@HunterBiden one of my favorite sections of the big book is pg 124 “the dark past is the greatest possession you have - the key to life and happiness for others.”
timing matters a lot… if you pass in a market correction, your shorts could have significant short-term gains. you can continue to run the strategy in the estate though… unwinding the strategy in a tax-efficient way. any net losses generated during the estate period can also be distributed out to the inheritors. average estate period is 4 years, so there’s plenty of time.
4/ Ownership - The endowment effect.
This one isn't about pride or fear - we value things more just because we own them. No story required. Owning the stock makes it feel worth holding
The fix: run the cash test. Would you buy this position today, at today's price, with cash? If not, you're holding out of ownership, not conviction.