Opportunity Trains

Over the course of my career, I’ve been asked to mentor a number of younger professionals and founders of start-up businesses, many of them trying to make their mark in fintech, regtech, or “anything tech.”

One metaphor I’ve often used with those individuals is to think about their careers in terms of a series of trains – opportunity trains. Having recently spent time in London, the train metaphor has been front of mind. A week on the Tube will do that to you.

Early in a career, the trains are everywhere. Doors are open. Movement is easy. If you don’t enjoy what you’re doing, or the experience isn’t what you expected, it’s relatively straightforward to change direction, whether that’s a new role, a different industry, or even an entirely new career. In your twenties, that process is almost consequence-free. You simply step off one train and onto another. And away you go.

But something begins to shift in your thirties, just as career momentum is starting to build. The opportunity trains don’t stop altogether, but they do begin to slow. At first, it’s almost imperceptible. Then gradually, in your forties you find yourself spending a little longer, waiting for the next opportunity train to arrive. But even then, you probably are not consciously aware the trains are less frequent and the ones which do appear have fewer doors that open.

At the same time, each career decision becomes more deliberate. Whether you choose to board a new train or stay on your current one, the consequences begin to carry more weight. Those choices are often difficult to reverse, not because you’ve lost capability, but because momentum has started to set you along a particular path. Direction compounds. Trajectory becomes more fixed.

Then there comes a point, different for everyone, when the number of opportunity trains is significantly reduced. For some, there may be none. If there was a station announcement, it might say: “This train will not call at your station.” But of course, there are no announcements. You must recognise that for yourself, the moment when certain opportunities are no longer realistically available.

That would be a rather grim place to end the story. But the reality is more nuanced.

In a world where AI is reshaping entire industries, altering how content creators monetise, how software developers write code, and how businesses operate, the types of opportunity trains are changing. New tracks are being laid even as others disappear.

The implication is not that opportunity diminishes it’s that it evolves. And from a career perspective, the sooner you understand how the trains move, the better positioned you are to choose which ones to board and when. That’s the best way to “mind the gap between the train and the platform” as they say on the Tube.

Dean Rea

An almost Gen-Xer with a passion for strategy, finance and governance - occasional early growth stage company investor and enthusiastic follower of financial markets, politics, and blue water fishing!
June 11, 2026

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