Alumni Hub, Cover Story

From Broke to Bestseller: True Badass, Jen Sincero ’87

Mandy Bray ’09

A woman in a floral top and white pants sits in a cream-colored chair, holding a yellow book below her chin in front of a large window with a tree-filled yard outside.
Jen Sincero ’87, author of You Are a Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life. Photo provided by Sincero.

Bestselling author and speaker Jen Sincero ’87 had never seen a mountain before arriving at CC in 1983. Waitlisted at first, she called the CC Admissions office and talked her way into a spot that changed her life.

“I’d never been out west, I’d never been camping, I’d never even been hiking. So, my activities were learning about that kind of stuff and exploring the west and going on road trips,” she recalls. “I was on the volleyball team when I got there, but then I learned that I couldn’t go on Block Breaks if I was on the team. So, I quit. I had my priorities pretty clear at that point.”

When she graduated, Sincero knew she could write thanks to professors like James Yaffee. But she took the scenic route to the bestseller list. Marketing for a record company, playing in a band, and life coaching were all part of her journey – often simultaneously – to publishing You Are a Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life.

“I’d always had a pretty fun life, I was in a lot of bands and traveled a lot, and had all these great friends, but I just never could figure out how to make any damn money,” she says. “I started reading all the self-help books and getting into life coaching. I was reading all these books that were actually incredibly helpful, but none of them were funny or edgy. I thought, ‘Okay, I could write the hell out of a self-help book.’”

“I’m just blown away by how much Colorado College changed my life. I met so many of my lifelong friends the first week at orientation and we’re still thick as thieves. They’re my second family.”

Jen Sincero ’87

In 2013, You Are a Badass broke out of the vanilla mold and resonated with audiences far and wide. The book won an Audie award and hit number one on the New York Times bestseller list. Subsequent books include You Are a Badass at Making Money and Badass Habits.

Now a resident of Santa Fe, NM, which she fell in love with on a Block Break, Sincero has carried some CC habits into her writing career.

“I am still 100% on the Block Plan, much to my shock and sometimes horror,” she says. “I have written six books at this point, and I have literally written them in three and a half weeks, almost down to the hour.”

Sincero has coached thousands of individuals, in everything from book marketing to life coaching. The most common and rewarding scenario she’s faced is helping someone take the leap into entrepreneurship.

Book cover of You Are a Badass.

“There’s that scary empty space between taking your foot off the dock of safety and putting it somewhere else,” she shares. “My big thing is, if you’re not scared, you’re doing something wrong. You have to take the risk if you want to really transform yourself.”

In reflection on her time at CC, Sincero says, “I’m just blown away by how much Colorado College changed my life. I met so many of my lifelong friends the first week at orientation and we’re still thick as thieves. They’re my second family.”

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