Over the past few months, I’ve been watching movies about the Great Financial Crisis of 2008. At the time, I was a freshman in college. While I knew something bad was happening, I’d be lying if I said I fully understood the gravity of the situation. My parents certainly did!

Some of the movies I watched:

The Big Short
The Last Days of Lehman Brothers
Margin Call
The Company Men
99 Homes
Too Big to Fail
Inside Job

Besides their entertainment value (most of these are excellent), two major lessons stood out:

The media’s obsession with the "big bet."
The importance of resilience and maximizing for endurance.

Let’s dive in.

The Media’s Obsession with the “Big Bet”

The media loves to celebrate the dramatic winners. The Big Short tells how Michael Burry and Mark Baum and others made billions by betting against the housing market. While compelling, this narrative is incomplete.

From the depths of the 2008 crash to today, the S&P 500 has risen over 600%. With dividends reinvested, that number climbs closer to 900%.

If you stayed invested (easier said than done), and better yet, kept investing, you would have done very well! Maybe not quite billions status, but very well indeed.

The media celebrates big winners—the Michael Burrys of 2008 or the hottest stocks of 2024—but that’s only one side of the story. For most of us, it’s not about making one perfect move. It’s about staying in the game long enough to let compounding do its work.

The Importance of Resilience and Maximizing for Endurance

This brings me to my second, larger takeaway: the need for resiliency. Three movies — Last Days of Lehman Brothers, Margin Call, and The Company Men — reveal a crucial truth.

Success Without Sustainability Is Fragile

They show how quickly fortunes can reverse when built on shaky foundations. In Margin Call and Last Days of Lehman Brothers, we see two separate stories of two companies who took on too much debt and risk, and the resulting consequences. In The Company Men, we watch a successful executive lose everything because his lifestyle couldn't withstand a single setback.

When headwinds came, they couldn’t endure.

A Better Approach: Strategic Mediocrity

I had the chance to hear the author Morgan Housel speak earlier this year, and his message stuck with me. He said:

“Most investors want to maximize the highest possible return. The variable I want to maximize for is endurance. [Because] If you can be an average investor for an above-average period of time, you will be in the top 5% of investors.”

Housel echoes this on a podcast with Howard Marks (an absolute masterclass in my opinion):

“There’s this great saying from PIMCO that I used to love…back in the early days of PIMCO, they had a phrase called strategic mediocrity, which meant that in any given one year period, they were rarely going to be in the top half ranked against their peers.

But in every 10 year period, they would always be in the top 10%, maybe top 5%. And that I think is really important.”

But this goes against everything the financial media celebrates! The media celebrates the people who make the big bets and win. The Michael Burry’s and Mark Baums in 2008. But also the highest flying stocks of 2024, and how much you could have made if you invested $10,000 in company X, 5 years ago.

If only it were that easy!

Housel also says in that podcast:

“Virtually every investor says, I’m a long term investor. That’s a core for the vast majority of investors. But what that really means you have to do is be willing to forego shorter term gains. And that is much more difficult to do.

It’s easy to say, I’m in it for the long term. It’s much harder to say, I’m going to go the next one or five years below my potential. And I think that’s where so many people get tripped up, is that you have to be willing to say, I could be leveraged up here and earn more over the next one year, over the next five years, but it’s going to make me less durable.

But if I can stick around for the next 30 years, the returns that compound to that are going to be absolutely extraordinary.”

The message is clear: you don’t need to outperform everyone in the short term. Instead, you need to endure for the long term.

Why This Matters: The Path To Long-Term Wealth

I can teach you to be rich.
The catch?

I can teach you to be rich… slowly.

Here’s the formula:

Money Invested × Smart Allocation × Time = Wealth

It’s simple but not easy. Why? Because life happens in the short term, even though wealth is built in the long term.

Ben Carlson puts it perfectly:

“No one lives life in the long term. Long-term returns are the only ones that matter, but you have to survive a series of short terms to get there.”

Creating Durability In Your Financial Life

In order to be able to survive these short-terms, your financial house must be durable. It can’t get knocked down at the first headwind.

We want to create the conditions for patience, so that you can maximize for endurance:

A healthy emergency fund: so you don’t have to sell investments during a crisis
An investment plan: one you can stick with in both good times and bad
Proper estate documents: to protect your legacy and make sure your wishes are met
The right insurance: to shield against unexpected losses

Putting It All Together

The most successful investors aren't those who make the biggest gains in any given year. They're the ones who stay invested, maintain their strategy through market cycles, and allow compound interest to work its magic over decades.

Remember: The key to enduring wealth isn’t chasing the next big win. It’s building a system that can withstand setbacks while steadily moving forward.

Invest early. Invest often. Stay the course.

It’s not flashy, but it works. And that’s what makes all the difference.