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In 2021, I quit a 15-year career as a tech executive in the finance industry and pursued content marketing and journalism. 

When I tell this story, I’m often met with, “You did what?” People can’t wrap their heads around such an unexpected career shift. 

While I quit my tech job, it wasn’t an overnight decision. In fact, it was something I’d been considering for a long time. 

A career pivot is much different than simply finding a new job in the same industry. If you’ve contemplated the same, you’ve probably asked yourself, “Can I do this? Will it be worth the change? What if it doesn’t work out?”

As someone who’s pivoted not once, but twice, in the past four years (first, I changed industries, and then I became self-employed), I can tell you yes, it’s worth it. But you need to be ready for the impact such a change will have on your career. Here’s how to tell if a major career change is right for you.

You can’t stop thinking about it

The first sign that you’re ready for a career pivot is that you can’t stop thinking about it. You dream not only of finding a new job, but doing something completely different. 

You start to explore new skills you might need to acquire, or how to prepare your résumé so it’s attractive to hiring managers in a new field. 

Once you start thinking nonstop about a career change, those feelings never go away. Trust me. They’ll only expand over time. 

You start to plan

Your dreams become more concrete when you start to consider a timeline. For me, it was, “Can I make this change within five years?” The more I thought about it, the shorter my timeline became. Staying in my current job instead of pursuing something different became unbearable.

You’ll start to think about a financial plan. A career pivot may involve a lower salary (at least in the beginning) if you’re starting in a new industry with little experience. 

Suddenly, my five-year timeline turned into six months. Then I quit without another job lined up (though I was at the end stages of several interviews and an offer came in a few days later). 

You’re comfortable with unknowns

Changing careers can be uncomfortable, especially once you start a new job. The saying “You don’t know what you don’t know” is particularly apt. All the research in the world can’t fully prepare you for your first day doing something completely different. 

As a longtime employee at my previous job, I went from being the most knowledgeable person in the room to one of the least. I went from being the boss to having a boss. I had no idea how long it would take me to catch on to the nuances of my new career. There were times I felt inadequate due to my lack of knowledge.

But I also knew that my previous career—though far different—had given me skills others in my peer group didn’t have. I understood contract negotiation, project management, and resource planning. I leaned into those, which helped me move past my discomfort. 

You’re willing to pivot again (if needed) 

As you plan to pivot to a new career, you have to ask yourself, “What if it doesn’t work out?” 

Maybe you end up hating the work. Maybe moving from a senior role to a junior role bothers you too much. Maybe it’s not the work itself, but you land at a company that isn’t a good fit, and now have to continue the job search.

I’m here to tell you: It’s okay to pivot again. Trashing your résumé is an outdated concept. After I pivoted to a new career and joined a marketing agency, I left within eight months and joined a different agency. One year after that, I pivoted again. Now I’m self-employed. 

As it turns out, that itch I felt to try something different was really a drive to strike out on my own. I didn’t know it at the time. I had to make a few stops along the way to figure out exactly what I wanted to do.

What you think you want and what you actually want might be two different things. But chances are, if you’re willing to make the leap once, you’ll be willing to do it again.


Anna Burgess Yang is part of the Creator Network at Fast Company, covering topics like work culture and the intersection of technology and work (including the impacts of AI). 

Anna is a former tech executive who spent more than 15 years at a financial technology company, including roles as a product manager and the director of customer success. In 2021, she joined the Great Resignation and quit her job to pursue content marketing and journalism. Today, she is a freelance writer who works with prominent B2B SaaS companies, specializing in fintech, automation, and AI. Additionally, her work has appeared in The Chicago Tribune, The Chronicle of Higher Education, and several banking publications.

You can learn more about Anna at annabyang.com. You can also follow her on LinkedIn, Threads, and Bluesky.


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