16 questions for free agents

Seth’s Blog

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:

1. Who are you trying to please?
2. Are you trying to make a living, make a difference, or leave a legacy?
3. How will the world be different when you’ve succeeded?
4. Is it more important to add new customers or to increase your interactions with existing ones?
5. Do you want a team? How big? (I know, that’s two questions)
6. 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?)
7. Are you prepared to actively sell your stuff, or are you expecting that buyers will walk in the door and ask for it?
8. Which: to invent a category or to be just like Bob/Sue, but better?
9. If you take someone else’s investment, are you prepared to sell out to pay it back?
10. Are you done personally growing, or is this project going to force you to change and develop yourself?
11. Choose: teach and lead and challenge your customers, or do what they ask…
12. How long can you wait before it feels as though you’re succeeding?
13. Is perfect important? (Do you feel the need to fail privately, not in public?)
14. Do you want your customers to know each other (a tribe) or is it better they be anonymous and separate?
15. 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?)
16. 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.

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