Everyone Has an Opinion From the Cheap Seats

By David Day on September 23, 2026

The NFL season is back, which means so is one of America’s favorite pastimes.

Criticizing quarterbacks.

We have quarterbacks on injury watch, teams underperforming expectations, potential MVP candidates emerging, and millions of people sitting on their couches explaining exactly what professional athletes should have done differently.

One of my favorite stories from the first couple weeks has been the controversy surrounding Caleb Williams.

For those who don’t watch football like I do, Williams is the quarterback of the Chicago Bears. And “quarterback of the Chicago Bears” isn’t exactly a low-profile job.

Williams has been polarizing since entering the league. He paints his nails. He wears lavish clothing. He speaks his mind. There were plenty of people who had opinions about him before he ever took a meaningful NFL snap.

Then he started winning.

And winning has a funny way of quieting critics.

Until it doesn’t.

During the Bears’ Week 2 game against the Minnesota Vikings, Williams went down on a non-contact play in the fourth quarter. He needed help getting off the field and was eventually carted from the sideline to the locker room. The Bears later confirmed a hamstring injury. [nfl.com], [chicago.suntimes.com]

Fortunately, the initial fear surrounding the injury subsided. But something else quickly replaced it.

Criticism.

People saw Williams’ reaction to the injury and decided it was excessive. One prominent sports personality publicly mocked him for how emotional he appeared and how seriously he seemed to react to the injury. [foxnews.com]

Suddenly, everyone had an opinion about how Caleb Williams should have reacted.

Maybe some of the criticism is fair.

Maybe he was being dramatic.

I’m sitting on my couch. I have no idea how badly his hamstring hurt.

But watching the reaction made me think about something that has very little to do with football.

The higher you climb, the more people seem to have an opinion about how you should live.

Being “The Guy” Comes with Something Else

Being the quarterback is different.

If an offensive lineman gets frustrated on the sideline, we might never hear about it.

The quarterback does it, and it’s a story.

Change your hairstyle. Story.

Wear something unusual. Story.

Say something confidently. Story.

Handle an injury differently than people expected. Story.

That’s the price of sitting in one of the most visible seats in sports.

And while most of us will never be starting quarterbacks in the NFL, I see a similar phenomenon with successful people in the business world.

Build a successful company and suddenly everyone has an opinion about how you’re running it.

Make a good income and people develop opinions about what you should do with your money.

Buy the nice house and you’re showing off.

Don’t buy the nice house and someone wonders why you’re so cheap.

Sell your business and someone tells you that you sold too early.

Keep working and somebody asks, “Why haven’t you retired yet?”

Pay off your mortgage and someone tells you that’s financially inefficient.

Keep the mortgage and someone else can’t understand why you’d want the debt.

Success has a strange way of inviting unsolicited advice.

Money Seems to Make This Even Worse

I’ve always found it interesting how comfortable people are giving other people financial advice.

Your coworker has a stock you have to buy.

Your friend can’t understand why you haven’t bought a rental property.

Your neighbor tells you that you’re keeping too much money in cash.

Your family tells you that you should buy the bigger house because “you can afford it.”

And the guy you’re golfing with tells you about the investment that has been absolutely crushing it.

Most of these people aren’t trying to hurt you.

They may genuinely believe they’re helping.

There’s just one problem.

They aren’t playing your game.

They don’t necessarily know your income.

They don’t know your expenses.

They don’t know your tax situation.

They don’t know what keeps you awake at night.

They don’t know whether you’re trying to retire at 55 or whether you love your company and hope to work until you’re 75.

Most importantly, they don’t know what you’re actually trying to accomplish with your money.

That’s why a perfectly reasonable financial decision for one person can be a terrible decision for another.

Not All Opinions Deserve Equal Weight

Now, here’s where I think this gets important.

I don’t think the lesson from Caleb Williams is to ignore criticism.

Quite the opposite.

If you’re an NFL quarterback, you probably should listen when your coach tells you that you made the wrong read.

You should listen to your trainer when he tells you that you aren’t ready to play.

You should listen to teammates you trust when they hold you accountable.

The objective shouldn’t be to surround yourself with people who tell you everything you’re doing is right.

The objective is to know whose opinion deserves weight.

I think the same principle applies to successful business owners, executives, retirees and investors.

You need people who challenge you.

You need people who tell you when you’re making a mistake.

You need people who occasionally tell you something you don’t want to hear.

But those opinions should ideally come from people who understand the entire picture.

There’s an enormous difference between someone saying:

“I would never sell that business.”

And someone says:

“I understand what this business means to your finances, your family, your retirement and your future. Let’s talk about whether selling it gets you closer to the life you actually want.”

The first is an opinion.

The second is advice.

And there’s a big difference between the two.

The Cheap Seats Will Always Be Full

I don’t know whether Caleb Williams overreacted to his injury.

Maybe he did.

But I do know it’s incredibly easy to decide how someone else should handle a situation when you don’t have to experience any of the consequences.

That’s true in football.

It’s true in business.

And it’s especially true with money.

The further you go in life, the more opinions you’re probably going to hear.

Listen to people you trust.

Listen to people who understand your situation.

Listen to people who aren’t afraid to challenge you when they believe you’re wrong.

But don’t build your financial life around satisfying the people watching from the cheap seats.

They’re not the ones playing the game.