I have a confession to make.
Years before I ever advised clients on six-figure portfolios, before the word “banker” was part of my title, I was sitting on my worn-out IKEA couch, staring at my phone. I had $100 in a newly opened brokerage account. One hundred dollars. The cost of a nice dinner out or a couple of new video games.
And I was utterly terrified.
My finger hovered over the “Buy” button for what felt like an eternity. What if I picked the wrong thing? What if the market crashed tomorrow? What if I lost it all? That $100 might as well have been a million. I felt like a fraud, convinced I was about to make a huge, irreversible mistake.
If this sounds familiar, you’re not alone. The biggest barrier to building wealth isn’t a lack of information or a lack of money. It’s fear. It’s that gut-wrenching, paralyzing feeling that you’re standing at the edge of a cliff, and the first step is a guaranteed plunge.
But what if I told you that first step isn’t about making money? It’s about buying something far more valuable: courage.
Why We’re Programmed to Be Afraid
Let’s get one thing straight: your fear is not irrational. Our brains are wired for survival, and for millennia, that meant avoiding loss at all costs. This psychological quirk, known as “loss aversion,” makes the pain of losing $100 feel twice as intense as the pleasure of gaining $100.
Combine that with a 24/7 news cycle screaming about market volatility, endless jargon (ETFs, P/E ratios, expense ratios… what?), and the highlight reels on social media where everyone seems to be getting rich off some meme stock, and it’s a recipe for analysis paralysis. You feel like you need to be a Wall Street genius to even start.
So you wait. You tell yourself you’ll start when you have more money, when you’ve done more research, when the market is “less crazy.” But waiting is the most dangerous decision of all.
A Banker’s Confession: The Biggest Mistake I See Is Inaction
The biggest mistake is never starting.
In my years in the financial world, I’ve seen all kinds of mistakes. People chasing hot stocks, people selling in a panic, people paying absurdly high fees. But I can tell you with 100% certainty that the single biggest and most destructive financial mistake is none of those.
From behind the banker’s desk, you see the devastating, silent cost of inaction. It’s the story of two people with the same income. One starts investing just $100 a month in their 20s. The other waits until their 30s, convinced they need a “real” lump sum to begin. A decade later, the first person’s small, consistent investments have snowballed into a significant sum thanks to the magic of compound interest. The second person is still waiting for the “perfect” moment that never comes, having lost the single most valuable asset in investing: time.
The wealthy don’t see the stock market as a casino; they see it as an ownership machine. Every dollar you invest in a broad market index fund isn’t a gamble—it’s you buying a tiny slice of the most powerful and innovative companies in the world. You’re buying a piece of Apple’s next iPhone, a sliver of Amazon’s next fulfillment center. You become a part of the engine of economic growth, not just a consumer of it.
That $100 I was scared of? Losing it wouldn’t have changed my life. But the wealth I would have missed out on by never investing it would have been catastrophic.
Your Three-Step Plan to Buy Your First Share of Courage
Forget about getting rich overnight. The goal of your first investment is simply to break the cycle of fear. It’s a psychological victory. Here’s how you win.
Step 1: Reframe the Goal. The Mission is “Experience,” Not “Earnings.”
Your first $100 is not an investment in the stock market; it’s an investment in your education. You are spending it to learn how the process works, to feel the emotions of a market dip, and to prove to yourself that you can do this.
Mentally, write this $100 off. If it goes to zero (which is nearly impossible if you follow Step 2), consider it the cheapest and most valuable financial lesson you’ll ever get. This mindset shift removes the pressure. You’re not trying to pick a winner; you’re just trying to get in the game.
Step 2: Choose Your “Sandbox”—Where to Play Safely.
When you’re starting, you don’t need a complex trading platform. You need a simple, reputable, and low-cost environment. As a banker, I advise against trendy apps that gamify investing. We’re building a lifelong habit, not playing a mobile game.
Instead, open an account with a trusted brokerage firm like Vanguard, Fidelity, or Charles Schwab. They are industry giants for a reason: they are built for long-term investors.
Once your account is open, what do you buy? You buy the whole haystack, not the needle. Start with a low-cost, broad-market index fund ETF. Think of something like the Vanguard Total Stock Market ETF (VTI) or the iShares CORE S&P 500 ETF (IVV).
Why? Because with one single purchase, you’re buying a tiny piece of hundreds or even thousands of the biggest companies in the US. You’re instantly diversified. You’re betting on the entire American economy’s long-term growth, not the fortunes of a single company. It’s the simplest, sanest, and most recommended starting point for a reason.
Step 3: Automate It and Make It Invisible.
You’ve reframed the goal and chosen your sandbox. Now for the final, crucial step. After you make that first manual purchase (and celebrate!), go into your account settings and set up an automatic investment.
Schedule $25, $50, or another $100 to be automatically transferred from your bank account and invested into that same fund every month. This is the secret weapon against fear and emotion.
By automating, you remove the most dangerous variable from the equation: you. You won’t have to psych yourself up to hit the “Buy” button every month. You won’t be tempted to panic-sell when the news looks bad. Your wealth-building machine will just hum along in the background, buying more shares for you, month after month, regardless of the market’s mood swings.
The Day After I Invested My First $100
So what happened after I finally got the nerve to press that button all those years ago?
The next day, my $100 was worth $99.17.
The old me would have panicked. But the new me—the one who had invested in experience—just shrugged. I had survived my first market dip. The world didn’t end. I logged out and went about my day. A week later, it was worth $102.
That first $100 wasn’t about the money. It was about proving I could. It broke the spell of fear forever. It’s the most important investment I ever made, and it’s time for you to make yours.
Open the account. Fund it with a number that won’t make you lose sleep. And press the button. Your future self will thank you for it.
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