Career Rejection Led Me to an Entrepreneurial Life
Lessons from hundreds of applications, a passed-over promotion, losing my job... and moving forward.
I don’t believe “everything happens for a reason.”
In the face of layoffs, not getting a job, being passed over for a promotion, or some other type of career rejection, it’s a phrase people often tell themselves. It opened the door to a different opportunity.
I’ve looked at various rejections throughout my career and asked myself: Did I learn something from this?
And in some cases, there was no takeaway. But eventually — eventually — it led me down a path of working for myself.
Passed over for an internal role
Early in my career, working at a tech company, I applied for a role as a business analyst. I was working as an implementation specialist and knew I understood the customer’s needs very well.
One of my peers in my department had also applied for the role. She’d been with the company for much longer. But I felt confident that I had a level of business knowledge that she didn’t.
I went through a panel interview with some of my co-workers. It included the head of the department, the senior analyst, and one of the developers. I could answer all of the questions about how I’d solve problems. How I’d interview customers to determine use cases. What I thought I’d bring to the role.
Then it was the developer’s turn to ask questions. He asked about my use of SQL. What types of queries I could write. I knew nothing… but assured the group I could learn quickly.
The developer looked down at his notes. I was positive he had more questions for me but had decided not to ask them. There was no point, since I didn’t know the basics.
The role was given to my peer. I congratulated her after I was given the news, even though I was crushed.
But I wasn’t ready. The role would have been nearly impossible for me, since it required technical skills right out of the chute.
I knew that if I wanted to rise within the company, I’d need the technical skills and the business knowledge.
I took a SQL class through the local community college. What the class didn’t teach me, I taught myself. I built a database for my department to use for project management.
Years later, I approached the head of the development group. I wanted to be the product manager, a far more complex role than a business analyst. The company (a very small startup) didn’t have a product manager at the time. I argued that it was necessary and outlined what the role would entail.
And I got it.
The company absolutely made the right decision not to give me the business analyst role. I wasn’t ready. But it motivated me to gain the skills I didn’t have so that later, I could go for something bigger. I took my career into my own hands.
Anna Burgess Yang
Many, many job application rejections
In 2021, I pivoted in my career. I left the tech startup and went into content marketing and journalism.
At the time, the job market was on fire. It didn’t take me long to find a full-time job at a marketing agency.
But I decided that I didn’t like being an in-house writer at an agency. I was burning out fast from writing all day, every day. So later that year, I was on the job hunt again. The market had shifted, a lot, in just eight months. I wasn’t getting any replies to my applications.
Imposter syndrome set it. Had I been found out? Could these companies tell that I lacked experience?
The market and hiring processes had changed, dramatically. I was being rejected because I hadn’t kept up with current trends. I was using the same tactics that had worked before.
I altered my cover letter, significantly, highlighting the skills I did have. I stopped worrying about comparing myself with others. I felt more at ease during interviews.
Once I did this, I found a new job within a few weeks.
And I learned not to let other people define me. What I lacked in tenure, I more than made up for in tenacity.
I wasn’t an imposter. I had a lot to bring to the table.
Losing my job
After about a year at the second agency, I was let go from my job.
I’d known for months the role wasn’t right for me (and it kept changing amid volatile market conditions). I’d raised the red flag with my manager several times but was repeatedly assured that “everything was fine.”
I finally broke down and told my manager that I felt terrible all the time. Like I wasn’t doing good work — because it had morphed into something outside my skill set — and that maybe we should part ways.
The next day, my manager said, “You’re right. This isn’t the right job for you. I think you should be done in two weeks.”
I was shocked. I knew what he was saying was true, but it was completely different than what he’d been telling me for months.
It didn’t end well. I met with the HR manager and told her how I’d been blindsided. After that meeting, my two weeks remaining with the company turned into two days. They wanted me gone.
There’s nothing like losing your job to make you question your self-worth. I’d been excellent at everything throughout my career. Why couldn’t I excel in this role? Why couldn’t I become what they needed? Was I not enough?
I didn’t have much time to dwell on this, because I needed money. The job market was tumultuous by that point, so I began life as a solopreneur.
It was absolutely the right move for me; I never looked back.
Taking control of my career
I spent 17 years in the corporate world. And if you’d asked me at the beginning of my career if I’d ever consider self-employment, I would have said, “Absolutely not.”
No one has a perfectly charmed career. We all face rejection at some point or another. And mine? Eventually led me to go out on my own.
I could take everything I didn’t like about working for an employer and fix it for myself.
Learn new skills at any time.
Define my own worth and value, rather than letting someone else define it for me.
Never be caught off guard. I’m in control of my business.
Did things “happen for a reason”? Or was I simply savvy enough to seize upon an opportunity when it presented itself?
It’s also worth noting that I had to be in the right headspace for reflection. This was never immediately after rejection. It would always sting.
Only later could I look back. Take what I needed. Leave what I didn’t.
You can read about the future of work and career pivots on my Substack.