Why Traders Self-Sabotage After Winning: A Deep Dive with Lia Holmgren

You hit your target. Your trade worked. Your system is solid.
So… why do you suddenly feel the urge to throw it all away?

If you’ve ever sabotaged a winning streak, spiraled after a big gain, or caught yourself “winging it” after weeks of discipline, you’re not alone—and you’re not broken. In the latest episode of Trading Truths, we sat down with Lia Holmgren—a trader, performance coach, and former relationship therapist—to unpack the invisible patterns that keep smart traders stuck in self-defeating loops.

🎧 Listen to the full episode on Spotify: Why Smart Traders Self-Sabotage – with Lia Holmgren


From Strategy to Sabotage: What the HeCK is Happening?

It’s one of the biggest mind-twisters in trading:
You can be at the top of your game, making sound decisions, managing risk… and then out of nowhere, you pull a 180 and torch your progress.

Lia has seen this firsthand—not just in markets, but in psychology. “We’re not just trading charts,” she said. “We’re trading our beliefs, our identities, and our unresolved stories.”

The self-sabotage doesn’t come from lack of knowledge. It comes from deeper emotional patterns that get activated when we’re under stress—or even when we’re finally succeeding.

“If you grew up believing you had to be perfect to earn love or approval,” Lia shared, “you’ll carry that into trading. Suddenly a loss isn’t just a loss—it’s proof that you’re unworthy.”


Trading Trauma: The Childhood Patterns We Bring to the Screen

In the episode, Lia walks us through a few powerful examples of how early life experiences shape our behaviors as traders:

1. Sabotaging After Success

You string together a few wins, and instead of reinforcing your edge, you deviate. You jump into setups that aren’t there. You oversize. You ignore your stop.

Why?

“Subconsciously,” Lia said, “many traders believe they don’t deserve to win. Or they fear what success might bring—visibility, pressure, higher stakes.”

It’s not a logic issue—it’s an identity issue.

2. Perfectionism Masquerading as Discipline

We all want to “follow our rules.” But Lia warns: perfectionism isn’t the same as professionalism.

“Perfectionism is a trauma response,” she said. “It’s the belief that if I do everything just right, I’ll be safe.”

That mindset is brittle. The moment something goes sideways—because it always does—you spiral. You blame yourself. You question your system. You try to ‘fix’ something that was never broken.

3. Reacting Emotionally and Calling It Intuition

We’ve all felt that itch to act: to chase, to double down, to ‘just do something.’

“Discipline isn’t about being robotic,” Lia said. “It’s about being emotionally regulated.”

She explains that many traders confuse emotional urgency with intuition. Real intuition comes from a calm, grounded place—not panic.


The Work Behind the Work: How to Change These Patterns

If you’re starting to see yourself in any of these patterns, good. That awareness is the first domino.

But what do you do about it?

Lia offers a few key practices traders can start using immediately to unpack and rewire these habits:

📝 Emotional Journaling (Yes, after your trades)

Not just what you did—but what you felt. Lia recommends writing down:

  • What was I feeling before I entered the trade?
  • What was I hoping this trade would give me?
  • Did I feel rushed? Anxious? Angry?
  • What part of me was trying to take control here?

This isn’t fluff—it’s data. And over time, it reveals patterns you can’t see in a P&L chart.

🔄 Pattern Recognition Through Reflection

After a losing streak, Lia suggests zooming out. Are you punishing yourself for succeeding? Are you reverting to the emotional age you were when you first learned “success = danger”?

Ask yourself:

“What am I afraid will happen if I keep winning?”

Sometimes the answer is revealing. And healing.

🧠 Identity Work

Lia also emphasizes the importance of redefining your identity as a trader. If your self-worth is tied to being “right,” you’re setting yourself up for constant internal conflict.

Try this: instead of chasing the identity of “a successful trader,” focus on becoming “a process-driven decision maker.” The more neutral your self-image becomes, the easier it is to stay grounded.


Real Trading Freedom Starts Inside

This episode hits hard because it dares to ask deeper questions. Questions most traders avoid.

“We think we want freedom from a 9-to-5,” Lia said. “But what we really want is freedom from the parts of ourselves that hold us back.”

That line stopped us in our tracks.

If you’re tired of repeating the same mental and emotional cycles—even when your technicals are dialed in—this conversation is your call to dig deeper.

🎧 Catch the full episode here:
👉 Listen on Spotify


Connect with Us

Want to go further?

🔹 Lia Holmgren

🔹 Mike Lamothe

🔹 Dennis Wilborn


Real trading breakthroughs don’t just come from new setups—they come from new self-awareness. Let’s keep going.

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