OH! And just to highlight how incredibly poor those flip/split decisions were. IFF I had simply rolled those ITM covered calls out 4 weeks, They would've ALL closed OTM today!
At least that's how I feel now. But hindsight being 20/20. I made the what I thought were the best decisions I could've made, at the time they were made. kicking myself with coulda/woulda/shoulda doesn't help. Just gotta live to trade another day.
You're onto something here. The hindsight / coulda / woulda / shoulda thing isn't helpful. We're all geniuses with the benefit of hindsight.
But what can be hugely valuable is contemplating what you knew then, what you did about it, and what you would do differently in the future given the same or similar situation and information.
As an example from my own trading - I've found that I improve my overall results when I take early positive closes. I don't know that I'm not leaving a lot of money on the table, and I know that I am on many individual trades. But the benefit of looking at overall results rather than individual trade results has left me in good shape (your results may vary, no warranty is express or implied, future results may vary substantially, etc ..).
Today is a particular example. I closed some 650/850 put spreads this morning when I noticed they were ahead ~55%. These were pretty big premium positions so I left a lot of potential earnings from this particular position on the table. They also weren't as far OTM as I'd like and I don't know what will happen on Monday. I consider another week of more down than up to be reasonable though I also think that to-the-moon is about to set in any moment. And besides my own objective is income and that 55% result might generate in 1 week my monthly target. Either way I got the 55% and now I'm free to re-enter if/when I get a good opportunity. Then later in the day the shares have traded from the 950ish range down to 930ish. It might already be a good re-entry!
If I had really been on the ball then I would have also closed the 1000 calls later in the day. With the late move down those have reached a 57% profit (from 25% earlier in the morning). If I'd have closed them then I'd be out of the market on both sides and ready to reenter on Monday whatever direction we open up with. That sounds like a better position to be in than what I'm in right now (but good either way).
Another example from 13ish years back. I found a stock that was paying out nearly 11% annual dividends, with -quarterly- increases to that dividend for several previous years. The company could also identify roughly 60% of the annual revenue for 2 or 3 years into the future due to contracted purchases of their service. Took me 2 weeks of looking at it backwards and forwards to finally figure out that it really was what it looked like.
Then I dabbled. I got $5k worth when I should have gotten $50k worth (or more). I was kicking myself for years afterwards as the investment worked exactly as I expected it to.
The learning - when I have a conviction (and they are rare), then don't dabble. Fortunately I learned that lesson before TSLA came along. When I found TSLA we opened the biggest position we were willing to open in any individual company at the time. Hello early retirement.
I couldn't change the previous coulda / woulda / shoulda situation, but I did learn something valuable.