FWIW I went through a similar "education." For roughly 3 months in 1999 I had a combined restricted stock (already granted with an 83b election filed but vesting over time) and incentive stock (fixed strike price, 1 year cliff, .25%/yr thereafter) options in a single stock that in 2003 (4 years later) if the stock was trading at the same price as it was in 1999 ($120) was "worth" $12,000,000.
In 2001 that stock was trading for $0.83/share[1]. And while I didn't have any opportunity to sell it, being an employee and all, what really pissed me off was that I had Sun stock that I could sell that would have been worth $360,000 after taxes (which would have paid off my mortgage). Instead I rode that stock down to about $9000 when Oracle bought them.
Similarly my 401k savings account, that I had put in the max amount every year for decades, had under-performed the S&P500 and even some lousy mutual funds.
So yes, I've had my share of ups and downs, and yes if I had put all of the money I ever had in my brokerage account into an SPX ETF I might have more in it now than I do.
But here is the thing for me, and perhaps spending my teen years in Las Vegas warped my perception of money enough to make this possible, I recognize that the equities market is essentially "random" and various studies have born that understanding out in the large view. As a result it doesn't "feel" to me like I somehow lost money through my own actions, it feels like the bet I made didn't pay off. That is a different approach than getting emotionally invested in the financial outcome of investment decisions. When I came to understand that I was not going to spend all of my time reading financial reports and resumes of senior management like my Dad's ex-swiss banker friend does to get an "edge" I had two choices, go the ETF route or let my financial manager manage some of my assets.
[1] At $0.83 that was about $40,000 in the restricted stock (nobody exercises their incentive stock options that are underwater :-), And yes, I recognize that $40,000 is way better than nothing, and because of my 83b election I have a long term capital gains loss that I can claim for $3,000 a year on my tax return every year and that will continue for the next 75+ years if I were to live that long (I won't).
In 2001 that stock was trading for $0.83/share[1]. And while I didn't have any opportunity to sell it, being an employee and all, what really pissed me off was that I had Sun stock that I could sell that would have been worth $360,000 after taxes (which would have paid off my mortgage). Instead I rode that stock down to about $9000 when Oracle bought them.
Similarly my 401k savings account, that I had put in the max amount every year for decades, had under-performed the S&P500 and even some lousy mutual funds.
So yes, I've had my share of ups and downs, and yes if I had put all of the money I ever had in my brokerage account into an SPX ETF I might have more in it now than I do.
But here is the thing for me, and perhaps spending my teen years in Las Vegas warped my perception of money enough to make this possible, I recognize that the equities market is essentially "random" and various studies have born that understanding out in the large view. As a result it doesn't "feel" to me like I somehow lost money through my own actions, it feels like the bet I made didn't pay off. That is a different approach than getting emotionally invested in the financial outcome of investment decisions. When I came to understand that I was not going to spend all of my time reading financial reports and resumes of senior management like my Dad's ex-swiss banker friend does to get an "edge" I had two choices, go the ETF route or let my financial manager manage some of my assets.
[1] At $0.83 that was about $40,000 in the restricted stock (nobody exercises their incentive stock options that are underwater :-), And yes, I recognize that $40,000 is way better than nothing, and because of my 83b election I have a long term capital gains loss that I can claim for $3,000 a year on my tax return every year and that will continue for the next 75+ years if I were to live that long (I won't).