“If it feels good, you’re probably too late. If it feels uncertain, you might be onto something.”

Introduction: The Myth of Certainty in Trading

Imagine standing at the edge of a cliff, peering down into the unknown. The air is thick with hesitation. Your gut screams at you to turn back, to seek solid ground. Yet, in trading, that moment of discomfort—where every instinct urges caution—is often where the biggest opportunities lie.

Think back to some of the greatest market trends in history: Bitcoin’s meteoric rise. Crude oil’s wild spikes. Cocoa’s stunning rally in 2024. In hindsight, these moves seem obvious. The charts tell a clean story, and analysts dissect them as if they were inevitable. But rewind to the moment when traders had to commit capital—these trades weren’t comfortable. They were terrifying.

That’s because financial markets don’t reward certainty; they punish it. When an opportunity feels obvious, it’s usually too late. The easy trade—the one that makes sense, that feels safe—is often a crowded one, already exploited. True outlier trades, the ones that define trend-following success, require stepping into the unknown. They demand action at the precise moment when most traders hesitate.

This is the paradox of profitable trading: the best trades often feel the worst. The reason? We are wired to crave certainty, yet markets thrive on uncertainty. This blog explores why discomfort is an essential ingredient of trend following, how our psychological biases work against us, and why those who embrace the unknown stand to capture the greatest returns.

1. Why Humans Seek Certainty in Trading

The human brain is an evolutionary masterpiece, built for survival, not for trading. For thousands of years, certainty meant safety. We evolved to seek patterns, to predict outcomes, and to avoid unnecessary risks. In the wild, hesitation and caution were life-saving instincts. In financial markets, they are often fatal to performance.

Several psychological biases conspire against traders:

• Loss aversion: The pain of losing outweighs the pleasure of winning. Traders hesitate to enter tough trades and exit winners too soon.
• Confirmation bias: Seeking information that supports existing beliefs, reinforcing “safe” but unprofitable decisions.
• Illusion of control: Many traders believe they can predict the market’s next move—leading to overconfidence in bad trades and hesitation in good ones.

When confronted with a trade that doesn’t “feel right,” our brains instinctively reject it. But in trend following, the most uncomfortable trades are often the most profitable.

2. Trend Following and the Discomfort Principle

Trend following is a strategy built on reaction, not prediction. It doesn’t seek certainty—it thrives on systematic uncertainty.

Unlike fundamental investors, who search for valuation “truths” or market mispricings, trend followers act only when the market itself moves. The key challenge?

• A breakout could be a false signal.
• A trend could already seem “too extended.”
• The market could reverse at any moment.

These uncertainties create discomfort. And that discomfort is precisely what makes trend following work.

If a trade feels too good to be true—if everyone agrees it’s a sure thing—it’s probably too late. The market has already priced in that certainty. The biggest trends are rarely obvious at the start; they begin in uncertainty, chaos, and hesitation.

3. Historical Examples of Uncomfortable but Profitable Trades

Let’s look at three moments in history where uncertainty ruled—yet trend followers thrived.

Bitcoin’s Reluctant Believers

Bitcoin’s 2017 and 2020 bull runs were textbook examples of discomfort. Each breakout was met with skepticism. Mainstream analysts called it a bubble. Traditional investors dismissed it as speculative hype. Many traders hesitated, waiting for a “safe” entry that never came. Yet those who followed the trend, despite the unease, saw exponential returns.

Cocoa’s Explosive Rally in 2024

Cocoa’s unprecedented price surge in 2024 is another perfect case. It was an outlier trade—unexpected, volatile, and seemingly “overdone” at every stage. Many trend followers hesitated, questioning whether it was too late. Yet those who ignored their discomfort and followed the system captured one of the biggest commodity trades of the decade.

Oil’s Extreme Moves (2008, 2022)

Crude oil has a history of trend explosions. Each time, traders hesitated. “Oil can’t go any higher” or “This move is unsustainable” were common refrains. And yet, trend followers who simply followed price action—despite all the uncertainty—profited massively.

The pattern is clear: the trades that feel the most uncertain are often the most rewarding.

4. The Cost of Comfort: Why “Easy” Trades Often Disappoint

There is a direct relationship between comfort and consensus. When a trade is comfortable, it usually means:

• The narrative is widely accepted.
• The price has already moved significantly.
• Everyone is already positioned.

But markets don’t reward consensus—they reward change.

Easy trades—such as mean reversion setups that feel “safe”—can work temporarily but often fail when the trend accelerates. Many traders prefer strategies that feel logical, structured, and controlled. Yet these same traders struggle to catch major outliers because they hesitate at key moments.

The cost of comfort is missing the very trades that define a trend-following strategy.

 

5. Embracing Uncertainty as a Competitive Edge

So how do trend followers embrace discomfort rather than avoid it?

• Small Bet Sizes Reduce Emotional Pressure: Large positions amplify fear. By sizing trades appropriately, trend followers minimize emotional biases and stay systematic.
• Systematic Execution Removes Decision Paralysis: Rules remove the need for gut-based decision-making. If a trade aligns with the system, the trader takes it—regardless of how it feels.
• Accepting Losses as Part of the Game: Discomfort often comes from fear of being wrong. Trend followers accept that many trades will be losers, but a few big winners will define long-term performance.
• Recognizing That If It Feels Uncertain, It’s Probably a Good Sign: The best trades often feel wrong at the moment. Recognizing this paradox gives traders the mental edge to execute without hesitation.

The Real Edge Lies in Doing What Others Won’t

In trading, as in life, comfort is often a trap. The market doesn’t reward certainty—it exploits it. The greatest outlier trades, the ones that define trend following success, emerge from moments of doubt, hesitation, and discomfort.

The challenge isn’t to eliminate uncertainty but to embrace it. The trader who can step into the unknown while following a systematic edge holds a distinct advantage over those still searching for certainty.

“If it feels good, you’re probably too late. If it feels uncertain, you might be onto something.” The next time hesitation creeps in, recognize it for what it is: a sign that you might be exactly where you need to be.