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Why the successful freelancer in the wild has to have a great sense of humour

Kara CoppleBy Kara CoppleSeptember 12, 2014Updated:October 22, 2025No Comments3 Mins Read
Why the successful freelancer in the wild has to have a great sense of humour

The successful freelancer in the wild has to have a great sense of humour, it’s a simple necessity if you want survive. See, as a freelancer you’re going to find yourself in some pretty ridiculous situations from time to time, even more so if you’re a freelance writer as the people who tend to hire freelance writers are often a bit… “Unique” and some of the requests they make can be just as “unique”

Funny story, I once had a client who claimed he was a “private investigator” he was a walking example of each and every detective cliché you can picture. Paid cash regardless of the amount, insisted on meeting in public places. His car was all black (even the windows had been tinted) and of cause, he used an autodialer to “signal contact” (what the hell is wrong with skype or a good old fashioned VPN?!).

I honestly woke up some days feeling like I had wondered into some kind of Ray Chandler novel. I was just waiting for the blond to wonder into my favorite coffee house and for no reason ask me to find her missing brother. Looking back, in all likelihood it was far more likely some nice policemen would turn up instead and ask about my “dealings” with the “investigator”…

SO, in order to help hapless new freelancer avoid the same fate, here’s a few tips on freelancing for possible evil company spooks (or special people)

  1. Get the money upfront. This is the biggest point as special people/investigators have a tendency to wander off after a while. The guy I knew dropped off the face of the earth after a few months, but I’d been paid so I was left to simply wonder if he ever got his hands on that German Passport…
  2. If you must meet face to face, do so in daylight and in a very open and very public place (somewhere like KFC or McDonalds)
  3. Be prepared for their ideas. Most will be insane to point of culture shock, but they may have one diamond in the so very, very rough. That said – in the case of the “investigator” his idea’s seemed a lot more sane once he started counting the money… strange that.
  4. When they come offering that “big score” it’s time to move on. Special people are forever after that big, quick score – and unless they’ve founded a start-up that’s gone viral it’s time to move on.

To summarise: keep your wits about you, use common sense and if they seem too good (strange/ and or different) to be true, chances are it’s a special person. Now they may have the money, but can you pay for that in a crazy tax.

Can you afford the crazy tax?

Freelance advice freelancers working from home
Kara Copple

An experienced business and finance writer, sometimes moonlighting as a fiction writer and blogger.

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