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  • Jenny Stallard

5 key ways that freelancing is like dating

Updated: Nov 17, 2022

The things I love about freelancing include the bylines-a-plenty in so many places, and never having to ask if my holiday dates clash with anyone else’s. I love being able to have coffee meetings that end up taking well over an hour, shopping in the daytime, watching daytime TV, or going to the gym for an hour and a half at lunch. There’s the joy of a new client or piece of work, the idea that I can choose to do some training without checking in with my boss or the training budget at work.

Then, there are the hate moments, where the chaos gets to me so much that I don’t know what to do first, and end up doing nothing and then berating myself. Searching for work and feeling unloved when I don’t get commissioned, or when my pitches fall on deaf ears. Scrolling through social media and feeling the weight of self-comparison like an anvil crushing down on my chest, telling myself that I’m not good enough, not achieving enough, not worthy of my freelance status.

Sometimes I compare Freelance Feels to other newsletters, sites and podcasts and think ‘what am I doing? Who wants to read this?!’. Then a comment or message comes in, or as happened recently, someone approaches me at an event to say how the podcast helped them through a bad spell, and I feel high as a kite again.

Dealing with all this alongside trying to run a business can be utterly exhausting. I have a real pride in being freelance, that I’ve made the leap and that I’m sticking with it. But I still feel, often, more ‘freelance fails’ than ‘freelance feels’.

My journey to freelancing today is a bit unusual — this is the third time I’ve been freelance. The first two times, I left jobs I wasn’t enjoying and struck out on my own. I was lured back into staff roles twice over the years. Then, in April 2017, I took redundancy from a job I really did like. Unlike the first times I went freelance, where it was 100% my choice, this time it was a case of going ‘back to freelancing’ which felt different. Getting dumped, rather than doing the dumping. There was less power in the decision; should I perhaps have handed my notice in sooner and given myself that power? Maybe. But it was a great job! And I did freelance on the side. I’d even written a book on the side. But there it was — ‘back’ to freelancing which felt a bit like something I’d experienced a lot, too. ‘Back’ to being single. Back to being self-sufficient in so many ways, to being in charge of all my own, well, everything.

Those first two times I went freelance, it’s like we were dating then I called it off and went into a relationship with someone else for a while. But freelancing kept texting. We had the odd coffee, and sometimes a drink. Sometimes we slept together. Ok, I admit it, I had one night stands with freelancing. I even cheated on one job with freelancing, when I wrote my book in my spare time. The job knew, but it was still that feeling that I couldn’t let freelancing go. Even though sometimes, just like all those ‘bad boys’ I dated, freelancing made me weep, stamp my feet and scream with despair.

So, how is freelancing like dating? Well, apart from the fact that we’re solo entities, single in a business world, there’s the idea that we need to be not just financially self-sufficient but emotionally, too. While we have friends to support us and tell us we’re great, we have to cheerlead ourselves. Here’s the other ways I think that being self-employed is a bit like being single…

We have to send ‘first messages’

Whether it’s a LinkedIn connection, an Instagram message, a cold email or even a cold call, we often have to send the first message. Just like on a dating app, we ponder over the wording (I’ve heard that ‘hope you’re well’ is now a no-no — but what else to say?!). When is it time to accept it’s a no before moving on to the next message? The first message counts so much and can be sent with so much hope and positive expectation, it’s really crushing to get no reply.

1: We have first dates

Coffees, breakfasts, lunches, desk side meetings… even the Zoom calls which are becoming a staple of working life. We have first dates all the time as freelancers. And just like first dates, they’re emotionally challenging — they can make us nervous, they can make us worry and they can make us wonder what the hell we’re doing there! Sometimes I’ll go to a ‘work first date’ and think ‘we should never have matched’ and other times I feel so glad I did as I find someone who’s on my work wavelength and I know I’ll build a friendship with. And we also go ‘speed dating’, AKA networking. It’s not for everyone and can be so nerve-wracking. I'll be writing more on the pros and cons of online networking soon!

2: We get ghosted.

Eurgh. The worst, right? Bad enough when you’re dating because it’s a total waste of time and an emotional kick in the balls. But when it’s taken in a freelance context, then there’s more at stake. Professional ghosting can lead to lost earnings, wasted time that could be spent elsewhere doing something that works for you rather than the client who is ghosting. Professional ghosting was something I talked about with my podcast guest Amy Nickell, where she also discussed the ‘pitching abyss’.

For me, professional ghosting can be when a client does a call out for people to come in-house and you email them, then they don’t come back to you — but you know they’re out there, because you can see them on social media. Or when you’ve pitched something, and had a maybe, then been asked for more info then they go quiet. You follow up, only to get an out of office. But there they are, on Instagram stories, mixing and mingling at a cocktail do. It’s hard because then you have the feelings of a ghostee, where you think ‘shall I message again? Do I look needy? I should just leave them, but, well, I know they’re not dead…’

Again, add this to having to do actual work and it’s pretty time consuming and exhausting.

But then, I admit, we ghost people too. Yes, I’ve been known to ignore someone when I want to. We all do it, of course we do. It’s hard to love freelancing when you’re in a ghosting rut. So what can you do? Well, just like when I was dating, I do always end up re-messaging those ghosters, ‘just in case’. I’m so stubborn that I will often say to myself ‘If it’s the last thing I do I’ll get a commission from them!’ and keep on messaging.

I’ve done this with men, too, trying to making things work so they eventually meet me for a drink. It feels like a bit of a triumph if they do, but in the long term, it’s never satisfying. The best thing you can do is put those ghosters where they belong — to the back of your mind. Don’t pitch to them. Let them float back to you, if they want to, and then when they do, you can make the decision about whether you want to meet up or not. You might just find that you’ve found a new client to hang out with that makes the ghoster suddenly seem, well, not quite so fanciable.

4: We sometimes settle down…

Yes, it can happen, and it carries (well, I think so, anyway) all the risk of a relationship. You have to trust that they’ll stick to their promises, and that they’ll stick around. There’s a commitment to not letting your head be turned again, and to working together towards a shared future. The thing about this is that you can obviously settle down with more than one client! Although that, too, can get complicated as you struggle to balance your loyalties and your time between them.

5: Benching and gaslighting

In the modern dating world there are so many different buzzwords; they are growing every day, and each one can be applied to how we interact with clients. Take Benching, where you’re put on the ‘subs bench’ for a bit. Ever had a call from a client you’ve not heard from but needs something ‘desperately’?! Or how about gaslighting, which is a serious dating problem, where someone’s sense of self-belief is undermined. There’s more on it here from Relate.

In freelancing terms, and in particular in my writing world, I think this can happen when a client gives you so many amends and edits that you begin to wonder if you have any talent at all. The edits come back again, and again, and even sometimes include questions about things you put in your original piece of work which then make you doubt if you were right in the first place or just couldn’t read what they wanted and when. Or they ignore loads of pitches then love one you send and need the copy within 24 hours. You’re left wondering if it’s just chance that you ‘got it right’ or good management…

The biggest thing about freelancing and the dating analogy is that we choose to be in it. Just like I did with dating, I have made a conscious effort to say I’ll put myself out there, have those ‘dates’, go to events, and keep hustling for a ‘match’. I’ll deal with the ghosting because it can lead to good things if I find the non-ghosters.

There is also a big lesson here, though. That we can choose to bench ourselves. To sit out for a while. Like when you delete Tinder off your phone, or think you’ll just go out for a night out and not see if you might meet someone — or even go travelling solo (very much recommended!) — there’s scope to take a step back from the freelancing merry-go-round.

Delete a social media app off your phone (or stop the notifications, at least). Have a break from networking events. Have a day off Instagram. You can stop pitching to those ghosters, even if just for a while. Have a look at your profile, rather than everybody else’s and see if it’s working for the kind of work you want to attract.

For more on Freelance Feels follow on Instagram @freelance_feels

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