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.…