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Why Freelancing is like Polyamorous Dating (How to Freelance: Part 2)


Yesterday, we covered steps 1-4 of how to freelance. Today, we’re getting to a post dedicated to Step 5: Clients. Seriously, go read part 1 first if you haven’t yet. I’ll probably combine these into a single blog post at some point, but yeah, go read that first.


CLIENTS: Like Dating, But Easier (since there’s contracts) Client management is like a polyamorous dating relationship: sure, you can have several partners, but you still gotta pick them well.

Would you enter into a 6 month relationship with any person off the street who offered? I sincerely hope not. You’d want to know the person was sane. Pleasant to be around. Able to support themselves. Emotionally stable. Communicative. All good things to have.

Clients are real, live people. They are not robots that write you checks. (If they were robots, they would probably pay you a lot faster.) They come with their own quirks, expectations, and personalities. Some are incredible people that you want to be best friends with. Some have unrealistic expectations and turn to verbal abuse when they’re not happy. So, pick well.

But what should you look for? The baseline:


The Perfect Client…

  1. Knows what they want.
  2. Has money to pay you.
  3. Isn’t a dick.

In order to have a happy working relationship, you need at least 2 of the 3.

I can deal with someone who doesn’t know what they want, as long as they can pay me and are a nice person. I can do work for a bit less, as long the project is straightforward and the client is nice. And I can work with a more difficult personality, as long as they know what they want and can pay.

So before we even get into how to find a client, remember that this is a service business. You are dealing with people, not products. Yes, you have to be competent, but making a client happy, fairly or unfairly, is the real gauge of success here.

1) Knows what they want.

Do they say things like, “We fired the last designer because they just couldn’t get it exactly how we wanted it”? Do they make you write 20 million proposals and string you along? Do they constantly ask for more free work and ideas before getting started? Do they actually know what “minimum viable product” means?

2) Has money to pay you.

Do they preface everything with, “I have a budget of $200”? When you tell them your hourly, do they try to buy a half hour? Do they promise to pay you later? Is the check always “in the mail”? Do they hassle you endlessly on tiny details, trying to get you to go down in price? Do they try to pitch unpaid work as being “good for the exposure and your portfolio”? (Sorry, that only works in media.) Are they about to go out of business? Did their last developer/designer quit for unknown reasons (probably because they never paid them)?

3) Not a dick.

Well, I hope you can figure this one out for yourself. But a few specific things: do they respect your professional opinion? Are they condescending? For designers: are they constantly complaining that it needs something “extra” without being able to voice what that is? (They’re allowed to do this once or twice, but if it’s constant, good luck.)

So, here’s my advice: have a phone call or Skype chat. See if what they say raises the red flags above. If they do, proceed with caution or don’t proceed at all.

If you’re thinking of embarking on a large, long-term project with a client, test the waters first. Make sure they pay a deposit. Try working on a smaller piece of the project together (that they agree to pay for), to get a sense of their working style.

It’s a relationship. You want to build a good one.


Clients can literally be anyone. I’m currently making a website for an author that I met 2 years ago at a random party. Another is a referral from a college friend. Another is a referral from an old client. I work 2 days a week at an agency, which an existing client put me in touch with.

I started off in college. I started telling friends I was a web designer, and would attend startup events and introduce myself as a freelance designer. That’s how I got my first few projects, which then spawned referrals, etc. It wasn’t extraordinarily systematic, but it worked. It helps state what you confidently, as a statement: “I am a freelance designer.” Do not say, “I wish I were a freelance designer.” Or, “I’m trying to be a freelance designer.” You are. Be.

You can find clients online as well, but the lowest hanging fruit will be personal connections. Avoid sites like Elance or 99designs. You’re competing against people willing to work for peanuts. In the case of 99designs, you’re doing work on spec (not guaranteed payment). That violates Rule #1 of the 3 Rules for money. Skip the headache, unless you just want to practice. For developer jobs, I asked my freelance developer/startup founder friend Ian for advice:

i got initial gigs because i’d been building my own product so i had something cool out in the world to point to. i think this is the single best way to get clients. have something that you – not you and a giant team of people, you – conceived of and built. when people see it (provided it looks good and works) they’ll want to hire you.

at the beginning of every month someone will make a  SEEKING FREELANCER / SEEKING WORK post on hacker news. look for these and add a brief comment with your background and skill set. if you write clearly and concisely and hit the buzz words people will seek you out. I get anywhere from 3 to 10 leads from each of these. most are gigs i don’t end up taking, but the ones i have taken have been great clients. i would avoid any general freelancing sites (like elance) because the clients there will be pretty low quality. you work at a pretty high visibility startup so you shouldn’t have a problem. other than using hacker news, let some people in your tech network know that you’re available. people are constantly being asked “know any good developers?” – so, you can become an answer to that question.

So let’s recap:

  1. Let your friends, family, coworkers, and random people you run into know what you do for a living.
  2. State what you do confidently. It’s extremely helpful to have something online you can point to. (You don’t even need a portfolio at this point, honestly. I didn’t have one for 3 months when I started, during which I signed up 5 clients.)
  3. Do some self-promotion in online communities, only when relevant. Make sure your work is visible online, and don’t be shy about putting it out in front of others. Link to your portfolio or projects on social networks, including Facebook and Twitter.

It doesn’t sound so hard. And really, it isn’t – things like client management and pricing were bigger sources of angst than finding clients. Finally, here’s my final insight: good-bad

A boring project with a good client beats an interesting project with a bad client. A bad client – one who refuses to pay you, insults you, haggles you on price endlessly, and doesn’t respect your professional opinion – makes your job not worth doing. A bad client fails to meet at least 2 of the “perfect client” attributes. Don’t take these jobs, no matter how cool they sound. You will be miserable, and worse, you might not even get paid.

Next up: Step 6, Don’t Get Screwed.


One Response to “Why Freelancing is like Polyamorous Dating (How to Freelance: Part 2)”

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Lana Lingbo Li

I'm a world traveler / enthusiastic eater who's now blogging and producing videos over at HelloLana.com. Visit me there!

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