How to plan a career pivot
From idle inkling to action
I’ve had two major pivots in my career. The first was in early 2021 and I completely changed industries — leaving a 15-year career in software and pivoting to content marketing and journalism. The second was in October 2022 and I pivoted from being a full-time employee to being a full-time freelance writer.
I get a lot of questions about career pivots, partly because my LinkedIn profile headline includes the phrase “Career pivots are fun!”
I try to share openly because while career pivots can be really fun, they’re also really scary. They can feel risky. You wonder if you’re making the right decision.
This series of my Substack will focus on career pivots and other major career decisions. I’ve gathered up many of the questions I’ve been asked over the past few years and will answer them honestly.
If you’re thinking about a pivot: you can do this. It doesn’t have to feel like an irrational decision. You can plan for your pivot.
Knowing when to make the leap
Around July 2020, I began thinking seriously about quitting my job. The pandemic exacerbated many of my frustrations, including a short-sighted and arrogant CEO.
A lot of things about the job were great. I had a boss I liked a lot and some colleagues that truly cared for the company’s customers. I’d been promoted several times over the years and my workday was really flexible.
But, as was the case for so many other people, the pandemic gave me time to reflect. I thought, “Well, maybe I should say until my youngest child is in kindergarten. After that I won’t care about flexibility as much.” She was 2.5 years old at the time. I thought maybe I could stick it out until the CEO retired in a few years.
But the more I honed in on the company’s problems, including some truly toxic employees, the less I could see myself staying. The bad things outweighed the good.
I thought about finding a similar job: a product manager at another software company. But I was also very honest with myself. The company was woefully behind in technology and, as a result, I lacked some of the basic skills required for product managers. I could take some online courses and try to gain those skills, but the pandemic had exhausted me. Product management on the whole tends to be a stressful job, at any company.
So I began to reframe my thinking: What else could I do? I had been an English major in college and loved writing. But at the time I graduated, back in 2005, writing didn’t seem like a stable or viable career.
Then I realized that a lot had shifted. Companies did hire writers. I’d never heard of content marketing, but tripped across it in my job search. It felt like something I could do.
When is the right time to make the leap? When you don’t see a path forward in your current industry or at your current company. When the idea of continuing with the same type of work feels suffocating.
How I prepared to pivot
In October 2020, I began freelance writing at a marketing agency alongside my current job. The pay was terrible, but the company allowed me to republish the work in my own portfolio.
I wrote blog articles early in the morning and late at night. I learned the basics of content marketing. The company had a giant queue of work for clients, and I selected topics that were in my wheelhouse: product management, banking and finance, and some other related subjects.
When I had a decent portfolio, I began to apply for full-time jobs in content marketing. The more I applied, the more desperate I was to leave my current job. I began to consider quitting before I had something else lined up.
I did the math with my meager freelance earnings and calculated how much I would need to write per day to earn enough to pay our bills. It would have required a lot of writing per day, but it was possible — especially as a short-term solution.
Every financial situation is different. I’m married and my spouse has a good job. We couldn’t afford for me to be unemployed, but we could adjust our lifestyle if I earned a minimum amount as a freelancer. It helped that at the time we weren’t paying for childcare due to the pandemic.
Even when I landed a full-time job, I knew that it would be much, much lower than my current salary. I would be starting over, the person with the least experience on a team.
Pivot Day
I planned The Day I Would Quit — whether I had a new job lined up or not. Psychologically, it helped to have an end in sight.
I chose January 15, 2021. I had a regularly scheduled meeting with my boss, so she wouldn’t suspect anything out of the ordinary. It was also the day that my year-end bonus hit my bank account and I didn’t trust the CEO not to revoke my bonus if I had quit sooner.
It was winter, but sunny. I went for a walk that morning before my 9:30 am meeting with my boss. I felt an extreme sense of calm. I knew it was the right decision.
The CEO treated me terribly after I left. Knowing his personality, I wasn’t surprised but it still hurt — especially since I’d given 15 years to the company as a loyal employee. But in his eyes, I had betrayed him. It was a reminder that, at the end of the day, the company will always put itself above the relationships with employees.
You have to be careful when planning a pivot and always protect yourself. You never know how the company will react. Companies, by and large, expect employees to be careful, even as mass layoffs remind us that they’re not loyal in return.
If you need to build skills or take courses or have a side hustle to prepare for your pivot, quiet quit your way through your current job.
Don’t give more than the minimum.
Focus your efforts on your pivot.
As for my second pivot about 18 months later, that’s a story for another day…
Thank you for your support of Work. Better. If you want me to answer a question about career pivots that you’d like me to answer in a future issue, send an email to annabyang@substack.com.
You can also follow me on LinkedIn for more insights about work, Threads where I’m a bit spicier, and my blog where I share tips for solopreneurs. Or, catch up on the personal side of my life here.