Your Investment Hustle Might Be Hurting You

For years now, I've watched high-achieving investors fall into the same trap over and over – a trap I know all too well from personal experience.

We're programmed from an early age to believe that more effort equals better results.

Work harder. Do more. Stay busy.

It's the fuel that propelled many of us through school, careers, and business ventures.

But here's the thing – when it comes to investing, this mentality can actually work against you.

 

Reconciling Action with Patience

Now, if you're a regular reader, you might be thinking: “Wait a minute – didn't you just write about the dangers of inaction and opportunity cost a few weeks ago?”

Yes, I did. And no, I'm not contradicting myself (at least not intentionally).

There's a critical distinction here:

Not investing at all is vastly different from investing strategically with patience.

In my previous newsletter, I was talking about folks who are sitting completely on the sidelines – watching their cash get eaten by inflation while waiting for some mythical “perfect” time or deal to come along.

Today, I'm focusing on the mindset needed after you've committed capital – the approach that leads to better long-term results.

The first step is always to be in the game. But once you're in, playing smarter often means making fewer moves, not more.

 

The Hyperactivity Trap

Investing operates by different rules than most areas of life.

While careers and businesses typically reward hustle and action, investing often rewards strategic inaction.

The data tells a compelling story: studies consistently show that investors who trade frequently underperform those who buy and hold. Warren Buffett's 50+ year track record versus the countless hedge funds that have come and gone in the same period help illustrate this well.

As a passive investor, constantly chasing the “next hot deal” often leads to:

 

The Expert Advantage

So restraint in trading frequency is almost always a net benefit to investors. The second dimension of “doing less” deals with operational involvement.

There's a significant skill gap between professional operators and DIY investors. While education is crucial (you should absolutely understand what you're investing in), you can't replicate years or decades of specialized experience overnight.

For most people reading this, your time is likely better spent:

  • Building your primary business or career

  • Leveraging your unique skills and expertise

  • Investing in relationships and pursuits that energize you

This is precisely why passive real estate investing makes so much sense for high performers. You leverage someone else's expertise while you focus on what you do best.

 

The Compounding Effect of Patience

Possibly the hardest part of doing less is simply being patient enough to let compounding work its magic.

Every time you exit an investment prematurely or redirect capital to chase a trend, you restart the compounding clock. For syndication investors specifically, this might look like selling your position early (if possible), passing on reinvestment opportunities with operators you know well, or constantly shifting your investment criteria based on what's currently “hot.”

I'll admit that I struggle with this. I have a textbook case of shiny object syndrome (as I've mentioned in previous newsletters). But I've trained myself to recognize when that impulse arises and ask better questions.

 

A Decision Framework for Smarter Investing

Given these principles of patience and delegation, how do we make better investment decisions?

I've found two questions particularly helpful:

  1. What truly deserves my active attention versus what should I delegate? Not everything needs your direct involvement.

  2. Is this a strategic portfolio change or am I just chasing the next hot thing? There's a big difference between thoughtful reallocation and performance chasing.

The most successful investors I know aren't the ones who work the hardest at investing. They're the ones who work the smartest by knowing where their attention genuinely adds value and understanding when to be patient.

This doesn't mean never making changes. But it does mean being intentional about why and when you do.

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