6 Things A Freelancer Doesn’t Miss About Startups

Shani Silver
6 min readAug 30, 2019

Lol have fun at All-Hands.

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.

I’m 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…