From feeling “off track” to finding her calling, Gretchen Rubin is proof that listening to your gut can lead to a happier life.
When bestselling author and happiness expert Gretchen Rubin joined Karen Finerman on the How She Does It podcast, she opened up about the winding path that led her from Yale Law School and a Supreme Court clerkship to becoming one of the most trusted voices on joy, habits, and personal growth. Here’s how she did it.
From Yale Law to the Supreme Court… to Starting Over
“I went to law school for all the wrong reasons,” admits Gretchen Rubin. It wasn’t until the Yale graduate was clerking for Supreme Court Justice Sandra Day O’Connor that she started to question her chosen path.
“ I did have a feeling that I was off track, [which I] can only describe as feeling on the side. I felt like [I was] not in the center.”
She said part of the issue was that growing up, she didn’t have a model for the type of writer she would become. “I thought at the time, well, you either wrote novels or plays or poems, or you were a journalist. Or you were an academic who wrote a biography of Samuel Johnson, and I didn’t want to do any of those things, so I didn’t really see a place for myself in writing.”
A Gut Feeling And A Bold Pivot
What Gretchen did love was research, a skill honed in law school, and during her time clerking, she became captivated by the topics of power, money, fame, and sex. She listened to her gut and came to the conclusion that, “I’d rather fail as a writer than succeed as a lawyer. So I should play my hand.”
She bought a guidebook called How to Write and Sell a Nonfiction Book Proposal, followed the instructions step by step, and began the long road of reinvention.
The Long Road to “Overnight Success”
It took Gretchen Rubin ten years and four published books before she hit upon the idea that would change her life: The Happiness Project. What began as a personal experiment, a year-long quest to increase her own joy, resonated deeply with readers.
The 2009 bestseller launched not just a writing career, but a brand: a podcast, newsletter, courses, and more. But while some called her an “overnight sensation,” Gretchen set the record straight: “I had worked for ten years to become an overnight sensation. Many people don’t even know that I wrote these other books.”
Becoming Her Own Kind of Teacher
Today, Gretchen Rubin continues to guide others toward greater happiness and self-understanding: whether through her books, her podcast Happier, or her ever-growing body of work. She’s not just a writer; she’s a teacher for a generation of women looking to live more fully, more intentionally, and more joyfully.
“They say, when the student is ready, the teacher appears, but each person kind of needs their own teacher,” she says.
And for many of her readers and listeners, Gretchen Rubin is exactly that.
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