In my 20 years on the trading floor, through the subprime crisis, through the pandemic, and now into an era where AI and algorithms are starting to place trades in place of humans – I keep seeing the same old investment mistake repeat itself.
It’s letting your portfolio drift with the current. Never satisfied with the gains you should have banked. Never willing to cut your losses.
A lot of people latch onto Dollar Cost Averaging (DCA) and memorize it, wrongly, as some immortal longterm investment strategy. But trust me. In the real world of trading, DCA doesn’t work across every market, and it doesn’t work with every asset class. If what you’re invested in is heading the wrong direction, averaging down is just feeding money into the same mistake over and over, then sipping your coffee and praying your portfolio grows back by some kind of miracle.
Whether you’re investing mid- or long-term, the real starting point was never closing your eyes and throwing money in. It’s coming back to ask: is what I’m holding still on the right track? Where’s the point where “good enough” is actually enough, and where’s the warning sign that says it’s time to pull out?
Here’s the scarier part: we use this exact same mindset to manage our own life portfolios. The result: most city dwellers have slipped into a state of “Passive Drift” – letting life run on Auto-Pilot.
Let’s look at our day, for example. Wake up. Check the feed. The algorithms behind our screens are fighting for our attention around the clock, news and social noise pouring into the smartphone in our hand very waking minute. Respond to a schedule set by other people’s expectations, then close out the day scrolling to see how everyone else is living. Even I catch myself scrolling into random dance clips on TikTok sometimes, sitting there wondering who these people are dancing for, and why I’m the one watching.
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