After I finished my session on creativity at the How Design Live conference, a woman approached me and handed me a note.

“I know now that I was meant to be here,” she said, dreamily. “I mean, I’m not even part of this conference.”


But before I had time to call security, she was gone. That woman is fast.

Her note was cryptic, too: She wrote that clearly the Universe had played a part in getting her to my session (the rest of us registered). If I want to know more, she says, I could call her.

Later in the conference I saw creative director turned creative activist and sometime troublemaker Jeff Greenspan (Buzzfeed, Facebook, BBDO) speak on how to make your work compelling to other people.

Jeff has made headlines over and over again with his “side projects” in which he does things like lay hipster traps all over the New York City, and erect a bronze bust of NSA whistleblower Edward Snowden in Brooklyn’s Fort Greene park.

He says that, yes, quite a bit of planning and expense have gone into the brilliant and disruptive stunts he and his creative partner Andy Tider have pulled off over the years. It is good to bear in mind that if there are any stunts being pulled, there is potential risk for injuries, and there could be legal precautions so be sure to take measures into account.

But, there have also been amazing things that just happened.

Such as when the police came and hung a tarp over Snowden’s statue—a lovely bit of stagecraft he couldn’t have planned for, which created the visual irony of the government covering up the face of the man who risked his life to expose the government. It was the icing on his rebel cake. (More on that whole project here.)

Lots of other very cool things have happened in Jeff’s creative life that have earned him headlines and accolades, paying work—and allowed him tap a wellspring of collective energy from all over the world.

Is he lucky? Guided by the invisible hand of The Universe?

“You don’t get happy accidents if you don’t put yourself in accidents’ way,” he says.

Ah. And given the risk in standing up and saying anything contrarian (which Jeff is not afraid to do), it’s no wonder most of us might defer, might instead stay where it’s safe and quiet, and out of the way.

Interesting, right?

One woman wanders into a conference she didn’t register for and calls it divine intervention; a man performs an illegal act that triggers a media event better than he could have imagined, and he calls it a happy accident.

Both had some kind of plan in place (though in truth I am very curious about what that woman was up to). But what they did was leave their doors open a crack.

Whether you believe your life is guided or a series of random events, a bit of magic is at play. Something that’s beyond your control.

So what does that mean? It means your job is to put some conditions in place, but it’s also your job to keep your heart open and, as creative sherpa Sam Harrison said at his session, “available for seduction.”

That is what an artist—anyone looking to discover or create something—must do.

In his book Creativity, famous psychologist Mihaly Csikszentmihalyi (who introduced the concept of “flow”) studied how creative people think and work, and one of my favorite takeaways is this:

“Creative people are constantly surprised.” – Mihaly Csikszentmihalyi

They don’t assume they know what’s going on, he says, nor do they assume anyone else does. I love this. Because that’s the source of childlike wonder and brilliant perspective.

You can’t discover what you’re not curious to know, and the fact that we can’t know everything is, I think, an advantage. Discovery requires a bit of darkness in order to shine.

I’ll add this: The dreamy lady and Jeff also broke the rules; they did things you’re not “supposed” to do. Now, I don’t think you have to perform illegal acts to make things happen. But to invite divine intervention, inspiration, or happy accidents, you need to be open to the unexpected, to the what ifs, to the flow of things outside your control.

We can all have happy accidents and find ourselves the recipient of some benevolence, some great wonder, if we’re willing to wade out into it, and, when we feel the lift of that mysterious tide, start swimming. Hard.

Writing letter to a friend. Selective focus and shallow depth of field.

During a recent interview on SiriusXM, Howard Stern asked Lady Gaga if she listens to what the “kids are into these days” so that she knows what to do next, if she’s calculated and preplanned each phase of her career.

The answer? No.

Sure, she likes to listen to music and know what’s going on—in dance clubs, the world in general. But she’s not nearly as calculated as people think. In fact, she laughs at the idea. What’s her priority? To make music. To make people happy. To create.

Sounds so great, right? Ah the life of an artist, and a successful one, to lie around and dream and write. Well, not so fast. You don’t think there are a million people screaming in her ears about what she should and shouldn’t do? Shit she has to do and doesn’t want to? At the end of the day, she is running a business; she just prioritizes the making, not just the “doing.” And it seems to be working for her.

You know what makes my head hurt?

The degree of calculation required to plan, launch, and operate an online business, or any business for that matter. Since I just launched an online business myself, I know first hand that it’s a pain in the ass. Marketing can be joyless and I try really hard not to let it be.

Too much SEO or CRM or data analytics? I feel like I’m being embalmed alive. 

In the end there’s no replacement for creating—and nothing you measure or calculate can be as brilliant and moving as something that’s born from a true creative effort. It’s easy to get stuck on box-checking, task-doing, to think that those things equal “productive.” They don’t. 

Look, we all have business to take care of. But, if, like me, you start to feel your energy drop and everything starts to feel stiff and pointless and dry as a bone, that’s a sign that you’re getting too focused on the pipes and not enough on what flows through them.

Create instead of do. Make instead of manage.

This is not just for artists, by the way. We have unfairly decided that some people are creative and others aren’t. Couldn’t be further from true. We are all creative by nature, and the less you make stuff, the more robotic and listless you will feel.

I just returned from a writing retreat, a non-negotiable event that I attend twice a year, no matter what I have going on. Spending a brief but intense period focused on the act of creating and supporting others’ work fills my tank and completely shifts my mental state. I feel in control, and calm, and rich with potential. And, far more able to put up with the regular drudgery.

Don’t wait for someone else to give you the time or opportunity to do what you do, whether it’s sketching or writing or woodworking. And yes, you have to make time for it—which is well, as critical as making just about anything else.

Screen Shot 2016-01-20 at 12.15.06 PMI’m not an incredibly patient person. I have a short fuse and I bore easy. It’s bad. I think it makes me good at a few things, like keeping people entertained and engaged, but makes me bad at other things, like coping with slow restaurant service.

Over the holiday break I turned away from the world a few degrees. I didn’t call anyone; no one called me. It was wonderful for a while. And then I thought: Why don’t I have anything going on? Why isn’t this person wondering what I’m doing or why does that one not seem to be interested in seeing me? There’s an underbelly to boredom that’s ugly indeed, because it reveals our neediness, our impatience, our hunger for attention.

But here’s what scares me most about boredom, and should scare you, too:

That I’m letting it dictate what I do. I get bored, restless, worried, anxious, and then I bail—not just on people, but on projects, situations. I lose interest and wherewithal and wander away. I make assumptions about it that aren’t true, all in the name of giving up because it fails to keep my interest. Right. If I subscribe to this theory, I’m saying that boredom shouldn’t happen, and that life only has meaning if I leap from peak to thrilling peak.

We give boredom perhaps a little too much power: We end up leaving instead of sticking around. Do something easy instead of something hard. Write off people who shouldn’t be written off.

Boredom has a role, no doubt. (Read what Bertrand Russell says about it in this piece on his book on Brainpickings). We need to get bored, to tolerate boredom, in order to appreciate real highs, real moments of deep, soul-filling satisfaction. But more than that, we need to wait out boredom for what’s on the other side.

On the other side of boredom is not just thrill and excitement. and it’s not busy. In fact, busy is not the opposite of boring, even though at first glance you think it is. And yet busy is what we do to combat it.

Sometimes to get past boring, you have to be the opposite of busy.

Our problem is not that we get bored (which our culture of distraction seeks to eliminate), but that we let it unseat us so easily. It’s that we aren’t willing to wait it out.

In Big Magic, a powerful and moving missive to creative souls, Liz Gilbert cites the wisdom of Buddhist nun Pema Chodron, who says that the biggest problem with people’s meditation practices is they quit too soon, or, “just when things are starting to get interesting.”

Gilbert writes, “they quit as soon as it gets painful, or boring, or agitating. They quit as soon as they see something in their minds that scares them or hurts them. So they miss the good part, the wild part, the transformative part–the part when you push past the difficulty and enter into some raw new unexplored universe within yourself.”

What’s happening is that we’re not hanging in there long enough, past the breakers of inhibition and self doubt. I’m guilty of this, and likely you are, too. The mistake is believing that interest, like an iPhone, starts to depreciate the moment you walk out of the store with it.

Not true. Interest is the opposite of depreciation. You pay back a loan with interest. And what Gilbert is saying is that it can grow in your own life, if you hang with it long enough. We have it backwards, just as we have passion backwards (a point I make in my TEDx talk, “Stop Searching for Your Passion.”)

You can’t “busy” away boring; you can’t distract away boring. Boring dissolves in the unblinking eye of attention…it’s just that we usually aren’t willing to wait that long.

Do you know how many times I’ve started to write a book, and got all excited about it, and then got bored? My problem was I burned up all my energy in the prospect of it, instead of allowing it the slow, steady burn of attention to ignite.

But I’m starting to change that. I’m not looking at just the goal, the prize, the finish line. I’m looking at the road. The road is far more interesting. It really is.

I am not trying to “finish” a book. I’m simply writing one. Don’t ask what it’s about, because I don’t know yet. And I find the most interesting part isn’t talking about or imagining, but doing it. Writing it. And seeing what happens.

So consider making yourself that promise this year:

That rather than flee from boredom too quickly, see it for what it is: discomfort, internal conflict, fear. Decide instead to wait it out, to stick it out. To stoke the fire of your energy enough to keep you going. Take a cue from Pema Chodron and be willing to see what happens after.  Because that’s what’s most interesting of all.

FearWhen she was eight years old, Elizabeth Gilbert (of Eat Pray Love) was so upset by the ocean that she begged her parents to get everyone out of the surf and back onto their towels, where they belonged. She was, by her own admission, afraid of everything—the dark, the deep end, babysitters, board games, grass, you name it.

I can relate. When I was eight, I didn’t like swimming in the ocean, and didn’t love the pool, especially with lots of other people in it. I was afraid of amusement parks and diving boards and going anywhere without my mother. I was terrorized by bees, and bugs, and dogs. When urged to go out and play, I famously responded, “What good is a house if you can’t stay in it?”

In her new book Big Magic: Creative Living Beyond Fear, Gilbert says that despite all the attention we give fear (and we give it a lot), the real turning point for her was when she realized the fear not only didn’t define her, but if it did, she was a real snooze:

“Around the age of fifteen, I somehow figured out that my fear had no variety to it, no depth, no substance, no texture. I noticed that my fear never changed, never delighted, never offered a surprise twist or an unexpected ending. My fear was a song with only one note–only one word…and that word was ‘STOP!'” My fear never had anything more interesting or subtle to offer than that one emphatic word, repeated at full volume on an endless loop: ‘STOP STOP STOP STOP!'”

Not only that, she writes, but what’s worse is that fear was not only one-note and predictable, but it was just like everyone else’s. There’s literally nothing interesting about that. And yet for years, she says, she fixated on her fear as if it were the most interesting thing about her. Fear isn’t the most interesting thing about anyone.

Part of what I do, for a living, is to help other people make themselves and their messages more compelling. And yet, people fight me on it, try to convince me of why they can’t do it, and it’s because of fear, of course. Often it feels as if I’m a personal organizer and their fears are a set of broken beach chairs they simply won’t part with. I know they think I don’t hear them or don’t understand, but in fact I do. I know it too well.

Fear is not a problem to be solved, because by design it never will be; fear has its own survival tactics, dirty ones at that. At its most extreme, it can paralyze us, and at lower levels, it worries at our edges, making us more and more dull.

Here’s the truth: Fear doesn’t make any of us stronger, better, or more lovable. But what if instead of clinging to fear as a life preserver, keeping our heads above the unknown, we saw it for what it is: A millstone around our necks, dragging us to the very depths of boring, to the lowest common denominator of our personalities. Because that’s what it is.

So, no, you don’t want or need to get rid of fear entirely. You can’t, and you shouldn’t. When Gilbert embarks on a creative journey, fear comes along for the ride, but it does not get to drive. It doesn’t even get to touch the radio. But if you wait for your fear to stop doing its job so you can do yours, you’ll be idling there a long time.