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“A non-linear career path isn’t a red flag”

You’re generally advised not to zigzag and move around a lot in the creative industry, but is it really that bad? In this week’s Creative Career Conundrums, Kat Wong tells us what it means to be a “squiggly” career.

Date
23 June 2026

Creative Career Conundrums is a weekly advice column from If You Could Jobs. Each week their selected panel of professionals from the creative industry answers your burning career questions to help you navigate the creative journey.

This week’s question:

“What does being a career zigzagger look like in the creative industry?

There are many sources claiming zig zag careers are the future for professionals, opposed to the traditional corporate ladder. In the creative industry how does one approach this? Since frequent role changes can seem unreliable on a CV, and my experience can be less credible because I can’t prove a traditional linear growth in one place only.”

Kat Wong, founder of career change platform Oh Yeah:

What a zig-zag career looks like, how you approach it, and why you should move on, are probably the most common questions I receive as an ‘established’ zigzagger. But it wasn’t based on a decision where I sat down years ago announcing, “I’m going to have a squiggly career!” – but more about making a considered choice at every turn across my 30-year career. How does this move nourish me? Does it help me grow in skill or my network in a way I value? Now, would I have articulated that back in my early twenties when I left my first full-time gig after uni to switch to freelancing? Absolutely not.   

“Here’s been the constant: giving myself permission to explore, experiment, and not to be defined by other people’s success.”

Kat Wong

But here’s the thing – in the creative industry, a non-linear career path isn’t a red flag – it’s actually a big asset. I’ve always had positive responses (and curiosity) to my own career journey across radio, retail, different platforms, audiences, creative indies, global corporations to becoming a founder. The whole journey, hand on heart, has been utterly fulfilling, despite the usual challenges in a career. But here’s been the constant: giving myself permission to explore, experiment, and not to be defined by other people’s success. It’s allowed me to grow at every single move – one of the things most important to me.   

When it comes to unreliable CVs, the only time I’ve ever viewed a frequent role change as a red flag (when hiring for new roles) is when an experienced person has consistently done less than a year, at several places, over a number of years. Something’s not quite right there, possibly underdelivering on what was expected of the role or not being able to build trusted work relationships.  

Approaching a successful zig-zag career is about having a proven track record and reputation: one where you’re known for delivering impact, whilst building a great network of trusted relationships. That’s gold in all disciplines and industries, but particularly in the creative industry, where you are also exposed to broader perspectives and experiences. And in turn, this builds your own individual confidence and understanding in what you value, therefore leading to quality decisions about the next career move that works for you.

This is how you don’t become defined by mainstream expectations or what you ‘should’ be doing. Actors, musicians, and artists don’t ever box themselves in with every new creative endeavour or identity they explore. Of course, they have privileges, but what comes for free is the ability to reframe your career in a way that doesn’t pigeonhole your path. Know that you can build your career with intention, experiment to gain clarity, and start owning your story.

In answering your creative career conundrums we realise that some issues need expert support, so we’ve collated a list of additional resources that can support you across things that might arise at work.

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Further Info

View jobs from the creative industries on It’s Nice That’s jobs board at ifyoucouldjobs.com.

Submit your own Creative Career Conundrum question here.

About the Author

Kat Wong

Kat Wong's 30-year career has spanned across a number of vibrant industries and renowned brands, including Apple and BBC Radio. Her path has been eclectic and fulfilling, from producing documentaries about the fall of apartheid to leading international teams at Apple and developing global initiatives to provide career-building mentorship worldwide.

Always at the heart of Kat’s career is her dedication to sharing knowledge and career opportunities at an equitable level. In 2025 Kat left Apple and founded Oh Yeah, a platform created to give better access to years of career wisdom, lived experiences, and balance for those thinking about changes in mid-career.

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