They say "the best story wins." How do take "financial planning" - an admittedly boring topic at times - and tell a better story?

I’m reading Morgan Housel’s recent book, Same as Ever, right now. One of the chapters is called “Best Story Wins.” 

[While I’m not sure it’s word-for-word the same, this chapter can be read (for free) via Morgan’s blog: https://collabfund.com/blog/story/]

Housel’s idea is fascinating – and probably makes sense to us all. The takeaway is that humans promote or discount particular ideas simply because of the story told around that idea. We ignore some great ideas because of a bad story. And we promote some terrible ideas because of a good story. Housel challenges us readers to ask in on our lives: 

• Who has the right answer, but I ignore it because they are inarticulate? 
• And what do I believe is true, but is it just good marketing?

I immediately thought of one of my former engineering colleagues.

In our early years working together, I saw him as quirky, obtuse, at times unprofessional, and an overall oddball. Over time, though, I realized: while all those things were still true, he was also one of the smartest people in the room – in every room. 

Now, call me a jerk, but I think the average person confounds “quirky” with “intelligent.” As in, “She’s so strange…she must be a genius or something.” No, no, no. Just because someone is weird enough to memorize Wikipedia doesn’t make them intelligent. Hollywood might have taught us to correlate “weird” with “smart,” but I don’t buy it. 

This former coworker, though – I know enough to know he was genuinely brilliant and coincidentally also quirky. 

But here’s the problem he faced: 99% of our shared colleagues, customers, stakeholders, etc., could not get past the strange exterior to see, understand, and appreciate the genius underneath. His “story”—the way he presented himself—was a perfect example of Housel’s idea that a bad story can discount a terrific idea. Nobody took him as seriously as they should have.

I thought of this idea again recently when one of my clients emailed me an insurance pitch they received. The video featured an affable, well-dressed, well-spoken insurance sales guy. He explained, to paraphrase, the untold downsides of all traditional retirement investing (e.g. everything I talk about here) while preaching the incredible upsides of his indexed universal life insurance. 

All the upside, none of the downside, and a free steak just to attend your seminar?! 

It was a great story. Delivered smooth as Irish butter.

I’ve seen these pitches before. The math they use is patently untrue. The language they choose is overly emotional, stirring up the audience’s deep fears (“If I can scare you, I can sell to you”). 

But to the unknowing outside viewer, I’m sure this insurance pitch works! It’s a good story! Is it dishonest? Of course. And if a viewer sees through the lie, the jig is up. But until that point, it seems like a conversation worth continuing. And looking at the size of the Big Insurance, there’s no shortage of people having that conversation.

Meanwhile, what’s going on my side of the “financial industry”?

The smart, long-term financial planning principles we discuss here are immensely valuable. And I think the stories I share here and on the podcast add some spice and flavor to the topic.

But is it exciting?! Or is it a little boring, repetitive, and lacking a “bogeyman” to fear?

So I’d like to present to you: The Man Who Never Looked Up

“The Man Who Never Looked Up”

Ryan had a plan. Or so he thought.

Work hard. Earn more. Save later.

He wasn’t irresponsible—he paid his bills, avoided credit card debt, even put a little in his 401(k). But retirement? That was a problem for “future Ryan.”

For now, he had bigger things to focus on: the next promotion, the next house upgrade, the next family vacation.

So he kept his head down. Grinding. Hustling. Living in the moment.

And then one day, he looked up.

He was 55. Retirement wasn’t some distant concept anymore—it was right there, staring him in the face.

But he wasn’t ready.

• His savings? Not nearly enough.
• His investments? Scattered, inconsistent.
• His timeline? Pushed back… again.

Ryan had done what so many people do—he spent decades focused on the next step, never stopping to see the big picture. Never looking up.

What if he had started sooner?

• Invested consistently—so time, not effort, did the heavy lifting.
• Built a real plan—so his future wasn’t just a vague idea.
• Optimized his choices—so he kept more of what he earned.

The truth about retirement isn’t complicated: You don’t drift into it. You plan for it.

Because someday, you’ll look up.

The only question is whether you’ll like what you see.

~~Fin~~

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On that note, our podcast “Personal Finance for Long-Term Investors” is by far outpacing this written blog. Tune in and check it out.

-Jesse

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