November 2016


You are a star. You have a vision, a calling, and a keen sense of smell. You have important things to say, you know exactly how to phrase them, and your spelling is pretty good. The world has a job opening for a Creative Genius, and you can expect your offer letter by today’s close of business.

I used to feel this way, and I let my feelings get the best of me for far too long.

be-a-self-worth-promotingAfter some early success as a radio host and writer, I fizzled. I slumped into a life of mediocrity and boredom. It took me a long time to grasp that my problem was my ego, and that my ego would need to die for my soul to live again.

When I was young, I was lonely, and I thought being creative might be a way out. So I wrote stories, played music, drew comics, and volunteered at a radio station.

In a way, I was correct.

It’s hard to describe the all-consuming thrill I felt the first time I spoke into a live microphone at age sixteen. For years, I had pretended to be a DJ and put on shows for an audience of stuffed animals.

Maybe a dozen-or-so people were listening, but the feeling of sending my voice out into the atmosphere gave me an intoxicating rush of power. I was speaking to people — lots of people — without my usual stammering anxiety.

I was hooked.

The first few times I wrote for publication, I got a similar rush. As a kid, my favorite toy was a typewriter. I devoured whatever reading material I could find, from encyclopedias to magazines to the fine print on food labels. Being a real, published writer — someone who told the stories that lit up imaginations — made me feel like a god. I got a few record reviews published in local zines and I felt like Hunter Thompson. I wanted to feel this awesome forever.

Radio and writing enriched every aspect of my life. I didn’t just feel less alone; I was less alone.

People want to be friends with people who do things. It was a lot easier to make friends when I had creative projects that could make introductions on my behalf. Because these radio stations and magazines had established audiences in specific areas, I found myself much more in-demand than I had been when I was a quiet daydreamer with bad eye contact.

My problem was that, for someone with grinding depression and rock-bottom self-esteem, I had a hell of an ego. I wanted my work to speak for itself, on my terms. The world owed me a living, and if it didn’t pay up, I would take it to court. I thought it was cool to alienate and antagonize strangers and to pose as much tougher and more cynical than I was. (To be fair, it was the ‘90s.)

By the time I had been out of college for a few years, my creative efforts hit diminishing returns, hard. Print media and radio were laid waste by the rise of the internet. It became much easier to put my words and my voice out there and much, much less likely that my work would gain any sort of an audience. I still had my old swagger, but I wasn’t doing good work or connecting with anyone new. I was an aging hipster running out of things to say.

It was fun while it lasted. Going through a period of arrogant self-indulgence helps you get to know yourself, which is more difficult than it sounds. If you haven’t given free rein to your creative vision, I recommend it. (You don’t need to share the results.)

Once you’ve gotten to know yourself and get comfortable expressing yourself, you may find that you’re still not quite satisfied. A few people praise your work because they know you and like you and want to feel good. But most people don’t really get it, and you’re not getting out of it what you put into it. You’re not living up to your potential. Even you are losing interest.

I’ve been through this several times. I’ve lost jobs because I alienated the people who supported my work and found that it couldn’t survive without their help. I’ve gone through years of alcoholism, extreme depression, and writer’s block. I’ve given up, started over from scratch, and given up again.

My problem, as I see it now, was that I got pretty good at expressing myself but never really learned how to communicate.

If you’re stuck in a rut, or you’ve got something to say but are afraid to clear your throat, this may help. Here’s how I healed my bruised ego, extracted my head from my ass, and gathered the courage to get back to work I cared about.

Harness the Power of Selfishness

It takes courage and creativity to be true to yourself. But it takes even more to pay attention, solve problems, and be true to others as well. You probably aren’t a genius, but you are smart enough to make yourself useful.

Fortunately, you have an ego, and you can be its master, not its slave. You can harness your desire to be a star and use it to help others. Like everyone else, you need attention. And if you strive to be the sort of person who deserves positive attention, you can make the day a bit brighter for everyone. Demote your ego from the C-suite and put it to work for you.

The Bad Idea That’s Killing Your Creativity

demote-your-egoGrowing up in the ‘90s, I dreaded being a “sellout.” I was terrified that making a living would mean sacrificing my integrity and becoming part of the problem.

As it turns out, there is no separation of church and state between art and commerce. Yes, some people make music or movies just to make money, but that doesn’t mean that people with genuine passion should have to go broke. If you have something important to say that can help people, learn how to say it where those people can hear it. That’s what account executives call a “win-win.”

Read books and blogs about marketing, activism, and social influence, and think about how you can express your ideas in ways that will resonate with others. The giants of advertising have a lot to teach about human nature. Instead of exploiting people’s weaknesses, you can empathize and do work that’s relevant. Expressing yourself is a lot more rewarding if someone else is paying attention, and it’s a lot more rewarding if someone is learning something from you.

I found that my experience as a storyteller came in handy in helping nonprofit organizations and mission-oriented startups with branding and promotions. My time as a DJ and comedian enabled me to communicate with other people suffering through addiction and depression. And my writing skills could help people understand urgent problems.

Yes, there is plenty of noise in the new media landscape. There are a lot of people talking. Most of them will run out of breath. If your signal is strong, your purpose is clear, and you know how to connect with the people who need you, you will find the strength to keep doing the work.

Don’t Learn From Your Mistakes. Do This Instead.

When I was young, I wanted to be a star because I was lonely. I didn’t get all the attention I wanted, and I felt even worse. I gave up. Then I sobered up, thought about what happened, and noticed that everyone else was lonely, too. With that, I wanted to be creative again. So far, this go-round has been a lot more rewarding.

Every day, do something to expand your capacity for empathy. Talk to someone who’s going through a rough time, or read the life story of someone who made it through a struggle. Don’t give advice. Don’t force your way into someone else’s story. Pay attention to the pictures, sounds, and feelings they describe. That’s what your art can be about.

Discover what you can learn from someone else’s struggles. At the least, you won’t have to make that person’s mistakes yourself. You can start my avoiding my mistakes. I already made them, and they weren’t that interesting the first time.

To be fully human, you have to care for people other than yourself. Not because you think they deserve it. Just because they are lonesome and suffering, and there may be small ways you can use your art to help.

As a keen observer, you can notice how other people are screwing up and suffering. As a creator, you can speak to that pain in a way that is inclusive, empathetic, and honest.

If you feel driven to create, there is probably an audience out there for your creation. Everyone with courage has something to teach. Hone your skills and supply the humanity that other humans demand. There will always be room for more art, and human connection is not a zero-sum game.

How To Define Creative Success

Life is an awkward mess of small talk and social status games. Meanwhile, we long for the sorts of crazy-meaningful connections that artists know how to create. If ad wizards can convince people to buy things they don’t need, there’s no reason you can’t use the same tools to make people feel less alone.

Salesmen get a bad rap because so many products aren’t worth buying. Promote yourself, and develop a self worth promoting.

Create to connect.

How I Didn't Crush It

I  don’t know how to “crush it!”

howididntcrushitI’m not Gary Vaynerchuk. I’m a recovering alcoholic, so wine was a net loss for me. 

I’m not Tony Robbins. When I walk on hot coals, I tend to get burned. When I shoot for the moon, I tend to end up floating around in space for a long time.

I’m not a superstar, a unicorn, a guru, or even much of a go-getter. 

I’m well acquainted with bitter loss and with snatching defeat from the jaws of victory. Sometimes I get up, dust myself off, and make it as far as the sidewalk. But I am also in the habit of ruminating over my failures.

Although I’ve never crushed it, it hasn’t been for lack of trying. I despise bosses and slaving away for causes I don’t believe in. I’ve attempted to take the wheel of my own ship and become the captain of my own destiny.

I heeded all the advice. I didn’t listen to naysayers, or anyone else, assuming my friends and family envied my rebellious spirit and would try to hold me back out of spite. 

Instead, I listened to some douches on the internet, whom I assumed had my best interests at heart. I jotted down lessons from their success stories, copied their repeatable formulas, and applied them to my own life. I burned the boats and didn’t look back, even when I needed a fire to cook food or keep warm.

In the process, I made some discoveries. Some of this might help you. I don’t know.

Sometimes, it is a good idea to listen to friends and family, even when they say things that don’t sound supportive. Sometimes, when they try to hold you back, they are trying to protect you from humiliating yourself, or they don’t want you to end up asking them for money.

By cultivating the habit of not listening to people who care for you, you might be closing yourself off from the people who could actually use your help. You don’t live in a vacuum. If you shut out the world and spend all your time looking inside yourself for your million-dollar idea, you may find yourself with your head wedged in your ass. Sometimes I’ve needed the Jaws of Life for this.

This happened to me. My ambitions weren’t even that grand. I didn’t sacrifice everything for my art or bring my wacky idea for an app in front of Mark Zuckerberg. I only wanted to make it as a full-time freelancer.

The main thing I learned is that poverty sucks. I learned how many days I could go without eating before I started hallucinating. I learned that it’s easier to start bullying yourself than it is to stop. I was never all that concerned with money until I didn’t have any.

I learned that, by failing to save any money and racking up significant debt, I was really upsetting my wife. I learned that I wasn’t the only person who cared whether I succeeded or failed — my wife cared, too, a lot. 

She didn’t care because she liked me, although I assume that she does. She cared because my terrible decisions hurt her materially, too. She saw something I didn’t see — sometimes the costs of pursuing a dream outweigh the benefits. Sometimes you aren’t the only one who needed those boats to get home. Sometimes you have to be an adult because the world can’t support another spoiled, deluded child.

I do think she believes in me. Sometimes, I even believe in myself. I believe in myself enough to make things easier on myself, not harder. I have enough confidence in my dreams to pursue them without putting our well-being at risk.

As my attempt at a freelance career came to an end, I had three options. I could find a regular job with regular hours and regular benefits, one that would support me and my wife. I could give up, move into my mom’s basement in the Chicago suburbs, and lick my wounds for a long time. Or I could hurl myself from the tallest building I could find. 

At one point, I came close to executing on the third option. Had I done that, it wouldn’t have been a setback I could have leveraged to my advantage or spun to make myself look like a winner. There was nothing romantic about that feeling. It was freezing cold. I was completely alone.. One sunny day in May, I came very, very close to crushing myself.

As I peered over the edge, it occurred to me that I had a lot to lose. I had people who loved me. I had ideas worth pursuing. I just couldn’t live the life of a compulsive gambler. This constant state of fear and scarcity was not helping me.

Although I failed to crush it, I learned that I have my own skillset. I am patient, persistent, and realistic, almost to a fault. I plan for the worst. I harbor no illusions about my own significance in the world. When things go well, I don’t take it as a sign that things will always go well. I can sit steady in the saddle and not be shocked when things go badly — it’s never a surprise. It isn’t the same skillset that Gary Vee has, but it has its advantages.

It is easier to dream with a roof over your head. When you’ve suffered, you appreciate relative comfort. There’s nothing wrong with grinding it out in a bad day job if you use your relative comfort to support creatively and spiritually fulfilling activities in your off-hours.

I now have a day job that I don’t much enjoy, but is usually preferable to a dry-dive from the US Bank tower. It gives me security and resources to invest in writing, podcasting, spiritual exploration, and the other things that make me happy to be alive.

When I encounter setbacks, I tend to take them quite badly. Disappointment hurts. It will never be easy or fun, I’ll never escape negativity for good, and taking a spill will always hurt.

After I fall down and realize my bones aren’t broken, I regroup and get up, because I remember the joy pursuing my dream brings.

We are not the sum of our experiences, but of how we react to them. Many of my experiences have been painful, and most of my reactions have been even worse: counterproductive, juvenile, and sometimes self-destructive. 

I pissed away most of my 10,000 hours on lashing out and feeling sorry for myself, but I always allow myself to started over from scratch. There’s freedom in that. When I’ve had a chance to grieve my losses for however long that takes, I always ask myself two questions. What can I learn about this? What is funny about this? From there, I begin anew.

When you fall apart, you have the freedom to reassemble the pieces of your life in a whole new form. Sometimes giving up is for the best. Just don’t give up for good.

I am not by any means crushing it. But I am not being crushed, either.