It’s the toughest thing about trading, and nothing has provided a bigger leap away from fear than my recent experience of managing an ITM call spread. I was short the August 2130/2155 call spread as the SPX reached all time highs of 2193. It was a big trade, too, over twice my normal size, and it sucked as the index went through my strikes (I had already rolled several call spreads, but let this one sit). But as it sat there ITM for days and then weeks, I grew more relaxed and started exploring ways to roll my way out. I figured a system, without increasing position size, and started rolling it one week before it expired. All it would take is a decent pullback or two and I’d be out. It took about 6 rolls and now I’m out with no loss, in fact retaining the profit I expected on the original trade.

Going ITM and realizing max loss seems to be a great fear for many option traders. To help overcome it, I suggest trading an ITM spread on an index. Indices do not have huge overnight gaps like stocks, and there is no possibility of early assignment, as they are cash settled at expiration, never earlier. Your risk never changes, whether you are 100 points OTM or 100 points ITM (except with Portfolio Margin, which is unpredictable).

Today, I sold a 1-lot:
Sold to Open $SPX Nov 25th 2175/2150 put spread for 14.00. I will wait until mid November to even worry about it. It will be similar to having a trade go against you, except we now have the benefit of a very fat credit upon entry, rather than the 1.30 or so for which we usually sell these spreads.

Feel free to join if you are looking to overcome some of your fear. If you do it, understand that if it remains ITM in November, we may be selling condors or extra options during the rolls. But as before, I do not plan to increase risk very much. #SPXcampaign #FearTrade #ITMrolling