10 ways that freelancing is like online dating

by Debbie Elkind
03 July 2015

Today’s blog post is written by journalist, copywriter and List member Debbie Elkind.

From painstakingly crafting that perfect pitch to the high of anticipating a first meeting – followed by crashing disappointment when your dream-partner-on-paper turns out to be a narcissistic control freak sans dress sense – there are some definite parallels between freelancing and looking for love online.

1. You have to constantly sell yourself Neither endeavour favours the modest wee wallflower. You have to be able to beat your own drum, both in print and in person, in a way that is simultaneously charming and confident, without being cocky, over-bearing, or needy. While it’s sweet to think that they’ll see past your amateurish website or pixelated photos to the brilliant wordsmith/inner beauty within, the reality is you’re swimming in a sea of contenders, so you need a savvy marketing approach.

2. You need to stand out in a crowded marketplace Being memorable becomes more important when it’s likely that whomever you’re trying to woo has plenty of other appealing prospects. Sometimes it pays to check out the competition and make sure that you look at least as appealing. Having said that, it’s still wise to…

3. Be honest about what you have to offer It’s a mystery why so many Internet daters lie about their age/weight/height and use ancient pictures – when meanwhile their weight gain has been in inverse proportion to their hair loss. After all, do you really want your potential soul mate’s first impression of you to be one of sinking disappointment when reality doesn’t match fantasy? Likewise, extravagant false claims made about your professional experience are likely to become painfully apparent during that first new client face-to-face. It’s always better to exceed expectations.

4. If you’re not in it, you can’t win it You can’t complain bitterly about not meeting Mr or Ms Right (or even Right Now) if you’re making zero effort – they’re not going to abseil into your living room. Nor is your dream client or editor going to magically commission you if you’re not getting (politely but persistently) up in their face. Or, as a wise fellow freelancer friend puts it: Pitch Don’t Bitch. There have been times I’ve had to repeat this mantra to myself daily but when you actually act on it, it never fails.

5. Don’t give it all up at once It may seem clever to hit up that editor with all 12 of your best ideas at once, but what are you going to follow up with when they say, ‘Great, what else have you got?’ As for the dating analogy here, it’s the decision you wind up regretting 9 times out of 10, as you stumble home with your best intentions balled up in your pocket and a miniature troupe of elephants stampeding through your cranium.

6. It pays to be brave and take risks The biggest problem with online dating is that sometimes people can look so perfect on paper but in person the chemistry is less than non-existent. Conversely, it’s easy to over-look someone who doesn’t tick all your boxes but keeps you up all night laughing. Life is best when you’re taking some risks – be it taking a punt on that intriguing person who is ‘so not your type’ or boldly sending off that pitch to the magazine/website/publisher you think you don’t stand a chance with.

7. They will snoogle you It’s astonishing – and creepy – just how much you can learn, and how quickly, about someone you’ve never met with just a tiny bit of clever snoopy googling. Anyone who says they have never done this before a date is either lying or not terribly resourceful. And whether it’s a prospective date or client doing the snooping, pictures of you wasted doing laybacks in a strip club probably isn’t the look you should be going for.

8. Don’t ignore the red flags If a client treats you badly, takes forever to pay, or consistently makes unreasonable demands, you can be sure that this situation is unlikely to improve over time. To think otherwise is a bit like being surprised that your partner who has cheated on you multiple times just did it again. In both cases, the only sane answer is pack up your bags and get the hell out of dodge. Trust me, there are far better things on your horizon and staying with Those Who Suck leaves you no freedom to find them.

9. Don’t be desperate Just as the dating can smell desperation – and it doesn’t smell pretty – I often feel like freelancing is some sort of psychic popularity contest. As in, either giant tumbleweeds are rolling through my apartment or the moment a big job comes in every client I’ve worked with in the past year suddenly needs something (everything) yesterday. The more elusive/expensive/unavailable you are, the more they want you.

10. Be persistent Just as online dating can be a deeply soul-destroying, dispiriting process, so freelancing will suck you up and spit you out some days. But years of experience with both have taught me that when that seemingly golden project or partner vanishes inexplicably there’s no great need to despair. Because the beauty of both is that your Next Big Love might ping into your in-box tomorrow.

Can you relate? We’d love to hear from you in the comments!

Photo by Aleksandra Mazur, Unsplash
Debbie Elkind

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