Top 5 freelance Halloween costumes

Oct 28, 2014

Halloween is just around the corner… and that means turning our attention to the grotesque, the stomach-turning, the terrifying. It’s a holiday that asks us to examine and magnify our worst fears – making a mockery out of our demons in order to exorcise them.

With that semi-serious introduction in mind, here is my definitely not-serious list of the best / worst ideas for freelancer Halloween costumes. These are all unspeakably punny and lame, of course, but it is my experience that the most eye-rolling-inducing, lamest costumes are the hits of any given party.

Don’t go as a sexy fireman, or a sexy rag doll, or a sexy Bazooka Joe Bubblegum wrapper. That’s so predictable and boring! Go as your worst freelance fear, and make BFFs with all the other freelance nerds instead!

1. The To-Do List

Wrap yourself in reams of paper covered with minor tasks and blank check boxes. Keep wrapping yourself until you are smothered entirely and fall unconscious, twitching, under the weight of your undone tasks. When you are finally dragged out from under it, remember that you forgot to brush your teeth and the cat hasn’t eaten in three days.

2. The Check that’s In the Mail

Loudly announce that this will be your costume. Never show up to the party.

3. The Tax Collector

Get a suit and a calculator. Prowl around your host’s house with a checklist and a clipboard. Write down everything that seems to be an invalid deduction for a home office.

Bonus points if you “collect” 30% of everyone’s drink.

4. The Freelance Stereotype

Show up pale and unwashed, in pajamas. Tell everyone you woke up at noon. Twitch when forced to make eye contact. Complain about how your grandma never sends you big checks anymore. Scrounge in the couch cushions for loose change.

5. Terrible Client Edits

Bring along a friend. Give everyone at the party vague, un-fulfillable notes on their costumes; for instance, ask them to make their vampire scarier, but not too scary – more like an EEK scary than an AAAH scary, and could their pointy teeth be a different shade of white? Just, like – a whiter white.

Then get your friend to give the exact opposite feedback.

Tell them that you expect the new draft of their costume to you by 5 PM tomorrow.

What’s your Halloween costume, fellow freelancers? Minus -150 points if you say “sexy witch”, or the like.