Realized Gains Getting Too Big

My account has a weird issue brewing in it.  I have very big paper losses, but haven’t done much to realize those losses throughout this year of Hell.  I’m still showing a realized gain and have a month and a half to go before I have to dump something for a loss and maybe two positions.  I pulled my November short option holdings into Excel today and calculated what’s going to happen at the end of this week.  I pulled these numbers around 12:45 today.

The first four columns came from TD Ameritrade’s interface.  The “Gains from Options” column is the combination of Quantity*100*Purchase Price (actually sale price, but that’s how they list it).  This shows me what I’ll have in gains from my options assuming I don’t buy any back for a loss.  It does not include commissions from selling the options originally or from any that may be assigned at expiration.  I’m lined up to record another $8,500 in realized gains this month. 

I have a wide variety of losers to pick from, but continue to wonder which will rally and which will fall deeper.  One avenue I could take would be to buy more shares now (or buy calls or sell options farther out), wait 30 days for the wash rule to fall out of play and then dump my losers for a loss while I still stay exposed to the same equities.  The risk on that is what could happen in the next 30 days.  I’m not a big fan of chasing losers as they fall (although I’ve done that recently), so I doubt I’ll take that route.

The “Value Total” was supposed to say “Time Value Total”, but I cut it off by mistake and I’m short on time and not updating it now (forgive me).  Anyway, that last column is the Quantity*100*Time Value.  This shows me that if everything flattened out for the next four and half days, I’ll have $1,126 more then than now.

Without double checking yet, I think I’ll have around $10k in realized gains after this Friday.  I’ll have more gains with all the options I plan to sell for December expiration, so I’ll be dumping something before long because I can’t stomach paying taxes on gains in a year when I’ve lost my shirt.