Essays & Confessions

How I Got Into (And Out Of) The Most Nightmare Job Of My Life

By | Friday, April 07, 2017

I’ve written about a lot of my life for TFD. It’s something I love doing — being as transparent as possible about things I’ve experienced — especially if I feel like someone else might relate, or laugh, or benefit. But there are still a few things I’ve held back, frankly for the fear of embarrassing myself on the internet. Today, though, I’ve decided I want to talk about one such thing that I’ve avoided writing about for a long time.

Last spring, I’d been working as a full-time freelance writer and editor for about six or seven months. I was growing sick of it; I was mostly copyediting for a shitty celebrity gossip website, and taking on low-paying copywriting gigs whenever I could get them. I didn’t feel like I could go after higher-paying work without continuing to “pay my dues” for a bit longer. But I was getting burnt out, and wanted a quick solution to start earning more money. I started applying to jobs, and I landed one as an editorial assistant at a startup. It was a startup in the extremely early stages (as in, it didn’t really exist yet), and I was one of three team members, not including the contracted web developer who would poke in and out of the office.

The company was going to be a website dedicated to telling stories of artists in New York. We were going to feature both written and video interviews with people who made a living doing some kind of craft, and we’d also invite people to buy into a membership program that would allow them to attend monthly events and meet these artists. The team consisted of a founder/CEO, an editor-in-chief, and me.

The founder, my boss, was a man in his thirties, and he seemed to me like a dream of a CEO: he wore jeans and t-shirts every day, encouraged us to voice our opinions about what we wanted the company to accomplish, and made us feel like we could do anything without bothering to consider a budget — which we especially believed when he would take us out to lunch almost every day. I couldn’t tell what he spent all day doing on his computer, but I didn’t think much of it. We’d spend most of our time talking about our personal lives and non-work-related topics, and it felt more like a friendship than a working relationship. I sincerely thought this was a dream job situation. I did not imagine that I’d eventually be owed five figures of backpay for more than two months I’d spend working there without a paycheck.

Of course, when I recount this experience to people now, the warning signs are all there. The first red flag was, of course, that there wasn’t any legitimate plan in place for how we were supposed to be profitable. I was more interested in my editorial duties, though, so even though I asked some pragmatic questions about the company, I was satisfied with vague answers, and knowing that we were going to “figure it out” as we went along.

The next was that I also never received any legitimate contract to sign. When I asked to get something in writing, my boss emailed me his confirmation of my position and salary, and I responded back with my confirmation of acceptance as a sort of signature. Another warning sign: we moved into a new suite in a new coworking space roughly four times in the three months I worked there, usually because my boss still couldn’t find a place with the right “vibe.”

The biggest red flag, though, was when the editor-in-chief got fired two weeks after I started working there. My boss cited her frequent lateness and general sense of unprofessionalism as his reasons. I thought it seemed extreme, but it made enough sense to me; sure, she was at least 10 minutes late every day, and yes, she did sometimes use her desk as a footrest. He offered me her now-vacant position, and I jumped at the title change in a heartbeat. The salary that came with the promotion was almost twice what I’d ever earned in any year of my professional life thus far. I couldn’t help but think that it was in some way deserved, that I’d just needed to wait for someone out there to recognize my talents in order for me to get a “big break.”

Soon after my promotion, we hired a videographer, and got to work on actually filming and interviewing the artists we would be featuring on the site. And about two weeks after she started — the same amount of time I’d worked there before the original editor was fired — my boss told me he was letting me go. His excuse for me was that he knew that they desperately needed to focus on video, and that maybe after getting off the ground, he’d be able to open up the door for editorial again. After a long and tearful (on my end) conversation, I defended myself well enough that he decided to keep me on board. We hugged, and got back to work.

At this point, my boss owed me one paycheck. He’d paid me for my first two weeks of work in cash, which I thought nothing of at the time — he’d said there was some issue with his electronic payment system, and he didn’t want to wait for me to get what I was owed. I’d appreciated him taking care to pay me on time. But the near-firing was a week and a half after I should have received my second paycheck. At first, my boss told me there was another issue with the platform he was using for payment. Then, after about a week, he told me he’d had his identity stolen, and that all his accounts were locked up.

I believed him, because it didn’t seem like there was any reason I shouldn’t. But because I already felt like I was on thin ice after nearly being fired, I didn’t push him to pay me like I probably should have. Another payday arrived; I confronted him about the fact that it had been more than a month since I’d received any sort of payment. He took me for a walk the next day, apologizing profusely, offering me things like full healthcare coverage and stake in the company once everything was settled. He even said his mother was coming into town to give him cash for the time being to pay me, because even though he was dealing with this identity theft issue, she couldn’t believe the position he’d put me in — and he couldn’t, either. When I thanked him for taking care of it, he assured me not to worry about it, because no one should ever have to ask for what they’re owed.

As you have maybe guessed by now, his mother never came through. I don’t even remember the reason why. My boss continued to delay paying me, offering one excuse after another, but still doing everything in his power to make me believe that my payment was coming. He opened his online accounts and showed them to me, and even took me in to meet his banker, who eventually sent me false confirmations that a wire transfer was on its way. I sincerely thought there was no way a guy who works for a national banking institution was going to get involved if this wasn’t legitimate.

And all of this time, I kept working. My boss praised every piece of writing I put in front of him, and said he couldn’t be doing anything he was doing without me. He constantly compared me with the woman who originally held my position, insisting I was a far superior right-hand person, and that he’d absolutely made the right decision in keeping me around. And he still seemed genuinely interested in getting to know me as a person, asking me questions about everything from my upbringing to how I met my boyfriend to my goals in life, and gamely offered up details of his own life. (And, while this is speculation on my part, I do feel like a part of him felt guilty for not paying me — so he made himself feel better by getting to know me, and reassuring himself that I’d have some sort of security blanket via my personal relationships.)

We eventually decided that it wasn’t fair for me to be coming in to work anymore amid all the payment issues he was having. I was coming home every day emotionally drained, crying to my boyfriend on the subway and over dinner about how stupid I felt for believing this person. I was unable to sleep each night after going to bed with the expectation that I would be woken up by a text message with yet another excuse at 5:30 AM. (This happened constantly.) Nevertheless, I was too invested in the idea of getting my money to leave my “job.” I felt like I had put in so much time and effort, there was no way he couldn’t pay me what I was owed (which was, by the end of everything, well over $10,000).

Finally, he called me into the office with the promise of an actual check. He sat with me for an hour before actually handing it over, lamenting about the fact that he was a bad person, that what he’d put me through was completely unfair. He handed me a check for more than what he owed me, as a thank you for what I’d had to put up with, and told me I could cash it the next day. He said he needed to take some time away, and he wanted to reconvene in regards to how I felt about staying with the company in a few weeks. He, of course, wanted me to stay, but he would be understanding of my decision regardless.

Later on that day, he called me asking me to bring back my company credit card, just in case I decided to leave. Against my parent’s advice — they were, obviously, invested and concerned by this point, and rightfully thought I should get what I was owed and be done with the guy — I said yes, I would swing by the office to drop it off the next morning on my way to cash my check. When I did, I also collected my books and other belongings I’d left there, “just in case” I didn’t come back. I knew I wouldn’t be returning, so when he confronted me about clearing out my things, I answered honestly.

“So, you’re really leaving, huh?” he asked, seemingly hurt. I said yes, though I truly thought he’d have figured that out (especially because he asked me to return my company card). I felt that couldn’t go on carrying like I was actually considering still working with him — which is what I’d been doing for the weeks prior, as resigning seemed like a surefire way to never get paid, but I felt more comfortable now that I had a check in my purse. But then he told me I actually needed to wait one more day to cash my check, because he needed to take care of something with the bank.

Eventually, he told me he couldn’t allow me to cash it. The extra money he’d given me was a gesture of good faith that I would be returning, and now that I wasn’t, he couldn’t afford to pay me that full amount. 

I ended up blocking his number, and my father and his lawyer got involved. After weeks of back-and-forth via my dad’s lawyer, attempts to settle, and more excuses from my boss (via his lawyer), I ultimately walked away with nothing. We even sent the packet of information we’d gathered for the lawyer — my written explanation of everything, plus countless emails and texts — to the New York City D.A.’s office, but they wrote back saying their resources were being used elsewhere.

I still don’t know why he did it. I assume he was moving money around in some shady way, and using me to make his “business” appear more legitimate. It’s very upsetting that there’s this large amount of money I’m owed, and I’ll never get it. Sometimes, I think about the fact that I worked all those weeks and months for ultimately nothing, and the Excel spreadsheet I’d made up listing all the places I was going to allocate my money to when I finally received it, and the fact that I’d had to use up the $1,800 I had in emergency savings (the largest amount I’d ever saved up at that point in my life), and the fact that I had to ask my parents for financial help for the first time in years…and I mostly feel numb, if also very naive. Chalk it up to an unplanned unpaid internship, I guess. 

Towards the end of the entire process, I started seeing my therapist for the first time in a year or so. At one point, she likened the way I talked about the situation to the way a person in an abusive relationship might talk. That was incredibly validating in one way; this person did manipulate me — likely because I was a naive, enthusiastic 24-year-old woman, who didn’t think this particular lesson was one she’d have to learn — and it wasn’t my fault, and I stuck around because I was both emotionally and financially invested. He made me feel like he actually cared about me as a person, which made the financial betrayal cut even more deeply.

But in another way, it was the sort of kick in the pants I needed to get my act together. Because I wasn’t in an abusive relationship. I just was in a shitty situation that I was privileged enough to be able to walk away from, relatively unscathed.

And I know my situation is still lucky. I was dealt a pretty good hand in life, and even though I desperately did not want to have to ask my parents for financial help for the first time in several years, when it finally got to the point where I needed to, I knew that I could. I know that, if I didn’t have that cushion in the back of my mind, I maybe wouldn’t have taken the risk of working with a “startup” in the first place. I was lucky that I was quickly able to get back on my feet, financially, and build up the professional confidence I’d lost in the whole process.

I still don’t think making the mistake of working with this company — if we can even call it that — is one of those necessary growing pains that I needed to go through in order to become a self-actualized adult. And god knows, I have so much more to say about it. But it happened, and at least I know a few warning signs now. I know when my time isn’t being valued, and I know when to walk away. And, most importantly, I know you don’t owe anyone your loyalty just because they bought you lunch a few times.

Holly is the Managing Editor of The Financial Diet. Follow her on Twitter here, or send her your ideas at!

Image via Unsplash

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