Any regrets?

In the months coming up to ER, I regret not adjusting my AA sooner as I FIRE'd in Jan of 2008 when the great recession was starting to slip, slide away.

But I hadn't planned to FIRE in Jan 2008, instead situations at Megacorp made that the right time.
 
First one is we wanted to buy a cottage. But we decided that would be too expensive, so we bought a trailer instead, one that was permanently settled on a little plot of land by a lake in a trailer park. $30k. It was a hassle commuting up there for weekends, and we had to mow the lawn which was huge. One time we went up, and the entire trailer was filled with flies. There must have been tens of thousands of them. Then, the owner announced the park had been sold and everyone had to remove their trailers. We were able to sell it for $1500, less than a year after we originally bought it. Oops.

My second is I bought a stock that had suddenly dropped around 60% due to a bad earnings release. I even talked my husband into buying some because I was sure it would rebound. A few weeks later, they announced the directors had been falsifying the financial reports and the stock is now worthless.
 
My only regret is that I wish I had done some of the things I am doing in retirement earlier in life. Lesson learned. I am off and running as best as I can.
 
After the government did not let Bear-Sterns fail, I took that as a signal that Lehman Brothers was a safe investment. We all know how that turned out.
 
I wish I'd been exposed to the ideas of ER and simple / sustainable living sooner. We could have retired years ago. C'est la vie - at least now we get it.

It has been pretty wild how much we cut from our budget just from small changes all adding up - LED bulbs, having more time to cook from scratch, eliminating most single use products, making use of the library, dropping cable, switching cell phone plans, etc.
 
I regret not learning about passive investing and AA sooner. And getting cheaper financial advice. Wow I think I would be ridiculously wealthy if I had, instead of just very happily wealthy.
 
I have been kicking myself for not doing a Roth conversion last year. We didn't have that much income, and it would have been a great time to do it. I won't make the same mistake this year - the last year before DH turns 59 1/2.
 
I have learned I take not making money much better than loosing money. So, I am ultra conservative. And am ok with it.
 
I was way too conservative when I was young. I was good at saving, but stuffed it all into conservative funds. Also, I was told that a house was a good investment. If I had it to do over, I'd understand that rather than "buy the most house you can afford", "buy the least house you can tolerate" would have been better advice. Rental real estate may or may not be a good investment, but the roof over your own head is mostly an expense.
 
Would not have refinanced our current home. Didn't need to - could have paid cash for the remodel and the house would be paid off in 2016. We did learn our lesson and paid cash to build our retirement home. We plan to sell our current home in 2015 or 2016 and move into our retirement home. I just think about all the extra interest we paid - UGH.
 
Being too conservative over my investment lifetime; probably would have 2-3X what I have now, although being conservative enabled me to sleep better at night.

I resemble that remark, pretty much my biggest regret as well.
 
Oh, and trading cars so frequently back in the "keeping up with the Jones" phase, learned about depreciation the hard way...
 
If I had it to do over, I'd understand that rather than "buy the most house you can afford", "buy the least house you can tolerate" would have been better advice. Rental real estate may or may not be a good investment, but the roof over your own head is mostly an expense.

I would have bought a small, newer house. Ours has been kind of a money pit.
 
I wish I had learned the fundamentals of low cost investing and invested in income real estate earlier. But overall I did not make too many bad decisions.
 
Would not have refinanced our current home. Didn't need to - could have paid cash for the remodel and the house would be paid off in 2016. We did learn our lesson and paid cash to build our retirement home. We plan to sell our current home in 2015 or 2016 and move into our retirement home. I just think about all the extra interest we paid - UGH.

It might not be as big as mistake as you think.

Have you considered the income that you earned on the funds that you would have spent if you had paid cash? In my case the extra investment results that I have earned far exceed the extra interest that I paid.
 
Speaking of financial regrets, I could have invested with a more aggressive AA during my working life in order to capitalize on the great bull market of 1980-2000. However, I still managed to end up with a decent net worth to ER. So, I have stopped beating myself up.

But the OP really asked about mistakes in post-ER life.

... I'm interested in regrets people have for financial decisions they've made in their planning for FIRE or since they called it quits...

This, I cannot really answer as yet, as my earned income only stopped coming in 2 years ago. So far so good is all I can say.
 
Regrets? I've had a few, but then again, too few to mention

I did what I had to do and saw it through without exemption.

A bit of trivia...

The song "My Way" popularized by Sinatra had its lyrics written by Paul Anka.

See: My Way - Wikipedia, the free encyclopedia.

The tune was taken from the 1967 French song "Comme d'habitude" ("As usual") by Claude François. The original French lyrics is nothing like the English lyrics.

See: Translation of "Comme d'habitude" by Claude François from French to English.
 
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I didn't recognize it when Michael posted it but when you reposted it I recognized it right away.
 
I was granted a large number of 10-year stock options by a tech company throughout the late 1990s. I could have exercised and sold for a ridiculously large sum of money prior to the dot com disaster. Most of us thought we would retire with millions before turning 40, and those who timed it right, did just that. All the way down, I was convinced it would eventually recover, and didn't want to sell for the smaller gain. The stock never recovered and the options ultimately went underwater and expired in the mid 2000s.

Me too. :( But it turned out OK, I just don't have that second home in Hawaii that I thought I might have.
 
My DW and I did what was probably the right thing by diversifying the holdings of the companies we worked for, but if we hadn't, our NW would be significantly higher, about 50%. We all know what happened with Enron, but we wish we hadn't diversified quite so much. Anyone else have regrets from decisions or mistakes made?


I have a similar story. I was a partner in a firm that IPO'd in 2001 which netted me a tidy sum. Having just witnessed Enron, Arthur Andersen, WorldCom, etc, I made it my policy to sell as many shares as I could, whenever I could (we had a pretty onerous lock-up scheme).

I got my shares out over about a six year period, with a sale price that probably averaged 1.5x the IPO price. Today that stock is trading around 6x the IPO price.

I can console myself with the fact that I paid 15% capital gains instead of the 28.8% that I would owe today - and as these were 'founders shares' the cost basis was zero. But still...

Having said that, I don't *really* regret it. If someone handed me another concentrated position tomorrow, I'd do the same thing.
 
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