• Advice, Lifestyle

10 reasons why freelancing is like dating

When you think about it, dating is the “freelancing” of romance. It’s for people who are looking for variety, who either don’t really want to settle down yet – or who are still looking for that perfect fit. Check out our ten similarities below… and how the eerie parallels inform both!

1. Playing the field is fun, but exhausting

You entrepreneurial Don Juan, you.

When you’re working as a freelancer, some part of you is always on the lookout for a better gig. With each new contact, comes new potential… and new negotiation about expectations. It can be exciting to jump from prospect to prospect – but it’s also remarkably time-consuming and enervating. Unseen surprises are waiting to surface with every client: sometimes good, sometimes hair-raisingly bad.

2. You shouldn’t commit until they do

Nothing is more bewitching than the first flush of romance. But don’t throw out that little black book on a whim – give it a little bit of time first.

It can be tempting to block out big chunks of your calendar for every prospective client; to start building freelance castles in the air and adding wildly optimistic figures to your budget. But every seasoned freelancer has horror stories of dream clients that promised the moon – and then suddenly disappeared. Don’t fully commit yourself until you know it’s the real deal… and that means a signed contract.

3. You’ll find a lot of mismatches and false starts

The description of the gig looked great. You sent in your resume and a few samples – and they replied enthusiastically, with one little catch: right now, they’re not actually, uh, offering pay? But it’s great exposure!

Back to the drawing board, freelance friend. You’ll find the One someday.

4. When it’s a great fit, you’ll know

Sometimes, it just seems like destiny.

The clients who give you interesting, engaging work; who want to develop long-term relationships with you; who pay well (and on time) – eventually, you’ll find them. And when you do, you’ll want to lock those suckers down… because true freelance love is hard to find.

5. Nothing is ever set in stone

So you recently found that Perfect Client. You’ve only been working together a little while, but everything seems to be running smoothly! Time to sit back on your laurels and start picking out wallpaper for your new office!

Unfortunately, even if you feel like you’re ready to put a freelance ring on it, given circumstances can change quickly. Projects lose funding, departments re-organize, supervisors want to switch directions. This isn’t to say that you should never, ever relax; it is an argument for valuing what you have in the moment, and for checking in with that client often… making sure your relationship stays strong. Perhaps you can even discuss what the future may hold, and ensure you’re on the same page?

Also, even though you’re excited – keep that resume and portfolio up-to-date; that’s the dating equivalent of continuing to develop as an individual, whether or not you’re in a new relationship. The happier and more stable you are, the happier your client will be – and you won’t be left desperate and flailing even if you have to part ways.

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6. You should be very wary of Too Good to Be True

Are they offering you twice your usual rate, while working flexibly? Do they promise the work will be easy and effortless? Do they insist that you don’t really need a written agreement, because it will all just run soooo smoothly?

And while they’re at it, hey, could they just get your bank account information?

Be careful of new clients who seem too good to be true, especially if they’ve popped up out of the blue and try to sweep you off your feet. You may just be dealing with a con artist – the professional equivalent of the compulsive liar with two families on opposite ends of town. Get any terms in writing, and proceed cautiously.

7. You shouldn’t make promises you can’t keep

You, dear freelancer, are just as capable of breaking hearts and frustrating expectations as your clients are.

Don’t make commitments you can’t keep; you don’t do anyone a favor when you miss deadlines or do slipshod work. Know thyself, and don’t string clients along with overly optimistic promises about your availability or productivity.

It’s normal to encounter little challenges, or realize that you want to choose a different path; just make sure you openly communicate your needs as they change. Deal with others fairly – because you want to be treated fairly yourself.

8. Sometimes people will just disappear

That interview seemed to go so well! They laughed at all your jokes! They ooh-ed and aah-ed over your portfolio! You even hugged at the end!


Endlessly obsessing about the Client that Got Away is an exercise in self-abasement. If you really thought that you missed a connection, you may send one – yes, ONE – friendly little query after a meeting with said client. The ball is thereafter in their court; if they never contact you again, chalk it up to fate and move on. Pint of consolatory ice cream is optional.

9. Loving yourself is the most important thing

The most obliging clients and best gigs in the world won’t make you happy if you don’t fundamentally enjoy what you do – if it doesn’t give you fulfillment. Do you like your work – and, just as importantly, do you enjoy most of the process of working? Keep relentlessly pursuing what you want and growing, and eventually those perfect gigs will fall into place. When you least expect it, the perfect opportunity will come to you – and you’ll be ready for it.


Life is too short to waste much time. Frittering away precious years with people you’re lukewarm about, doing the things that you hate is a great to become old before your time. That’s how bitter, jaded, depressed misanthrope are made.

You don’t do anyone favors by settling for them – whether they’re romantic prospects that you’re “meh” about or clients that you’re doing half-hearted work for. Giving up does everyone a disservice… yourself most of all. If you find yourself unhappy, unsatisfied, and uninspired, take an honest look at yourself and then your surroundings. Is it time to find something that challenges you to grow, that makes you really happy and strong, that builds you up instead of breaks you down?

Don’t ever settle. Shoot for the goal that makes you the best person you can be. And if your current situation doesn’t have the potential to realize your dreams… well, there are plenty of freelance fish in the sea!

What do you think, fellow freelancers? Is freelancing more like marriage, or child-rearing, or deep-sea fishing? Leave it in the comments…

Kate Hamill lives and works in New York City, where she consumes an inordinate amount of Sriracha daily. You can catch up with her on Twitter at @katerone.