Regret of selling winning stocks early

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virw
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Regret of selling winning stocks early

Post by virw » Thu Jan 28, 2016 11:16 pm

I used to work at a public company and got some stock compensation. Since it was a large part of my portfolio back then, when I received the shares I decided to diversify and sold most of them to buy index funds. However the company's share has since done very well compared to the overall market and thus I would gain significantly more if I hold the shares instead of diversifying. But I know I made a right decision, so should I not regret? Did anyone get to the same situation?

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saltycaper
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Re: Regret of selling winning stocks early

Post by saltycaper » Thu Jan 28, 2016 11:32 pm

I missed out on a quarter-million-dollar profit by selling Apple too soon. All I had to do was nothing. But don't waste time on regrets. There's always something you could have done in hindsight that would have produced a much greater return than what you chose. Remember this saying by Larry Swedroe: "Don't confuse strategy with outcome." If you have a sound strategy--and I think diversifying out of a single company's stock is part of a good strategy--don't worry about outcomes that never were.
"I guess I should warn you, if I turn out to be particularly clear, you've probably misunderstood what I've said." --Alan Greenspan

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randomizer
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Re: Regret of selling winning stocks early

Post by randomizer » Thu Jan 28, 2016 11:34 pm

This is happening to me right now. My company has out performed the market for multiple years now.

I'm fine with it though. I stick to my plan and sell and diversify. This hasn't made me rich, but I have no interest in betting on a single horse.

I sleep well at night.

EHEngineer
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Re: Regret of selling winning stocks early

Post by EHEngineer » Thu Jan 28, 2016 11:41 pm

When I converted to indexing I sold my REGN (regeneron) holdings at about $70 per share. Less than 6 years later they are trading above $400; they were nearly $600 for a time.

Don't confuse strategy with outcome. I sold Regeneron because I wanted to diversify and take an appropriate amount of risk. The fact that it went up after I sold doesn't mean I was wrong. It proves what I admitted when I switched to indexing: I don't know which stocks will go up or which ones will go down. You don't know that either, and neither does anybody else (that doesn't have illegal-to-trade-on insider information).

If it makes you feel better, as an indexer you also avoided owning any individual stocks that recently tanked.

Don't regret! 8-)
Or, you can ... decline to let me, a stranger on the Internet, egg you on to an exercise in time-wasting, and you could say "I'm probably OK and I don't care about it that much." -Nisiprius

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Re: Regret of selling winning stocks early

Post by Wagnerjb » Fri Jan 29, 2016 1:19 am

I know a fair number of people who used to work at Enron and who lost a bunch when the company collapsed. For everyone who got lucky with company stock and options, there is an Enron story.

Best wishes.
Andy

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k66
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Re: Regret of selling winning stocks early

Post by k66 » Fri Jan 29, 2016 1:30 am

Yes, absolutely. My company stock often has periods of great performance, but regardless, once a year I sell all the shares that have vested and convert to index holdings.

I haven't done the actual math, but I am sure that I could have been further ahead had I kept everything in the share ownership plan. But then again, it could have all imploded on me too--and could still yet.

I have never lost any sleep over it, in fact, maybe even sleep better knowing I have much better diversification this way.
LOSER of the Boglehead Contest 2015 | lang may yer lum reek

quantAndHold
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Re: Regret of selling winning stocks early

Post by quantAndHold » Fri Jan 29, 2016 2:33 am

I work for one of those companies now. I think about whether or not I'd hold the stock if I didn't work there. The answer is yes, but much less than they give me. So I hold the small bit that I'd hold anyway, sell the rest as soon as it vests, and invest it in something else. I don't worry about missing out.

My current company is doing fine, but I have been left holding the bag when my employer at the time went bankrupt. The stock was $23 one day, $2 the next, and $0.26 when I sold it a few weeks later. Fortunately I'd been selling all along so I only lost about $20k, but I had coworkers who were wiped out.

Goal33
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Re: Regret of selling winning stocks early

Post by Goal33 » Fri Jan 29, 2016 2:39 am

Sometimes being smart isn't always the most profitable. I think you did the right thing.
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Toons
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Re: Regret of selling winning stocks early

Post by Toons » Fri Jan 29, 2016 4:19 am

"However the company's share has since done very well compared to the overall market and thus I would gain significantly more if I hold the shares instead of diversifying."

Isn't that the beauty of looking in the rearview mirror?
In hindsight everything is 20/20.
Shoulda, coulda, woulda,
Move On.
Hmmm,,,,,,if I had only kept those Amazon shares I bought 10years ago. :D :D
"One does not accumulate but eliminate. It is not daily increase but daily decrease. The height of cultivation always runs to simplicity" –Bruce Lee

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Maynard F. Speer
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Re: Regret of selling winning stocks early

Post by Maynard F. Speer » Fri Jan 29, 2016 4:51 am

Simple rule: never sell anything that's uptrending (i.e. price above its 100-200 day moving average)

I think of opportunity cost as very real ... Trends aren't crystal balls, but they take a helluva lot of guesswork out of things
"Economics is a method rather than a doctrine, an apparatus of the mind, a technique of thinking, which helps its possessor to draw correct conclusions." - John Maynard Keynes

sambb
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Re: Regret of selling winning stocks early

Post by sambb » Fri Jan 29, 2016 7:00 am

Yes it would have been financially better to keep the stock
Unfortunately, (as with relationships, marriages, children, careers, etc.) it is impossible to predict.

Indexing is great, but won't beat the right stock picking. Hard to get it right though for decades and decades. I hit it big on two stocks - one of which was apple, that allowed me to pay off my mortgage. It went up after i sold it too. Nevertheless, I am so glad i didn't index and kept that stock for most of the ride.

I hope you prosper in the boglehead philosophy, but who knows what the future will bring.

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Re: Regret of selling winning stocks early

Post by Call_Me_Op » Fri Jan 29, 2016 7:30 am

virw wrote:I used to work at a public company and got some stock compensation. Since it was a large part of my portfolio back then, when I received the shares I decided to diversify and sold most of them to buy index funds. However the company's share has since done very well compared to the overall market and thus I would gain significantly more if I hold the shares instead of diversifying. But I know I made a right decision, so should I not regret? Did anyone get to the same situation?


You can still regret, but you made the right decision. If only we had a clear crystal ball.
Best regards, -Op | | "In the middle of difficulty lies opportunity." Einstein

Snowjob
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Re: Regret of selling winning stocks early

Post by Snowjob » Fri Jan 29, 2016 7:36 am

Maynard F. Speer wrote:Simple rule: never sell anything that's uptrending (i.e. price above its 100-200 day moving average)

I think of opportunity cost as very real ... Trends aren't crystal balls, but they take a helluva lot of guesswork out of things



do you make broad shifts in your asset allocation the trend shifts negative like today?

Snowjob
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Re: Regret of selling winning stocks early

Post by Snowjob » Fri Jan 29, 2016 7:38 am

haha, I remember one stock that I sold after a triple, could have had a 10 bagger if I waited, but is now bankrupt. sooooo yeah I'll take the smaller gain and roll into the index. I'm ok with placing preservation of capital over return of capital at this juncture of my life.

synpacket
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Re: Regret of selling winning stocks early

Post by synpacket » Fri Jan 29, 2016 7:51 am

You made the right call! If you play that game enough times, you will lose.

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fortyofforty
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Re: Regret of selling winning stocks early

Post by fortyofforty » Fri Jan 29, 2016 7:57 am

Toons wrote:"However the company's share has since done very well compared to the overall market and thus I would gain significantly more if I hold the shares instead of diversifying."

Isn't that the beauty of looking in the rearview mirror?
In hindsight everything is 20/20.
Shoulda, coulda, woulda,
Move On.
Hmmm,,,,,,if I had only kept those Amazon shares I bought 10years ago. :D :D


:oops: That was me. Sold Amazon at around $13, when the "experts" said it was more than fully valued at that price. I made a profit, but not a PROOOOOOFIT. Anyway, I realized that individual stocks are not for me. Now I just try to own all of them. :beer You made the correct long-term decision. But, you'll always regret the ones that got away.
"In a time of universal deceit, telling the truth becomes a revolutionary act." - George Orwell

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Maynard F. Speer
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Re: Regret of selling winning stocks early

Post by Maynard F. Speer » Fri Jan 29, 2016 8:04 am

Snowjob wrote:
Maynard F. Speer wrote:Simple rule: never sell anything that's uptrending (i.e. price above its 100-200 day moving average)

I think of opportunity cost as very real ... Trends aren't crystal balls, but they take a helluva lot of guesswork out of things



do you make broad shifts in your asset allocation the trend shifts negative like today?


I tend to rebalance too often, so it doesn't really happen .. But you learn and work out things you could maybe do better

In principle, if I had a target allocation of 10%, for (say) something that's done really well - like a Biotech ETF .. Then if it's going to keep climbing 20% a year for years and years, and generate quite strong compound returns, I could let its allocation drift up .. Then rebalance back to 10% when the trend starts wavering

I think if you're very systematic and disciplined with these kind of approaches, they could be an improvement on rebalance bands
"Economics is a method rather than a doctrine, an apparatus of the mind, a technique of thinking, which helps its possessor to draw correct conclusions." - John Maynard Keynes

johnubc
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Re: Regret of selling winning stocks early

Post by johnubc » Fri Jan 29, 2016 8:05 am

or one could have kept their money invested in great companies like GE, SUN Micro, City Bank, etc.

livesoft
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Re: Regret of selling winning stocks early

Post by livesoft » Fri Jan 29, 2016 8:24 am

I wrote about selling early about 5 years ago in this post:
viewtopic.php?p=914981#p914981

Isn't it amusing to re-read it now? Especially, since last year I wrote this about it:
viewtopic.php?p=2366008#p2366008 (corrected the link)
Last edited by livesoft on Fri Jan 29, 2016 9:20 am, edited 1 time in total.
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BlackStrat
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Re: Regret of selling winning stocks early

Post by BlackStrat » Fri Jan 29, 2016 8:29 am

Don't feel bad. I held on to a large amount of company stock with the idea to let it go up 'just a little more'. Since mid 2015 it's gone down over 35% and now I'm wondering whether to hold it a little longer to let it go back up 'just a little more'.

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Re: Regret of selling winning stocks early

Post by clip651 » Fri Jan 29, 2016 9:17 am

(no longer relevant, deleted)
Last edited by clip651 on Fri Jan 29, 2016 9:37 am, edited 1 time in total.

thomasbayarea
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Re: Regret of selling winning stocks early

Post by thomasbayarea » Fri Jan 29, 2016 9:24 am

I have always sold ESPP & RSUs immediately on vesting.

Some years I was unhappy because waiting would have been profitable.

Last 2 years selling immediately has been profitable.

Who knows the right answer :confused

Move on :sharebeer

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SeeMoe
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Re: Regret of selling winning stocks early

Post by SeeMoe » Fri Jan 29, 2016 10:58 am

Growing up I would occasionally hear the elders mention " losing out" on Xerex or Packard, Etc. stocks when they were cheap . Then the sad sigh: "If I had bought 100 shares back then , it would be worth $$$ because it split 10 times, Etc ." Always " The coulda, woulda, shoulda" stories by losers who always would be losers in the markets because they were inept speculators and gamblers,...Not long term investors .
SeeMoe.. :moneybag
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printer
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Re: Regret of selling winning stocks early

Post by printer » Fri Jan 29, 2016 5:42 pm

There are a lot of ways to think about it. Regret is only one. Another is that you could have used the proceeds to invest in a company that went up 100x in the same period. Do you regret not doing that, too?

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Re: Regret of selling winning stocks early

Post by LeeMKE » Fri Jan 29, 2016 6:28 pm

Just one more story to back up the premise that you can't plan your investments by using a rear-view mirror.

I've missed several lucrative opportunities by doing the right thing and diversifying. And I remember the ouches with some pain.

However, I have no memory of the problems I've avoided. One employer's stock rises to new highs, after I sold it to diversify. Another former employer goes bankrupt, but I don't remember because I diversified out of their stock years ago. I bought shares of all the stocks that became blockbusters, only because I diversified away from employer stock, and those blockbusters are buried in the overall performance of the funds I chose.

In the long run, be smart. The smart alecks only win in the short term.
The mightiest Oak is just a nut who stayed the course.

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Re: Regret of selling winning stocks early

Post by Artsdoctor » Fri Jan 29, 2016 6:32 pm

Virw,

You can carry over those thoughts to every aspect of your life. Could you have done things differently with your career? Your marriage? Your kids? Your friends? It will never stop if you go down that rabbit hole.

We learned as medical students that you cannot play Monday morning quarterback. You can look back and learn from mistakes, and you can learn to do the best you can in real time, and you can definitely learn to do things so that you can look back and say you did the best you could. But looking back with regret over something like selling an investment is an exercise in futility. If you feel as if you made a mistake, learn for it. Otherwise, move on.

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Re: Regret of selling winning stocks early

Post by joebh » Fri Jan 29, 2016 8:30 pm

virw wrote:Since it was a large part of my portfolio back then, when I received the shares I decided to diversify and sold most of them to buy index funds. However the company's share has since done very well compared to the overall market and thus I would gain significantly more if I hold the shares instead of diversifying. But I know I made a right decision, so should I not regret?


You diversified to reduce risk, not to take a chance on maximizing your return.
You made the right decision for the right reason. It doesn't matter what "could have been" in any alternate scenario. Move on and don't look back.

EarlyStart
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Re: Regret of selling winning stocks early

Post by EarlyStart » Fri Jan 29, 2016 9:30 pm

virw wrote:I used to work at a public company and got some stock compensation. Since it was a large part of my portfolio back then, when I received the shares I decided to diversify and sold most of them to buy index funds. However the company's share has since done very well compared to the overall market and thus I would gain significantly more if I hold the shares instead of diversifying. But I know I made a right decision, so should I not regret? Did anyone get to the same situation?


You effectively managed risk. There's nothing to feel bad about.

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Re: Regret of selling winning stocks early

Post by sawhorse » Fri Jan 29, 2016 9:40 pm

I can't speak about employer stock because I've never been in that position.

In terms of non-employer stocks, my experience has been that in the long run, the regret of selling winning stocks early (definitely can relate!) is balanced out by the relief of not hanging on too long. Like you, I've kicked myself for selling winning stocks too early, but when I look at the whole list of transactions, there were also a bunch of stocks that I'm glad I didn't hang onto.

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Re: Regret of selling winning stocks early

Post by ge1 » Fri Jan 29, 2016 9:59 pm

I wish I had that problem, my company stock goes down all the time :-)

On a serious note, I never regret taking a gain, even if it could be bigger. Yes I probably "lost" 100k by selling Starbucks too early, but I also sold Citi in the 20s before it went to $1, sold IBM in the 180s or Caterpillar with a 10% gain before it lost 30%. Don't get greedy.

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Re: Regret of selling winning stocks early

Post by magneto » Sun May 01, 2016 3:17 am

Maynard F. Speer wrote:Simple rule: never sell anything that's uptrending (i.e. price above its 100-200 day moving average)


It has been suggested that stocks spend one third of time :-

1. At All Time Highs
2. Making New Lows
3. Recovering

When a stock position is hitting All Time Highs seems the more sensible option of the three as to when reduce. :?:

If however some measure or over-arching criteria such as Portfolio Construction or even Momentum is bothering the investor, then the position can be reduced back to a higher target level than at the last transaction. The investor is thereby creaming off some of the capital gain, while leaving part of the capital gain to add fuel to the fire. Sort of have your cake and eat it. :!:
'There is a tide in the affairs of men ...', Brutus (Market Timer)

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Re: Regret of selling winning stocks early

Post by sambb » Sun May 01, 2016 5:23 am

If your goal was to accumulate wealth, then yes, you made the wrong decision, as the stock has done better.
If your goal was to spread out your risk, then you have done better, because you are spread out over more companies.

I think it comes down to what your goals were. I would feel bad also if I had given up extra gains. Sometimes it doesn't work out in your favor when you index, if an individual stock pick did better. But your risk is definitely lower in an index.

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Re: Regret of selling winning stocks early

Post by afan » Sun May 01, 2016 8:51 am

I have a friend whose company stock is up about 20% over the past year, but he is bummed because it is down about 3% in the last month.

I tell him he is driving himself crazy.

Take a look in 40 years and meanwhile, don't worry about it.
We don't know how to beat the market on a risk-adjusted basis, and we don't know anyone that does know either | --Swedroe | We assume that markets are efficient, that prices are right | --Fama

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Re: Regret of selling winning stocks early

Post by jjface » Sun May 01, 2016 9:35 am

I sold apple stock when it was $93. I was sad for a while but not anymore. No joke.

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Re: Regret of selling winning stocks early

Post by nedsaid » Sun May 01, 2016 11:57 am

virw wrote:I used to work at a public company and got some stock compensation. Since it was a large part of my portfolio back then, when I received the shares I decided to diversify and sold most of them to buy index funds. However the company's share has since done very well compared to the overall market and thus I would gain significantly more if I hold the shares instead of diversifying. But I know I made a right decision, so should I not regret? Did anyone get to the same situation?


Yes, you have suffered from the "Nedsaid effect" which occurs when the investment you sell outperforms what you bought to replace it. This seems to have happened to me at a ratio of 2:1 or even 3:1. Thus my reluctance to sell investments, heck I don't even like to rebalance my portfolio! A trader I am not.

That being said, you need to diversify your portfolio. You don't want too much of your net worth riding on just one stock. Think of what happened to employees of Washington Mutual and Enron who had most of their net worth tied up on their company stock. A lot of folks were pretty well wiped out. The company stock effect can work both ways.

I also believe in the principle of wide diversification versus narrow diversification. In index funds, you have hundreds if not thousands of securities and not just one. Though you missed out on a potentially large gain, you also sleep much better at night.
A fool and his money are good for business.

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Re: Regret of selling winning stocks early

Post by JustJim » Sun May 01, 2016 12:04 pm

virw wrote:I used to work at a public company and got some stock compensation. Since it was a large part of my portfolio back then, when I received the shares I decided to diversify and sold most of them to buy index funds. However the company's share has since done very well compared to the overall market and thus I would gain significantly more if I hold the shares instead of diversifying. But I know I made a right decision, so should I not regret? Did anyone get to the same situation?


If it makes you feel any better I was mulling over investing 1000 dollars in bit coin when it was super cheap back in 2010. Yeah I am kicking myself at this point. :oops:

capgain22
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Re: Regret of selling winning stocks early

Post by capgain22 » Thu Nov 02, 2017 2:41 pm

I became a Boglehead a few years ago as I'm approaching retirement, and started stock indexing and moving more into bond funds
.
I had an Amazon that had increased in value about 10 times. So, over- positioned in one stock I sold all of it at 300 to diversify. It is now over 1000!! That's a pretty penny to look at "what if.....?"

With the few individual stocks I still own I'm now selling winners;
but only on half the shares on a 10% stop loss.
I realize that this "system" would not work over the long haul, but it makes me feel better if I don't sell all shares too early on a hot stock.

Comments?

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Re: Regret of selling winning stocks early

Post by MotoTrojan » Thu Nov 02, 2017 3:51 pm

JustJim wrote:
Sun May 01, 2016 12:04 pm
virw wrote:I used to work at a public company and got some stock compensation. Since it was a large part of my portfolio back then, when I received the shares I decided to diversify and sold most of them to buy index funds. However the company's share has since done very well compared to the overall market and thus I would gain significantly more if I hold the shares instead of diversifying. But I know I made a right decision, so should I not regret? Did anyone get to the same situation?
If it makes you feel any better I was mulling over investing 1000 dollars in bit coin when it was super cheap back in 2010. Yeah I am kicking myself at this point. :oops:
Do you think you'd still be holding, or would you have sold in 2014 during its first major crash?

Atgard
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Re: Regret of selling winning stocks early

Post by Atgard » Thu Nov 02, 2017 4:24 pm

That's the problem right there. You're probably one of two types of people:

Type A: Hew to a plan or allocation, when your stock doubles, sell half of it, etc. This type of investor will probably sell all or most of the stock before it goes to the stratosphere.

Type B: LET IT RIDE! While this guy may hold a stock going up up up (reinforced in his behavior all the way up), what happens as soon as there is a dip? Does he sell? Does he hold it all the way? Does he hold it all the way up, miss the high, and hold it all the way to the bankruptcy as well?

Most people in hindsight seem to think they could be some magical blend of Type B while a stock goes up then suddenly (bolstered by always being right and making money) switch to Type A at just the right time to get out.

The odds of (a) picking the right stock, (b) getting in at the right time, (c) AND getting out at the right time are just pretty low. (For the record, with Apple, I had (a) and (b) but failed on (c). Ah well.)

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Re: Regret of selling winning stocks early

Post by Lillibelle » Thu Nov 02, 2017 4:46 pm

Tweets led me to sell some great defense stocks (drat) ... but can't argue with profit-taking.

Next time must remember to take some profit, not all, and tone down the noise.

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Re: Regret of selling winning stocks early

Post by Dandy » Thu Nov 02, 2017 5:47 pm

I worked for a stock company who had their shares rise to 120 do a 2 for 1 split rose to about 120 again and then in the 2008 crisis drop to 8 and only a rescue from a Japanese bank helped it survive. Lots on longer term employees saw their nice retirement plan go out the window as they followed the stock most of the way down - and then some lost their jobs as well.

I kept my exposure to about 5% of my portfolio. Lost all my small amount of stock options which I never counted on and some of my pseudo shares granted that had a holding period to exercise.

Company stock is enticing but often risky.

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Re: Regret of selling winning stocks early

Post by LeeMKE » Thu Nov 02, 2017 10:26 pm

I'm old enough to have lived through the dot.com crash, and watched as folks with piles of company stock lost both their savings and jobs.

Though I'd had plenty of company stock bonuses early in my career, I was always selling it off as able because we already had too much riding on DH's job there. Common sense ain't so common.
The mightiest Oak is just a nut who stayed the course.

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llama
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Re: Regret of selling winning stocks early

Post by llama » Thu Nov 02, 2017 10:45 pm

My company's stock has been going crazy for years. I don't for a moment regret selling my RSU and ESPP shares as soon as they vest, despite all the glee I hear in the hallway from those who have held onto theirs. It allows me to sleep well at night, especially in an industry where ageism runs rampant and I could be shown the door any day.

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Re: Regret of selling winning stocks early

Post by harrychan » Thu Nov 02, 2017 11:07 pm

My previous company's ESPP stock went as high as $150 then dropped till $9 at the dotcom bust. I put 30% of my salary into the espp for 6 months then cashed out when it went up to $80. It helped with my downpayment for my house. When I left the company earlier this year, it dropped back down to $30 due to some accounting malpractice in EMEA :shrug:
This is not legal or certified financial advice but you know that already.

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Re: Regret of selling winning stocks early

Post by exigent » Fri Nov 03, 2017 6:23 am

saltycaper wrote:
Thu Jan 28, 2016 11:32 pm
There's always something you could have done in hindsight that would have produced a much greater return than what you chose.
It’s a bit like picking a line at the grocery store. There are multiple choices and everyone is trying to optimize their decision of which line to get into. Odds are, you won’t happen to pick the very best one.

Personally, I like to diversify... I get in one line and my wife or one of my kids gets in another line. That helps protect us against getting stuck in the very worst one. :-)

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Re: Regret of selling winning stocks early

Post by nisiprius » Fri Nov 03, 2017 6:38 am

Feel good if your stock picks made money. Wishing that you could sell at exactly the right time instead of at a good time is greed. "Bulls make money and bears make money, but pigs get slaughtered."
Annual income twenty pounds, annual expenditure nineteen nineteen and six, result happiness; Annual income twenty pounds, annual expenditure twenty pounds ought and six, result misery.

goblue100
Posts: 343
Joined: Sun Dec 01, 2013 10:31 am

Re: Regret of selling winning stocks early

Post by goblue100 » Fri Nov 03, 2017 8:07 am

virw wrote:
Thu Jan 28, 2016 11:16 pm
But I know I made a right decision, so should I not regret? Did anyone get to the same situation?
You should not regret. In poker, we call this results oriented thinking. In the short run, you can do the right thing and get unlucky and lose, while the person who made a terrible decision gets lucky and wins. Over the long run, the good decisions are rewarded.
Some people are immune to good advice. - Saul Goodman

Broken Man 1999
Posts: 808
Joined: Wed Apr 08, 2015 11:31 am

Re: Regret of selling winning stocks early

Post by Broken Man 1999 » Fri Nov 03, 2017 10:09 am

jjface wrote:
Sun May 01, 2016 9:35 am
I sold apple stock when it was $93. I was sad for a while but not anymore. No joke.
I must have bought some of your Apple stock, as I bought at $93!

Tempting to sell now, but I'll hold just a little longer, I'd like to see a double first. Then maybe I'll sell part of it.

Broken Man 1999
“If I cannot drink Bourbon and smoke cigars in Heaven than I shall not go. " -Mark Twain

a5ehren
Posts: 28
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Re: Regret of selling winning stocks early

Post by a5ehren » Fri Nov 03, 2017 3:51 pm

My company stock has traded between 17 and 25 the whole time I've been here. I take my ~10% real return via ESPP and cash out immediately.

No regrets, though I would probably feel differently at a FAANG.

bikechuck
Posts: 111
Joined: Sun Aug 16, 2015 9:22 pm

Re: Regret of selling winning stocks early

Post by bikechuck » Fri Nov 03, 2017 4:17 pm

I have some company stock from a previous employer that I am waiting to sell in January as 2018 which will be my first full year of retirement and when I will be in a lower tax bracket. This stock is in a retirement account so I plan to take advantage of the NUA rules which is why I held the stock and am waiting.

A couple of years ago the stock began rising and it is up approx 51% in the past 12 months. Of course with my luck it will crash just before I sell it.

Funny thing is I debated whether to unload it and just not worry about taking advantage of NUA. For now at least it looks like it is a good thing that I just stood there and did nothing while patiently waiting for January 2018 to roll around.

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