The missed buys are hard to 'regret'...we all should have gone all in in 2009 or bought FANG at the IPO or Apple and no one could have predicted which was gonna go up 10,000% or which was gonna go down 100%.

My real mistakes and regrets are that:
I gambled a lot of money away trading options with very little options education

I tried multiple times to trade stocks

I got cold feet and wasn't 100% invested in stocks the last 10 years

That's how I learned options. No better way to learn on the fly than to lose a ****load while trying to do it.

This thread is off to a great start. Thanks for sharing your experiences. I read Millionaire Teacher, at recommendation from this board, when I was 23. I am so thankful for that.

My biggest regret so far is not maxing out my 401K earlier. I only started doing that this year.

Yes, originally bought for me in mid 80s. Can't remember exactly when it was sold but wasn't going anywhere at the time. The lesson in it (other than me not being mid 7 figure rich) is that it's very hard to foresee what will be the next big thing (iPod).

IrishTxAggie said:

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That's how I learned options. No better way to learn on the fly than to lose a ****load while trying to do it.

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I lost a ton (for me, at the time) of money in Round 1. Took a long time off from trading...especially options.

Accumulated real (again, for me) money, then repeated it all again...this time with more knowledge AND margin. ALMOST lost my ass in a big way (6 digits), thankfully didn't, and finally called it quits on the options trading.

El Chupacabra said:

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IrishTxAggie said:

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That's how I learned options. No better way to learn on the fly than to lose a ****load while trying to do it.

---

I lost a ton (for me, at the time) of money in Round 1. Took a long time off from trading...especially options.

Accumulated real (again, for me) money, then repeated it all again...this time with more knowledge AND margin. ALMOST lost my ass in a big way (6 digits), thankfully didn't, and finally called it quits on the options trading.

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I have a really difficult time believing that anyone not sitting on a trading floor full time beats the market playing options and actively trading.

Wife gave me an IPOD in 2003, and I still think it is the coolest thing I've ever seen at a given point in time. AAPL was trading in the $3 range at the time. I was so burned by tech in 2000-01 that I didn't pull the trigger.

Holding restricted stock shares in my employer's stock instead of selling them as soon as they vested . Should have sold them if for no other reason than diversification in my personal finances. I have rode them down from an average of over $15 per share at vesting to less than $3 per share. They were all gifts and I really had nothing to lose but the lost opportunity $ makes me sick. I guess when I do sell them I'll be able to take a tax loss . I don:'t ever see getting back to a net gain.

Wrong thread

Do we work for the same company!?

I paid off low interest debt too early. I could have put in min payments and invested the rest to shave a few years off of my retirement age using the sorcery of compounding interest.