Trading Education

Why I decide the risk before looking for an entry

Richard SarsfieldPublished 1 February 2025Updated 7 September 20264 min read

Because by the time I have found an entry I am no longer neutral about it. I settle the thesis, the position size, the correlation and the exit first, and only then go looking for a level. Many self-directed traders do it the other way round, and I did too for a long time.

This piece used to argue about who loses money and why. The narrower comparison is more useful: the two habits do the same things in a different order, and the order is what changes.

I am not describing one group as clever and the other as careless. I have used both habits myself. What follows is four places where the sequence differs, and what each difference costs or buys.

1. Order of operations

A chart-first sequence usually runs: find a setup, decide direction, enter, then work out a stop.

A portfolio-first sequence runs the other way: describe the economic setting, form a view, decide what size that view justifies, check what else in the book moves with it, write the exit, and only then look for an entry.

Both end with a position. The difference is that in the second sequence the size and the exit are decided while you have no money on the line. Nothing about that guarantees a better result. It does mean the two hardest decisions get made when you are calm.

Chart first

Position opensFind a setupDecide directionEnter the tradeWork out the stop

Portfolio first

Position opensDescribe the settingForm a viewDecide the sizeCheck correlationsWrite the exitFind the entry
The same decisions in two orders. A filled marker is a decision taken before any money is on the line. Neither order predicts a result: what changes is how many of the hard decisions are made while you are calm.

2. What "risk" refers to

In a chart-first habit, risk usually means the stop loss: the distance between entry and the level at which you get out.

In portfolio work, that is one input among several. The others are how large the position is relative to the whole book, how volatile the holding is, and how correlated it is to everything else you own. Five positions that all depend on the same interest-rate outcome are one position wearing five names, and a stop on each does not change that.

This is the part I would put first if you are only going to change one thing. It is also the part ITPM's Introduction to Professional Level Trading spends its time on, mostly through spreadsheet exercises where you calculate volatility and correlation yourself instead of reading about them.

3. What a chart is used for

Technical analysis is used in both habits. It is used at different points.

A chart-first habit uses the chart to generate the idea. Portfolio work generally uses macro and fundamental analysis to generate the idea and the chart to time the entry and exit once the idea already exists.

That is a real difference in function, and it is worth knowing which one you are doing on any given trade. I would not claim every institution works this way. Approaches at that level vary as much as they do anywhere else.

4. What a long/short pair actually changes

A single directional position needs you to be right about direction, timing and size at once.

A long/short pair changes what the outcome depends on. Buy one company and sell another in the same sector and most of the broad market move cancels out, leaving the difference between the two businesses. That removes a variable. It does not remove the risk: both legs can go against you, and a hedge that stops working is worse than no hedge, because you thought you were covered.

The aim of building positions this way is to make the result depend on the analysis rather than on market direction. Aim is the accurate word. It is not a promise, and no construction removes the possibility of losing money.

Changing the order

The sequence is learnable and it does not need an institutional desk. What it needs is somewhere to write the thesis, the size and the exit down before the entry, and the discipline to check afterwards whether the trade followed the plan you wrote.

ITPM's Professional Trading Masterclass is where I learned this version of it: the macro setting, long/short construction, position sizing and correlation risk, taught as one sequence and not as four separate topics. My PTM review sets out what the course covers, what it assumes, and who I think it suits.

I am describing a way of making decisions, not an outcome. Taking a course does not produce trading profits, and nothing here is financial advice.

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