When A Career Detour is NOT Career Suicide

by Pranav Ramesh
May 12, 2021
Seeing Signs that a Career Detour Was the Right Choice

“Not all storms come to disrupt your life, some come to clear your path”- Anonymous

“I did everything from investment banking, to being a toy buyer, to marketing diapers online, to coming to Vimeo to do marketing and finding myself in my dream job now as the CEO.”

Anjali Sud, CEO of Vimeo, is one of the youngest and biggest success stories of the decade. Anjali found her dream job, and success, after many years of trial and error. As she demonstrates on her path from leading in marketing to leading the whole company to a multi billion dollar valuation, not everyone is lucky enough to find a firm career path on the first try.

The idea of being a “career man” with a job for life is becoming as outdated as the term itself. People no longer aim to have a single profession for their entire life. There is a growing recognition that people have varied interests, some of which change over time, and are capable of transferring skills between different roles. According to the U.S. Bureau of Statistics, the median job tenure of adults in the U.S has been in decline since the 1980s and most people over 25 do not spend more than five years with a single organization. In today’s gig economy, switching roles is a legitimate way of getting some perspective, gathering experience, picking up new skills, and making the most out of your professional life.

Finding a New Perspective

Taking time off to go exploring other roles, or experimenting with your skillset won’t give you a deep understanding of these new roles, but it will give you additional perspective on your current role, or career. What do we mean by perspective? Having perspective means being able to look at your job, your career, even your life in general, from a new vantage point. Why did you choose this career? What is it about employing a certain skill set that satisfies you? Why are you passionate about your job, and if you aren’t, what are you truly passionate about?

A detour is an opportunity to employ skills you already possess but in a way that differs from what your main job might require you to. A good example of this is the movie Chef. In it, a chef in a high-class restaurant decides to take a sabbatical from his daily job, and travel around the country in a food truck. While doing so, he rediscovers his passion for cooking and re-connects with aspects of his life (as a father, boyfriend, etc.) that he could not make time for earlier.

Perspective can also come from outside yourself. If you do launch into an alternative career path, even temporarily, use the opportunity to ask those around you for feedback on your performance. You might find that the people around you have a better insight into the change than you do. If your relationship with your colleagues and managers is much better now, than it was in your previous role, for example, this might be a good time to think about why.

Conan’s Prohibited DeTour

Conan O’Brien is a talk show host, comedian, actor, and much else besides. He has been a regular feature on the American late-night circuit since the early ’90s and has millions of fans around the globe. Most people know about Conan’s short-lived stint as the host of the Tonight Show, when he was abruptly replaced by former host Jay Leno after less than a year on the job.

What a lot of people don’t know, however, was the little career detour Conan took after being replaced, to help him find his bearings once again. In his own words,

“I went through some stuff. And I got very depressed at times. It was like a marriage breaking up suddenly, violently, quickly. And I was just trying to figure out what happened. When we started putting this tour together, I started to feel better almost immediately. And then there is almost a no better antidote to what I’ve just been through than to do this every night.”

When Conan finished his short run on the Tonight Show, he decided he needed to get some perspective on his career, and launched into a nationwide live tour called the Legally Prohibited From Being Funny on Television Tour. He decided to employ his skills as a performer, and as a comedian, to take an adventurous little detour with a job that matched his skill profile, but was still a significant departure from his career as a late-night talk show host. By taking this detour, Conan was able to get some perspective on his skills, his passion, his career. At the end of the tour, he was offered a show on TBS which he has gone on to host for another decade.

Linear is so last year

In the past, careers were linear in progression, rising upwards at regular intervals but fixed to one definite path. By the time you finished high school or college, you already knew what you wanted to do and you set about doing it. This type of career progression is becoming less common. The advantage of operating