Pete the planner: An open letter to the investments I passed on

Dear missed investments:

I think about you more than I should. I’ve tried to move on, tried to tell myself I made the best decision with the information I had at the time. But sometimes, late at night, I’ll find myself staring at the ceiling, wondering what my life might look like had I taken the plunge. You weren’t just investments; you were doors, each leading to a slightly different version of me.

Let me start by apologizing. It wasn’t you, it was me. I wasn’t ready. I didn’t have the risk tolerance, the cash flow, the patience, or maybe just the courage. The truth is, you scared me. And yes, now I see that some of you went on to become household names, multi-baggers, the stuff of CNBC victory laps. Others? Well, some of you fizzled into irrelevance, which if I’m being honest, helps me sleep a little better. But the ones that thrived? You haunt me.

Remember me, Google? I was fresh out of college when you IPO’d in 2004. I distinctly remember thinking, “$85 a share seems awfully steep.” I had no concept of what a revolutionary search engine could become. I thought of you as just a website I used to look up the cast of “The Wire.” Had I invested a modest $5,000, I’d have turned it into well over $150,000 by now. Instead, I bought a leather couch that squeaked every time I sat down. That couch is long gone. You, on the other hand, are still here, dominating the planet.

Or how about you, Apple, circa 2001? I remember standing in line at CompUSA, staring at the very first iPod. It was chunky, it only worked with Macs, and it felt absurdly expensive. I thought, “No one needs this.” Turns out, everyone needed it, and your little music device became the gateway to the iPhone, which became the gateway to the modern economy. I should have seen it, but I didn’t. Instead, I smugly told friends that MP3 players were a fad. (If you’re wondering, yes, I also thought email was a fad. I was on a roll.)

It wasn’t just tech stocks. Real estate, you and I have a complicated history, too. In 2010, when the housing market was wobbling, friends whispered about scooping up foreclosures for pennies on the dollar. “Too risky,” I told myself. “What if the housing market never recovers?” I was convinced I was the sober voice of reason. Today, some of those very houses are worth triple what they were then, producing rental income like dependable little ATMs. Instead of buying, I sat on the sidelines, clapping for everyone else as they built wealth I could have had.

And then there was Bitcoin. Oh, Bitcoin. In 2011, a colleague suggested I could buy one for a few dollars. I laughed. I thought it was the Beanie Baby of finance. A fad wrapped in hype, destined for irrelevance. I’m not sure what stings more: the missed fortune or the fact that I once compared blockchain to a stuffed animal. Either way, you win, Bitcoin.

But here’s the thing, dear missed opportunities: I can’t be too mad at myself. Passing on you was, in many cases, the right choice for who I was at the time. I wasn’t reckless. I wasn’t greedy. I was cautious, sometimes overly so. But that caution allowed me to build stability in other areas. Sure, I didn’t turn $1,000 into a fortune with Tesla, but I also didn’t blow $10,000 on the hot stock tip my barber swore was a “sure thing.” In hindsight, the boring investments like index funds, bonds, steady savings habits, have quietly carried me pretty far.

Regret is a funny thing. It pretends to be about the past, but really, it’s about the present. When I dwell on you, I’m not just mourning what might have been; I’m wrestling with what I want from my money now. Security? Excitement? A shot at legacy wealth? The truth is, my relationship with risk has matured, just like I have. Younger me needed predictability. Middle-aged me, while still cautious, can stomach a little more adventure.

So maybe this letter isn’t just an apology. Maybe it’s also a “thank you.” By passing on you, I learned what kind of investor I am, and what kind I’m not. I learned that FOMO (fear of missing out) is a poor investment strategy. I learned that every dollar I didn’t put into you was still a dollar I put toward something else such as my family, my business, my health. Those returns aren’t listed on the stock exchange, but they matter just as much.

And so, missed opportunities, I release you. I won’t forget you. I mean, how could I? You’re literally in every article about “if only I’d invested back then.” But I won’t pine for you either. I’ll use you as motivation, a reminder to keep an open mind without abandoning prudence. There will always be another opportunity, another door, another choice that could shape my future. And when it arrives, I’ll be a little wiser, a little braver, and maybe, just maybe, a little quicker to act.

Fondly,

Pete•

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Dunn is CEO of Your Money Line powered by Pete the Planner, an employee-benefit organization focused on solving employees’ financial challenges. Email your financial questions to [email protected].