The Pain of Gain – Dealing With Making Money In the Markets

Staying with the trend is at least as important, if not more important, than identifying the turn. If you can’t stay on board, what’s the point of the exercise of trying to identify the change in trend? Of course, some folks like to prove how smart they are, while others prefer to simply make money.

— Jeff Cooper

One of the parts of trading that I still struggle with is the psychological aspect.  I have no problems coming up with trading ideas (as you might have surmised from reading my blog).  But even after trading for over 10 years, I still have trouble with the mental aspects. 

My problem isn’t cutting my losses.  I’m insecure enough to know I can’t take on the market and win.  I also hate losing money so this aspect of trading is already ingrained in my persona.  And cutting losers has allowed me to stay in the game long enough to figure out what works for me and what doesn’t. 

I have the opposite problem.  For me, the hardest part of trading is letting winners run.  It might seem like an easy thing to do.  You identify a potential reversal point, make your bet and voila…you’re right and you start making money.  I bring it up because the energy stocks are finally pulling back as I expected three times before.  I’m finally making money.  But whenever I make money on a short position, I begin to wonder…

Now what?  Is this reversal going to start a sustainable trend or is it just a minor pullback?  Will the stock bounce on support or will it cut through it like a razor?  Are too many shorts going to cover at the same time causing a short squeeze?  Should I ring the cash register on the whole trade and be happy I put money in the bank?  Should I sell half my position?  If I l let it ride and I get another double, I could make up for all my other losing trades this month.  But if I let it ride and the stock moves against me again, I’ll be in the same position I was in before I made this great trade.  There…the stock has already ticked 0.10 cents against me…it’s going to move all the way back…I better cover.   Phew!  That was great…I made 30% in a day on one trade…oh wait…no…no…the stock is starting to tank!  Without me!!!  Ahhhh!  Why did I cover my put?  I knew the stock was going to tank!  What was I thinking by covering before the stock reached my target price?  I’m so stupid.      

You see where I’m getting at with this.  Making money in the market turns me absolutely neurotic.  Paul Tudor Jones affectionately calls this "the pain of gain."  He was talking about making such absurd amounts of money that it overwhelms you…not the couple of bucks I take out of the market.  But the thought is still the same — you have to be prepared to deal with both the best and worst case scenarios. 

Since I’m of German descent, the worst case scenario is easy for me to plan for…I expect the worst to happen (pessimism is baked into the German psyche.  Exhibit 1 – Steffi Graf’s father used to place a bet against her before every tennis tournament she entered).  I have rigid sell stops on all new positions. On options trades, its usually 25 – 50%, depending on the volatility of the underlying security.  I’ve made one mistake not following the sell stops and it cost me.  That was all the lessons I had to learn. 

The best case scenario is always difficult to for me to prepare for.   I have a system of selling 25%, 50% and 25% of my position as it moves in my favor.  Why 25-50-25?  It just works for me.  I like to have something to show for my effort but I know that usually my first instinct to take profits is too early…therefore, my first trade is to just take 25% off the table.  That gives me enough psychological "relief" to be able to hold the rest of the position without constantly second guessing myself.  If I continue to make money on the 75% I have riding on the trade, I will take a 50% off the table at some pre-determined stock level such as support trendlines, DeMark countdown signals, etc.  That gets me out of the majority of the trade with a nice gain.  The rest of the 25% I let ride using a 15-20% trailing stop.  That way I’m still in if the stock really starts to tank, but if the position moves against me, I get stopped out for a decent gain.  If at any time after the first 25% is taken off the table, the stock goes past my cost basis, I’m out.  Therefore, I made enough to cover my commission costs and am ready for the next trade.

It’s a good system but it’s easy to make excuses and not follow it.  For instance, if I don’t get a full position initially (say I want to buy 50 put options but I only get 20), it’s difficult for me to follow the guidelines because I feel like I get eaten up by commission costs.  But that’s just an excuse to not trade correctly.  In reality, the commission costs are so minimal these days that even scaling into and out of small positions is not that expensive.  Likewise, I find it easy to make "market analysis" excuses, even though the market often has nothing to do with the security I’m trading.  For instance, I often think "the market is turning higher, so I should take profits right now…or the market is tanking, so I should let all my short position ride."  Wrong.  Follow the system that works for you and don’t start second guessing based on external factors.   

Despite my well thought out system, I still find myself making trading mistakes.  The only solution I have is to keep working at it.  I’ve gotten better over time understanding my own inherent psychological flaws and I’ve been working at fixing them over time. 

If you have similar frustrations or problems, I suggest the following beginning resources…

www.innerworth.com – Despite the cheesy name, this is a great site if you’re wrestling with trading daemons.  It’s one of the first daily emails I read every morning.

Trading in the Zone and The Disciplined Trader by Mark Douglas – Mark will reveal psychological hang ups that you didn’t even know you had.  They all need to be dealt with before you can consistently take money out of the markets. 

Trading for a Living by Alexander Elder.  While this book covers a lot of ground, it goes into the basics of the psychology of trading.

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