Mine is a really painful lesson in stupidity. Got into MU at a good price (stock and some options through September). Then I got hyped on knowing it would go up and decided to sell that position for 3x more leverage for more gain at my price target (e.g $3m instead of $1m) I switched everything overnight right before huge volatility pushed MU down 20% over the course of a week, and I had written a playbook out before of what changes to make at what price levels and it hit a trigger to sell most of it to average down and go back in later. So basically just bought at the top and sold at the bottom and if I just held what I had initially and did noting else I will be ITM at current MU price of $1m. Biggest lesson learned for me was honestly just about (A) how to moderate how much leverage to take, (B) to average in to a big bet instead of going big overnight - you see a lot of the opposite in WSB, (C) take more stock vs options in volatile stocks to be able to manage the risk overnight, and (D) to ride longer time horizon hypothesis on undervalued companies rather than try to day trade - e.g model the loss scenarios better and get to a loss you’re really comfortable riding for a while to then have it flip to a gain. A good lesson, but instead of ITM $1m, it’s more like $40k earned back with recent gains.

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How I changed my strategy with similar frustrations, I have been buying almost ITM long calls, like a year out. Buy almost ITM TSM call a year out and thank me in 11 months.

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You can also buy deep itm calls and just excersize them to have that cost avg too.

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