timothy sykes logo

Trading Lessons

Why I Want You To Lose

Timothy SykesAvatar
Written by Timothy Sykes
Updated 12/10/2025 7 min read

You read that subject line right.

While everyone else in this industry is wishing you holiday profits, pumping you up with motivational garbage about “crushing it” and “going to the moon…”

I’m hoping you lose.

Not because I want you to fail. Because I want you to succeed.

I’ve helped create over 50 millionaire students.*

You know what they all have in common?

None of them had immediate success.

Zero. Not one.

Even Jack Kellogg (who turned $7,500 into over $25 million)…*

Or Matt Monaco (who made $900,000 in the past five months)…*

If you look at their journeys, their first 6 to 12 months are filled with the same pattern:

Bone-headed mistakes, blown opportunities, and easily avoidable missteps.

They bought pumps at the top. They held losers too long. They ignored their stop losses. They revenge-traded after getting stopped out. They FOMO’d into setups they didn’t understand.

Every mistake you can imagine. They made it.

Just like I did when I started.

But one thing separated them from the 90% of traders who fail:

They didn’t make the same mistakes over and over.

They lost early, lost smart, and took invaluable lessons from every single error.

Now, they’re all millionaires.*

And that’s not an accident…

This Is Why You Need To Take Losses…

The Best Lessons Don’t Come From Wins

Wins barely teach you anything.

You buy a stock. It goes up. You sell.

You feel smart, accomplished, and validated.

But what did you actually learn?

That you got lucky on timing? That the setup happened to work this time?

You’re not walking away from that with a priceless lesson.

Losses teach you everything.

A loss forces you to ask the hard questions:

  • “Why did I enter this trade?”
  • “Did I follow my rules or did I break them?”
  • “Where was my stop loss, and did I actually cut it there?”
  • “Was this a valid setup, or did I get FOMO and chase?”
  • “What would I do differently next time?”

Those questions build pattern recognition, expose your weaknesses, and force you to refine your process.

Stop Fearing Losses

Nearly every trader fears losses in the beginning.

They treat every minor red day like a disaster, every tiny loss like a failure…

Image created by Google Gemini
Image created by Google Gemini

So they actively avoid risk. They stop trading after a loss.

And 90% of them lose money with no improvement at all.

Year after year. Same mistakes. Same results.

Why? Because they never learned from their losses.

They just kept making the same errors on a loop, hoping something would magically click.

It doesn’t work that way.

If you’re new to trading, or if you’re still struggling to find consistency, you need to hear this:

Early losses are small investments in your trading education.

Every mistake you make with a small account is a lesson you won’t have to learn later when the stakes are higher (and the losses more devastating).

Every blown trade that forces you to examine your process is building the discipline you’ll need to scale up.

Every time you cut a loss quickly instead of hoping it comes back, you’re programming the right behavior into your brain.

Grow your “knowledge account” first.

More Breaking News

That’s how you build long-term fortitude, wherewithal, and ruthlessness…

The One Rule That Changes Everything

All that said, your losses have to be controlled.

There’s a massive difference between a small smart loss and a catastrophic dumb one.

A smart loss: You enter a trade with a plan. The setup fails. You cut it at your predetermined stop, down 5% to 7%.

You journal the mistake, vow not to make it again, and move on with your life.

A dumb loss: You chase a stock at the top. It reverses. You hold, hoping it comes back. You’re down 15%, then 25%, then 40%.

Now your account has taken a kick to the chest when it should’ve been a slap on the wrist.

Smart losses teach you. Dumb losses destroy you.

Rule #1: Cut losses quickly.

If you can master this one rule, you can survive long enough to learn everything else.

Small losses don’t hurt your account. They don’t damage your psychology. They don’t put you in a hole you can’t climb out of.

They just provide feedback. And feedback helps you improve.

What I Really Mean

When I say “I hope you lose this week,” I’m not wishing ill will on you.

What I really mean is:

  • I hope you take trades that test your rules.
  • I hope you take a handful of controlled losses that expose gaps in your process.
  • I hope you cut those losses quickly, journal what went wrong, and adjust for next time.
  • I hope you build the pattern recognition that only comes from reps, even when those reps don’t go your way.

Because that’s how all 50 of my millionaire students did it.*

If you’re waiting to trade until you’re “ready,” you’ll never start.

If you’re avoiding risk because you’re afraid of losses, you’ll never learn.

Even the world’s most successful traders still make mistakes.

They lose on trades all the time. They just cut those losses before they become disasters.

They have bad days, bad weeks, even bad months.

But they study those periods, learn from them, and come back stronger.

That’s the difference.

So this week, don’t hope for profits.

Hope for lessons. Hope for growth. Hope for progress.

Write a letter to Santa, put it next to his milk and cookies…

Image created by Google Gemini
Image created by Google Gemini

Cheers,

Tim Sykes

 

*Past performance does not indicate future results



How much has this post helped you?



Leave a reply

Author card Timothy Sykes picture

Timothy Sykes

Tim Sykes is a penny stock trader and teacher who became a self-made millionaire by the age of 22 by trading $12,415 of bar mitzvah money. After becoming disenchanted with the hedge fund world, he established the Tim Sykes Trading Challenge to teach aspiring traders how to follow his trading strategies. He’s been featured in a variety of media outlets including CNN, Larry King, Steve Harvey, Forbes, Men’s Journal, and more. He’s also an active philanthropist and environmental activist, a co-founder of Karmagawa, and has donated millions of dollars to charity.
Read More

* Results are not typical and will vary from person to person. Making money trading stocks takes time, dedication, and hard work. There are inherent risks involved with investing in the stock market, including the loss of your investment. Past performance in the market is not indicative of future results. Any investment is at your own risk. See Terms of Service here

The available research on day trading suggests that most active traders lose money. Fees and overtrading are major contributors to these losses.

A 2000 study called “Trading is Hazardous to Your Wealth: The Common Stock Investment Performance of Individual Investors” evaluated 66,465 U.S. households that held stocks from 1991 to 1996. The households that traded most averaged an 11.4% annual return during a period where the overall market gained 17.9%. These lower returns were attributed to overconfidence.

A 2014 paper (revised 2019) titled “Learning Fast or Slow?” analyzed the complete transaction history of the Taiwan Stock Exchange between 1992 and 2006. It looked at the ongoing performance of day traders in this sample, and found that 97% of day traders can expect to lose money from trading, and more than 90% of all day trading volume can be traced to investors who predictably lose money. Additionally, it tied the behavior of gamblers and drivers who get more speeding tickets to overtrading, and cited studies showing that legalized gambling has an inverse effect on trading volume.

A 2019 research study (revised 2020) called “Day Trading for a Living?” observed 19,646 Brazilian futures contract traders who started day trading from 2013 to 2015, and recorded two years of their trading activity. The study authors found that 97% of traders with more than 300 days actively trading lost money, and only 1.1% earned more than the Brazilian minimum wage ($16 USD per day). They hypothesized that the greater returns shown in previous studies did not differentiate between frequent day traders and those who traded rarely, and that more frequent trading activity decreases the chance of profitability.

These studies show the wide variance of the available data on day trading profitability. One thing that seems clear from the research is that most day traders lose money .

Millionaire Media 66 W Flagler St. Ste. 900 Miami, FL 33130 United States (888) 878-3621 This is for information purposes only as Millionaire Media LLC nor Timothy Sykes is registered as a securities broker-dealer or an investment adviser. No information herein is intended as securities brokerage, investment, tax, accounting or legal advice, as an offer or solicitation of an offer to sell or buy, or as an endorsement, recommendation or sponsorship of any company, security or fund. Millionaire Media LLC and Timothy Sykes cannot and does not assess, verify or guarantee the adequacy, accuracy or completeness of any information, the suitability or profitability of any particular investment, or the potential value of any investment or informational source. The reader bears responsibility for his/her own investment research and decisions, should seek the advice of a qualified securities professional before making any investment, and investigate and fully understand any and all risks before investing. Millionaire Media LLC and Timothy Sykes in no way warrants the solvency, financial condition, or investment advisability of any of the securities mentioned in communications or websites. In addition, Millionaire Media LLC and Timothy Sykes accepts no liability whatsoever for any direct or consequential loss arising from any use of this information. This information is not intended to be used as the sole basis of any investment decision, nor should it be construed as advice designed to meet the investment needs of any particular investor. Past performance is not necessarily indicative of future returns.

Citations for Disclaimer

Barber, Brad M. and Odean, Terrance, Trading is Hazardous to Your Wealth: The Common Stock Investment Performance of Individual Investors. Available at SSRN: “Day Trading for a Living?”

Barber, Brad M. and Lee, Yi-Tsung and Liu, Yu-Jane and Odean, Terrance and Zhang, Ke, Learning Fast or Slow? (May 28, 2019). Forthcoming: Review of Asset Pricing Studies, Available at SSRN: “https://ssrn.com/abstract=2535636”

Chague, Fernando and De-Losso, Rodrigo and Giovannetti, Bruno, Day Trading for a Living? (June 11, 2020). Available at SSRN: “https://ssrn.com/abstract=3423101”