In the past few weeks we’ve been talking about risk, specifically the universe of hazard that the artist and entrepreneur willingly and consciously inhabit. We’ve talked about operating on two tracks—the commercial track and the pure-soul track—and about betting on yourself. Today I want to take the discussion deeper into the realm of nuts and bolts. When you and I sell our novel or cookbook to Simon & Schuster (or our screenplay to Warner Bros. or our album to Interscope or our videogame to Electronic Arts), we willingly and consciously take ourselves out of the sphere of risk. The company…

If you’re an artist or an entrepreneur, your working life is by definition about risk. You’re already rolling the dice or you wouldn’t be doing what you’re doing. But beyond the inherent hazards of the artist/entrepreneur’s life, how should you manage risk? (I’m not referring, by the way, to the Seinfeld episode featuring George Costanza and his protégée.) My theory is to bet on yourself. If I have $10,000, should I put it in the stock market? Or should I use that cash to back my own dream? My stuff has crashed and burned 90% of the time. But always…

When I came out to Tinseltown from New York in the 80’s, one of my first paying gigs was working with a grizzled, old-time director on a low-budget action script. (This post is picking up from last week’s, about “Track #1” and “Track #2.”) The director and I used to work at his house in the Hollywood hills. We’d sit side by side at a huge oak table in his kitchen for eight or ten hours at a crack. I’d drive home exhausted, but I was having fun. The director and I started becoming friends. One day during a break…

When we complete a work of art or commerce and expose it to judgment in the real world, three things can happen: 1. Everybody loves it. 2. Everybody hates it. 3. Nobody notices that it even exists. All three responses present you and me—the artist or entrepreneur—with serious emotional challenges, and all three drive deep into the most profound questions of life and work. It will not surprise you, I suspect, when I say that in my opinion all three responses are impostors. None is real, and none should be taken to heart by a professional. When we work in…

Each day I get one or two invitations to speak at events or conferences. People have read The War of Art, and the concepts of Resistance and “turning pro” have struck a chord. They’d like to hear more; they’d like to see who I am in-person. Maybe they’re seeking “inspiration” or “motivation” for their group or association. All the invitations are proffered out of respect and in the most generous and elevated spirit. They’re well-intentioned; the groups themselves sound interesting and fun; and I certainly appreciate the thought behind all of them. Some even come with offers of significant remuneration.…

[The following is a slightly-tweaked-and-updated version of one of Writing Wednesdays’ most popular posts.]

I have a recurring dream. In the dream I’m invited to climb into the back seat of a limo that’s about to drive off to someplace fabulous. The dream always ends badly. It’s trying to tell me something.

Trust me, this baby is taking us nowhere

Publication day—or any date when we launch a project that we’ve worked on long and hard—is like getting into the back seat of that dream limo. Launch day gets our hopes up. We’re human. We’re prey to the folly of anticipating rave reviews or long lines outside the theater; we’re itching to check the grosses or the day’s sales on Amazon. I’ve been up and down with these expectations through ten books and a bunch of movies and I can tell you one thing:

Of the two possible outcomes—a flop or a hit—both are delusions.

One of the things you learn writing fiction is to think in metaphors. The first draft of any novel or screenplay usually spills forth in blissful cluelessness. You tell yourself, I’m writing a detective story, or a Western, or some crazy genre that I don’t even know the name of. Then comes Draft #2 and you have to ask yourself, “What the hell is this thing about?” That’s when metaphor comes in. It took me a long time to learn this, and a lot of people had to hammer me and my work pretty hard. Words like “shallow,” “slick” and…

Here, thanks to Alexandra Choi, is a day we can all relate to.  (Viewing time: 1:52.) I will say no more. Except for more of Ms. Choi, click here.

My friend Paul is writing a pilot. He’s never done a piece of writing this serious before. The work is totally on spec. Paul has a full-time business and has to do his writing at odd hours. A couple of weeks ago he had a crisis that made him almost suicidal. When I describe it to you, you’ll say, “Man, have I been there!” A script for a TV pilot is about fifty-five pages long. Paul was on Page 52. He went home after work, sat down at his laptop and opened up the script to (blank) page 53. But…

Ask me what I envy most about people who have lots of money. My answer: “I’m jealous that they have secretaries to say no for them.” Saying no is hard for me. Always has been. It’s hard for a lot of people. Maybe we want to be thought of as nice guys. Maybe we remember people turning us down when we asked them for help, and we don’t want to be that kind of person when other people ask us. Maybe we truly have empathy for the plight of whoever is asking us for something. Maybe we really do want…