Cherry Glossed Thoughts: Tech Layoffs, 634 Job Rejections, and Why I'm Building My Own Thing

Anna R.
November 3, 2025

I really enjoy working, like a lot, and while I've done a lot of work to unpack my relationship with work, I'm not going to lie—I'm still majorly concerned about my career. Embarrassingly, I'm someone that puts a lot of her own worth in her title and how advanced she is in her career, so as you can imagine after two layoffs in two years my entire sense of self has really been uprooted.

This summer, after six months of looking for a job, I fucking broke and had to have real honest conversations with myself, my therapist, and my partner. The career and life I dreamed of, I fear isn't realistic in today's world, and it's a disservice to myself to not pivot. My hope with putting this out there is that other people, specifically women in the corporate world, feel less alone. Because one of the hardest parts of getting laid off is the isolation of rejection.

all jokes over here babe.

So to rewind: I didn't grow up dreaming about a career. I went to a Chicago liberal arts college on my own, worked nonprofits, did sex work for consistent income, then clawed my way into ad agencies and eventually tech. I wasn't technical, felt like a fraud at every turn, but I pushed. Networking events, conferences, hackathons. I learned the social norms, became comfortable in my skills, and finally thought: fuck, I've got a place here.

A few months after the Twitter layoffs of fall 2022, where Elon cut nearly 80% of their workforce and everyone just... let him, I got my first layoff. My entire team, gone. It came less than five days after I lost a friend unexpectedly. And I'm not going to lie, that layoff really fucked with my ability to process her passing. I was thrust into: fuck, what am I going to do for money?

It took me eight months to get a job after. And while I loved my team, the company was in peril. I managed to survive four rounds of layoffs in a year, including one that happened on my first day. And right at the year mark, a sweeping cut at the company. The product I'd been working on was acquired and my role was a redundancy.

That was earlier this year. From February to August, I spent countless hours applying to jobs. I eventually started applying for lower title and salary jobs, which didn't do well for my self-esteem. I couldn't even land a job as a junior social media manager. I told myself it was because I was too dumb, that I wasn't worthy of having a career or dreams.

But 634 job applications, 83 screenings with recruiters, 52 first round interviews, 6 final round interviews, 4 assignments, no offers had me feeling worthless.

And then I fucking snapped. I was staring at my spreadsheet after what I thought was a particularly successful final round. A senior role at a major software company, I vibed with the team, did well on the assignment, they said I was a perfect fit. And then I had to change that column in my job tracker to red. Another rejection.

What didn't happen.

I work in social media. I look at data all day. I know when numbers are bad, when ROI is fucked. And I'm sitting there thinking: what the fuck are you doing? This is insane. I started calculating the hours I'd spent. I was in a deficit, spending hours on something with a) no promise of a positive outcome and b) potentially terrible ROI even if I got the job. What if I was in the same place in a year because I got laid off again? I also knew a third layoff would actually break me.

I couldn't do it anymore. I felt worthless, moronic, deeply inept, and fearful for my future. I'm embarrassed to admit I had some not-great mental health thoughts. I would randomly start crying, become so overwhelmed with anxiety and this crippling sense of self-doubt that I would just stop what I was doing and freeze. I started losing ambition, something not like me. I felt like I had no control over my life—spinning, bidding, playing a rigged game.

My life could be worse, I could be this loser.

I felt like so much of my life had been put on hold. I had been planning to freeze my eggs in Q1 of 2026, but suddenly that felt really stupid and unfeasible. My partner and I had been planning and saving for overseas travel, but that money felt frivolous to spend. I even had a friend visit—she came specifically to see me—and I rescheduled so much of our time together for job interviews. Interviews that went nowhere.

Also, and this was the hard part: I was never going to get a CMO title. Which was the goal. I wanted that c-suite title for some sort of sick validation. Maybe then I could be proud, or my work would mean something.

But I'm not quite the type of person they want in c-suite. Marketing itself has its own weird set of rules and games, and I don't feel like I fit well with them. There's my appearance—I'm aware that my size and propensity for goth things do not mesh particularly well with marketing executives. Too weird, too fat, too queer to take a risk on.

Channeling the confidence of this crypto icon.

But my mind shifted to trying to understand where my energy best lies. And it wasn't in playing this failing job application game. I cannot afford to not make something for myself—not emotionally, not financially, not creatively. I have to build my own table.

And so my partner and I (who also works in tech, and was also laid off, lol) decided to build our own agency. At first, I felt like a loser. Like I couldn't cut it, so I had to give myself my own title.

But the conversation shifted. We talked about needing to make money because, bills, and this being the quickest way. We talked about AI deeply changing both our fields and needing to get ahead. We talked about what kind of life we want—I want kids maybe, depends on the day you ask me—and what kind of parents we want to be.

And yeah, we talked about the state of tech. When Elon cut nearly 80% of Twitter's workforce in fall 2022 and everyone just... let him... it normalized what we're seeing now. These unreal layoffs, these brutal cuts. Suddenly every company was doing it. I don't know a single person who works in tech who hasn't been impacted by a layoff. 80% of people I know have been laid off themselves. The other 20%? They're on teams that got decimated. Stretched thin, emotionally checked out, in some cases earning less than years prior.

Another fun joke!

Beyond that, we're in such an interesting time with AI. And I think the whole industry is going to change because some companies are struggling to keep up and they're making bets that might not come to fruition. But what then? And honestly, I don't think nearly enough professionals are being given the time to learn how to implement AI into their workflows. Experimentation takes time, and often times might not be profitable initially. And in a climate where the only concern is that quarter's profits, it doesn't seem like there's much time for learning.

And honestly? I worry about what this is doing to tech itself. Teams of burned-out, disengaged, and scared people who are too stressed to do their best work. Distracted, under-resourced, overworked. What kind of products are we building? I think of moments like the CrowdStrike outages, which caused massive issues across airlines, banking, and countless other industries. Since then the company has cut 5% of its workforce. How can you continue to cut workforces when your product is having major malfunctions and deeply ruining your brand? And what does this mean for the future of everyone in the country who inevitably has to use products that rely on this service? Are we to subsidize their greed?

There's no stability in corporate America anymore, yet we're all expected to give it our stability and loyalty? I think in some ways white collar jobs are falling victim to the gig economy. I've observed marketing teams become increasingly reliant on freelancers. Which objectively I don't think is bad, but I do think it speaks to the instability of the corporate world.

I want off this ride. Granted, I still work with tech clients and I love it, but I want to have autonomy and agency over my own work and time. I don't want to be at someone else's whim.

I spend a lot of time thinking about the impact these environments have on women and other marginalized groups. With the rollback of DEI, how will this affect millions of people's ability to advance in corporate? In some ways I think that the best thing people can do for themselves right now is not only find additional streams of income, but to also really build something of their own—providing they have the self-discipline and desire.

hoping for a very bright future for us all.

For what it's worth, with all the amazing talent being laid off, I do think tech will be fucked when the pendulum swings. People are building their own things, and I'm particularly very excited to see it.

If you're someone feeling burnt, scared, alone post-layoff, or just living in fear of a layoff—you aren't alone. What you're feeling is normal, and it's not fair. But you can't let it define you. You have to find something that makes you feel good. You have to laugh, to cry, to rest, and to run towards something.

The pendulum always swings back. And I believe the industry is not ready for it.

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