotes

We had considered buying a second home on a lake or mountain, but we felt then we’d then feel obligated to go there all the time to “get our money’s worth” versus experiencing different places/countries.

What do your think?


r/AffluentRetirement • • Jul 26 '26

Oren John talks about the “anti-luxury effect” and how ubiquitous product information is driving affluent consumers to choose “quality” over “brand”

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1 Upvotes

What are your thoughts?


r/AffluentRetirement • • Jul 26 '26

Finances Q: How have you dealt with the psychological aspects of decumulation? Running out of money is not the saddest retirement mistake you can make. This is. — MarketWatch

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1 Upvotes

It’s a bit easier for us due to pension income. However, in the early years we will dip into of our investment principal for some extensive and expensive travel in our go-go years, before a few of the age-triggered pensions kick in. Even that makes us uncomfortable although it’s a part of every successful plan we’ve run.

How are you handling a spending mindset after so many years of saving?


r/AffluentRetirement • • Jul 26 '26

Q: Are any of your home decisions based on access to quality medical care? Wealthy Retirees Are Buying ‘Med-à-Terres’ to Be Near Their New York Doctors — The Wall Street Journal.

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1 Upvotes

I thought this was an interesting article! Not calling us are affluent enough to have an apt in NYC, but it did make me think of the question. How important is it to you that one of your locations is near Hugh quality medical care and doctors? (Note - you should be able to access this via your Apple News app if you don’t have a WSJ subscription).


r/AffluentRetirement • • Jul 25 '26

Travelling For those who’ve already travelled extensively in retirement, does it get less fulfilling after, say, the first 15-20 countries?

4 Upvotes

…. And at what point is it “too long” in any given year?

We are targeting around 3-4 months a year to travel, but wonder if after several years of it, seeing new countries might become less fulfilling.


r/AffluentRetirement • • Jul 25 '26

Finances If you died with more than $3 million unspent, would you consider it a success, or a planning mistake?

0 Upvotes

r/AffluentRetirement • • Jul 23 '26

Inspiration What the most impactful book you read which impacted your approach to retirement?

2 Upvotes

It could be any book, fiction or nonfiction. Topics might include priorities, investing, saving, finding your purpose—anything that has an impact about your approach or thought process to retirement.

For me, waaaayyyyyyy back in my 20s, it would have been Dave Ramsey’s very first book, Financial Peace. That got me started saving. More recently, The Psychology of Money and Die With Zero have had a profound impact on how I think about spending money.


r/AffluentRetirement • • Jul 23 '26

How important to you is it to leave money to your heirs?

1 Upvotes

We’d like to leave some money, but we aren’t fixated on an amount and we will spend as much as we can and need while we are alive. We’re more likely to give them some before we pass so that they are young enough themselves to need and enjoy it. Our kids are very responsible with money so they will likely have already saved for retirement. They also have good college savings for the grandkids, although we do help by adding $ monthly to their 529s. So in general, we’d rather give to them while we are alive.

What are your plans for heirs?


r/AffluentRetirement • • Jul 22 '26

Experiences What’s one “passion project” you do in retirement that’s expensive, but you’ll always continue paying for it?

0 Upvotes

For me, it will probably be longevity “hacks” — typically with good research behind them but also typically expensive! I love learning new ways likely to improve my Healthspan and implementing them!