Do You Make This Huge Mistake, When Trying to Help Someone (or Yourself) to Change a Habit?

Recently, after I spoke about my personality framework, the Four Tendencies, a woman came up to me and said, “Because of your talk, I’m going to do something different.”

“What?” I asked, curious.

“My daughter plans to take the GRE. She keeps telling me, ‘Mom, I need to take a class.’ And I kept saying, ‘No, if you’re motivated to take the test, you should be able to buy a book and study from that.'”

When I heard that, I wanted to jump up and down and say, “No, no, NO! You’re making the classic mistake! You’re saying the dreaded ‘You should be able to…!’

Fortunately, she continued, “After hearing your talk, I realize that she’s right. If she needs to take a class, she should take a class. She’s an Obliger, and she needs the accountability of a class.

I was very relieved to hear that. I’ve found that one reliable sign that we’re about to make a big mistake, when we’re trying to help someone else (or ourselves) to change a habit, is to say “You should be able to.”

  • “If you want to exercise more, you should be able to get up an hour early and go to the gym before work.”
  • “If you want to eat more healthfully, you should be able to indulge in just half a dish of ice cream each night.”
  • “If you want to stop spending so much time on your phone, you should be able to limit Candy Crush to just twenty minutes a day.”
  • “If you want to get that report written, you should start early and work on it a little each day.”


When we say “You should be able to,” we’re talking about a fantasy person, one who may bear no relationship to the actual person we’re talking to.  And usually we’re talking about what habits would work well for us.


If there’s one thing I’ve learned about habits, is that each of us must change our habits in the way that’s right for us. There is no “should be able to” — it’s just a matter of what works.

“Should be able to” is harmful, too, because it makes people feel bad about themselves — “I should be able to get up early and exercise; I must be lazy” “I should be able to eat half a dish of ice-cream; I must lack self- control.” No! This habit is just being set up in the wrong way.

If someone keeps telling that you “should be able to” do something, but it’s not working for you, try something else! Night people shouldn’t try to do things early in the morning. Abstainers find it easier to have none than to have some. Sprinters find it easier to work for a shorter, intense period than to work over a long period. There are many ways to build better habits and the lives we want.

There’s no right way or wrong way — just what’s right for you.

How about you? Have you found yourself telling someone — or yourself — “You should be able to...?”


  • Katherine

    YES! And what’s more, when you find yourself saying, “I should be able to. . . ” you may be about to make an excuse that’s going to derail you. “I should be able to have a slice of cake without hurting my diet.” “I should be able to have this drink, because I had a bad day”– loopholes. Just as we are individuals in how we change habits, we’re also individuals in how we sabotage them. The point is to get away from whatever notion of *should* and *ought* and work toward what works.

    If a habit is worth acquiring for you or bad habits are hurting you, then there are good reasons to alter behavior that go beyond whatever we’ve promised ourselves as *should*.

    I wonder where this *should* comes from. According to what authority *should* all this occur? I wonder if *should* is a mutually agreed-upon kind of fiction? Or some concept of Platonic rightness, which carries with it the implication that anything practical and workable is flawed and doomed?

    If you’re going to buy into *should*, it’s like saying you have to be somebody other than you before you can begin. You can’t get there from here. Or you can just accept that we’re all cobbling ourselves together from spare parts and get resourceful.

  • This is incredibly helpful! I see the differences in my family members and how I’ve been judgmental in the past. Thank you for this.

  • I love this Gretchen! I’ve been sorting through all the expert advice for new business owners and there are so many different things experts say you *should be doing* to get results. And there’s almost no one is saying what kind of character traits or previous experience will help you get those results.

    Your framework is giving me new ideas on how to sort out those recommendations for my clients. I’m excited.

  • ChrisD

    I’ve learn that ‘should’ is a big red flashing light. There is a gap between the real world and what we want.
    Usually we need to change our expectations, but sometime we do need to change the world (little children ‘shouldn’t’ work in mines, for an extreme example).

  • Moly

    This is a very insightful post. I have never thought of it that way. Maybe the best thing to say to someone who really wants to make a change is: What do you need in order to make the change? If it’s our children and it involves larger sums of money, maybe we should ask Why? Just to be sure…haha 🙂

  • Leigh

    Ha ha, *I* spend a lot of time saying *I* should be able to… Clearly the imaginary me that should be able to do things doesn’t do them. Time to re-evaluate my own strategy for my self!

    • SallyVee

      It’s a trap that Obligers especially fall into. We see the way that society works, the way that adulthood and responsibility is “supposed to work” based on what we see from Upholders and Questioners, who are more naturally self-motivated. But when we don’t live up to that expectation on our own (and sometimes the expectations of others – of all tendencies), we think that if we try to convince ourselves that we “should” be able to do something just because we’re adults and we’re dependable, we end up beating ourselves up over trivial things like not doing the dishes or not getting to work on time, even though beating ourselves up takes away much more mental energy than just letting it go and trying again tomorrow.

      The problem is that we often set unrealistic expectations for ourselves. We see people who look like they have it all together and we try to reach to their level on our own willpower, but the truth is that they not only tend to have tendencies that make them more naturally self-motivated, but they have strategies for keeping themselves together, and their success is neither accidental nor easily attainable. That’s why Better Than Before is such an important book, at least to me, because it names each habit strategy so that you can figure out which strategies will help you be able to achieve your goals, YOUR way. It’s never a matter of should. Should is a harsh, unrealistic judgment. We only have so much willpower per day (or maybe even per week, I’m still trying to figure that out), and every individual person is different. If you want to change, expecting yourself to be able to magically do the right thing at the right time merely because it is the right thing at the right time is actually a little bit silly. No one learns how to play the piano merely by saying, “I should be able to play the piano.” Mastery takes time, practice, patience, and learning from mistakes.

      • gretchenrubin

        Such excellent points. Very true.

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  • Anne-Marie

    “There is no right way and no wrong way, just what’s right for you” sounds very Rebel to me, lol.

    Also, I once heard someone say that when a person says you should do such and such, they are “shoulding” all over you. It’s always stayed with me.

  • Kate Vansuch

    One of my nursing school professors used to tell us “don’t SHOULD all
    over yourself.”!!