Reverse Engineering a 20% Return Target Before Entering a Trade

Most traders start by searching for entries. They look for chart patterns, indicators, market narratives, or signals that might identify the next profitable opportunity. While these tools can be useful, they often address the final step of investing rather than the first.

A portfolio manager typically approaches the problem differently. Before considering an entry setup, the manager defines a target return, acceptable drawdown, position sizing framework, and expected opportunity set. The goal is not merely to find good trades. The goal is to build a process capable of achieving a specific financial objective.

This distinction may seem subtle, but it fundamentally changes decision-making. Instead of asking whether a trade looks attractive, the investor asks whether the entire strategy can realistically deliver the desired outcome while remaining within acceptable risk limits.

Observation: Start With The Desired Return

Consider a hypothetical account worth $100,000. Suppose the objective is to achieve a 20% annual return. The requirement is therefore simple: generate $20,000 of profit over the course of a year.

Next comes risk allocation. Assume the investor is willing to risk 1% of capital per trade, or $1,000. This immediately creates a common unit for evaluating performance. Every gain and loss can now be measured relative to the amount of capital placed at risk.

Now assume the average holding period is five trading days. With approximately 250 trading days in a year, the strategy can deploy capital roughly 50 times. The exact number is not important. What matters is recognizing that opportunity frequency is part of the investment equation.

At this point, a useful question emerges. If the annual target is $20,000 and there are approximately 50 opportunities, how much must each trade contribute on average? The answer is $400. Relative to the $1,000 risk amount, the required expectancy becomes 0.4R.

Explanation: Why Expectancy Is The Critical Variable

Many traders focus on individual outcomes. They celebrate large winners and become frustrated by losses. However, long-term performance is determined by expectancy rather than any single trade. Expectancy measures the average amount earned per trade after accounting for both winners and losers.

In this example, the strategy does not need every trade to generate 2R or 3R. It only needs to produce an average expectancy of 0.4R across a sufficiently large sample of opportunities. The challenge is therefore not finding extraordinary trades. The challenge is building a repeatable process.

Consider a strategy with a 40% win rate, average winners of 2R, and average losers of 1R. The expectancy calculation is straightforward:

  • 0.4 × 2R = 0.8R
  • 0.6 × 1R = 0.6R
  • Net expectancy = 0.2R

At first glance, the strategy appears attractive. The average winner is twice the average loser, and the strategy remains profitable. However, profitability alone is not the objective. The objective is achieving a specific return target.

An expectancy of 0.2R with $1,000 risk per trade generates approximately $200 per opportunity. Across 50 opportunities, expected annual profit becomes $10,000. That translates to a 10% annual return rather than the desired 20% target.

This exercise highlights a reality many investors overlook. A profitable strategy can still be inadequate. The correct benchmark is not whether a strategy makes money. The correct benchmark is whether it meets the investor’s required return while remaining within acceptable risk limits.

Implication: Three Levers Determine The Outcome

Once the economics of the strategy are understood, improving results becomes a matter of adjusting a limited number of variables. There are only a few ways to bridge the gap between a 10% expected return and a 20% target.

The first lever is expectancy. Better trade selection, improved exits, stronger risk management, or a more robust edge can increase the average profit generated per unit of risk. Small improvements in expectancy often have significant long-term effects because they are applied repeatedly.

The second lever is position sizing. Increasing risk per trade raises expected profits, but it also increases drawdowns and portfolio volatility. This lever is powerful, but it must be used carefully because survival remains the foundation of compounding.

The third lever is opportunity frequency. A shorter holding period or a broader universe of opportunities can increase the number of independent decisions made each year. More opportunities allow the investor to deploy an edge more frequently.

Connecting Skill To Opportunity

This relationship is captured by the Fundamental Law of Active Management:

IR = IC × √Breadth

The formula emphasizes that performance is influenced by both skill and opportunity frequency. Information Coefficient represents forecasting ability, while Breadth represents the number of independent opportunities available to apply that skill.

An investor does not necessarily need extraordinary predictive ability. A modest edge, applied consistently across many opportunities with disciplined position sizing, can produce attractive outcomes. Conversely, even a strong edge may struggle to generate meaningful returns if opportunities are scarce.

This perspective shifts attention away from predicting the next trade and toward designing a repeatable investment process. Rather than obsessing over individual outcomes, the investor focuses on expectancy, position sizing, opportunity frequency, and risk-adjusted performance.

Ultimately, entries matter, but they are not the starting point. The process begins with defining return objectives, acceptable losses, risk per trade, and opportunity frequency. Only after these variables are established does the entry setup become relevant. The trade is simply the final expression of a portfolio construction decision that began much earlier.

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There Are Only Two Ways To Become A Better Investor

There Are Only Two Ways To Become A Better Investor

Most investors spend their entire lives trying to make better decisions.

They read more books.

Study more charts.

Follow more experts.

Analyze more data.

The objective is simple:

Make better investment decisions.

There is nothing wrong with this approach.

But there is another path that many investors overlook.

You can either:

  • Make better decisions.
  • Make more decisions.

Understanding the difference changed the way I think about investing.


The Formula Behind The Idea

In portfolio management, there is a well-known relationship:

Information Ratio = Skill × Breadth

You do not need to understand the mathematics behind the formula to understand its message.

The formula says that investment performance comes from two sources:

  • The quality of your decisions.
  • The number of opportunities you have to apply that skill.

I prefer to think about it in plain English.

Better decisions.

Or more decisions.


My First Investing Framework

In the early years of my investing journey, I focused almost entirely on making a few high-conviction decisions.

One example was my investment in GAS after oil prices experienced a significant decline.

I spent time studying the industry.

I built a thesis.

I developed strong conviction.

The entire outcome depended on a relatively small number of decisions.

This approach has one attractive feature.

If you are right, the rewards can be significant.

It also has one major weakness.

If you are wrong, there are very few opportunities to recover.

Your results become heavily dependent on a handful of large bets.


What Changed

Over time, my thinking evolved.

Trading, options, and even poker exposed me to a different framework.

I became less interested in finding a few perfect opportunities.

I became more interested in creating a process that could be repeated consistently.

Instead of asking:

How can I make this one investment work?

I started asking:

How can I make hundreds of decisions with a small edge?

This shift fundamentally changed my approach.

Poker players understand this naturally.

The objective is not to win every hand.

The objective is to make enough good decisions over a large number of hands.

The same principle applies to investing.


Two Paths

Every investor eventually chooses one of two paths.

Path One: Increase Decision Quality.

This path focuses on research, analysis, expertise, and insight.

The goal is to improve the accuracy of each decision.

Many successful value investors follow this approach.

Path Two: Increase Breadth.

This path focuses on process, repetition, and scale.

The goal is to apply a small edge across many independent opportunities.

Many systematic traders and option sellers follow this approach.

Neither path is inherently superior.

The important thing is understanding which game you are playing.


The Question Most Investors Never Ask

Most investors spend years searching for better opportunities.

Very few stop to ask:

Am I trying to improve my decisions, or increase the number of decisions I make?

The answer influences everything.

Your strategy.

Your process.

Your portfolio construction.

Even your expectations.

An investor making five decisions per year needs a very different framework from an investor making five hundred decisions per year.


Reader Exercise

Think about your own investing approach.

Which description sounds more like you?

A. I make a small number of high-conviction decisions.

B. I make a large number of repeatable decisions with a small edge.

C. I am trying to combine both.

There is no universally correct answer.

But understanding your answer may help you understand your investment process more clearly.


Final Thought

One of the biggest changes in my own investing journey was realizing that performance does not come from a single source.

It comes from a combination of decision quality and decision frequency.

Some investors win through exceptional insight.

Others win through disciplined repetition.

Most successful investors eventually develop a balance between the two.

The important question is not which path is better.

The important question is whether you know which path you are currently following.

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How I Determine Position Size

One of the most common questions investors ask is:

How large should my position be?

Unfortunately, most people ask this question after finding an investment idea.

I believe the process should work in the opposite direction.

Position size should not be determined by conviction.

Position size should be determined by risk.


The Wrong Approach

Many investors follow a process that looks like this:

Find an opportunity → Become excited → Increase size.

The stronger the conviction, the larger the position.

This approach feels logical.

It is also responsible for many large drawdowns.

Markets do not care about conviction.

Markets care about outcomes.

A highly convincing idea can still be wrong.


The Framework I Use

I start with portfolio objectives rather than trade ideas.

Step 1: Define your return target.

What annual return are you trying to achieve?

10%? 15%? 20%?

Step 2: Define your maximum acceptable drawdown.

How much pain can you tolerate before the strategy becomes unacceptable?

10%?

15%?

20%?

Step 3: Create a risk budget.

I generally think of a single investment idea as consuming between 1/10 and 1/20 of the maximum drawdown budget.

This means no single idea should be capable of significantly damaging the portfolio.


A Practical Example

Assume the following:

  • Portfolio value: $100,000
  • Target annual return: 12%
  • Maximum acceptable drawdown: 15%

A 15% drawdown means the portfolio can tolerate a loss of $15,000.

If we divide that risk budget into 15 equal units, each investment idea receives approximately 1% of portfolio risk.

In this example:

  • Risk budget per idea = $1,000

Only after determining this number do I think about position size.

The question becomes:

How large can the position be if I am willing to lose no more than $1,000?

This is very different from asking:

How much money should I put into this trade?


Why This Matters

Many investors fail because they focus on maximizing returns.

Professional investors focus on controlling losses.

Large drawdowns require disproportionately large gains to recover.

A portfolio that loses 50% must gain 100% simply to break even.

Avoiding catastrophic losses is often more important than finding extraordinary opportunities.


Reader Exercise

Before entering your next investment, answer the following:

  • Portfolio size: ________
  • Target annual return: ________
  • Maximum acceptable drawdown: ________
  • Risk budget per idea: ________

If you cannot answer these questions, you may not be sizing positions.

You may simply be allocating capital based on confidence.


Final Thought

Most investors spend years searching for better entry signals.

I believe a more useful exercise is learning how much to invest before deciding what to invest in.

Position sizing will not guarantee success.

But it can prevent a single mistake from becoming a permanent setback.

That is why I continue to believe:

Position sizing before strategy.

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The First Rule Is Survival

One of the biggest investing lessons I learned did not come from a textbook.

It came from almost blowing up a trading account.

When I started trading seriously, I was obsessed with growth.

Like many traders, I set daily profit targets, 2%/day!!! . I wanted consistency. I wanted momentum. Most importantly, I wanted to maintain a winning streak.

At first, the results looked great.

Then I started increasing position sizes.

Not because the opportunity was exceptional.

But because I wanted to protect the feeling of success.

When a position moved against me, I sometimes averaged down. The logic felt reasonable at the time. If the market came back, the loss would disappear and the winning streak would continue.

Eventually, the account suffered a drawdown close to 80%.

That experience changed the way I think about capital forever.

Growth Can Be Dangerous

Most investors assume the biggest risk comes from losses.

I disagree.

The biggest risk often comes from success.

Success creates confidence.

Confidence creates larger positions.

Larger positions create fragility.

Many traders blow up shortly after their best periods, not their worst ones.

The market rewards them just enough to encourage behavior that eventually becomes destructive.

The Same Lesson Applies Outside Trading

I have seen a similar pattern in corporate finance.

As a CFO, I rarely worry about businesses growing too slowly.

I worry about businesses growing too aggressively.

A company can survive a missed opportunity.

A company may not survive a decision that commits too much capital to a single project.

This is something I think about frequently when evaluating large projects.

Survival comes first.

Why Survival Matters

Markets provide endless opportunities.

Capital does not.

If you lose 80% of your account, your next challenge is no longer making money.

Your next challenge is survival.

Every large drawdown reduces flexibility.

Every large drawdown reduces future opportunities.

Every large drawdown increases the pressure to make perfect decisions.

That is why professional investors spend so much time thinking about risk.

Not because they fear opportunity.

Because they understand that opportunity only matters if you are still around to take it.

The Shift

Today, I think differently.

I no longer ask:

How much can I make?

I ask:

How much can I lose?

I no longer focus on protecting winning streaks.

I focus on protecting capital.

Because the market always gives another opportunity.

Capital does not always give a second chance.

Final Thought

Looking back, the biggest mistake was not a bad trade.

The biggest mistake was prioritizing growth over survival.

The same mistake destroys trading accounts, investment portfolios, and businesses.

The first rule is not making money.

The first rule is survival.

Everything else comes after that.


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