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“Should” is SUCH an informative word

When you hear it come out of your mouth, listen up! It has a lot to say.

Bookmark this to walk through the next time you hear yourself say "should"

Last week, I had a coaching client say “well, I know I should be doing X.”

I perked up and said: “SHOULD!!”

And he said, “yeah, I know, you hate that word!” Which is interesting, because I have never once said that.

I think he was braced for yet another person lambasting him. He may have even been hit with the “fun” refrain Don’t Should Yourself!

There are, at minimum, three problems with people saying that.

It's valuable data

First, when you’re feeling conflicted and trying to work it out with someone you trust, the last thing you need is for someone to scold you for not being positive enough. Not only are you feeling bad about something, but now you should feel bad about your word choice too!

Second, when you’re saying “should” about something, it’s probably something you’ve been dragging around with you for quite some time. You’ve spent a lot of time feeling bad about it.

But you’re still dragging it because something’s wrong. Something’s not lining up. Otherwise you would have already done it or dropped it, and we wouldn't still be talking about it.

The way through is not to chirpily pretend you’re not dragging a weird lump around. It’s to actually look directly at the lump.

Third, they’re throwing away valuable data. When working through a behavior change, whether it’s mine or with a client, I like to run experiments, collect data, and iterate. This has many benefits, including exploring a huge possibility space very quickly to find the few things that actually work.

A crucial source of data are your specific word choices. They can often reveal hidden beliefs and assumptions that are tripping you up, but may not be visible to your conscious brain. (This, by the way, is one of the things that a good coach can speed up. You can’t hear it anymore because you’ve said it so many times, but they listen for these telling phrases and help you unravel them.)

One of the most densely packed words is “should.”

But what's it saying?

⚠️ I picked my words very precisely here so slow down for this bit.

It's telling you:

You don’t actually want to do the thing. And you think other people want you to want it

Often the second one is people wanting you to do something (like a task) but I'm not focusing on that here, because the more insidious dynamic—where more people get stuck—is when they want you to WANT something that you don't actually want.

This is really painful for everyone involved, because whether they realize it or not, it means they wish you were a different person. Oof.

Now pick it apart

You've already done step one, which is noticing. This is huge! Because now you can lay it out on the table in front of you and poke the lump you've been dragging around.

I like to systematically pick it apart this way. It seems like a lot of steps, but with practice you can do this in just a few seconds:

1) Get real honest about your motivations. You can accept that you don’t really want to do the thing very much, which can be freeing! Or maybe part of you does but part of you doesn't. Life and work have more ease with realistic grasp on our motivations.

2) Who, exactly, are the other people? Sometimes they are an actual person, like your partner or your manager, but with a couple pokes you may realize they’re a person-shaped smoke cloud like “investors” or “just people, generally.”

3) How, exactly, do you know what they want? Sometimes they do actually want something, and you know because they told you.

But a lot of times, they don’t actually care that much. Maybe they just made a comment in passing, or they were just brainstorming, or it would be nice but they didn’t realize the cost would be so high.

And sometimes it didn't come from them at all. It's really common to project things onto them that are more about you and your past than the actual desires of the person in front of you. People who were really good at school—you probably have a lot to unpack here!

4) How much do you want to weigh their wishes? People are going to expect all kinds of things from you, more than you could ever possibly fulfill.

The default is to reflexively adopt the others' expectations, starting with our parents' expectations when we are young. But if you want to avoid burnout, it is crucial to deliberately decide who you are trying to please and at what cost.

Some typically intense expectation sets can come from your parents, managers, direct reports, and any online audience you’re cultivating. And some identities, like "mother of small children out in the world," come bundled with a lot of scrutiny and unsolicited opinions.

You also need to shed old expectations like a snakeskin in order to grow. This sounds positive and worth celebrating—and it is!—but it can provoke surprising resistance. People may be grieving the Old You and your closeness, they may be uncertain what comes next, they may not like your new direction as much, or they may just be projecting their own stuff onto you. Preparing for these reactions can help you not overcorrect on them.

5) DECIDE. Now you can make an informed, confident decision about what you're going to do. Do the thing or cross it off your list. No more dragging it around.

So no. I don’t hate the word “should.”

I love it. It tells us so much.



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