Does anyone regret not buying individual stocks/staying with index

[wideopenspaces]

If I were you I would only sell 50% of it to cover the original vest. I would leave the 50% gained to see how it rides in the future.

I can't handle it!!!!! ;-)
But he will vest more stock every 6 months moving forward so I *could* keep some of that. The problem is that we are getting so much stock in the next couple years that even if we only kept half of it, it would make up too big of a chunk of our overall portfolio and I'm not comfortable with that. If he leaves current employer in 2 years, we might keep 50-100k of the last portion that vests but only if it stresses me out less by then.

[Tom Kazansky]

I can't handle it!!!!! ;-)
But he will vest more stock every 6 months moving forward so I *could* keep some of that. The problem is that we are getting so much stock in the next couple years that even if we only kept half of it, it would make up too big of a chunk of our overall portfolio and I'm not comfortable with that. If he leaves current employer in 2 years, we might keep 50-100k of the last portion that vests but only if it stresses me out less by then.

RSUs?

[Max Power]

Indexing is not nearly as bad as it once was... the ER fees are much more reasonable than the dreaded mutual fund fees, minimums, etc or the early ETFs with much higher ERs... kinda like the nasty 1-3+ percent robbery way most 401ks still are functioning, lol. Modern DIY index low ER funds like VTI and VOO and IVV and ITOT in the cash accounts or IRAs are the fine option for the masses who "never liked stocks" or "don't have time" or don't have the stomach for it, though.

Likewise, trading also got a ton better with lower cost and now free trades on stocks, options, funds, etc. It has gotten tremendously more profitable for me and others who do it (like to trade but not doing huge quantities... so those $6-$12 trade fees really did become problematic).

...I still see indexing as accepting the average IQ, average income, average BMI, etc and taking that as your own. It is a fine choice... you could do worse, but it is just not too difficult to do better. I do indexing with a portion of my portfolio... although for my "indexing," I mostly sell weekly or monthly calls on SPY. The index funds popular here on this forum are fine but mostly mutual funds with no action available or index ETFs with snail volume for selling calls.

In the end, with the individual stocks, it depends on personality type. Most people can't help but tinker. We are a puny and fickle folk. They make a choice and then over-analyze it, don't buy it, maybe change it, change again. They can't take the volatility and just give up and eternally refer to it as "gambling." Pro and novice traders and funds eat them for lunch since it's a zero sum game. They should just index. Trading and picking is a confidence thing as much as a logic thing. They marry their stocks or funds and hold onto losers or ride winners up-up and then back down to a lower price. They apply analysis and logic and then freak out or have a tantrum when what happened last year or last quarter or what "should" happen doesn't. A lot of the best traders (and entrepreneurs) have above average - not elite - smarts... they just have elite cojones. Again, not for most folks.

[PedsCCM]

How do you get rid of individual stocks if you pick winners? I used a small bit of my portfolio to buy Delta, Southwest, Boeing and Airbus in April, May and June when the overall stock market was recovering but the airlines were lagging behind. I got lucky and they went up. But now what? These are all in a taxable account. I suppose I can flush them as a part of my normal charitable giving, but how else do you deal with winners if you're not at all confident that the trend will continue for 20+ more years?

[Max Power]

My husband's amazon stock vests in 6 days and I've literally been counting it down for months. I hate it, even if it's doubled since he got it. We will immediately sell, pay taxes, and invest the rest in index funds in our taxable account. Individual stocks are not for me. Too anxiety provoking. I don't know how people sleep at night investing in single stocks!

Sleep well. Looks like it's not your problem to worry about?

[Max Power]

How do you get rid of individual stocks if you pick winners? I used a small bit of my portfolio to buy Delta, Southwest, Boeing and Airbus in April, May and June when the overall stock market was recovering but the airlines were lagging behind. I got lucky and they went up. But now what? These are all in a taxable account. I suppose I can flush them as a part of my normal charitable giving, but how else do you deal with winners if you're not at all confident that the trend will continue for 20+ more years?

You sell when you like the profit and/or have potential from better buys on your watchlist than present holdings.

Never focus on the taxes. You want 50% gains with 50% taxes over 5% gains with 5% taxes.

Make money first and foremost. Let the accountant sort it out later. Tip him well.

[Random1]

How do you get rid of individual stocks if you pick winners? I used a small bit of my portfolio to buy Delta, Southwest, Boeing and Airbus in April, May and June when the overall stock market was recovering but the airlines were lagging behind. I got lucky and they went up. But now what? These are all in a taxable account. I suppose I can flush them as a part of my normal charitable giving, but how else do you deal with winners if you're not at all confident that the trend will continue for 20+ more years?

I would wait if you can to make the gains a long term capital gain vs short term at least for tax purposes.

[wideopenspaces]

Sleep well. Looks like it's not your problem to worry about?

Hahaha I do all the investment/saving/spending decision making in the house! Of course I talk it over with him but I'm pretty sure all he hears is "blah, blah, blah."

[wideopenspaces]

RSUs?

Yeppers. We're just now getting to the time period where the amount of shares and vesting frequency increases significantly and. . . I don't like it. We just never planned to have individual stock so I'm still kinda trying to figure out how to handle it. I don't want 500k of a 1M portfolio in 1 stock!

[jacoavlu]

Sleep well. Looks like it's not your problem to worry about?

can I unlike a post? I realize by quoting this maybe I’m not helping. But, wtf is your point?

[Tom Kazansky]

Yeppers. We're just now getting to the time period where the amount of shares and vesting frequency increases significantly and. . . I don't like it. We just never planned to have individual stock so I'm still kinda trying to figure out how to handle it. I don't want 500k of a 1M portfolio in 1 stock!

What I've found most helpful with RSUs has been to ask myself if the amount that vested was in cash instead of stock, would I buy the same amount of company shares?

[xraygoggles]

How do you get rid of individual stocks if you pick winners? I used a small bit of my portfolio to buy Delta, Southwest, Boeing and Airbus in April, May and June when the overall stock market was recovering but the airlines were lagging behind. I got lucky and they went up. But now what? These are all in a taxable account. I suppose I can flush them as a part of my normal charitable giving, but how else do you deal with winners if you're not at all confident that the trend will continue for 20+ more years?

If I were you, I would hold for one year to get LTCG, then sell if you don't think they can keep growing after this recovery.
Or, you can also sell now, take the STCG hit and be happy you were lucky/skillful. But I would only do that if I really needed the $ for a large purchase, or I had a better investment opportunity with potentially higher return than the tax hit difference (STCG v LTCG).

[Balance1969]

How do you get rid of individual stocks if you pick winners? I used a small bit of my portfolio to buy Delta, Southwest, Boeing and Airbus in April, May and June when the overall stock market was recovering but the airlines were lagging behind. I got lucky and they went up. But now what? These are all in a taxable account. I suppose I can flush them as a part of my normal charitable giving, but how else do you deal with winners if you're not at all confident that the trend will continue for 20+ more years?

Agree with xraygoggles and Random1. Hold for a year to minimize LTCG.

As an aside, I think odds are they will continue to improve with the vaccine and lotsa peeps aching to travel for relief from cabin fever. Last time I checked (recently), some air travel related stocks were still halfway from where they were before the virus. Keep in mind, this is speculation and I have as much of an idea as a dancing monkey as to where anything is actually going to go.

[Turf Doc]

Max Power, how is it easy to beat the index? All data shows it's insanely difficult to do over a long enough time horizon. Can you point to me some people who have done that on average over 30 years? And if not, how could you expect Dr. Joe Schmo to do it?

[EntrepreneurMD]

Grace Groner, who was not a financial professional is a good example. We've discussed her on this site before. Outperformed index with stock. Time frame is well over 30 years.