Jasmine Wei

In May 2026, I left the big tech company where I’d spent the last four years without another job lined up. I thought I’d take some time to reflect on what I’d learned from ten years of my corporate career, and think about what I wanted the next ten years to look like before jumping into another job.

In the first few weeks after I sent in my company laptop, I felt oddly exhilarated and started exploring things I’d always been curious about but had dismissed as irrelevant to my education and background. I set up an influencer account on a social media platform, spent about two days deciding on my account name, profile picture, and the focus of my content, and stopped there because I really didn’t like how my face looked in a post and didn’t want to be posting pictures of my family and children. I browsed a bunch of freelancing websites to see what looked interesting, applied to a few opportunities, and I think most of my applications remain on “unread” to this day. I read books. In hindsight, my choice of books probably wasn’t the most appropriate, as my faith in big corporations further deteriorated after reading Careless People and Empire of Pain.

About a month into this break, I found myself walking around the mall trying to decide which luxury jewelry or watch store had the lowest barrier to entry as a salesperson. And after a few applications and a few more trips to the mall, I somehow got offered an operations position at one of the stores. The job was literally taking the jewelry from the safe in the back in the morning, putting it on display, checking to make sure everything was fine and nothing weird had happened overnight, and then doing all of that in reverse again at night after the store closed. I was really quite grateful for the store manager at David Yurman, who thought I was trustworthy enough to handle expensive jewelry, and I really needed the confidence boost after some tough interviews I had failed and rejection letters I’d gotten from the corporate world earlier that month. My rosy bubble of starting as an operations associate and getting hefty employee discounts quickly burst when I was asked to fill out an availability sheet that required at least two nights and one full weekend day per week. I couldn’t commit to that with two young kids, so that chapter closed before I got my hands on any jewelry. 

On the topic of interviews, I had quite a few. Maybe 30, maybe 50—I lost count after five. Good thing my AI chatbot kept track of all my live processes, reminded me to follow up with recruiters and hiring managers if I hadn’t heard back, tried to figure out where I was falling out of the funnel most often, and gave me pointers on what I should do about it. After a while, I started to suspect that interviews were mostly testing how good I was at interviewing– not how good I was at the job. I got better at pulling out the right story at the right moment, sounding convincingly enthusiastic about whichever company I happened to be talking to, and answering yet another version of “tell me about a time.” Some of that was skill. Most of it was luck.

There was one job that I particularly cared about. I fell for it instantly, if I dare say, the moment I read the job description; it was different from everything else I had seen. The qualifications fit me like a glove. The responsibilities section included everything I had ever enjoyed doing in my career and almost nothing I hated. The company was making an exciting product, growing quickly, and the founder seemed smart, driven, and not particularly money-hungry –at least on paper.

It was an ordinary Thursday morning when I saw the posting, and I gave it the whole day. I wrote a courting email – or a cover letter, in less romantic terms – and hand-edited my resume, matching every bullet to the tone and style of the qualifications section in the job description. In this day and age, I can’t think of a more serious way to treat a job application than refusing to use AI to edit your resume or write your cover letter.

I waited anxiously for a response. I got one the next day. I talked to the recruiter the following week and a week later I had interviews lined up with the hiring manager and the founder.  I spent the next few days soaking up every detail I could find on the internet about the company, the product and the founder. Things were going swimmingly up until then. 

The hiring manager interview was about as uneventful as it could be, except he casually mentioned one possible gap he’d want more signal on towards the end of the conversation. For the next few days, I mentally excavated every project, accomplishment, half-forgotten conversations and examples that might prove this was a gap I could easily overcome. I was ready for rounds of interrogation on this topic by the time I appeared in front of the founder a week later, along with a bank of examples illustrating why I’m the best person in the universe for this job.

The founder was young, clean-cut, with two small dimples that appeared when he smiled and softened his whole face. It was an easy face to trust. For the first few minutes, I thought, this is good, he seems smart, I can see myself working for him. 

Then the conversation went on. Nothing catastrophic happened, and there was no single comment that should have sent me running. Things just started to feel slightly off. Little warning signs started popping up like mushrooms after rain – each one easy enough to explain away on its own, but increasingly hard to ignore together. Somewhere around the halfway point, I realized the job he was describing looked increasingly unlike the one I had spent an entire Thursday courting.

At the end of the ninety-minute interview, I felt like I had been catfished—not by the founder, exactly, but by the job description. It was as if LinkedIn had set me up on a blind date with someone who, on paper, was everything I had been looking for. The first drink had gone well enough. Then, little by little, the lighting changed and the music quieted down, and I began to realize that the person sitting across from me bore only a passing resemblance to the one I thought I was meeting.

I concluded my job search about a month later and started at a new company just as posters for pumpkin spice lattes began appearing in coffee shop windows and you couldn’t finish a grocery run without getting startled by at least one Halloween figurine in the store. The scenery changed quickly, and I only started to realize what a strange four months they had been after I sat down and thought about everything that had happened. I usually care a lot about how things turn out, but this time the ending felt almost beside the point. The last time I remember feeling that way was during my first maternity leave. Both felt, in hindsight, like stretches of time that had somehow been handed to me, even though while I was in them I mostly wanted to get to the other side.

For four months, I had inhabited a strange, private daytime life that nobody else was really inhabiting with me. Before it, I had work; after it, I had work again. In between, there were long weekdays filled with whatever I had decided to try, whatever interview I happened to be preparing for, and whatever I happened to be worrying about.

There wasn’t really a grand lesson I was hoping to share at the end of all this. Part of me was quite glad that I would be getting a paycheck again. Part of me regretted not doing anything more dramatic with the break. I had never actually wanted to backpack through the Amazon or go on a phoneless retreat in Bali, but in retrospect, those seemed like the kinds of things a proper career break was supposed to contain. Mostly, I think I was surprised by how quickly something that had occupied so much of my mind became a season that was already over.