When A Career Detour is NOT Career Suicide

“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 […]by Pranav Ramesh

May 12, 2021

“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The idea of being a “career man” with a job for life is becoming as outdated as the term itself.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.

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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 in a gig economy is that it gives people the option of spending time trying out different roles, to find out what fits.

According to Stewart Butterfield co-founder of Flikr, “Some people will know exactly what they want to do at a very young age, but the odds are low… I feel like people in their early- to mid-20s are very earnest. They’re very serious, and they want to feel like they’ve accomplished a lot at a very young age rather than just trying to figure stuff out. So I try to push them toward a more experimental attitude.”

Anjali Sud of Vimeo is a perfect example of someone who found success with a non-linear career path. After facing multiple rejections from big-name investment banks, Sud finally found employment as an analyst for a small firm with a varied client base. Over the next ten years, she worked in many different roles—finance, e-commerce, and media communication—before transitioning into operations, marketing, and eventually becoming the CEO of Vimeo at the age of 36.

Sud advises taking a non-linear career path for a robust career experience,

“You don’t have to follow a traditional career path. There’s no rule book or playbook for success. Write your own roles. Don’t take people’s paths as the way that you have to do things. You have to do it yourself.”

The S-Curve of Performance

You may be familiar with the ‘S- Curve’ as a concept applied to explain disruptive innovation. It explains why a growth curve can stay flat for a long time, before a drastic climbing only to plateau again. The same idea can also be applied to career development. When we begin our careers, we spend a long time building our skills and growing. Once we’ve settled into our roles, however, things start falling into place, and our performance gets better. But if we get too comfortable, then our performance will plateau, and we run the danger of settling into autopilot. This would be the perfect time to consider taking a voluntary detour.

For example, if you’ve spent the last five years working in the same role, say as a retail manager in a supermarket, without seeing a noticeable increase in your skillset, you might want to think about making a parallel move to another department within the organization like warehousing or transportation. Your current management experience will make this move easier, and the skills you develop in your new role will add value, should you choose to return.

Many organizations today encourage their employees to spend time working in many different departments at the start of their careers, to give them a chance to develop a more holistic skill set. Such employees gain a complete overview of the organizations which makes them more suitable for leadership roles in the future. You can think of a career detour as a cross-training opportunity, but one that is driven by your interests, rather than any one organization’s needs.

Ify Okoli-Watson’s 4 Year Adventure

Ify Okoli-Watson was born in the middle of a civil war in 1960s Nigeria. She was admitted into a British boarding school at 14, before going on to study law at the University of Reading. She faced her share of setbacks early in her career. As a woman and a person of color in ‘80s Britain, she had to struggle to make it in a profession still largely dominated by men. She was rejected by a number of law firms in London, forced to take a training contract at a small organization, and was made redundant after the birth of her first child. In many ways these challenges made her appreciate the benefits of developing an alternate career path.

More than a decade into her career as a lawyer, Okoli Watson decided to switch roles and spend time working in management. She moved from the UK to South Africa and became the Chief of Staff to the CEO of Barclays Africa. Okoli-Watson admits that the learning curve was steep initially, but the experience made her a better leader. She says, “Being Chief of Staff in a hierarchical organization like a bank gave me a great insight into the way a modern, multinational organization works. Apart from learning how various moving parts need to interconnect efficiently, I gained a real appreciation of the importance of strategy execution, corporate governance, and hands-on leadership. Watching talented senior leaders navigate first-hand the threat of competition, technological disruption, and increasingly costly regulation, instilled in me the importance of communication, trust, and emotional maturity.”

Returning to a legal role at the end of her detour, Okoli-Watson confesses loving her job even more. It made her a better lawyer, and the experience and knowledge from her detour job transferred easily into her old career. She maintains that the detour was the best thing she could have done for her career. After returning to law, Okoli-Watson has gone on to become the Assistant General Counsel at Thomson Reuters and continues to work there today.


Finding yourself being forced to make a detour in your career, or maybe having an opportunity to take a detour voluntarily, can be a great way to start a new chapter in your life.

First, career detours can also give you perspective, not just about your work, but also about your life as a whole. It is a chance to re-examine your priorities, your interests, and goals. Are you really as invested in your current career as you thought?

Secondly, it is an opportunity to expand on your experiences and pick up new skills. Employers today appreciate individuals who have more to offer than the basic necessities of the role. Having performed successfully in multiple roles shows that you can bring more to the table than just your professional skill set. Having added experience makes you more creative with problem-solving.

Finally, and perhaps most importantly, there are many paths to success. Why limit yourself to one path when you can walk along many? As long as you have your goals firmly in sight, why not get creative with your methods? We live once and are young only briefly. Let’s make the most of it.

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About the Company:

Peterson Technology Partners (PTP) has been Chicago’s premier Information Technology (IT) staffing, consulting, and recruiting firm for over 22+ years. Named after Chicago’s historic Peterson Avenue, PTP has built its reputation by developing lasting relationships, leading digital transformation, and inspiring technical innovation throughout Chicagoland.

Based in Park Ridge, IL, PTP’s 250+ employees have a narrow focus on a single market (Chicago) and expertise in 4 innovative technical areas;

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