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.

How to Freelance and Travel the World: Part 1

Several friends have asked me for advice on freelancing. Since I’ve been at this for two years (!), I thought it’d be fun and helpful to write up a blog post.

Remember Maslow’s hierarchy of needs from psychology class? I thought it was strangely appropriate to use it as inspiration for this post – except inverted. Because you gotta self-actualize first. Let’s start there.

I even made some graphics to go along with this post!



Actualization #1:

Whether you’re looking to do this full-time, or just make some money on the side, the most important step is defining what you want out of freelancing.

When I graduated from college, I wanted to travel, so I had two requirements: no full-time gigs, and I had to be able to work remotely. I said no to everything that didn’t fit that requirement (including job offers). One of my friends freelances to bootstrap his startup, so he limits his freelance work to 15 hours a week, working remotely.

Work backwards. Start at the end, then figure out how you’re going to get there. Start off with what you happy and successful means to you, no matter how mundane and obvious it sounds. Once you have that in hand, use that to filter for clients and make your constraints clear to them (“I can spend up to 15 hours a week on this project”).

Great. You’re already 20 steps ahead!

Actualization #2:

Clients don’t pay you for a website. They’re paying you to build something that will generate leads, market their product, or sell a service. It’s easy to get caught up in the nitty gritty of what you offer, but clients rarely care about technical intricacies – they care more that you deliver a product that achieves their goals.

In fact, if you’re worried about not being a “rockstar” developer/designer, here’s a dirty little secret: it doesn’t matter. Clients care equally, if not more, that you’re pleasant to work with, trustworthy, and deliver things when you say you will. Competence will get you very far.


When I talk to people about freelancing, their first concern is finding business. If you’re a designer and/or developer, particularly one living in a startup hub, the world is your oyster. Freelancing isn’t scary because you have to find clients, but because you have to chart your own path.

There aren’t performance reviews, bonuses, or promotions. There are no ladders to climb, and no benchmarks except your own. If your goal is to make $3k/month working 5 days a month, and you hit it – congratulations, you’ve been successful. Figuring out what’s next is up to you.

You need to be self-motivated and self-directed. That includes your social life. There isn’t the easy camaraderie and built-in social life of an office environment, and you’ll be working alone a lot. Plus, People Just Won’t Understand What the Hell You’re Doing. They’ll ask you, what’s next? a lot. Acquaintances won’t give you the respectful nod at cocktail parties that comes with names like “McKinsey” or “Google”. (Personally, I never enjoyed being judged by the institutions I was affiliated with.) If you’re the kind of person who craves social affirmation, this isn’t the right gig for you. You’ll get respect, too — it’ll just be a different kind, and from different people. And you’ll hear a lot of, “I wish I could do that,” to which you’ll reply, “You probably can.”

And it’ll be awesome. But sometimes clients will try to stiff you, or things will go pear-shaped. But things would go wrong in a traditional job, too – and besides, gotta fail forward.


Remember that time you waited an hour in line for a free Benny and Jerry’s ice cream cone? Yeah. Time to reevaluate.

As a freelancer, time – not money – is your most valuable resource. Let me elaborate.

MONEY: A salaried employee gets the same paycheck, regardless of how much they’ve actually done. If they take afternoon naps, they’re still getting paid. On the flip side, if they have to stay late and finish up a report, they’re not getting paid more.

As a freelancer, you won’t get paid if you aren’t working. But if you line up work and get it done efficiently, you can make multiples of what you would make in a salaried position.

TIME: Employees can’t just decide they’re going to work really hard for 2 months, take a month off, then come back. If they need Friday off to go to a best friend’s wedding, they need to ask permission first.

As a freelancer, you don’t need to ask anyone for permission. In fact, if you set your business up to serve your needs, you will only take on clients that respect your constraints (whether that be working remotely, responsiveness, or length of contract). Moreover, you can work really hard for 2 months then take a month off – if that’s what you want to do.

All of this has completely changed my view of the relationship between time and money. Waiting an hour in line for a free ice cream cone… a really dumb idea.


There’s a popular venn diagram in the service business that looks like this:


Here’s the trick to freelancing: forget about cheap. Don’t promise cheap. Cheap is a trap. It gets you cost-sensitive clients who view your work as a commodity. Price acts as a signal and a filter: I am worth this rate, and I will only work with people who are serious and respect my time. As demands on your time grow, your rate should go up accordingly.

Here are the other rules to freelancing:


Don’t work for free.*

Get money upfront.

Don’t compete on price.

(If you work for free, do it without strings attached, because you want to. Don’t do “I’ll do this for free now because they said they’ll have money in the future”. I have not heard of this working.)

Developers charge around $50-200 (most that I know run $100-150) per hour. Several I’ve talked to have day rates of $800-1000. I know fewer designers, but somewhere in the $30-100 range seems about standard. Start off with what feels comfortable, and experiment with raising your rates as you gain experience and build your portfolio.

Read Part 2: Why Freelancing is like Polyamorous Dating here.

A magical 2012: The recap

I went to a fortune teller last month. I was out for dinner with a friend, and we thought it’d be a hilarious exercise.

I paid $25 to have my palm read. She started telling me about myself – how I’d had my heart broken before, how I’d get what I wanted.

But I knew she wasn’t actually psychic when she said the past year had been difficult and painful for me. When she said there were too many jealous and negative people in my life.

She got some of the specifics correct – who hasn’t had their heart broken? – but really, the past year has been more incredible than I could have ever asked for or imagined, thanks to supportive friends, family, and clients. Here’s a few highlights from the 2012:


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My birthday (December 23rd), Christmas, and New Year’s were spent in Koh Phangan, Thailand at Full Moon Party. This involved 20-30,000 tourists on a beach, wearing day glo and drinking red bull and vodka out of buckets. I was with a group of people I’d met through Couchsurfing: a German tourist who’d just spent 10 days eating vegetarian food and meditating in total silence, a Malaysian girl who’d organized the whole thing, and Jared, a thoughtful Kiwi who I ended up traveling with for another few weeks afterwards.

Haad Rin, Koh Phangan’s beach party headquarters, was a charmingly charmless island enclave of drunken tourists. Christmas morning, I woke up at 8am and headed out to the water. The tide was so high that it had partially submerged a picnic table – where a group of girls were still dancing to house music as the sun rose.

The parties themselves involved a lot of fire. There were slides with fiery arches to bellyflop through, ropes soaked in gasoline and lit on fire to jump rope with, chains with lit torches to spin, giant signs written in fire. The crowd ranged from happy to obnoxious. On New Year’s Eve, I walked around with a pair of light up Minnie Mouse ears and eventually took them off because guys kept grabbing them.

What I learned: In Thailand, you are responsible for your own safety.




I was supposed to visit my friend Lena Chen in Singapore, but heavy rains flooded the Thailand/Malaysia border crossing. With no buses running through Haat Yai, I looked up flights – both expensive and sold out until the next week. That left so little time that I opted to nix the idea.

Jared was heading north to Cambodia, so I decided to tag along. We headed back to Bangkok, caught a scammy bus to the border, obtained our visas to the Kingdom of Cambodia, and found ourselves in Siem Reap.

Angkor Wat was wild and beautiful. We went to Battambung and Sihanoukville after that, then Kampot, a sleepy countryside town. One of my favorite days of the trip was buying picnic ingredients, renting a motorbike, and eating overlooking the misty vista from Bokor Mountain. After Kampot, Jared was headed home, and I continued on alone.

My first night in Phnom Penh, Cambodia’s capital, I met up with Couchsurfing folks and talked to a Chinese-Dutch expat who mentioned he was going to Burma next week.

“You can fly direct from Phnom Penh now,” he said.

“Yeah, but I don’t want to bother with going back to Bangkok and getting a visa.”

“Actually, if you fly on the government airline from here, you can get visa on arrival!”

This little bureaucratic detail seized my imagination. I had already purchased a Vietnam visa while I was in Cambodia, anticipating heading east for my next big move. Right then, I decided to launch into a surreal 3 week solo adventure.

I spent the next few days squaring away travel plans: withdrawing money from the bank and exchanging it for perfect, crisp $100 USD bills (the only legal tender in Burma), buying plane tickets, and having my online assistant make reservations.

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My last few days in Phnom Penh were made memorable by Simone, a gregarious Italian expat who showed me around and ate deep-fried tarantulas with me.

What I learned: Num Pang is Cambodia’s version of Banh Mi, and it is delicious. Many Cambodians make as little as 30 dollars a month, which depressed me and made me more aware of the ridiculousness of my job.


Burma was absolutely nuts. Looking through my photos, I’m filled with nostalgia and wanderlust.

My itinerary was Yangon, Mandalay, Hsipaw, Monywa, Kalaw, Bagan, Inle Lake, then Tuangoo. Since I spent the entire 3 weeks alone, I interacted with more locals (the perk of solo travel) and fell down more rabbit holes.

I’m not sure how to even recap that time. I guess there’s always photos…

IMG_9101 IMG_9087 IMG_9070 IMG_9273 IMG_9251 IMG_9219 IMG_9112 IMG_9094 IMG_9021 IMG_0041  IMG_9890 IMG_9844 IMG_8769 IMG_8557

It was all capped off by meeting a local on a 10 hour bus ride back to Yangon. Turned out he spoke Mandarin Chinese, and we ended up trading stories about our respective home countries. He invited me to visit his chicken farm, so I rented a taxi for the day and met his family and chickens. I hope he’s doing well.


I arrive back home! My skin is sun damaged and eczema-ravaged. I promptly get sick from eating yogurt in my parents’ fridge that’s been expired for year. And they say street food is dangerous.

I start working more. I visit my friend Nick in Buffalo, crash on Bostonians’ couches, and eventually decide to get a sublet in Boston for the summer.


I spent 2 weeks in Italy, where I eat my weight in gelato and buffalo mozzarella. I buy my first designer handbag at the Prada outlet in Tuscany, meet up with a college friend in Lake Como (where I also hitchhike for the first time), and finish it off in Bologna. In Bologna, I serendipitously meet a friendly Canadian girl and I watch the Eurocup soccer match at her boyfriend’s bar. More gelato.

My entire time in Italy, I keep thinking – what am I doing here? Sick of always moving around, I decide to rent an apartment in Boston.


A hundred person trip in Provincetown! I go for the second time with my good friend Evan, and cap it off with another amazing meal at the Beachcomber in Wellfeet.


I sign the lease for a 400 square foot studio in Boston’s Back Bay. I have ambitions of making a coffee table. (That never happened.)


My second Burning Man! I attend a Reddit meet up, hand out chapsticks, wear many wigs, and get very, very lost in the dust.

One of my fondest memories from this year is talking about design, technology, and emotions with Evan on burn night. I realize that my empathic, emotional nature is what makes me a good friend and designer. I learn to appreciate my positive qualities and focus on cultivating those. (Versus trying to always fix what’s “wrong”.) I leave Burning Man with lots of fuzzy, warm feelings and more aware of the positive effect I can have on others.


I move into my very first solo apartment! I promptly spend 3 weeks and waste countless hours agonizing over furniture decisions.


Chicago trip! I visit my high school friend Rachel, currently a math PhD at UChicago, along with college friend Spencer. It’s a restorative and really fun weekend.


After an unbroken string of good months in my freelance business, realize that maybe I should focus on higher-level goals. A work project – designing an iPad app for Puma – gets installed in New York and Japan. So weird to see something I designed out in the wild!

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Puerto Vallarta, Mexico with Rachel. My first vacation where I really let myself take a vacation. We sun ourselves, drink dirty monkeys (some magical blend of banana, Kahlua, and coconut), and take a taxi into town in the evenings. Things go so well that we decide to go on another trip together to Thailand in a few months.



My friend Mark hosts a lovely New Years party in his investor’s apartment. I spend the preceding days with my foodie friend Sam, eating NYC classics like Russ and Daughters gravlax. I take the bus back to Boston New Year’s Day, with promising developments for the new year.

Closing thoughts

Since I graduated from college, I’ve experienced a few things. (“Learn” is the wrong word – I already knew these before, I just didn’t really believe them deep down.)

– Making more money doesn’t make you more happy. It switches around your priorities (namely, time becomes more valuable) and makes some things easier, but introduces a different set of anxieties that are no less real. I also traveled more last year on a much, much smaller income.

– The only way to get have the job/life/love of your dreams is to 1) define what that is and 2) say no to everything that doesn’t fit your criteria. You must believe that there will be another opportunity down the road that you can’t see just yet – and there will be.

– Take lots of photos. Memories fade. Sometimes I feel dumb taking tons of photos in the moment (when I should be “experiencing” instead of recording), but I’m always glad I do. And when I don’t, I’m much more likely to forget.


What do you want, anyway?

Last summer, I lived in a $450 sublet with a grease and filth-covered kitchen and 2 roommates. I didn’t make much money, but because rent was so cheap, I swung a trip Mexico for a week and attended my first Burning Man.

There was an amazing Chinese bakery across the street, a fantastic thrift shop next door, and Super 88 was a 5 minute walk away.

I was happy as a clam.

From September 2011 until mid-May 2012, I didn’t have a permanent address. While traveling through Asia, I didn’t work much and managed to break even after 4 months on the road. The entire trip, including airfare, cost about 8k. If I’d been even more cost conscious, I could probably done it for 6k.

After I got back to the US, I stayed on friends couches and with my parents for a few months. I thought about moving to Buenos Aires for the summer and learning Spanish. I looked up airfare, apartments, language immersion classes.

Still, I couldn’t shake my weariness. You know how people become lawyers to win their parents’ and peers’ approval? It’s crazy, but I was doing the same thing. I felt obligated to live out other peoples’ aborted dreams. That I was disappointing some phantom audience if I didn’t learn every language, visit every country, do this whole “travel thing.” Just because I knew that I could.

Not entirely sold on Buenos Aires, I got a short-term Boston sublet and picked up more clients, waiting to see what transpired.

Summer crept in, thick and golden. In July, I took a 2 week trip to Italy, because I could. I wandered beautiful miles of coastline and ate a few kilo of gelato. I hung out with backpackers, and saw the same travel stories play out: transient relationships, chance encounters, pantomimes.

A college friend happened to be in Lake Como. We rode the funicular to admire an panoramic view, then took a ferry to visit a villa.

As we walked back to the ferry, dripping wet from a dip in the water, I said to him: “You know what my problem is? I shouldn’t travel… unless I actually want to.”

The American couple walking behind us burst out in unmuffled laughter.

I felt a dark flash of embarrassment. I sounded spoiled. All the money and time in the world, whatever will I do?

I know what you’re thinking: give me a fucking break.


In order to succeed at anything – absolutely anything – the first step is always the same.

Get clear on what you want. Define the goal.

But why is the wanting so unclear?

Most people don’t want to grapple with the underbelly of this question.

It calls all your life choices into doubt. If you want something different than what you’re doing, it makes you feel like a hypocrite. And you already have a great resume – no one’s ever accused you of screwing up your life, so everything must be fine.

But that’s not the actual issue.

Consider this: if someone held a gun to your head, you’d give an answer.

It’s not that you don’t know. It’s that you don’t trust yourself.

Who are you to make that call, anyway?


After I got back from Italy, I thought: what am I waiting for?

I signed the lease for a studio apartment in downtown Boston after 2 days of hunting. It was much more expensive than last summer’s accommodation, and not a whole lot more luxurious – but it was mine.

I started working more and reattempted dating. Work went a lot better than dating, as is often the case. I stopped worrying so much about what I was going to do after freelancing, and began to focus on what I enjoyed about it. Things have gone well. I’m surprised and grateful.

I feel strange about writing this post. There’s no conclusion. And then I lived happily ever after? That would be boring and a lie.

And if I don’t post it now, I’ll just keep tacking things onto the end, or rewriting sections. But I suppose that’s ok – unless I get hit by a bus tomorrow, no one’s expecting a neat ending.


Tips for Getting Around Las Vegas

After last year’s Burning Man, Vegas felt like a strange, corporate Disneyland: a city imagined from a small-town conception of glamor. It’s also not small. I brought extra walking shoes (which I lost a club, sadly) so here are a few options for making your way around, should you decide to take the plunge:

Easy peasy, and not so cheap. Also, be careful – one of our drivers decided to take the long way around because of “traffic” (it was a decidedly non-trafficky time of day). Another lamented being fired from his job after 40 years of dedicated service. But that’s another story. But the fact remains: after checking out nightlife in Las Vegas, you’ll generally find a cab the best option for getting back to your hotel room safely.

Las Vegas Transit System
Yes, there are buses too! I didn’t actually use this. Buses scare me. I never know what stop to get off at and I turn into an anxious ARE WE THERE YET mess.

Casino Shuttle
No price quite as good as free. Some casinos (and other venues of entertainment) offer shuttles for getting around Vegas depending on your destination.  Some will only take you to specific casinos that they are affiliated with and others will take you to a set number of locations. Your casino host will be able to tell you about what shuttle service they provide.  If you are going somewhere near a casino serviced by a shuttle, this could be a quick and free mode of transportation.

Renting a Car
… Or you could rent a car. With all its attendant upsides and downsides. This makes more sense if you have a group, are staying for awhile, and need the flexibility. Try shopping around online, and don’t forget to take advantage of daytrips and other excursions if you have a car. For example, there’s a machine gun shooting range… a junkyard of vintage signs… all kinds of interesting stuff off the strip that I regret never seeing. So go see it!

Oh hey! I'm Lingbo.

I've eaten cow brains, bull penis, and Icelandic fermented shark. Otoro, campari caviar, and meltingly tender pork belly. McDonald's Big Macs, Bertucci's rolls, and Starbucks coffee. Grrr.

Lana Lingbo Li

I'm obsessed with food. Now blogging over at Hello Lana.

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