A Conversation with Gretchen Rubin on Success & Happiness

Four years ago, a friend sent me The Happiness Project, by Gretchen Rubin, author of several books, blogger at her popular blog, and co-star with her sister of the podcast Happier. I was going through a rotten time in my life, feeling like a failure, and the book took me by surprise. It inspired me to apply Gretchen’s idea of studying happiness to the question of how I could redefine success. I began reading up on the topic and blogging about it. A few weeks ago, I had the opportunity to sit with Gretchen Rubin  - in person - and ask her about success.

The New York Times described Gretchen Rubin as “the queen of self-help.” That’s a darn good moniker. I myself think of her as “the Martha Stewart of happiness.” Like Martha with her practical advice to create the Good Life, Gretchen tackles practical ways to create the happy one. But she’s a lot wonkier, i.e., more intellectual, than Martha. I had the good luck to review her latest book, Better Than Before, which is all about habits and how they contribute to or detract from happiness. She’s great at illuminating home truths we take for granted – for example, if something is easy to do we are more likely to do it.

However, her particular genius is breaking down complex ideas into practical, useful tips. She eschews deep introspection. We couldn’t be more different. If I have a genius, it’s for existing in a state of conflict or ambivalence, and examining all facets of it. Then making fun of myself.

What is success? What makes you feel successful? And how can you tweak the definition so that you can feel successful even if you actually, well, fail? These are the questions that led me to the small office at Politics and Prose Bookstore in my hometown, Washington, DC, sitting at a round table with the Queen of Self Help. She was generous with her time and her enthusiasm*, and offered some interesting ideas for me to consider, which I am now passing along to you, Readers.

Although before I get to the good stuff, let me just come right out and say this. I learned the hard way the first rule of interviewing, which is as follows:

Shut up so your interviewee can talk.

Okay, I’m no expert, so I don’t know if this is the first rule, but it should be. I tell you this after listening to the recording of my conversation with Gretchen Rubin. She talked, she responded, but oh my, so did I. Yes, I was aware, even as it happened, that she was drawing ME out, and yet still I talked on. Was I afraid of silence? Maybe that was it. Maybe that she herself was interested in probing ME was gratifying. That probably contributed to my blathering. Nevertheless, our conversation was revealing.

I told her I write a humorous blog about redefining success triggered by a midlife crisis.

Me: How do you define success? Do you see a connection between happiness and success?

GR: Well, it’s an interesting question, because what does it mean to be a success? I guess I don’t think about it very much.

Me: All the successful people that I’ve talked to say that. Because it’s not like they started out to be successful.

GR: Right. Because that’s sort of a general term. Well, that’s one thing I think about it. Like with happiness, it’s much more effective to think about very concrete things you can do rather than to think about vague goals. If you think about being successful it feels overwhelming, and like, well, what would that look like? Which probably for some people would be, 'I’d lose 30 lbs., I’d get a promotion, my kids would get into a great college.' It could take over every field of life. Instead of thinking, 'These are my three things I want to tackle and that’s what I want to get done.' It’s an interesting question.

Me: My [initial] definition [of success] I always considered was the standard definition, at least for someone who is college educated: You get a degree from a good college, you get a good job, you move up the ladder. You have vacations and a home and your kids go to good schools and it continues. But I didn’t take that path. Eventually, I thought, well, where does that leave me?

GR: So how did you deviate from that path?

Me: I became a writer, and a person who took jobs to support the writing.  As opposed to - well, I considered law school, and I became a teacher for a while. There were other things that went into it. I became a full time mom. I felt like I veered off the path. For a long time I was close enough to the path that I could still see it and I could get back on it. But eventually I got to a point where I was nowhere near the path.

GR: So what precipitated the midlife crisis?

Me: Well, I was trying to find an agent for my second novel. I tried 39 agents. I didn’t have enough of a platform.

GR: Is that what they were telling you?

Me: They didn’t use that word so much at the time, but as a debut writer, without a journalism background or some kind of background that would bring guaranteed readers, it was hard to sell my book, even though the feedback I was getting on the writing was good. My husband is a doctor, he was doing his residency and fellowship at Mt. Sinai, and then it was time for him to get his first job and we had to leave New York City. And suddenly it hit me: you decided to be a writer and a mom, and therefore you are a single income family. And it came to me that I hadn’t given a lot of thought to what were my goals in life and how I was really going to achieve them, as opposed to sort of just drifting along.

GR: I talk about drift a lot. Making a decision by not deciding. Or going along because you want to avoid conflict, or you don’t want to disappoint somebody, or you don’t want to face uncomfortable truth… So how long ago was that?

Me: That was six years ago. We moved to the suburbs of Albany because my husband got a great job. And I’m a writer, so my work is portable. And I was writing a blog -  Because my friends in New York wanted me to write about moving to the suburbs - it was so exotic to them.

GR: Right! Driving every day!

Me: Now I’m talking the whole time and it’s not you!

GR: No, no, it’s so interesting. I feel like I haven’t thought about it [success], in a way. One of the things I’m thinking is that there are a lot of ways to be successful. I always say that to people when they’re waiting for their books to come out. For example, when your book comes out - there are lots of ways for a book to succeed. There are a lot of hopes and dreams attached to when your book comes out. There are many ways for a book to succeed. There’s not one way to succeed.

Me: Right. Well that was part of it [the impetus for me]. You have to figure out how to live your life and feel successful even if you don’t get published.

GR: It sounds like what you’re bringing up is how do you feel like a success when things aren’t necessarily turning out the way you want them to turn out.

Me: Yeah. What I finally have come up with, something I can look at as an umbrella - and I do have specifics you can do to help you feel successful, and that’s where I think happiness and success overlap -  is that success is like light. Light is a particle and a wave. And success is outcomes or achievements, but it’s also process.

GR: Yes, yes, that’s a hundred percent true. When you enjoy the process the outcome doesn’t matter as much. It still matters, but it doesn’t matter as much. I think of this haunting conversation I had at a New Year’s Eve party. The guy sitting next to me at dinner was a seventh year associate at a law firm. And he desperately wanted to make partner. They had just bought a new apartment, they had two kids in private school. And he hated his job. He hated his job so much. I’ve never talked to anyone who hated his job so much. And the thing about making partner is it’s like the old joke about finding out you’re the winner of the pie-eating contest and the prize is more pie. Because it’s not like you work less [being partner].  I’ve never met a man more trapped. Because he desperately wants something that he desperately doesn’t want. Either way he loses. I said, ‘Can’t you just escape this cage that you have put yourself in?’ And he just refused to believe he had any volition in it whatsoever and that every decision he had made had put him there. That they lived in an apartment that they otherwise couldn’t afford. That his children went to school that they otherwise couldn’t afford. Everything was predicated on this job he hated. There’s no way for that guy to succeed.

Me: A lot of people would say he is successful. But he doesn’t feel successful.

GR: No. It was the worst. It was like being with a dementor. If he didn’t become partner, everything would be a horrible waste. He would have wasted seven years in this job he hated and he would still be out there involuntarily trying to make partner. But if you enjoy the process, then it doesn’t matter as much.

Now, one thing, though, I wonder. Sometimes we wish that we didn’t want the things that we want.  Do you think that maybe you don’t think you should want the life you have? Like to say I want to be a full time mother is not acceptable?

Me: Yes, definitely. I’ve talked about the shoulds that are imposed on you and that you then impose upon yourself. And something like being a parent is kind of low status, so if you feel you should be doing something that has status, but then if you’re happy to be mother and write a little blog — I mean, I have a really good friend - we were writers in college — and she said her nightmare was that she would grow up to be a middle aged lady who sends wonderful, entertaining Christmas letters. And at the time I thought, Yeah, that’s a terrible thing. But now I think, is it that awful?

GR: A friend of mine was dragging her daughter to some speaking engagements. I was saying to her does your daughter want to go? I mean, my daughters would never want to go hear me speak. She said, ‘Well I think it’s really important for her to see that women can have jobs.' And I was like, that is not going to be your daughter’s problem. Your daughter’s problem is not going to be that she feels that it is wrong for her to have a job. Your daughter is going to feel much more pressure not to choose to be a stay-at-home mom. That’s the reality of it now.

Me: Yes, because the message of feminism from the 80s was really all focused on work. Also part of it for me was lack of self-knowledge when I was younger. I mean, my parents both worked. My parents were both lawyers. My mother’s satisfaction came from her job. So I thought I would be working full time and have a nanny and my kids would kiss me good night and go to bed. But in the end that was - actually, my mother died. That was my stepmother - my mother died when I was a toddler. So it was pretty obvious that I was going to have a strong attachment to being with my kids. If I’d thought about it. If I’d known myself better.

But yeah, it’s not considered high status. So I think that’s part of it. Having a hard time accepting that the things I wanted to do were ok. You’ve never had that? [accepting that what you want to do is not ok?]

GR: I had that to some degree and that’s part of why I went to law school. I always wanted this feeling of legitimacy…And it’s funny because my sister, who knows me super, super well, when I was thinking about becoming a writer and wondering if I would feel legitimate, my sister said to me - this was when I was clerking for [Supreme Court Justice] Sandra Day O’Connor, - ‘Well, tell me, do you feel legitimate now?’ and I was like, ‘NO!’ And  she said, ‘Look, face it, this may be part of your personality. You may never feel legitimate so don’t use it as a basis for making decisions. It just may be this thing about you.’ And I thought, that’s so true. I can just ignore this part of me.

Writing is tricky, too, because there’s this element of luck to it that both gives you hope but is also very distressing.

Me: Right, but when you write and you get in the flow of things, in flow…then it’s very satisfying.

GR: Right, then it’s very satisfying. But in terms of what book does well and what book doesn’t do well. There are great books that nobody reads. There are terrible books that everybody reads.

(More musings on the mysterious ways of popularity followed.)

GR: So what’s your big takeaway about success? Do you have a thesis?

Me: My big takeaway is to have a process, a thing you’re doing, just to keep going. So if the creative cycle or part of it breaks down, you have other things in place. So - I know you’re not into it - but mindfulness or some kind of centering activity. There is the whole piece about working with your brain. There is so much in cognitive behavioral science that helps you shape yourself. So working with yourself that way.

Note: I really flubbed that answer on the articulamometer. I could have talked again about success being like light - achievement, but also process - and enumerated my process better. Alas, I did not. I was aware that we were running out of time before her talk.

GR: Another one is multiple identities, which I’m sure you talk about. If you’re only identified by one thing then your success or failure there matters totally. But if you have multiple identities then you’re like, ‘Well I got fired from my job, but I’m head of the PTA, or I had a big fight with my co-head of the PTA, but I can go to my spin class and everyone things I’m great.’ That’s one thing I really liked when I went from being a writer, to a writer and a blogger, to a writer and a blogger and a podcaster. You do feel more secure in your identity, because it’s not all in one avenue.

Me: Do you think that’s a female thing?

GR: No, I don’t. You know what I think? I think women way over-attribute things to being a woman. I think a lot of it is human nature. I know so many women who say, 'Why do we women feel this way?' Well, have you asked a man if he feels this way? Because I think in some ways they probably feel less free. Does your husband feel he could be a stay at home dad and tell you to make a living for everybody?

Me: I don’t know.

GR: Because I think some men would take that deal and they feel like they can’t. Some men do anyway, and they are smart because they pick women who are up for that.

Me: I mean, he’s a doctor, but he loves to sing. So, if he’s having a crappy period at work, is he going to say, 'I’m a success because I sing well?' I mean, I don’t know. He might say, I’m a pretty good dad, or my marriage is okay.

GR: Yeah. Well, maybe because he’s in an intense job he doesn’t put a lot of value on it [those other things], but there are probably people who are like, ‘I’m the choir master of my large congregation and we give multiple concerts throughout the year and I’m seen to be doing a good job, so that identity is important to me.’ Some people maybe over-identify with one identity. Like parenting. I think for some people that’s a super important part of their identity. For other people, not so much. And I think that probably shows up in their parenting. If you just don’t think it’s that important to be an excellent parent then….And sometimes you can be too invested in something…

Me: Do you think that you need to be successful to be happy?

We are interrupted by the promoter of the event who says it’s time to start.

GR: What were you saying?

Me: Do you feel like you need to be successful in order to be happy? In the sense that, if you look at our need for autonomy, mastery, and purpose, in something that you do in your life. So there’s the element of struggle, there’s the element of reaching for a goal —

GR: Atmosphere of growth. Right.

I had a boss who told me ambitious people could never be happy. I don’t think that’s true. But I got his point. I don’t know. Is a feeling of growth and mastery important? I guess I have trouble with the word “success” because the word success can encompass so many things. So is a pursuit of your own goals important….? 

The event’s announcer signaled that it was really time to start.

GR: Oh, okay, I’ve gotta go. Anyway, This was so fascinating. You’ve given me so much food for thought. I’m going to have to ponder all this.

And she was off to give her talk on Better Than Before. I wished for another few minutes to discuss the link between happiness and success, but I was thrilled to have had such an interesting conversation.

* Gretchen Rubin did me a big favor by granting me this interview. I was very pleased to discover that her segment, “Try This at Home“ on her Happier podcast #50 recommends asking someone for a favor. Specifically, if you want to build a friendship with someone, ask a favor of them. People like to do well by others, and the theory (credited to Benjamin Franklin, the original American self-help guru) is that by putting yourself in someone else’s debt causes them to look kindly upon you. She also talks about how granting a favor increases your happiness – as well as the happiness of the favor-requester. So any lingering guilt I felt over asking this favor dissipated. You should check it out! Thank you again, Gretchen!