Stay Wealthy Retirement Newsletter

Mar 27 • 3 min read

How to Lose Money Investing (Without Even Trying)


Want to sabotage your financial future?

There's an art to it.

While the market averaged a 10% annual return for the last 30 years...

...the average investor only captured close to half of the total returns delivered.

Year after year, we witness a masterclass in self-destruction through poor decision-making.

In response, author, psychologist, and behavioral finance expert Dr. Daniel Crosby published a satirical guide on investment self-sabotage.

It isn't just amusing—it's a mirror reflecting the irrational behaviors that separate successful investors from everyone else.

I enjoyed it, and trust you will, too.

So, with his permission, I'm excited to share it with you in today's email.

Want more from Dr. Crosby?


10 (Surefire) Ways to Ruin Your Financial Future

1. Ignore the Impact of Your Behavior

Over the last 30 years, the market has returned an average of 10.15% per annum, but the average investor only earned 8% due to poor investment behavior (Source: Dalbar).

Making prudent decisions is much less interesting than, say, trying to time a bottom in oil prices. So, by all means, allocate your efforts there.

2. Trust Your Gut

A meta-analysis comparing rules-based approaches to discretionary approaches in decision-making found that adhering to rules surpasses or matches expert human judgment 94% of the time.

Rules are boring, so just do what feels right with your money!

3. Live for Right Now

The worst ever 25-year return for stocks (that includes the Great Depression) was 5.9% annualized.

Patiently planning over an investment lifetime is tedious, so be sure to check your stocks every single day, where you will see red about 45% of the time.

4. Do as Much as Possible

When things get scary, it feels good to act, right? Right.

Disregard the research showing that the most active traders in Sweden underperformed their buy-and-hold counterparts by 4% per year.

Also, forget about the fact that across 19 major stock exchanges, investors who made major changes trailed those who did nothing by 1.5% a year.

5. Equate Volatility with Risk

Stocks outperform other asset classes by about 5% annualized after adjusting for volatility, but the ups and downs can be a lot to handle.

Volatility also provides opportunities to buy once-expensive names at a bargain.

Go ahead and ignore all of the upsides to volatility and do something “safe,” like buying treasuries that don’t keep up with inflation and lose real dollars every year.

6. Go it Alone

Aon Hewitt, Morningstar, and Vanguard all place the value of financial advice at anywhere from 2% to 3% per year in excess returns, but don’t let that stop you.

With multiple 24/7 news channels and hysteria-inducing magazines available to you, who needs personalized advice?

7. Try and Beat the Benchmark

You could argue that beating an impersonal market benchmark like the S&P 500 Index has nothing to do with your goals or risk tolerance, but that takes all the fun out of it!

Just go watch The Big Short and pick up a few pointers there.

8. Read Every Article that Mentions “Recession”

The US economy has been in a recession nearly 20% of the time since 1928, meaning the average investor will experience 10 to 15 recessions over their lifetime.

But by all means, read every scary article you can rather than accepting the historical trend that recessions are a common occurrence and haven’t materially impacted the long-term ability of the market to compound wealth.

9. Tune in to Dramatic Forecasts

David Dreman found that roughly 1 in 170 analyst forecasts are within 5% of reality, and Philip Tetlock’s examination of 82,000 “expert” predictions shows they barely outperform flipping a coin.

So, ignore the robust body of evidence saying no one can predict the future and pick a market prophet to follow.

10. Ignore History

JP Morgan reports the average intra-year drawdown over the past 35 years has been just over 14%.

What’s more, the market has ended higher in 27 of those 35 years.

Forget the fact that the horror of 1987’s “Black Monday” (a 22.61% single-day drop in the Dow) ended in a positive year for stocks.

Ignore historical suggestions that double-digit volatility is the norm and instead imagine vivid Doomsday scenarios that leave you in financial tatters.


Behavioral finance continues to demonstrate that our greatest obstacle to investment success is our own decision-making.

As Dr. Crosby cleverly illustrates, the gap between market returns and average investor returns stems directly from predictable psychological pitfalls.

Ultimately, your retirement hinges not on market timing or predictions but on your ability to master your emotions and make rational, informed decisions consistently over time.

📚 Don't forget to grab Dr. Crosby's new book, The Soul of Wealth!

(This is not an advertisement—I'm just a huge fan of his work and find myself gifting this book more than any other at the moment.)


Thank you for reading!

Hit reply to this email with comments, feedback, and/or questions.

Stay wealthy,

Taylor Schulte, CFP®

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