From A To Z: A Short History Of My Professional Successes And Failures

I was supposed to be a journalist.

That’s what I told everyone I wanted to be.

Or a television producer. I wanted to be one of those, too.

And I did everything millennials were instructed to do, in the name of attaining the American Dream and Everlasting Happiness. I went to college. I got my degree. I even landed some stellar internships at major networks. I thought I’d be good to go when I left school, and entered the real world with student loan debt — bright-eyed, bushy-tailed, and ready to Have It All.

Me at 20, ready to take on the world.

And… as we all know, all of us out here in the real world, anyhow, we all know that life’s not that simple. Wishes don’t come true with the wave of a magic wand. Dream jobs exist, but in tiny quantities, and with hundreds, if not thousands of highly-qualified applicants to compete against.

I’ve had a few successes. I’ve made even more missteps. And overall, I, like everyone else playing the Game Of Life, have rolled the dice on my chances to win big. And mostly, I’ve come up empty-handed.

This missive isn’t meant as a pity party. It’s a factual, objective observation of how I went from Point A (on my timeline, me at 17, a highly ambitious writer assured of future success) to Point Z (me at 30, right now, freelancing, and trying to figure out What Will I Be Doing Next?)

If my life were a museum, I’d be carbon-dating my ambitions and dreams, trying to understand where the fossilized remains once stood in the natural landscape of my mind, and how, if it’s even possible, to put them back together again.

I can understand my obvious mistakes. That time I worked in IT? Success was highly unlikely, especially since my one year of Apple Store retail experience didn’t extend to particulars such as “server administrator” and “network troubleshooter”. (I’m super glad I no longer do this for a living.)

Other mistakes, however, retroactively appeared. Hindsight is 20/20, after all. The IT job exposed me to startup culture, and I decided I wanted in.

And startups? They’re the bad boys of the professional world. Like James Dean, they’re mysterious, sexy, bold, and risky to hang out with. Just like last week’s Tinder date ghosted you, startups will chew you up and spit you out faster than you can say “Like AirBnb, but for dogs.”

But startups are brutal, punishing environments. So many pixels have been spilled in the name of extolling their virtues (Flat hierarchy! Free beer!) and their multitude of drawbacks (Long hours! Beer belly!)

And I haven’t even mentioned the numerous incidents of sexual harassment that I, like so many other women in technology or venture capital firms, experience on a near-daily basis. And I wasn’t even a developer–imagine that!

Behind and beyond this, there are additional insidious factors at play when you work for a startup — and I’d imagine that to be the case for any other similarly-demanding industry, such as finance. And when I say insidious, I’m alluding to the B-word.

You know. Burnout.

The unspoken requirement for 24/7/365 availability is, for me at least, one of the most anxiety-provoking aspects of working for a startup. Your overflowing Gmail inbox is supplemented by constant pings on Slack, or text messages when coworkers think you’re not responding quickly enough to email or Slack.

It creates a feeling in which the time I take to make dinner for my partner and I, or catch a movie on the weekend, or try to take care of General Life Stuff is wrong, and bad, and I should be ready to respond to coworkers’ requests every single second of every day.

Now, this isn’t meant to be confused with emergencies. The kind of emergencies in which something is totally broken, and you’re the only one who can fix it. By all means, at that point, email me, any time of day, anywhere in the world I might be. Heck, you can call me if it’s a real, true emergency.

But for small requests, inane requests, to call me on my cell when I’m walking to the subway in the freezing cold night of a New York winter, and forcing me to duck into the vestibule of Whole Foods to have a 45 minute discussion, and thereby delaying my ability to get home for over an hour, is extreme.

It’s extreme when a coworker expects me to respond to a similarly low-priority request while I’m trying to have brunch on Mother’s Day with my family. Or when I’m in transit, on a highway, with limited access to Internet and my laptop.

It’s extreme when my C-suite boss sets the example of working 24/7/365, even though she works from home, in a different country, to boot, and the rest of my team exist on the East Coast, in a difficult-to-reach co-working space in Midtown. But no matter, we’re expected to show up and work, and work, and work until every single item on our to-do lists are completed for the day, even if we’re ahead of deadlines.

It’s extreme when this same manager expressed the feeling that my quarterly goals were “bullshit”, despite only having joined the company with three weeks left in said quarter. Of course my quarterly goals were going to be modest. How much growth can anyone expect in under a month?

It’s extreme when the startup founder you work for is legion in his methods of taking advantage of every single person he hired. This came primarily in the form of missing payroll for months on end, forcing us, his employees, to continue coming into the office while not being able to pay basic living expenses. But we still had projects, and deadlines, and the pressure to grow the company while not being able to feed ourselves.

I basically went bankrupt by the time I was able to find another job which enabled me to leave.
Me at 27, at work, nearly bankrupt.

It’s extreme when you learn this founder was charged with rape in the mid-1990s, and games his Google search results to push down newspaper articles of the incident. (He also games his Glassdoor reviews with glowing, fake reviews, to hide the nightmarish reality confronting every employee he manages to con into working for him.) It’s extremely indicative of how far this guy would go to get what he wanted — by not only draining the life out of everyone around him, but by projecting a false exterior vision of himself to the world at large.

It’s extreme when coworkers, at every job I’ve ever had, stay at the office late into the evening hours, for no apparent reason. What am I supposed to do, when I’ve completed as much work for the day as I could, when there’s a partner and a cat at home, waiting to make dinner with me, and to be fed? Should I stay for the hell of it, too?

Because everyone has these things at home too, in different quantities, both people and animals. Why are they still in the office so late at night? How can people work for 10 to 12 hours, every single day?

What job is so important, outside of actually saving real people’s lives, that it requires such an insane commitment?

I find all of this, all of my experience, to be completely exhausting. It’s almost traumatizing, to the point of my current hesitancy to return to an office setting. And maybe this is where I’m wrong, and why I’ve failed at working for startups.

Maybe this — the requirement for constant availability, long hours, horrible managers — is part and parcel of participating in the corporate world. Maybe This Is What It’s Like To Have A Job, and I just need to suck it up, and get with the program?

It doesn’t seem like much to ask — to be able to go home at night, and on the weekend, and not be constantly pinged by coworkers who apparently have nothing better to do with their free time than impinge on mine. How is this normal? Because it shouldn’t be.

But, am I wrong? Can someone tell me what they think? What has your experience been in the workforce? Is it overwhelming? Or do you find it balanced?

Is this the new world order?

Or have I been living in reality distortion fields for far, far too long?