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Most Americans believe financial success is about making the right decisions.
I disagree.
After more than 30 years helping families build wealth and managing billions of dollars, I’ve learned something different from experience. Financial success is often about avoiding the wrong ones.
WE ALL ARE DESPERATE FOR A FINANCIAL CHECK-UP. TIME TO SAY, ‘SHOW ME THE MONEY!’
That’s why one habit separates people who consistently build wealth from those who struggle to keep it. They don’t make major financial decisions alone.
The New York Stock Exchange (NYSE) in New York, US, on Wednesday, July 2, 2025. (Michael Nagle/Bloomberg)
Ironically, the more successful you become, the easier it is to believe you don’t need advice. You earn more, accumulate more assets and start trusting your own judgment above everyone else’s.
That’s exactly when mistakes become the most expensive.
Buying a vacation home. Selling a business. Exercising stock options. Investing a large inheritance. Taking Social Security. Retiring a few years early.
One poor decision in any of these areas can cost hundreds of thousands or even millions of dollars. Yet many people spend more time reading online reviews before buying a $500 television than they do seeking advice before making a $500,000 financial decision.
That doesn’t make sense.
The most financially successful people I know all have what I call a Financial Board of Directors.
Businesses have boards because even exceptional CEOs have blind spots. Your financial life deserves the same level of accountability.
Your Financial Board of Directors doesn’t have to be formal. It simply needs to include people who bring different perspectives and aren’t afraid to challenge your thinking.
Here are four people worth having in your corner.
Ironically, the more successful you become, the easier it is to believe you don’t need advice. You earn more, accumulate more assets and start trusting your own judgment above everyone else’s.
Someone who asks hard questions
We naturally seek out people who agree with us. That’s comforting but it’s also dangerous. The best financial decisions are often sharpened by someone willing to ask, “What if you’re wrong?”
Someone with nothing to gain
Good advice is easiest to trust when the person giving it isn’t earning a commission, selling a product, or benefiting from your decision. Every major financial move deserves at least one truly objective opinion.
Someone with experience
Financial markets change. Tax laws change. Human behavior doesn’t. Someone who has lived through multiple recessions, bull markets, housing booms and crashes has perspective that no spreadsheet can provide.
A professional who knows what you don’t
Even successful people have knowledge gaps. Tax planning, estate strategies, insurance, investments, and business succession all require specialized expertise. Knowing when to ask for help isn’t weakness. It’s wisdom.
Behavioral finance has repeatedly shown that emotion is one of the biggest enemies of good decision-making. Fear causes people to sell at the bottom. Greed convinces them to chase investments after they’ve already skyrocketed. Pride keeps them from admitting a mistake.
The Riverside Plaza apartment towers dominate the skyline of Minneapolis’ Cedar–Riverside neighborhood. (Michael Dorgan/Fox News Digital)
The problem usually isn’t intelligence. It’s emotion. That’s why perspective is so valuable.
One of the biggest myths in America is that financial independence means doing everything yourself.
It doesn’t.
It means building a team that helps you make better decisions.
The wealthiest families rarely rely on a single opinion. They ask questions. They challenge assumptions. They seek different viewpoints before making life-changing financial moves.
Maybe we should as well.
Before your next major financial decision, ask yourself four questions:
- Who can challenge my thinking?
- Who has nothing to gain from my decision?
- Who has experience I don’t?
- Have I allowed emotion to outweigh logic?
Good advice is easiest to trust when the person giving it isn’t earning a commission, selling a product, or benefiting from your decision. Every major financial move deserves at least one truly objective opinion.
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Those four questions may save you far more money than finding the next hot stock. Because building wealth isn’t about getting every decision right. It’s about avoiding the handful of mistakes that can permanently set you back.
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The smartest financial move you’ll ever make may not be the investment you choose.
It may be the conversation you have before making it.
CLICK HERE TO READ MORE FROM TED JENKIN