Mindset Alpha: The Modern Edge Is Between Your Ears

Most people think investing is about math. Morgan Housel reminds us it’s really about psychology. His book The Psychology of Money is a masterclass on how emotions, habits, and fears shape financial decisions far more than charts or spreadsheets.

Why People Don’t Invest (Even When They Should)

One of Housel’s most striking points is that fear, not ignorance, keeps people from building wealth. We fear losing money. We fear volatility. We fear looking foolish. So we sit on the sidelines, telling ourselves we’ll “wait until the timing is right.”

But as Housel explains, there is no perfect time. Waiting feels safe, but it’s actually the riskiest move of all — because every year spent waiting is a year of missed compounding. Time in the market beats timing the market.

Key Lessons from the Book

• Wealth is built quietly. The biggest returns come from consistency, not luck (but, if you’re not in the market, luck can’t help you).
• Compounding is useless if you don’t actually save—no amount of math can help money you never bothered to set aside.
• Know how much is “enough”; true freedom comes from contentment—not comparison. 
• Money’s greatest value is giving you control over your time and choices.
  
• Your behavior matters more than your knowledge. Emotional discipline beats IQ.
  
• Taking no risk is the biggest risk. Inflation and missed opportunities quietly erode wealth.
  
  

What This Means for Us as Investors

At Fearless Investor, we see this play out every day: talented, hardworking people who know they should be investing more, but let fear or hesitation hold them back. Fear of not being “smart enough” to invest keeps people parked on the sidelines or locked in the golden handcuffs of a 1% babysitter calling the shots. 

Housel’s book is a wake-up call — reminding us that smart risk-taking isn’t reckless, it’s essential. If you’re waiting for someone to give you the green light to take charge of your own money, Housel’s book is your permission slip—go be your own asset manager, a Fearless Investor.

The Next Step

Reading The Psychology of Money will open your eyes to how emotions can sabotage financial freedom. But knowledge alone isn’t enough. You need a supportive community to turn that insight into action.

That’s exactly why we created the Fearless Investor Community — a space for investors who want to stop letting fear dictate their decisions and start building wealth with confidence.

👉 Ready to apply these lessons and invest with courage?

Join the Fearless Investor Community → https://neil-winward.kit.com/community 

Percentage math has a flair for drama.

It loves to paint recovery like a Sisyphean struggle—an investor’s uphill battle in hurricane winds. “You’re down 50%? Buckle up. You’ll need to double your money just to break even.”

Cue the anxiety.

But here’s the real story: if you focus on absolute numbers, not percentages, the path back isn’t a cliff. It’s just a walk back to where you started.

Let’s break that illusion—and show you how smart investors avoid the percentage panic trap.

The Percentage Panic (And Why You Should Ignore It)

Let’s say you invest $100 and lose 50%. You’re down to $50.

Math says to get back to $100, you now need a 100% return. Sounds terrifying—until you remember that you only lost $50. You don’t need to “double” anything. You just need your $50 back.

This is the mental trick of percentage math. The recovery sounds harder because the base number has shifted. But the real-world effort—the actual dollars—hasn’t changed.

The Emotional Toll of Percentage Framing

This mathematical trick isn’t just academic—it has real psychological consequences.

Investors internalize that 100% gain as a monumental task. They panic. They hesitate. Or worse—they make reckless decisions trying to “win it back” quickly.

In reality, this fear is based on flawed framing.

Once you zoom out from percentages and look at absolute recovery, the fog clears. The path is calm. Predictable. Even empowering.

The Power of Absolute Recovery

Here’s the antidote to percentage panic:

• Lose $50, gain $50—you’re back.
  
• No math games. No emotional rollercoaster.
  
• Just arithmetic: subtract, then add.
  
  

It’s the same whether we’re talking about money, distance, calories, or steps on a hiking trail. The road back is exactly the same distance as the road down.

That’s not just reassuring—it’s actionable.

Why This Matters More Than You Think

1. Real Life Operates in Absolutes

If your wallet is $20 lighter and you find $20 in your jacket, you’re whole again. Nobody says, “Well, I need a 100% gain from this jacket to recover my 50% wallet drawdown.” That would be absurd.

But in finance, we allow that kind of thinking to dominate.

In real life, people think in units, not percentages. And investing should reflect that.

2. The Psychology of Simplicity

When you reduce problems to absolute terms, they stop feeling overwhelming.

Compare these two statements:

• “You need to double your money to recover.”
  
• “You need $50 to get back what you lost.”
  
  

Same math. Very different feeling.

That’s why the best investors don’t just watch the numbers—they manage the narrative.

So Why All the Percentage Drama?

Because percentages are sneaky.

When you lose 50%, the next gain is calculated from a smaller base. That’s what inflates the percentage requirement. It makes recovery seem twice as hard—when it’s not.

This leads to unnecessary risk-taking. It warps expectations. It confuses effort with math.

But here’s the truth:

• Absolute recovery never changes.
  
• Fall $X, climb $X. Done.
  
  

Don’t let percentage math turn a round trip into a guilt trip.

Investing Implications: What This Means for You

Savvy investors focus on liquidity, fundamentals, and signal—not just math tricks. If your portfolio is built to handle volatility, then drawdowns aren’t existential. They’re manageable.

You don’t have to hit home runs. You just need to keep walking forward.

If you’re down $50, structure your recovery around regaining that value with clear-eyed, long-term strategy—not magical percentage targets.

The Takeaway

Don’t let percentage math psych you out.

Recovery isn’t harder—just framed differently.

• Lose $X? Gain $X.
  
• The universe is balanced. You’re back on top.
  
• No anxiety required.
  
  

Next time someone tries to scare you with “you need a 100% return to make back a 50% loss,” just smile and say:

“Nah. I just need my money back.”

💼 Want a portfolio that responds to macro signals instead of gambling on timing?

→ Book a call with Dakota Ridge Capital

Want to surround yourself with other clear-eyed investors?

→ Join the Fearless Investor Community

Why the biggest threat to your portfolio isn’t the Fed—it’s you.

Let’s review 2025 so far.

• February: I escaped the 1% prison and reallocated to a mix that was driven by a model portfolio I was trying to follow.
• It was ~50% precious metals, split between gold and silver and some individual mining stocks.
• The rest was individual energy stocks and a leveraged inverse ETF on NASDAQ
• The strategy involved a highly technical wave analysis strategy that I respect but find hard to reproduce in a way I can get comfortable.
• I discovered levered inverse ETFs can be very volatile. I made money trading but lost a lot of sleep.
• Same with silver: it moves in a different way to gold because of its industrial use cases. Tariff concerns impact the price. I traded in and out, used inverse ETFs to escape the worst, but took a beating anyway. That cost my $20k I would not have lost had I simply held.
• I can’t own individual stocks unless I understand them. I feel obliged to do the work of underwriting them. I don’t have time for that, so I sold them.
• TLDR: I concluded I needed a different approach. I cut my losses, kept the gains, swore off inverse, levered ETFs and trading generally.
• I outline the strategy I have been following since then in a previous edition of this newsletter.

I sleep better and have a more balanced approach.

• Unless you are a great trader, staring at the red and green urging both to go in ‘your’ direction is a foolish way to spend your time.

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The Real Problem: You’re Too Smart for Your Own Good

Most people think investment losses are due to poor asset choices.

But if you’re reading this, your biggest threat isn’t stupidity—it’s behavioral bias.

You’re smart. You read the right things. You try to time it just a bit better.

And that’s what screws you.

Let me show you the four silent killers lurking in your head:

1. Recency Bias

You assume what just happened will keep happening.

If markets drop 3 days in a row, you expect a crash.

If Bitcoin pumps, you FOMO in.

This makes you chase highs and sell lows—the exact opposite of what works.

2. Loss Aversion

You feel a $1,000 loss twice as painfully as a $1,000 gain.

So you’ll hold losers hoping they recover and sell winners too early to “lock in” gains.

You become emotionally attached to outcomes, not strategies.

3. Overconfidence

You think you can outthink the market.

You believe this time you’ll sell at the top and buy at the bottom.

Most pros can’t do this. What makes you so special?

4.  Confirmation Bias

You only seek opinions that agree with your existing view.

Bullish on gold? You read gold bulls. Bearish on stocks? You ignore good earnings data.

It feels good to be “right” in your echo chamber—until reality hits.

The Solution: Systems, Not Feelings

Professionals don’t rely on emotional judgment.

They rely on systems—rules, processes, and review cycles.

Here’s what I now do:

• I track allocation in a simple dashboard
  
• I review my portfolio every 30 days, not daily
  
• I log every trade I make and the reason why
  
• I rank my emotional confidence in the trade (1–10)
  
• I don’t trade outside of my plan
  

Do I still make mistakes? Of course.

But they’re fewer. Less expensive. And easier to learn from.

What You Can Do Right Now

1. Create your Investor Operating Manual
   Write down your rules: asset mix, rebalancing dates, allocation limits, and emotional triggers.
   
2. Track decisions in a journal
   Note why you bought or sold something. It’ll expose your patterns.
   
3. Talk to people who challenge you
   Not everyone in your circle should agree with your outlook. That’s how you grow.
   

Final Thought

Markets are complex. But your brain is worse.

The best investors aren’t the smartest. They’re the most disciplined.

They know the enemy isn’t inflation or China or Powell.

It’s themselves.

Ready to Build a System That Works?

📈 Want a real-world portfolio strategy backed by macro fundamentals?

Book a call with Dakota Ridge Capital

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