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9 Questions to Ask Before You Start Something New

Priority Management

One of the subjects which I have written and thought the most about is what I like to call priority management. Ultimately the goal of priority management is to spend your time and energy in a way that aligns with your priorities (which themselves are derived from your values).

I think there’s a lot to be said on the nuances of the subject (and I’ll link to further reading below), but, ultimately, it boils down to saying yes to some things that become your priorities and saying no to other things that don’t become your priorities.

Sometimes, it’s very clear that something is a priority and sometimes it is clear that something is not, but there are a lot of cases at the margin where it can be hard to decide.

A simple and effective rule of thumb is Derek Siver’s Hell Yea or No, elaborated on more colorfully by Mark Manson as F**k Yes or No. The title more or less says it all: if you have an opportunity that isn’t a hell yes do it, if not, don’t.

Since basically every project takes twice as long, costs twice as much, and works half as well as you would hope (a result of reality having a surprising amount of detail), you want to make sure you are pretty psyched about it upfront.

If you are “meh” when you get started then you are likely to quit halfway through and a half-completed project is about as useful as a half-cooked turkey.

While Hell Yea or No is a pretty good general rule, there’s still a lot of cases at the margin that is hard for me to decide on. As a result, I’ve tried to keep a more detailed list of criteria for deciding on whether to take on a project. If all the criteria are met, it’s a clear “Hell yea” for me.

  1. If I didn’t make any money, would you still have had a great time?
  2. Is the project a purple cow? Imagine having a conversation at the last cocktail party (or even better, actually have one) do people’s eyebrows raise and say “cool”?
  3. Does the project leverage your unique ability? Why are you uniquely qualified to do it?
  4. Imagine that you are selling a million dollars worth of this product. Are you happy with how you spend your time?
  5. Do you respect your customers? Would you be happy to see one if you were walking down the beach on vacation?
  6. Does this solve a pain point people already know they have? I.e. Can you sell this without needing to re-educate the market? If not, can you position it that way?
  7. Is the problem a ‘tooth-ache level’ pain point? Will they do anything to get rid of it? Does it itch or does it burn? (You want something that burns).
  8. Is it something I Personally Need – Are you scratching your own itch?
  9. Does it follow the Star Principle – Is the market growing at least 10% YoY so that the overall size of the pie is growing?

If you’re interested, here are some other Priority Management resources I’ve put together over the years:

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