Automation and Investing: A Cold Code Meets Human Connection

Automation and investing have become a frequent theme in this blog—not just because the headlines keep rolling in, but because there’s something strangely satisfying about watching large firms stumble as they attempt to replace human connection with cold, calculated code.

Here’s what I’ve learned: (1) humans are historically terrible at predicting what jobs will fall to automated, and (2) I won’t be replaced by a robot. Those two ideas may seem to contradict each other but stick with me. The real issue isn’t what robots can do—it’s what people are willing to allow it to do. When it comes to high-stakes financial decisions and deeply personal emotions, automation still struggles to earn our trust.

There’s a natural split in the financial industry: back office vs. front office. Back-office automation? That’s a no-brainer. Let the machines take over the repetitive tasks so human minds can focus on strategy and complexity. UBS is doing just that—a robot now completes a 45-minute task in two minutes. That’s a win.

But UBS is also venturing into front-office automation, marketing what it calls the first “adaptive strategy” investment product. While it sounds futuristic, they haven’t secured a single client. Why? Because investors aren’t ready to hand over emotional, financial decisions to an algorithm.

Robots, Emotions, and the Limits of Automation

Robots and investing have become a frequent theme in this blog—and for good reason. With the rise of automation in finance, we’re watching a fascinating tug-of-war between efficiency and the irreplaceable value of human connection. I’ll admit, there’s a certain satisfaction in seeing large firms stumble as they try to replace people with machines.

Here’s what I know: (1) humans are historically terrible at predicting what jobs will be automated, and (2) I won’t be replaced by a robot. Those two ideas might seem contradictory but hear me out. The real issue isn’t whether robots are capable—it’s whether people trust them in emotionally complex roles. And when it comes to finance, trust is everything.

There’s a natural split in the industry: back office vs. front office. Let the robots have the back office—tasks get done faster, and people are freed up to solve more complicated problems. UBS is already doing this: one of their robots now performs a 45-minute task in two minutes. That’s smart use of automation.

But the front office? That’s different. UBS is experimenting with a robot-driven investment product and pitching it directly to clients. While it sounds impressive, not one client has signed on yet. Why? Because in finance, where stakes are personal and emotions run deep, humans still want to deal with other humans.

Retail Nostalgia and the Curious Case of T.J. Maxx

Though I rarely write about retail, it holds a nostalgic space in my heart. My career began in that world—and like many first jobs, my affection for it is part fond memory, part Stockholm Syndrome.

Traditional retail is clearly on the decline. Just as travel agents and bank tellers have faded, department stores like Macy’s are slipping into history. Online giants like Amazon have changed the game. But T.J. Maxx is the exception. They’ve posted sales growth for 33 straight quarters.

Analysts cite market strategy and adaptation, but I think there’s a simpler reason: the type of shopper T.J. Maxx attracts. They’re not looking for convenience—they’re looking for a win. There’s a rush that comes from spending time and effort digging for a deal.

Time vs. Money: Why Some People Love the Chaos

Today’s economy is all about speed and convenience. You can order anything online and get it in a day. But not everyone wants that. Some people get more satisfaction from the search than the find.

These shoppers view time spent as an investment. The more they dig, the better the deal feels. It’s not logical, but it’s real. T.J. Maxx has tapped into this deeply human quirk. Their stores are barely organized, and that’s by design. It’s a game—a treasure hunt. And that emotional reward? That’s something a robot will never replicate, whether it’s in retail or finance.

If retailers ever go full gamification and start hiding merchandise on purpose, I might just rejoin the industry. But only if I get the title: Chief Officer of Hiding Things. That sounds like a pretty fun job.

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