Gretchen Rubin: Former Supreme Court Clerk, Author of The Happiness Project

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Author Gretchen RubinBitter Lawyer recently caught up with Gretchen Rubin, former lawyer who turned to writing and is now the best selling author of Forty Ways to Look at JFK, Forty Ways to Look at Winston Churchill, Power Money Fame Sex, Restatement of Love, and Profane Waste.

Her latest book, The Happiness Project, is an account of the year she spent test-driving the wisdom of the ages, the current scientific studies, and the lessons from popular culture about how to be happier. It just hit its 62nd week on the New York Times Best Seller list.

Law school and first law job?

Yale Law. I clerked for Pierre Leval on the 2nd Circuit and I clerked for Justice Sandra Day O’Connor on the Supreme Court. After that, I went and worked for FCC Chairman Reid Hundt as the advisor for broadcasting and cable, then I made the jump into writing.

Tell us about working for Justice O’Connor?

It was an amazing experience and incredible opportunity to be able to do that. Justice O’Connor is an incredible person and it’s an extraordinary institution of government, I really loved it.

Did you get to write any opinions?

One of things the clerks never talk about is what the process is.

So it’s like Fight Club?

Yes, just like that.

So, we’ll just assume you wrote all the important ones.

Yes, you can think that.

Did you always know you wanted to be a writer?

I have to confess; I’m kind of amazed at this in retrospect. I thought about it almost not at all. I went to law school for all the wrong reasons. I was good at research and writing and my father was a happy lawyer.

I told myself all the usual things, it’s a great education, I’ll keep my options open, I can always change my mind. So when I was there, I was like, oh I can do this next, and this next, and then this other thing. It was really when I was clerking for Justice O’Connor that I began to realize it was hard for me to envision a career in law. I just didn’t see a lot of things I wanted to do. I was also realizing I was surrounded by people who loved law. They were really good at it and they loved it. I could see I did not bring that enthusiasm to it.

So how did you transition out?

It happened in several stages, the first thing was I was walking during my lunch hour and I was looking up at the Capital bell and started thinking, if you were going to write a book that everyone in the world would be interested in, what would it be about?

It hit my like a thunderclap: Power, Money, Fame, Sex. So I felt compelled to start writing about that. I didn’t originally conceive of it as a book, but I wanted to start researching and investigating these things, which to me felt very unified.

So when I was clerking for Justice O’Connor, I was doing a massive amount of research, which I now know is my process. I was doing that in my free time, and it slowly started to dawn on me that this was turning into a book. It also dawned on me that this could be a career; this was something people did for a living. It didn’t have to be a hobby.

So did you quit right there?

I didn’t immediately leave. I worked one more year at the FCC, but all that time I was thinking I would not get another legal job. That I was going to somehow figure out what to do next. So I bought a book from the bookstore called How to Write and Sell Your Nonfiction Book Proposal.

At the same time, my husband—who was also a lawyer—started taking financial accounting at night at GW. We moved from DC to NY and we both stopped our legal careers at that point. He got a job in finance and I started working on the book proposal. It was easier to leave in tandem. It was also easier because everyone in my family was very supportive of my decision. At the moment where I had every feather I could possibly have in my cap, and I was starting over, everyone around me was willing to see me take a risk, did not discourage me from trying.

So you started writing the book and now you are on your sixth book. How did we get here?

I got an agent, which is in a way the hardest part of the whole thing and then just started writing books. I’ve been mainly a book writer. I do some freelance now as a consequence of the happiness project.

Can you tell readers something interesting about Winston Churchill?

He wore pale pink silk underwear. His daughter Mary Soames reported that. I had a military man email me with great indignation about that, and I was like sorry, buddy, it was his own daughter who reported that. A pretty reliable source.

Can you tell readers something about JFK?

He said his own best quality was curiosity and his worst was irritability.

I think about it with respect to happiness. It’s interesting because Kennedy was in terrible pain from his back; I think that’s not recognized enough. He said he started managing himself to keep him from being on the edge of irritability because so much depended on his decisions.

I think in our ordinary lives, make sure you don’t get to hot or too cold or too hungry or have a headache when you make decisions. Being uncomfortable or in pain makes you edgy or short or not thoughtful. And so, I think I can understand why he felt irritable, because he was in pain a lot.

What is the Happiness Project?

It’s an account of a year that I test drove the wisdom of the ages, the current scientific studies, and lessons from pop culture about how to be happy. I reported on what worked and what didn’t. And I have a blog where I write about my daily adventures in happiness and the pursuit of happiness.

Can you give us an example?

I divided the months into themes and what I could do in that area to make my life happier. The first month was energy, so one resolution was getting enough sleep; the other was getting rid of clutter. You wouldn’t think it is tied to energy, but it is. Another month was marriage. I decided to quit nagging. I knew that would make me happier and it definitely made my husband happier.

There’s a conventional wisdom that lawyers are unhappy as a group, what’s your take on that?

One argument is that lawyers are always trained to look at the negative. Either being belligerent or nitpicky, always looking for the negative.

Another big issue is that a lot of people go into not wanting to be lawyers. If you look at tax lawyers they really enjoy it. If you go into that, it’s because you have a certain kind of mind. They really like it, they seem happy.

But a lot of other people choose law as a default. If it were sound engineering and everyone went into without wanting to do it, we might have a ton of unhappy sound engineers. I think a lot of people back into it and don’t think it through and you’re not really making a choice.

I think there is a lot transition in the legal profession right now and that creates anxiety and then there’s the debt, which makes people unhappy because it limits their choices.

What job is a good default for everyone in the world?


The thing about happiness is that I truly believe you can only build a happy life of happiness on a foundation of your own nature and your own interest, your own values. The better you know yourself, the more you can make sure you life reflects your nature your temperament your values and if you accept other peoples choices and go with the flow, maybe it will make you happy, but maybe not.

You’re not mindfully choosing something that’s right for you. It’s very hard for you and it’s very painful to do. I did it that way, so I know exactly why people do it, I was right there. I do think the more you understand yourself, what you want, why you want, then you can figure out what to do about it. But just not dealing with it, it’s not a very useful way to approach it.

Can you give us a few simple happiness tips for lawyers?

Get enough sleep. Most adults need 7-9 hours. You cannot train yourself to get by on less. So don’t kid yourself.

Be active. That will do a lot of for your energy and your health. Make time for fun, its easy to push that to the bottom of the to do list. Have a little playtime. Real playtime. Not playtime where you just plop down on the couch and channel surf. If you’ve been looking forward to Downton Abbey all week and you race home to watch it that’s good, but if you too tired to do anything but watch bad TV, go to sleep.

If you had to pick one element to a happy life, I think ancient philosophers and contemporary scientists would agree its strong relationships. So do anything in your life that strengthens or widens those relationships. Go out to lunch with a friend or take 15 minutes to joke around with the lawyers on your floor. Don’t feel like that time is badly spent. You need to do things to strengthen relationships. Make an effort to go to weddings, baby shower or birthday parties. These things are important for relationships.

Tell us about the new book, Happier at Home

I decided that for me and for a lot of people, home is the foundation of happiness. There’s a great Samuel Johnson quotation: ”to be happy at home is the ultimate result of all ambition.” Whether or not you agree with that, it’s certainly thought provoking. So I wanted to do another happiness project but focused on home. So it’s narrower, but deeper than my other book was. It’s things like time, possession, body, marriage parenthood, and neighborhood and really on this idea of what your home is.

Since I started working on it, I’ve met people that say I hate my home. I think gosh, how can you live your life and hate your home? Then there are people that love your home. If you feel like you have that place to come back to you, I think you are a lot happier. I wanted to work on my experience of home, to make it feel happier to me.

Do you get any weird emails or requests from your readers?

Not really, but a Danish guy told me he got a tattoo of the Happiness Project. That seemed extreme.

Yeah, that’s kind of cool though. Three things you can’t live without?

Diet soda, my laptop, and something to read.

Book you’re reading right now?

I’m rereading A Tree Grows in Brooklyn by Betty Smith and I just read a book Punished by Rewards by Alfie Kohn.

Any last words for Bitter Lawyers who are trying to write a book?

There is a great book that a friend of mine wrote called The Creative Lawyer by Michael Melcher. It is a fantastic resource. If you are a lawyer and you want to add something to your experience, maybe you’re trying to figure out how to get into a different kind of career or just be happier in your career. It has some very practical ideas about how to do that.

How can you think about it in a way that’s practical but moving you forward? Sometimes you get this advice “be free, break out of the box, don’t let anything stop you” and you’re like I can’t do that it’s not realistic, so you feel paralyzed. This book walks you through your options and makes you feel like you have more choices, people really find it useful. It’s a short book, but really helpful.

Get your daily dose of happiness on Gretchen’s blog. And catch up with other successful lawyers, typically in alternative careers, with our Bitter Lawyer interviews.

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  • Guano Dubango

    Too bad this woman is already married. She has all the qualities that my Aunt Ooona is looking for me to secure in a spouse. I am not sure she would have moved back to Ghana with me to live with my Aunt Ooona. Oh well, as they say, there are other fish in the ocean. I just need a fresh one.