One Olympics, Four Cities: A Better Model for Your Career

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The 2026 Milano Cortina Winter Olympics has done something unprecedented. If you want a hint as to what it is, just look at the name.

The Olympics are bid on and assigned to a city (e.g. Sydney, Lillehammer, Tokyo). For the first time, the Games are being run as a multicity event. While the 2026 Winter Olympics are named for the city of Milano and the mountain resort of Cortina d’Ampezzo, events will also be held in Valtellina and Val di Fiemme. One Olympics, four cities.

We can apply a similar, non-traditional framing to our careers.

Most people think of themselves as having one, singular career. You very well may, but that’s not the only option. There are several ways to have a non-singular career.

The best known is referred to these days as “polyworking” (e.g. working two jobs, having a side hustle). It’s nothing new, as any actor will tell you. The classic narrative for actors is waiting tables between casting calls, waiting for a big break. My brother, in addition to being a very successful stage actor, is also an ASL interpreter, something for which he needed extensive training (unlike waiting tables in the US), ultimately giving him two careers, both of which he enjoys (not just one job to pay the bills until the other hits some milestone). Or consider how many people have a day job but play in a band on weekends? It may not be for the money (though no one would object to making it big), but for the fulfillment. Multiple careers bring multiple benefits, which aren’t always financial.

A second model is having multiple careers over time. Not simply job changes, but different professional paths across decades of work. As technological acceleration pushes change ever faster, from centuries to decades and sometimes just years, the creative destruction of capitalism will continually destroy and create new jobs, causing significant professional volatility. Instead of one lifelong career, it may be helpful to think of several distinct careers over your lifetime.

Finally, even if you have a single career your entire life, it can be helpful to view it as multiple “sub-careers,” each one oriented to a different stage of work. All four cities are hosting the Olympics, but they each focus on different events. Similarly, different phases of your career may emphasize different goals.

The dawn of your career may focus on exploration, looking at different roles, industries, or specializations. The next career phase may focus on growth, building skills, growing your network, and achieving ever bigger accomplishments. A professional capitalization phase would focus on maximizing your earnings. Some may even have a more relaxed chapter like second-semester seniors who are now just waiting for the next phase of life.

Your career doesn’t have to follow those phases. It may be more or less than four, may not be those specific phases, or could be in a different order. Importantly, your career is only one part of your life, and other lifetime goals may suggest or constrain your career goals in any phase. (For suggestions on how to think about your career more holistically, see Career plan questions from The Career Toolkit.) These are simply models, not absolutes. Like any model, they may or may not be applicable to you right now.

Just as the Olympics reframed their view as being constrained to a single city into a multi-city approach, so, too, can we reframe our career view from that of a single career to one of multiple careers, and the meaning of “multiple” can vary. What matters most is that you don’t limit yourself to just one way of thinking about your career. The 2026 approach to the Olympics combined different locations each of which brought something to the table and which together created a winner. Your winning career strategy may also benefit from multiple aspects, not all of which are alike.

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