The end of a job: an untold story
Ending one job and launching into the unknown
One year ago, to the day, I met with my boss at a small content marketing agency. I was coming up on one year with the company, so the meeting was supposed to be a retrospective of sorts.
During the meeting, I broke down. I’d been feeling, for months, that the job was not a good fit for me. I’d brought this up repeatedly, but my boss assured me that I was doing great. Still, I didn’t feel good about the work. But I continued to plod along because I’d already changed jobs twice in the prior 18 months and the idea of searching again was overwhelming.
But I finally couldn’t take it anymore. I felt like I was doing myself — and the company — a disservice.
My boss listened. He asked me to list off my accomplishments, as if to say, “See? You’ve done some great things.” But he also told me that he would support whatever decision I made and that we would figure it out.
The next day, in the late afternoon, he asked to meet with me. And he said, “I think you’re right. I think you’re not a good fit for this job and we should part ways.”
I was shocked.
Not because he was telling me anything that I hadn’t already been feeling. But because he had been telling me for months that everything was fine.
He thought I should work for two more weeks and could let the team know that I was “choosing” to leave.
I was offered two weeks of severance beyond my final working day. I spoke with the HR person and let her know that I would work the final two weeks, but I didn’t want to talk to my boss anymore — I was so blindsided. She told me that was fine, and that I could work with her to wrap things up.
The next thing I knew, my working period was changed from two weeks to two days. I was being effectively kicked out the door. And along with that came a financial impact: I was only paid for two days and two weeks of severance, far less than the four weeks total I’d planned on.
I swiftly made the decision to go out on my own as a freelance writer. But it shouldn’t have been that way: it should have been my decision rather than one borne from necessity.
I haven’t shared this story publicly for a lot of reasons. The primary one is shame: I was let go from a job.
But over the past year, I’ve reflected on this a lot. People lose their jobs for so many reasons — sometimes for things far outside their control. Sometimes it has nothing to do with performance. Sometimes companies are just shitty. And there shouldn’t be shame in acknowledging that a job is a bad fit, although I wouldn’t wish an ending like I experienced on anyone.
And as I’ve thought about my own final experience with an employer, I recognize that yes, some of it was about me. But a lot of it was also about the company, the economy, and one terrible boss.
The backstory
I joined the company in October 2021 as employee #9. A friend had recently joined the company and posted on LinkedIn that she thought she’d found a dream employer: a company that truly put people first.
I’d been casually looking for a new job, so I looked at the company’s website. The only open role was an account manager, someone to connect with existing clients and also bring in new business. I applied and interviewed with the person who would eventually become my boss.
I was very clear during the interview that I had no outbound sales experience. But I had a ton of experience managing relationships with clients. He told me that the lack of sales was fine: most of the company’s work was inbound anyway. I only needed to meet with prospective clients, understand their needs, and write up proposals. I was comfortable with that and was offered the job.
I realized quickly that my new boss was an intense micromanager. I wasn’t used to that: having come from an executive role, I had been working autonomously for a long time. But my colleagues were incredibly kind. And the company observed a four-day workweek, which was a nice bonus.
I implemented a CRM for the company, introduced a new retainer model for the business, and closed some of the largest contracts in the company’s history. For the first few months, everything was fine.
The spiral
In early 2022, layoffs began to permeate the tech industry. Many venture capital-backed companies had been swimming in money throughout 2021, but “growth at all costs” wasn’t sustainable. The agency’s clients were hit hard by budget cuts and layoffs.
Inbound inquiries began to slow. Contracts were for smaller dollar amounts. The company had no marketing strategy, so I was also fighting an awareness problem: prospective clients had never heard of this tiny agency. An internal person was promoted to a marketing role in March, but my boss drastically overestimated how quickly marketing efforts would impact sales.
I was asked to do cold outreah. It was uncomfortable for me, mostly because I hate being on the receiving end of cold emails. And cold outreach to marketers of all people? An even more difficult task. And cold outreach when budgets were being slashed across the board and I was pitching a boutique agency? Yikes.
I did a ton of reading about best practices for cold outreach and even met with an email coach. I felt like the most effective strategy would be to hang out on LinkedIn, connect with marketers, and then soft pitch them later (or hope they’d remember me when they needed marketing services).
But that was a long-game strategy and the company needed money in the short-term. I told my boss in early 2022 that I didn’t feel like I was good at my job — specifically, the cold outreach needed to bring in new sales. He replied by asking, “Is it imposter syndrome?” (since I had changed careers). I acknowledged that maybe this was the case.
Sales didn’t pick up. I brought up again that I wasn’t feeling good about the work or my results. My boss assured me that it wasn’t my job to generate new leads, it was marketing’s job (even though marketing was a brand new effort) and that ultimately, I wasn’t responsible for results, he was.
Over and over, I raised my concerns. Over and over, I was told that everything was fine.
The breaking point
I began to feel guilty. I felt like the company would have more sales with a more seasoned sales professional. And no matter what I did, I couldn’t make up for the lack of experience. Moreover, I felt like I wasn’t naturally good at sales and that I might never be good at sales.
It wasn’t the job I’d signed up for. But the market conditions had changed, and this was now the job I found myself in.
I was miserable. I was also scared by the prospect of finding a new job in a tanking tech environment.
I didn’t plan to melt down during my 1:1 meeting with my boss on September 28, 2022. But as he started to talk about my results (or lack thereof) over the past year and my goals for the future, I started crying. I shared with him everything I’d been feeling about the job and that I just wasn’t good at it.
I told him that I thought we should find a path to part ways gracefully. Maybe that would happen over a few months’ time, so that I wasn’t leaving the company without a salesperson at all. My boss told me that he’d support whatever decision I made.
And the next day, he told me that my job was over.
This was a person who had repeatedly positioned himself as understanding, supportive, and looking out for the best interests of the employee as well as the company. That’s why I’d felt safe approaching him with how I felt, rather than simultaneously looking for a new job and then quitting when I found something.
But his true colors showed at that moment. He knew as well as I did that the role (or what it had morphed into) was not a good fit for me. He’d never been able to say it. When I brought it up, he seized the opportunity to get rid of me — something he’d been too cowardly to address on his own.
When I told the HR person, she was horrified: both by what had happened and because I’d been told repeatedly that my performance was fine. She said, “I’m so sorry. It never should have gone down that way.”
I guess “people-first” was a lie. And I’d bought into that lie, truly believing that this company was different. It wasn't. It was like every other company that puts itself first.
The pivot
Truthfully, I’d been thinking about becoming a full-time freelancer for a while. But I was scared. It seemed so risky. I wanted our family to have more in savings before I made the leap.
When I quit my career of 15 years in early 2021, I carefully planned the timing. The timeline kept shortening as the idea of leaving became more and more appealing, but still — I kept my family’s best interests at the forefront. I didn’t quit until I felt ready.
I wasn’t ready to leave full-time employment when I finally found myself out of a job. I know that I was headed down the path of self-employment anyway, but it doesn’t change the fact that the decision wasn’t mine.
I caution other people to be careful when opening up to an employer. You may think that your boss will be sympathetic or willing to work with you if you’re struggling. But you actually have no idea.
“People-first” may be an ideal, but not a reality. It’s a label, but not the core of the company’s identity. In the end, when push comes to shove, it’s “company-first.”
What happened to me removed any sense of psychological safety I had in the workplace. It was a massive burn, one that made me feel like I could never trust an employer again. For me, it fueled the path I was headed down anyway.
The aftermath
As it turns out, the company was struggling on many levels. Things didn’t magically improve after I left. A series of missteps and mismanagement led to full-blown collapse and all employees were laid off. Perhaps, in that sense, I dodged a bullet.
My former boss reached out to me shortly after my last day. He felt bad about how things ended, he said. After several (unwelcomed) emails, I finally told him that I needed some space. I wasn’t ready to interact with him because I felt so betrayed.
As for me? I’ve been fine. More than fine. My freelance income has far surpassed my salary at the company. But I think about the employees who were laid off more recently, some of them still struggling to find jobs. They trusted that the company was functioning well, and it wasn’t. They were also burned.
I was already cynical about employers after leaving a fairly toxic environment and realizing, “It doesn’t have to be this way.” Surely a company that purported to be “people-first” would be the antithesis.
I was wrong.
Most issues of this publication are free because I love sharing ideas and connecting with others about the future of work. If you want to support me as a writer, you can buy me a coffee.
If you love this newsletter and look forward to reading it every week, please consider forwarding it to a friend or becoming a subscriber.
Have a work story you’d like to share? Please reach out using this form. I can retell your story while protecting your identity, share a guest post, or conduct an interview.