Any regrets?

[Dash man]

No, I'm not talking about regrets for RE, since there most likely wouldn't be any responses. I'm interested in regrets people have for financial decisions they've made in their planning for FIRE or since they called it quits.
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?

 

[Fishingmn]

Around 2000 my software company announced a partnership with a firm that made expense management software. I decided to buy 4,500 shares of their stock since it was only at .90. I then sold it when it got to $2.00 thinking I made it big.

Today Concur Technologies (cnqr) is over $90/share. That $400k would look nice about now.

 

[MichaelB]

Regrets? I've had a few, but then again, too few to mention

 

[REWahoo]

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

 

[pb4uski]

I think the only regret I have is not having the courage of my convictions to stick to my AA and sell bonds and buy stocks in the depths of the great recession. I've never checked but I suspect it cost me 10% of my NW or perhaps more.

 

[aim-high]

Around 2000 my software company announced a partnership with a firm that made expense management software. I decided to buy 4,500 shares of their stock since it was only at .90. I then sold it when it got to $2.00 thinking I made it big.

Today Concur Technologies (cnqr) is over $90/share. That $400k would look nice about now.

That reminds me of a funny story. Back in 1986 a couple of friends and I ran a College Storage business at our college. We rented tractor trailers, marketed the services, and stored students belongings over the summer in the trailers so the students didn't have to take them home and back. Altogether we netted about $3k each in profit. We figured we'd settle up at the beginning of the next school year so the guy handling the money put it all in Microsoft over the summer. When we got back he said we could either have the shares or take the cash. We all took the cash (it was beer money for the year) and none of us had brokerage accounts or knew much about the market.

Today's equivalent would have been around $1.2 million. So the opportunity cost of two fun loving semesters of beer cost over a million.

I didn't realize that is the choice I was making when I was 20!

 

[Pleeplus]

Today's equivalent would have been around $1.2 million. So the opportunity cost of two fun loving semesters of beer cost over a million.:

OUCH!! Well I hope you at least did not spend it on cheap beer!!

My only regret is that I wish I would have educated myself sooner in regards to personal finance and investing. My fear of the unknown and perception that investing was too complicated for me to tackle kept me on the sidelines.

 

[travelover]

For the first 10 years that I worked at MegaMotors, I didn't contribute to the pension fund. Indeed, everyone that I met there said I'd be a fool to do so, as they expected the company to collapse at any time.

Now retired, that costs me about $20K a year in lost pension benefits. The good news is that I did save and invest the whole time and even so, my collectable pension has covered all my costs, so far.

 

[martyb]

I am a soon-to-be retiring federal employee. In 2008, I made a career move within the fed system that increased my pay by some, but more importantly increased what my eventual pension will be. However, I regret not making the decision to make that career move about 10 years sooner. I did consider it, but procrastinated, because I was comfortable with what I was doing. Had I made the move 10 years sooner, my pension would be substantially more than it's going to be. I could keep working and achieve the same or similar results, but I'm not going to work into my mid-60's or beyond. Lesson learned, I'll do better next time.

 

[RunningBum]

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?

My situation was the counter to yours. It wasn't an Enron, but I stayed too strong with my company. It had doubled every year during the tech boom. Luckily I was forced to exercise (and smart enough to sell) some of my initial options due to expiration, and exercised just part of another set right around the high at 2000. But the bubble burst and a lot of my options went underwater and stayed there. It delayed my ER 10 years. I did well by holding it through the 90s but when I hit a number I'd have been very comfortable ER'ing with I didn't pull the trigger. One reason I remember is that I was planning to move to a state with a lower tax rate the next year so I looked at how much that 2% would add to it, and I thought the stock would still go up. I don't beat myself too much because it basically amounted to not timing it right, even though I could see some of the signs, like the company expanding into areas beyond their expertise.

 

[ERhoosier]

Around 2000 my software company announced a partnership with a firm that made expense management software. I decided to buy 4,500 shares of their stock since it was only at .90. I then sold it when it got to $2.00 thinking I made it big.

Today Concur Technologies (cnqr) is over $90/share. That $400k would look nice about now.

I felt the same way at the casino last week after I resisted my gut instinct to put my nest egg on 17 Black at the roulette wheel....at it hit
Seriously- you cannot predict the future. You make your best decisions based on the best info you have at the time & move on. Congrats on doubling your investment!

 

[eytonxav]

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.

 

[Rustic23]

No regrets. I would rather be happy with the investments I have and retired, than still working lamenting the decisions I made. I propose you look at the glass another way, and be thankful you did not work for Enron. Every financial decision I have made could have been made better, some a little some a lot. They also could have turned out worse.

 

[Cobra9777]

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.

Also at the time (late 90s), about half my 401K was in the company's stock (my choice). And to make a bad story worse, I accumulated a mountain of additional stock via voluntary ESPP. It wasn't until around 2003-4, that I liquidated all that cr@p and found AA religion.

Ten years later, I ER'd at 52, which was largely enabled by doing the exact opposite in the 2008 meltdown... I had continued to accumulate low-priced options in the bloodbath of 2001-2003. I sold it all in early 2008 for a tidy sum. I then held the cash through the '08 meltdown and bought stock index ETFs like crazy in early 2009, along with rebalancing the rest of the portfolio to my target AA, which was 70% stock at the time.

So yes, I have deep regrets for decisions I made in 2000. I was young and got sucked into a fervor about the company's prospects. But the good news is I learned from it, recognized what was happening in 2008, and made an opportunistic move that enabled FI and ER a few years later.

 

[RockyMtn]

In 1978 I bought 1000 shares of a company called Blue Ribbon Sports for $1 a share. I had seen a number of students wearing these waffle soled shoes with a checkmark logo around the University of Oregon where I was a student.

Sold the stock a couple of years later after it doubled. The stock has now split 2 for 1 five times. My initial 1000 shares would be 32000 shares. At the current stock price those 32000 shares would be worth $2.34 million.

Yes the company is Nike.

 

[FIREd]

No regrets. With hindsight, we could have made better decisions, like cashing in our stock options at the top of the market. But without the benefit of hindsight, I think we did the best we could.

 

[travelover]

My only true regret is not picking parents that were wealthier and better looking.

 

[nash031]

I've purchased 3 cars since graduating college 14.5 years ago. I wish I had skipped the second one, where at 26 I traded in a perfectly good, paid-off, four-year old car with about 50,000 miles. Three years later, I figured out that the second car didn't meet my needs, and I traded it for my current car which I've now had for over six years (effectively paid cash, now with 70,000 miles, aiming for 150k or until the wheels fall off.)

It was a "whim" purchase and I'd likely have about $20k more saved (not counting compounding). I had fun with it, but not $20k+ fun. Less of an investment regret than a LBYM regret.

Otherwise, most of the investing lessons I've learned the "hard way" - speculative stock investing in pre-dotcom bubble 2000s - have been relatively inexpensive (less than $2000), but invaluable nonetheless.

I did think to myself in the early 2000s that I should buy Apple stock - I always loved their computers - when I heard about this neat little "iPod" thing in the works. Unfortunately, I didn't have the funds to move on it at the time. That would've been an 80-90-bagger if I had...

 

[rodi]

I wish I hadn't used the credit cards issued to me while still a starving college student. My ignorance and free spending left me dealing with debt for several years after college.

 

[TimSF]

My only regret is that I wish I would have educated myself sooner in regards to personal finance and investing. My fear of the unknown and perception that investing was too complicated for me to tackle kept me on the sidelines.

+1

 

[jayc]

Limit order for 200 shares CMG (ipo) at $44. Should have been a market order.
It closed at $552 today.

 

[KingB]

I should have put my 401K contributions into 401K Roth IRA to reduce my RMD. I am now trying to do IRA - IRA Roth conversions and time is running out.

 

[KingB]

Another 1:
I should have delayed receiving SS benefits until I reached FRA instead of taking it when I retired.

 

[RetireAge50]

Had big gain in yahoo stock held in IRA. Converted it to Roth and paid taxes. Later stock went to almost nothing so ended up paying those taxes for nothing.

 

[Sanbenito1]

I wish I had made an appointment with a financial planner when I was 30, not 40. That initial visit was very embarrassing - I knew absolutely nothing, except to save (which I guess is something, as I ER'd at age 55). That first talk with my CFP started me down the path of self-education. Better late than never, I guess.