16 Questions for Free Agents

Posed by Seth Godin:

• Who are you trying to please?
• Are you trying to make a living, make a difference, or leave a legacy?
• How will the world be different when you've succeeded?
• Is it more important to add new customers or to increase your interactions with existing ones?
• Do you want a team? How big? (I know, that's two questions)
• Would you rather have an open-ended project that's never done, or one where you hit natural end points? (How high is high enough?)
• Are you prepared to actively sell your stuff, or are you expecting that buyers will walk in the door and ask for it?
• Which: to invent a category or to be just like Bob/Sue, but better?
• If you take someone else's investment, are you prepared to sell out to pay it back?
• Are you done personally growing, or is this project going to force you to change and develop yourself?
• Choose: teach and lead and challenge your customers, or do what they ask...
• How long can you wait before it feels as though you're succeeding?
• Is perfect important? (Do you feel the need to fail privately, not in public?)
• Do you want your customers to know each other (a tribe) or is it better they be anonymous and separate?
• How close to failure, wipe out and humiliation are you willing to fly? (And while we're on the topic, how open to criticism are you willing to be?)
• What does busy look like?