Looking off your trades alone, starting from the MSFT trade as the most dated, most of your trades have been the "lottery ticket" type. The NTRI long OTM put spread, the VIX fly, the MSFT OTM calendar, the NXTP puts. These are low probability, low risk, high reward types. So get used to losing a lot of those and hitting the occasional big winner. Now the CSCO double OTM calendar is a different story. 1st, have a look at the premium you are selling, 0.1 and 0.2. That is virtually negating the long gamma in the longs with no compensation by theta. 2nd, CSCO has been dead for a few years. Volatility is low and this is reflected in the premiums. Chances of a IV increase are slim. So it looks like you like defined risk type trades. Naked short strangles/straddles, ratio spreads etc are out. If you like low risk type directional trades, learn to get real good at feeling the underlying.