You want to have a good year freelancing?  Don’t we all?

But how do you do that? 

I’ve been asking questions, swapping stories, and debating with my fellow bandits and independents. They include grizzled pros, as well as some annoyingly successful upstarts

All of us have racked up good years, galactically stellar years, and not-so-good years. What works? What doesn’t? 

Some fascinating themes kept coming up again and again. I’m relaying them here.

We started in Part I, which involved focusing on having good days. And on skipping the happy resolutions and goal-setting. 

We continue . . .


Cultivate some luck

None of us liked to talk too deeply about this. Partly for fear of jinxing it, and partly because the idea is a bit unsettling.

But it’s about as true as it gets: Your career can often be pushed along — at high velocity and on short notice — by luck. Pure dumb luck.

You can go from pooping along to soaring in a matter of weeks, all due to an unpredictable and random chain of collisions out there in the universe. But that is not entirely a bad thing.

I was once catapulted into a lucrative run of work for six months (where that 25K thing happened) primarily because a VP at a big technology company shattered her ankle on a ski trip.

A designer friend landed a semi-famous client mainly because she happened to be at her desk at 1:15 am, and answered her phone. “Ah, a fellow night owl,” said the client.

I guarantee you, there’s a scriptwriter out there who fell into an unexpected assignment last week only because I screwed up and couldn’t get to a meeting downtown and was summarily kicked off the project.

My friend Bill, a freelance composer and sound designer, started a side venture where he took parts from an old junk car and fashioned musical instruments from them. He wrote some original music and formed a band. But the concept never took off. He shelved the whole thing.

Six months later he got a call from a big-ass film company in Europe. They were creating a high-budget commercial for Ford. They had seen stories about his project. They wondered if he could create futuristic instruments from pieces of the new Ford. They had six figures to spend. Was he game? (Duh.)

For weeks, you send out emails, make calls, work your network. Nothing much happens. Then, when you’re about to apply for a job at Starbucks, you get a call from a friend of a friend of someone who was once your brother’s boss. You have no idea who he is, but he has plenty of money and inexplicably thinks you a genius.

Work can land on your desk through an improbable chain of hops, skips and ricochets that you couldn’t map out if you tried. It can make for a hell of a year. And it often does.

Does that seem unfair? Too capricious? It most certainly is. But all of us have seen it happen. All of us owe a chunk of our careers to luck no matter how much we like to think otherwise.

But there is a catch.

This is not an excuse to sit around and wait to be ‘discovered.’ That never works.

This is not an excuse to whine about not getting any breaks. Nor is it an excuse to bad-mouth that buffoon with no talent who blunders ass-first into a pile of money and recognition. (It is more professional to curse the guy only in private, to yourself.)

Okay. So what do?

“Sure as hell,” says a fellow writer even more veteran than me, “The minute I start counting on luck, and come to expect it, that’s when the freelance gods turn off the spigot. Those sons of bitches are smart.”  He tends toward ‘woo’ a bit. But he’s dead right.

You can’t force luck. But you can nurture it, set it up. But you can’t game it.

There’s an old golfer’s maxim: “The harder I practice, the luckier I get.”

So put yourself out there. You can’t get lucky holed up at your desk.

Put your work out there. Interview yourself on your web site on video. Designer Andrea Mignolo has released a bunch of WordPress themes out into the world. All for free. Her name and karma benefit immensely.

How many people even know you exist? (No this is not about PR, this is not ‘exposure’. This not about gaming SEO for your name. This is about making things and trying stuff.)

Send complimentary and appreciative emails to people. Make sure everyone you meet knows what you do. The more ping-pong balls you fire into the universe, the better your chance of bouncing off something good. Be generous. Encourage a young freelancer who is even more clueless than you. When you see something you like, send a note and say so. (Without asking for work.)

Most of the time, nothing will come of this. But do it well and sincerely and you will tip things in your favor. Just enough.

Here’s the other half of luck.

Be ready.

If your dream client called this afternoon, out of the blue, with a luscious high-profile project, could you pull it off? Would you have the chops?

(This is why, of course, you are always trying to get better. You are always honing and practicing. You want your spear limber and sharp. Just in case.)

Or if you really weren’t ‘qualified’, would you have the stones to try it anyway?

“Say yes first,” says my late-night designer. “You can always panic later if you want.”

Oh. And when you’re touched by luck, offer up some gratitude. Really. In whatever manner you wish. I don’t know why it should matter, but it most certainly makes a huge difference. Forget this at your peril.

Embrace that pain

Is there something about freelancing really sucks for you right now?

Something that causes a god-awful ache in your gut in the middle of the night? Something that chafes and burns at you all day long?


You have most of what you need to crank up your business a few notches. And fast.

Fact is, the more we thought about it, the more we realized that pain and discomfort are perhaps the most unsung, most unheralded motivators of freelancers and other human beings. Fear works, too. (Fear is just pain, anticipated.)

Most of us will run longer and faster away from pain, than we would run toward glory. That hazy, beckoning vision on the horizon? Nice. Pretty. But you’ll get much farther if something’s behind you, trying to chew your ass.

You know that freelancer with that cast-iron discipline, the endless energy and impeccable self-organization? The one who puts up five blog posts, wraps up three assignments, does a quick conference call, gets interviewed on a podcast, then has breakfast?  The kind of freelancer you want to smack, just once?

Here’s our observation:  What’s cranking this guy’s engine isn’t “ambition.” It’s not that he has built up his willpower. It’s not that he’s learned how to be ‘results-oriented’, or has mastered ‘productivity.’

What gets him up and working at 5:30 am is the absolutely intolerable thought of somehow not making 250K a year. The ghastly pain of crapping out. Having two empty hours in his schedule makes him twitch and fidget uncontrollably. He just can’t help himself. There is no decision-making, goal-setting, visualizing, daily affirmations or any such happy talk.

It’s just too painful not to do it. He cannot help himself. There is no discussion.

(And all those years I figured I was just lazy? Nah. I just have a higher pain tolerance, I guess.)

Watch the YouTube video of Olympic swimmer Michael Phelps. Watch the race where he doesn’t come in first. Notice the look on his face when he checks the scoreboard. He looks as if his liver had been pulled out and his dog just died.  I’m guessing that’swhat pushed him into a cold practice pool every morning year after year. The spectre of coming in second was too awful to contemplate. So in he dove.

That’s the good thing about working from pain. You don’t have to remind yourself to get to work. You don’t have to write lists or read blog posts for inspiration. The itch is so bad, you get up and work. Sort of like a full-body case of restless leg syndrome. There is no sitting down.

And it doesn’t matter if you don’t know the fix, can’t figure out the right answer.

Okay, so what sort of pain propelled our renegades onward and upward?

“How about having to borrow from your daughter to make the mortgage? So humiliated, I kicked in the afterburners and cracked three big clients in 32 days. For work I was too scared to pursue before.”

“Trying to wangle assignments from creative directors fifteen years younger than me. And getting turned down.”

At the desk at 9pm, plowing through most numbing, low-paying dreck there is. For clients who don’t give a shit. Just because it’s ‘safe.’”

“Seeing kick-ass design work on the web. And realizing I wasn’t doing anything like that.”

“Realizing that I’m clinging too hard to a craft that doesn’t much matter any more.”

“Watching the look in my wife’s face.”

“The thought of telling the kids we couldn’t go to the beach this summer.”


That’s the kind of pain that can change things, get things moving.

Man, I didn’t want to end this post on a down note. It took too long to write as it is. I was hoping it would be good.

Maybe this will pick it up.


I used to be far too intimidated by big, important clients. They had work. They had money. I wanted work, I wanted money. I was hoping they would give me some. I spent way too much time being intimidated.

Once, I was in a client’s office. (Back when we used to go to client’s offices.) He owned a big company.

We were sitting at his conference table. He was chewing me out. I was apparently hopeless and talent-less. Maybe I was. I was nineteen seconds from getting fired.

Anyway, back on his desk, his phone rang. He got up to answer it, but caught an ankle on the leg of the conference table. He fell and went skimming across the white oak floor, like a walrus in a suit.

A $200 shoe flew off. (The other $200 shoe stayed on.) A button popped on his shirt. His glasses went sideways. He flailed on the floor.

I went to help him up. He grabbed my hand, with his glasses all askew, and his stocking foot slipping on the floor. As I hoisted him up, he let loose a fart. There was no way to pretend it didn’t happen. It was a full-on executive fart.

When he finally got himself together again, he was a pussy cat. No more yelling at me. He realized he had lost some status.

Now, when I feel myself getting too intimidated by a client, by someone who seems way smarter and richer and better than me, I remember that incident.

I think, “I bet if you tripped over the conference table, and I went to help you up, things would pretty much even out here.”

And I feel better.

Did that help?