6 Things A Freelancer Doesn’t Miss About Startups

Lol have fun at All-Hands.

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Photo by Nicole Honeywill on Unsplash

Last summer, for a variety of reasons not all awesome, I became a full time freelance writer after working for roughly a decade in startup environments. Naturally there was a level of fear that set in, knowing full well how difficult it is to actually get people to pay invoices and that for some reason it’s always been super easy for me to negotiate salaries but somehow hourly rates which are actually saving a company the need for an expensive full time hire are a trick or two to get a yes on. Anyway.

Im roughly a year into this new take on earning a living and amid all the change, one of the things I take joy in noticing is everything that’s missing. The things I used to deal with as part of the literal cost of doing business. I thought they were table stakes, entirely normal things that, while annoying, can’t be avoided as part of our unfortunate need to pay rent once a month. As a freelancer, there are certainly things to deal with that I’d prefer to toss into a candle flame, but I thought it might be fun to reflect on those startuppy bits that aren’t a part of my life anymore, to see what I’ve learned. Spoiler: I’ll never miss ’em.

  1. Leaving the house. There are so many gloriously sweet freedoms about becoming a work-from-home freelancer, but I think not having to deal with any of you is one of them. There are days when the weather is foul, or just the notion of smiling and saying good morning to others is foul, that I bask in the bliss of never needing to cross my own threshold unless I want to. I can’t even fathom what it would take at this point to convince me to purchase an unlimited monthly subway pass. Maybe there’s one client out there who will push me over the invoice edge and back to the land of the commuting masses, but we haven’t met yet.
  2. Rolling up my sleeves. This phrase is a very clever way startup C-suites shame people into doing tasks they have no skillset for. The overall startup mindset that everyone’s supposed to “wear many hats” is just cleverspeak for: we don’t 100% know what your role is or what we need exactly so we’re just going to give you whatever tasks happen to pop up that we haven’t yet hired someone for. And that’s cool right, because you’re working at a cool startup where the culture is very “roll up your sleeves?” Because if it’s not cool you’re going to come across as lazy and having a bad attitude, just FYI. Also, that thing we asked you to do that you have no experience or interest in, you’d better be amazing at it, thanks.
  3. Super unnecessary perks. Is a keg full of rosé cool? Yes. Should it ever be trotted out as a reason to give a company 40–60 hours of your time every week? Absolutely not. I’m not much of a bells and whistles gal, never have been. I guess you could all me a purist, focusing primarily on benefits that are vital to my wellbeing like healthcare and a 401K plan. In my experience, I’ve seen direct correlation between the number of bullshit perks lying around and volume of actual bullshit I have to put up with while working there. The nap pod is awesome, but do I get dental?
  4. Appearances. I’m not a big fan of other people giving a shit about how many hours they physically see my ass sitting in a chair. No matter what that ass is doing, they want it in a chair, in an open floor plan, during the hours they are also there, and still there when they leave and before they arrive. Eyes on me apparently matters more than my work product, and eff that. Appearances do not mean anything to a person who enjoys starting her workday at sunrise and ending it while there’s still enough time to take the subway home without getting nervous. I care about doing actual work, at a time of day of my choosing, and I really don’t have patience left for what people think of how late I stay at an office I arrived to by 8AM and answered emails for beginning at six. I now work when I want to work, during the hours I want to work, I deliver excellent work product on time, my time, and your full-time job could never.
  5. Meetings: It hurt you just reading the word “meetings,” didn’t it? Because you know. Startups love meetings. Constant meetings. Meetings upon meetings in cleverly named conference rooms with glass walls that people outside the meeting stare into like we’re operating in some kind of fishbowl society. You’re probably reading this in a meeting right now and you’re not going to pay attention until someone says “thoughts?” and then you’ll be in a bit of a pickle unless you say, “what’s the ROI here” and then you’ll sound forward-thinking and smart and it will be fine. I don’t have meetings anymore. A conference call now and again, sure—but I only look great from the belly button-up and they take far less time than meetings because there will inevitably be some technical glitch that’ll convince us all we could just email about this offline. Which is a weird way to describe something inherently online but whatever. Meetings are fake, you know meetings are fake, so just walk up to someone’s desk and talk through something with them real quick because that’s how shit actually gets done and you know it. Stop with the meetings, I’m at work, not a one-act play.
  6. Hierarchy: If being a freelancer has taught me one thing, it’s this: We’re even. We are all even. We are all operating at the same level, because we’re alive human beings who all matter equally. Work is an exchange. Someone does work, someone else pays them what that work is worth. Any belittling of the worker by the boss or required groveling or culture of constantly needing to impress is, to be quite frank, sewage. To think of the years I spent allowing myself to feel so small around my bosses, like a piece of gravel in a poorly maintained driveway, being rolled over by an ego with four-wheel drive. In work, in life, things are an exchange. I am doing work for you, and you are compensating me for that work. If we are both doing things right, neither of us should feel let down by or beholden to the other. We shouldn’t ever put each other in ranks of importance. We should be, at all stages of our careers, equally important to each other. And in startup environments, I never felt that way. So I’m not there anymore. Put that in your invoice and pay it.

I like to think that the workplace is an ever-evolving thing. We’re certainly not sitting on giant balls anymore, are we? Maybe one day I’ll go back to a life in an office with a real desk and free temperature control. And when I do, I hope all of the things I lived with for so long and never really should have are washed away and replaced with workplaces that inspire and uplift all of us to do genuinely amazing work. And if for some reason they never do, if you need me, I’ll be at home.

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NPR once called me a humor essayist, let’s go with that. Host of A Single Serving Podcast. shanisilver[at]gmail

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