The Gap Between Assumption and Reality

There’s a simple truth about life—and money—that most people overlook: you don’t know what you don’t know. And that gap between what you think you know and what you actually need to know? It can cost you.

This became glaringly obvious to me over the weekend through two very different conversations. One was with an Uber driver who had dabbled in finance decades ago; the other was with a highly educated executive navigating a complex financial landscape. Both reminded me of how easy it is to fall into the trap of thinking we’ve got it all figured out—when we don’t.

A Conversation in the Backseat

My Uber driver was 59, a New Yorker who had moved to Palm Beach to care for his elderly mother. When he asked me what I do, I told him I manage money for educated, high-income earners in tech, biotech, and healthcare. That sparked a story from his days working briefly on Wall Street in the 80s—specifically, at a boiler-room-style brokerage like the one depicted in The Wolf of Wall Street.

He described selling penny stocks to rich people, a world of inflated promises and inevitable jail sentences. He assumed my work was similar—selling high-commission products to wealthy investors.

I quickly set the record straight. I explained that I’m a fiduciary, which means I operate with my clients’ best interests in mind. I don’t sell annuities, whole life insurance, or mutual funds with high-load fees. I don’t pitch stocks, and I certainly don’t gamble with speculative assets like crypto. My focus is on building sustainable wealth through thoughtful planning, not chasing quick wins.

The misunderstanding wasn’t surprising. His brief experience decades ago had left him with outdated perceptions. He didn’t even know what a fiduciary was or how it differed from the brokers he’d worked with.

A High-Powered Executive’s Wake-Up Call

The next conversation was with a tech executive who had reached out after reading one of my articles. He wanted advice on managing his RSUs and addressing some time-sensitive financial concerns.

As we talked, it became clear he didn’t know what he didn’t know. Despite his education and income, he was leaving critical opportunities on the table:

  • He didn’t have a plan for his RSUs.
  • He was filing his taxes on his own—despite owning real estate, managing concentrated stock positions, and facing a potential liquidity event.
  • He hadn’t taken full advantage of employer-sponsored investment programs.
  • His retirement account was parked in a generic target-date fund, with no thought how it supports his actual goals.
  • He had hundreds of thousands in cash sitting idle instead of earning interest in at at least a attractive yielding money market fund.
  • and the list goes on...

Then there was the bigger picture: he and his spouse weren’t aligned on their financial strategy. They were managing their future without a plan, simply spending less than they earned and assuming things would work out.

After our conversation, he realized how much he’d been leaving to chance. He didn’t understand the value of working with a fiduciary advisor, the importance of a CPA or tax attorney in his situation, or how to create a cohesive financial plan that works for his family’s goals.

Why You Shouldn’t Wing It

This isn’t unique to one person. Whether it’s a construction worker or a corporate executive, the most common financial mistake I see is “winging it.”

Here’s the truth: you wouldn’t diagnose your own medical issues or train for a marathon without guidance. So why approach your financial life without professional help? Even the best athletes, corporate leaders, and policymakers rely on advisors to sharpen their focus and execute their plans.

A fiduciary advisor helps you:

  • Understand the difference between speculation and strategy.
  • Align your investments with your long-term goals.
  • Avoid costly mistakes that could derail your future.
  • Stay on track, even when life throws curveballs.

What Don’t You Know?

No matter how successful you are, there are always gaps in your knowledge. The right advisor doesn’t just help you fill those gaps—they create a roadmap, hold you accountable, and help your money work for you, not against you.

— Mateo