Most of my retirement is in ETFs and such but I do have a good amount in single stocks that I actively manage. My largest position is a stock that is currently trading at around $136/share. I own about 150 shares with a cost basis of around $120. As of today It’s down over the last year (-3%) but has trading as high as \~$160 just a month ago. It’s biopharma so volatility is pretty common.
I’m still very bullish on the stock as I’m familiar with their products, pipeline, and upcoming catalysts (I work in the industry). That said, I’m wondering if it makes sense to replace 100 of those shares with a LEAP (furthest out right now is December). I’m thinking deep ITM like $80 (breakeven at the current ask would be +3%).
Note that these are long positions for me so they do have long term capital gains tax status should I sell.