• Advice

Confessions of a sometimes terrible freelancer

There are lots of fantastic perks to being a freelancer. Making your own schedule! Being your own boss! Forging your own path!

The downside, of course, is that you don’t have anyone else to blame when the structure of your business isn’t thriving. You figure out what your weaknesses are pretty quickly – because you smack into them over and over again.

A friend of mine who works as a freelance designer is a Champion Procrastinator. The deadline will come closer, and closer, and closer – and until the last minute, all that will get done is her dishes. “On the upside, my house is very clean,” she said, “on the downside, I do a lot of work at 3 AM while panicking.”

Another friend, who works as a freelancer in the film industry is terrible at talking on the phone – so he’ll put off important phone calls for days, even weeks. Fortunately, the majority of his business is done by email, but the very sound of a ring tone makes him fill with dread.

And my secret freelance shame? The thing I am truly sub-par at?

Invoicing on time.

Just thinking off the top of my head, I have eight – EIGHT – invoices overdue. I just have to do them, and send them to my clients, who are all good at paying me on time. I just have to take a few minutes and finish them! It’s the simplest thing in the world!

And yet, I have not done them.

I’m blushing even writing this.

The only nice thing about this extremely shameful bad habit is that it serves like a sort of de-facto budget tool; I certainly can’t spend the money that I don’t have yet.

It’s the world’s stupidest, least efficient savings plan!

I don’t know any freelancer who doesn’t, at some point, find themselves in a less-than-ideal situation because they’ve run into their own professional or personal weaknesses. And every single one of them finds their own weaknesses deeply embarrassing; it’s easy to feel completely alone in one’s singular ineptitude.

But what’s comforting about revealing one’s freelance weaknesses is that WE ALL HAVE THEM – and we’re all mortified. An informal survey of Secret Freelance Shames amongst my friends reveals some common themes: procrastination, difficulty setting rates, difficulty promoting oneself, workaholism, laziness, ambivalence about clients.

If we can reveal our Secret Freelance Shames and accept that none of us are completely self-realized – that freelancing, like anything else, is about trying to do one’s fallible best – perhaps we can start actually addressing the issues behind them. Do you procrastinate because you fear doing imperfect work? Do you hate the phone because you feel uncertain of how to present yourself? Do you delay submitting invoices because you hate asking people for things – even payment (ahem)?

Admitting one’s problem is the first step, they say, to getting help.

Hello, my name is Kate Hamill, and I have a problem with invoices.

What’s your Secret Freelance Shame?

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