When to Say “Yes” and How to Say “No”

Say “Yes” Until You Have to Say “No”

Early in your career, you need to jump into every opportunity you can get, so you say yes to everything. Even the things that seem kinda dumb or pointless or weird or inconvenient. You say yes and do them anyway. Because you never know what doors they will open.

Then, as you start building your skills and reputation, you begin to find yourself in situations where you have more opportunities than you need. This is when you begin to strategically start saying “no.”

By saying “no,” you’re able to focus on the opportunities that present the biggest upside and you get even further, faster. Eventually, you arrive at a point where you are forced to say “no” to almost every opportunity.

Congratulations. You have now “made it.”

The “say yes until you have to say no” principle doesn’t just work in business, but in many areas of life:

  • If you move to a new city and want to make friends, say yes to everything until you’re so popular you can start saying no to invitations to the lamer parties.
  • If you’re single and want to find a relationship, say yes to meeting everyone until you find people you like enough to say no to people with terrible Tinder profiles.
  • If you’re trying to figure out what you’re good at or what you love to do, say yes to everything until you’re forced to start saying no. Eventually, you’ll be left with what matters most to you.

The Skills of Saying “Yes” and “No”

I’ve found that most people tend to naturally be good at saying “yes” or saying “no” but few people are naturally good at saying both.

Those who struggle to say “no” turn into people-pleasers. They will have a busy social life and lots of career opportunities, but because they can’t cut out what’s not important to them and they’re unwilling to disappoint others, they often feel “trapped” in a life they didn’t choose or want.

People who struggle to say “yes” are contrarians and loners. They often feel smart and superior because they are correctly able to spot bullshit. But because they’re unable to fully trust and commit, they struggle to build something they’re proud of. These are the hipsters and has-beens of the world.  

Being unable to say “no” will give you plenty of short-term opportunities but gradually wear you down in the long run. Being unable to say “yes” will eliminate most short-term opportunities, but it occasionally pays off by allowing you to spot something everyone else missed.

The secret sauce is knowing when and how to say (and hear) both.

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