Job Security

Edward Hopper New York Office painting
Edward Hopper “New York Office”

At the holiday party, a coworker came up to me on the dance floor.

“Isn’t this so much better than contracting?” 

He was shouting, but I could barely hear him over the music. I assumed he thought that contractors were usually not invited to company holiday parties. And this one – he looked around pleasingly at the mostly young, gyrating, presumably salaried, benefit-outfitted bodies around us – was probably one of the rowdier ones I’d been to, given my past as a freelancer.

“I am a contractor,” I shouted.

“What?” He leaned in, attempting to dance.


He leaned out.

“Oh, really?”

I nodded. Was it too soon to get another tequila on the rocks?

“Oh, well.” He shrugged, not knowing how to continue the conversation in such a loud environment, and eventually shuffled away.

We met in the elevator during my second week, as we were both leaving the office. He said hello and we chatted about our respective departments for nine floors down. He was a relatively new member of the data team, having just joined four months before I did. He was well-acquainted with my teammate, who’d he got to spend time with at Summit.

Summit was a much-anticipated event that involved the company flying all two-thousand-or-so employees to the south of France for a four days of endless parties, booze, and team-building.

“I got my offer and they said, ‘Oh by the way, Summit is next week. Get ready.’ and I was like, ‘What?’ But it ended up being so, so great because I got to know my team so much better. I felt like we really bonded.”

By the time we crossed Park Ave., I learned that he’d also come from advertising, from an agency owned by the same conglomerate I worked at during this time last year.

“It’s way better here,” he said, “The problems we do are actually challenging.”

I nodded. This was promising. Normally I would have smiled blankly towards any thing that hinted at Kool-aid drinking, both tiny sips and large gulps. But I’ve now been through enough jobs to know that the work is a very small part of whether you like the job. So far, I too was enjoying myself. Everyone was cheery and helpful. I got along with my boss and my coworkers, and even when I was knee deep in “content,” enjoyed listening to the conversations around me.

I also liked the general belief in work-life balance. It was incredible to me that people could (mostly) work from home whenever, but that many still chose to come into the office, which was beautiful and filled with light and greenery and organic snacks. And despite the office’s accommodations, by 5PM, the cheery, helpful people headed out to get drinks with friends, or attend shows, or write for two to three hours, as my boss said he sometimes did.

At my last company, I would see the clock hit five and sadly turn my head back to my monitor along with three hundred other overworked souls. Five PM just meant we might be there for anywhere between two to five hours more.

At this job, if I stay until 5:30 my boss will say, “You should leave.”

And that first month, even before I got the job, it seemed too good to be true.

For one thing, they had found me. For another, they were willing to interview me purely via video because I happened to be in Taiwan that month. They had even arranged for one of the Directors on the corporate marketing team – a Taiwanese woman who happened to be in Taiwan visiting family – to meet with me. All I had to do was take the train down to Taichung for an afternoon and meet her in a hotel cafe.

We ordered our coffees in Chinese, laughed about the fact that neither of our Chinese was good enough to do the interview, and chatted about writing and content strategy. It was going well, but a lot of the job details remained a bit fuzzy to me.

“Don’t worry,” the woman said, “We’ll have a ton of trainings set up for you to understand the products. I had no idea either what was going on when I first started.”

Sitting in the warmly lit lobby across from a kind, Taiwanese face a few years older than mine, I felt like maybe I was looking into the future.

I asked about benefits, including maternity leave. The first time I’d ever done so in an interview. Because, you see, I was getting married soon and starting a family was not too far off.

“Of course,” she said. “It’s smart to ask and to plan for things like that. I wish I worked here when I had my kid because they offer four months fully paid maternity leave.”

She went on to tell me about the travel opportunities, free yoga and pilates classes and massages, and of course, the excellent health insurance and 401k and stock options.

At the end of the interview she shook my hand with a twinkle in her eye. “I really really enjoyed meeting you and will be giving the rest of the team my feedback right away.”

It was the easiest interview I’d ever had.

By the time I had returned from Taipei, they were ready to give me an offer.

“Man,” said Tom, “Looks like you just fell ass backward into a damn good opportunity.”

Except. It was too good to be true.

There was a vague explanation about missing some headcount deadline by one day.

“But we have the offer ready to go, which we’ll give you in December,” they said, “In the meantime, you’ll be a contractor on a 40-hour week. But by January 1st, you’ll be full-time.”

I was disappointed. Until I had a contract in hand, I was still a freelancer. But I was also, for the most part, unemployed.

Two weeks before our New York wedding, I started the job and tried hard not to make the same mistakes I’ve made in the past. Essentially, I tried to distinguish what’s useful and what’s valuable. If I figured it out, I hoped, the company wouldn’t be able to give me a full-time job fast enough.

In November, my boss and I were having one of our weekly check-ins. By then, I’d been at the company just ten weeks. I was still feeling out some parts, but mostly I knew what was going on.

“Why don’t we get one of those phone booth rooms,” he said. I thought that was weird because usually he’s happy to just sit in the open kitchen. But it was only the middle of November. I had only gotten great feedback since starting. I didn’t think anything was the matter.

We talked through the usual things: what I was working on, the projects I had coming my way. Vitals all good… right?

“Okay yeah, that sounds good,” he said. He seemed to hesitate.

I looked at him. “Anything else?”

“Yeah,” he let out a sigh, “I have some bad news.”

The aforementioned full-time contract never materialized because it couldn’t. Some vague details about a hiring freeze and financial “blah blah blah,” as my boss put it. There were some impending changes to the entire business itself that made the leadership spend more conservatively than usual. But the corporate marketing team could guarantee me another short-term contract through March.

Beyond that? My boss shrugged, “I don’t know. If you don’t want that, and you want to stop doing what you’re doing and leave, I understand.”

I tried to keep my disappointment in check, which was easy because my boss looked more uncomfortable than I did. I wanted to pat him on the shoulder and say, “Hey man, it’s okay. At least you’re not firing me. And if you are, at least you’re doing it in person.”*

But I also thought about the way he phrased it: “If you don’t want that, and you want to stop doing what you’re doing and leave, I understand.”

Was he actually letting me go but in a nice way? Did he actually want me to leave before December? Was the March thing just a nice way to say, ‘But feel free to leave now’?

Was I seriously that unemployable? I could have, if I let these thoughts get the better of me, burst out laughing and then cried and made my boss feel seriously uncomfortable, but I gathered my thoughts.

I remembered the past few (fine, several) times when I could sense that my job was on the line and did the bare minimum, if anything at all. No. This time would be different.

“Does this have anything to do with my performance?”

“No, we are bought-in on you. There is just no money.”

That was kinda bullshit, kinda not, because as big public companies go, there is always money.

“Okay, then what do I have to do to prove myself? What projects should I focus on?”

As he spoke, I began to think it a bit unfair that just ten weeks in, when I was barely wrapping my head around the people that owned which products never mind the products themselves, I now had to wade through the myriad tasks and projects coming my way to figure out which would be most valuable to the organization….

But that kind of thinking was also not productive. The whole, “Oh but it’s not my fault!” mindset. So I shut it up and listened.

“…so yeah, those projects are probably the most important,” my boss concluded. “I know it sucks. We want to keep you, and we’ll continue to push to keep you, but I just want to set your expectations. It’s not because of your performance or anything.  I phrased it like that because I didn’t know where you were at with health insurance and stuff.”

I held up my wedding band. “Well, luckily, I got married and am now on Tom’s plan.”

“Oh nice,” my boss said, “So you don’t even care. You’re like a mercenary.”

I had never thought about it like that, mostly because I didn’t know what mercenary meant. Later, back at my desk I looked it up.

He was partly right. The other part was that I liked my job and the people, the environment; for the first time in a long while, I could imagine myself building a semblance of a career.**

But it’s all TBD. Come March I may very well be unemployed again, but it won’t be without warning. And for the time being (and considering my history), that’s job security enough for me.

*Which is more than I can say about my last boss. Cowardly asshole.
**Though admittedly this is a complicated thought because sometimes it’s easy, after a long day of writing for someone else, to come home and push aside the urgency you feel to create something of your own…. but that’s for another day.


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