My 3 BIGGEST trading mistakes in 2025 (-$208k)
get my risk rules and squeeze more out of your trades
In 2025, I lost $208,000
Not because I didn’t understand markets or lack of research
But because I stopped following my own rules
On Monday morning at 9am, sitting in my co-working space with a plain black coffee, I wrote down every mistake that led to that number.
Then I figured instead of keeping all this valuable information to myself…
I’d share with you so you don’t repeat it in 2026
Here are the top 3 mistakes that cost me $208,000 in 2025 in 1:30min (and the rules I rebuilt because of them):
Mistake #3: Increasing Risk After Strong Performance Periods (-$50k)
In July, I booked $90,000.
The correct move after a month like that would have been to go to the beach in August and not trade.
Instead, I got greedy.
You see, before August I was only trading 40% of my capital.
Risk was controlled. Position sizing was deliberate.
After the $90,000 July win I:
• increased risk to the maximum
• started trading with 100% of my capital
• loaded full $20k positions instead of $5k
I got overconfident.
This mistake removed my ability to:
adjust entries
scale into positions
wait for confirmation
August performance: -$13,000
September performance: -$37,000
Total damage: –$50k
The rule I rebuilt:
Cap the risk per trade independent of recent performance.
Phase capital deployment so reserves are always preserved.
These guardrails should help me to avoid betting too big too fast on a trade.
If you’ve had a big winning month recently, this mistake will cost you too. Unless you cap risk immediately
Mistake #2: Initiating New Ideas Instead of Focusing on What Was Already Working (-$58k)
You can only trade 3,000 stocks with options.
At the time, I had 300 stocks fully researched in my Notion database.
That should have been enough.
Instead of squeezing more profit from proven names, I kept hunting for the “next better idea”…
This is shiny-object syndrome.
This cost me:
lower capital efficiency
missed scaling opportunities
mental fatigue from constant research
My execution suffered because my attention was scattered.
Total damage: –$58k
The rule I rebuilt
Limit new ideas added to research
Increase exposure only to trades with validated behavior
If you have over 100 trade ideas in your research database then stop. Focus on what you have, not the next big stock.
Mistake #1: Letting Emotions Override Risk Discipline (-$100k)
I still have bad dreams about Birkenstock ($BIRK).
You know the German sandal brand…
This trade alone cost me $20,000
Here’s why I took it:
Birkenstock is a global brand.
Q2 2025 earnings looked strong.
60% of revenue comes from the US.
Tariffs were introduced. Prices were raised.
Growth was 10%+. The brand moat looked real.
So in August, right after my $90k July, I opened a full-size position.
To win big.
A few days later everything broke:
earnings missed expectations
Chinese competitors undercut pricing
the brand moat wasn’t as strong as assumed
Growth stocks get punished when expectations slip.
So did Birkenstock.
I knew the trade was broken, but I didn’t want to admit I was wrong.
So I held.
I told myself it was temporary.
I hoped for a rebound.
Every day I held:
winners stayed under-allocated
losers grew larger than planned
the portfolio skewed weaker
Total damage: –$100k
The rule I rebuilt
Mechanical stops only
Predefined scaling rules
No discretionary overrides. Ever
If you sit in trades that you should have cut then you risk getting bigger losses.
The 3 Rules That Will Make You More Money in 2026
If you remember nothing else, remember this:
Cap risk per trade independent of recent performance
Phase capital deployment with reserves preserved
Enforce mechanical stops with zero discretion
Simple rules. Expensive lessons.
I could have made twice as much as I did in 2025 if I had gained that experience earlier.
Talk soon,
Iskan
Founder of Constellation Stocks
P.S. Want the exact risk rules, position sizing logic and live option trades?
The same framework I rebuilt after losing $208k
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Risk caps before emotion kicks in
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About the author
Iskan is a full-time professional trader and investor who managed a private equity fund with $120 million in Assets Under Management. He has invested over $80,000 in his trading education and spends more than 50 hours per week researching stocks.
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