Quote from aeliodon:
Because every step of the way you are faced with the temptation of 'taking profits' at new equity high water marks because you know there will be a pullback and you don't know how long or how large the pullback will last. And you're also constantly bombarding by the conflicting 'fundementals' spin machine.
Holding onto your winners is the toughest skill to master and adding to your winners on pullbacks as you hold is nearly impossible. But if you can master this skill, all you need is one huge move: whether its a bubble going parabolic, or a bubble popping to make enough money to be rich.
Doesn't this depend on the size you are trading?
I've traded positions ranging from small to large, and my own experience is that the gut-wrenching only occurs when you are trading too big. As the old trader saying goes, if your position is so big that you can't sleep at night, then "Sell down to the sleeping point". The flip side is that you are not going to retire from one trade if you are trading sensible size. But how many market legends made their reputation from making a killing on one trade? It was normally success over a lengthy career that established their credentials, not an enormous killing on one trade. George Soros had a great 23 year track record of superb returns before the British Pound trade, for example. Paul Tudor Jones made a name for himself in October 1987, but it is his record since then that elevated him from flash in the pan to legendary hedge fund manager. So, I think your comments are based around the idea of betting way too much on one trade, rather than looking at the long game of trading - how you perform over the next 10-20 years, rather than the next big trade you put on.
I've had my share of losers and winners, and from time to time I have managed to ride a market for the majority of a very large move. Whenever I have been trading sensible size, I have found holding on to be pretty easy. Whenever I have traded very large size, I have found it much more difficult. Suddenly, every small movement assumes greater significance. It makes it much harder to focus on what matters - the broad move taking place - and much easier to get distracted by what doesn't matter, i.e. the random noise. Furthmore, I have found it much harder to correctly adjust a position when I am trading too big. If the market changes tone, and suddenly your trade is not so hot anymore, then you need to be able to completely objectively realise that and act on it promptly. Trading large, it becomes harder to do this because you are more attached to the position.
I think this is the real problem with trading big - it causes you to become emotionally invested in your position. With big size, all of a sudden a huge amount is riding on this one trade. It thus becomes much harder to be objective and flexible, to listen to the market action and respond accordingly. If your gut is wrenching then you are liable to get faked out by every slight move against you, to second guess yourself constantly, and to hesitate when you need to be decisive. That is not the way it should be, because you are going to have hundreds and hundreds of trades over your career. The results of any given one, even if you wait for the odds to become stacked in your favour, are not going to be what determines the end result. Personally I have found it far easier to make the correct trading decisions when I am trading medium size, with a few % of capital at risk on any given trade.

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