The biggest headache I have now is dealing with a trade that has gone wrong.
$WMT is giving me a run for my money.  I opened my bull put spread 5 contracts for $75/$70 end of March 2015 when $WMT was trading at $81.32 per share.  I collected $202.08 in premiums after commission.  
In the past three months, $WMT dropped a good 12% after reporting their earnings.  Today, $WMT closed at $71.94.  This is $3.06 under my $75 short strike price.
In order for me to keep my $202.08 premiums, I need $WMT to move and stay above $75 per share.
If $WMT does not move up, I will have to close my position for a loss.  Take for example, by Friday, $WMT closes at $72/share.  My total loss would be around $3 x 5 contracts x 100 per contract = $1500. 
$1500 loss in this trade would be devastating to me.  But my exit plan is to roll this bull put spread out to a later date in hopes that $WMT will recover and bounce back to its original glory.
My worst case scenerio is I get assigned 500 shares @ $75.  So I rather close my position earlier than later.  
Couple of other smaller headaches in scale are my call for $V for $70 and my put for $PEY.TO for $34.  Both are expiring this Friday.  I am really counting on a nice bull frenzy streak that we've been getting for the past few months.
To manage my positions better, I need to take profits earlier than later.  I need to take them @ 50% capture instead of waiting for the "possible" 100% capture at the end of expiration.  I've let $WMT become a problem.