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100% agree. Don't put all of your eggs in one basket. That said, by following this advice, I've now got $800k post-tax cash vs $4-5 million in stock, assuming

100% agree. Don't put all of your eggs in one basket. That said, by following this advice, I've now got $800k post-tax cash vs $4-5 million in stock, assuming I would have held on to my shares. Oh well.

eloisant 3y ago
"Don't put all of your eggs in one basket" doesn't mean "stay away from that specific basket". There is a middle ground between holding everything and selling as soon as it vests.
- stouset 3y ago
  Your income is already tied to your employer. For most people in most situations, attaching a significant fraction of your net worth to that same employer is an extremely risky position to be in. Of course you don't have to sell everything always all the time the moment you can. As always, use your own judgment. But your default tendency should be to divest and diversify.
stouset 3y ago
> I've now got $800k post-tax cash vs $4-5 million in stock Of course that's true of any investment though. With that $800k in cash, you could have bought any stock. Including your employer's! And if someone is going to beat themselves up over not holding RSUs ("I knew it was going to go up!") that same logic would warrant putting even more money into company stock. On the flip side, I was holding on to some ISOs that were very nearly bringing me to my retirement stretch goal. I just wanted to squeeze out 5% more. That was December 2021. Within a month or two they'd dropped to less than 25% of their value, and I lost well over six figures. The rest of the market recovered, my company didn't. If I'd sold instead of holding on for just a little bit more, I'd be retired today. C'est la vie!
- jebarker 3y ago
  I'm also in the position of feeling regret over selling stock to diversify that I would have been much better off holding on to. Even though I understand why logically I shouldn't feel bad, it feels like I made a mistake. I assume Kahneman and Taversky could tell me the particular mental bias that makes this happen whether you sell and it goes up or hold and it goes down, i.e. it feels more like a loss because you already held the key to the gain. Loss aversion maybe?
  - stouset 3y ago
    I feel like there's some structural similarities to the trolley problem. With hindsight, inaction (not pulling the lever) would have had the better outcome but you explicitly intervened. This is more painful than a similar situation where the default was reversed and where you would have explicitly had to act to buy those same shares with cash.
GaryNumanVevo 3y ago
I'm on the flip side, I have around $3 million in stock from my former employer that I'm trying to sell off as tax-advantaged as I can. It's tough

eloisant 3y ago

"Don't put all of your eggs in one basket" doesn't mean "stay away from that specific basket". There is a middle ground between holding everything and selling as soon as it vests.

stouset 3y ago
Your income is already tied to your employer. For most people in most situations, attaching a significant fraction of your net worth to that same employer is an extremely risky position to be in. Of course you don't have to sell everything always all the time the moment you can. As always, use your own judgment. But your default tendency should be to divest and diversify.

stouset 3y ago

> I've now got $800k post-tax cash vs $4-5 million in stock Of course that's true of any investment though. With that $800k in cash, you could have bought any stock. Including your employer's! And if someone is going to beat themselves up over not holding RSUs ("I knew it was going to go up!") that same logic would warrant putting even more money into company stock. On the flip side, I was holding on to some ISOs that were very nearly bringing me to my retirement stretch goal. I just wanted to squeeze out 5% more. That was December 2021. Within a month or two they'd dropped to less than 25% of their value, and I lost well over six figures. The rest of the market recovered, my company didn't. If I'd sold instead of holding on for just a little bit more, I'd be retired today. C'est la vie!

jebarker 3y ago
I'm also in the position of feeling regret over selling stock to diversify that I would have been much better off holding on to. Even though I understand why logically I shouldn't feel bad, it feels like I made a mistake. I assume Kahneman and Taversky could tell me the particular mental bias that makes this happen whether you sell and it goes up or hold and it goes down, i.e. it feels more like a loss because you already held the key to the gain. Loss aversion maybe?
- stouset 3y ago
  I feel like there's some structural similarities to the trolley problem. With hindsight, inaction (not pulling the lever) would have had the better outcome but you explicitly intervened. This is more painful than a similar situation where the default was reversed and where you would have explicitly had to act to buy those same shares with cash.

GaryNumanVevo 3y ago

I'm on the flip side, I have around $3 million in stock from my former employer that I'm trying to sell off as tax-advantaged as I can. It's tough