How I'm Skirting the Rules

I’m Uncovering Life’s Hidden Architecture So Others Can Discover Their Own Path to Happiness

Bestselling author and happiness guru Gretchen Rubin has long since learned it's easier to trust your intuitive instincts than try to change yourself.

To say that Happiness Project author Gretchen Rubin is a rules skirter when she’s most known for uncovering the unseen rules that make up our behavior might seem like a contradiction. And yet, it all makes sense when you discover a fundamental drumbeat of her research is that it’s our habits that make us happier, and finding practical work-arounds to shift them—rather than the arduous work of trying to change ourselves—is a lot simpler. In her bestselling books, The Happiness Project and Happier at Home, she investigates everything from ancient wisdom to science-backed strategies to discover the path to greater contentment. And in Better Than Before, her fascinating framework for self-understanding, which she calls the “Four Tendencies,” (see if you’re an Upholder, an Obliger, a Questioner or a Rebel, here) offers an entirely new way to go about skirting our most stubborn habits. She explores habit change, happiness and more each week with her sister Elizabeth Craft on her popular podcast, Happier, and is now working on curating a wider collection of podcasts on living a better life called The Onward Project. Here’s why the infamous Upholder thinks we can all learn a little from the Rebels among us.  

I’m Skirting the Rules by… giving myself permission to shape a story by leaving out the boring parts. My roommate in college used to keep a Post-it note on her computer screen that said, “Down with boredom,” as a reminder to herself as she was editing her senior thesis. I was enchanted by this motto and it always stuck with me. So now, if I’m writing something and there’s a part of it that’s boring, I just figure out a way to write around it. If it’s not interesting to me, I doubt that I would make it interesting to you, the reader. In my book about habits for example, I was having trouble with a section on neurobiology and asked my editor, “Can I just not get into any of that?” and she said, yes you can. So I did. It was so freeing. Now when I go through a draft, every page should have something that’s really interesting. If I have a page where it’s not really interesting, I ask myself why is it even there? That’s been really helpful.

A time when I found the possible, (i.e. a creative solution), within the impossible (i.e. against incredible odds) was…when I left law to become a writer. I had all of these credentials: I clerked for Sandra Day O’Connor as well as an appellate judge, I had been Editor-In-Chief of the Law Review at Yale, I just had every feather in my cap that I needed, and told myself, now I’m going to start over. I did not have a clip, I didn’t have a short story, I had nothing. So I went to the store and bought a book called, How to Write and Sell Your Nonfiction Book Proposal and I just followed the directions. Looking back on it now, I’m astonished. At the time, I think I was just like, “Huh, I guess this is what you’re supposed to do.” I don’t remember being that freaked out. Now, I’m just so impressed by myself that I did it! It’s unbelievable but I did.

That’s not to say there weren’t plenty of obstacles. It took me a while to get an agent. At one point I was told I had too many ideas! When I heard that, I thought Who has too many ideas? That’s just crazy talk. But I told myself, this is the process. It’s going to take a while. We’ve all heard stories like the one with Madeleine L’Engle, who submitted A Wrinkle in Time 26 times, so I was prepared for the idea that it would not come easily.

Even after multiple drafts of The Happiness Project, I remember my agent saying in the saddest, most kind voice, “I really wish I could say something different, but it’s just not there yet” and realizing that that was the kindest thing she could do because she pushed me. That was very hard, but I was convinced something was there; I knew that there was a good book there. I just was groping my way there. Structure. For me, it’s always structure.

An example of how listening to my intuition has helped me is…  observing the ordinary and trying to see patterns that other people haven’t quite identified. My favorite thing is when I identify something and people are like, “Oh my gosh, it’s as if my whole life I’ve recognized that about myself but now you’ve given me vocabulary for it.” Once you see the pattern, it’s absolutely clear. That’s my intuition. Like when a friend of mine once said, “I don’t understand it, because when I was in high school, I was on the track team and I never missed track practice so why can’t I go running now?” Every important bell went off in my head but I didn’t know why it was important. My intuition was telling me, there’s something really important going on, pay attention. Or when someone said, “I had such a great time training and running for the marathon but I haven’t ran since.” It took me months and months of thinking about it to figure it out, but each of these stories became important in helping me uncover what I now call the Four Tendencies. My intuition recognized when people say these things that somehow I think have a deeper significance or signs of something important.

My secret talent is… I think this goes back to the intuition. I think my secret talent, first of all, is recognizing when people say things that somehow fit into a larger pattern. I’m just constantly listening to people talk and reading all the time and trying to pick up these patterns of how people are alike and how they’re different from each other.

That’s what I love about my sister. She says these things constantly. I tell her: “You’re the sage, you just don’t know it. You need me to go ‘Oh my god, this is really important.’” Like when she said, “Oh, now I’m free from French fries,” I practically fell to the floor, I was like, that is the most brilliant phrase I’ve ever heard in my life. She says these things constantly: “Yes comes right away, no never comes.” “No one has an opinion until someone else has an opinion.” She has a million of them. Seriously, she’s a genius. I pick up on them.

A woman is most powerful when she…first off I don’t think men and women are all that different from each other. I think individual differences trump gender differences and that women often are overly focused on their being a woman as an explanation for things that I think are just part of their individual nature so that’s my two cents on that. But men and women, both, I think they’re at their strongest when they know themselves.

What I wish I had told myself when I was starting out is to be Gretchen. I wish I had spent a lot more time asking myself: What do I want? What am I interested in? What are my values? I just didn’t think about it that much, but today if I had to say what is my subject, I’d say it’s human nature. Happiness is a very important aspect of it and so are habits.

My favorite skirt is…from a practical standpoint, you don’t have to have the sound notifications on your phone turned on. People are like, ‘Well, what if it’s an emergency?’ There’s rarely an emergency. You just can glance at your phone every once in a while. It’s much more peaceful.

But in general, I would say that the thing that I’ve learned from Rebels is that we’re more free than we acknowledge. If I decided that I was going to wear only yoga pants for the rest of my life—even to my sister’s wedding or to my grandmother’s funeral or speaking in front of a thousand people—no one could stop me and it probably wouldn’t be that big of a deal. In big things and small, we just have a lot more freedom than we think. And that has been so powerful for me to realize.