16 questions for free agents
If you're starting out as an entrepreneur or a freelancer or a project manager, the most important choice you'll make is: what to do? As in the answer to the question, "what do you do?"
Some questions to help you get started:
- 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?
In my experience, people skip all of these questions and ask instead: "What can I do that will be sure to work?" The problem, of course, is that there is no sure, and even worse, that you and I have no agreement at all on what it means for something to work.