Dare, Dream, Do: How Whitney Johnson Found Her Path
This article is the next installment in our “Finding Your Path” series. Over the next few months, our friends at 40:20 Vision will feature successful 40-something women sharing their stories on how they found their career path, and the lessons they’ve learned along the way.
Whitney Johnson, Author, Dare, Dream, Do; Co-Founder, President, Rose Park Advisors
Education: Brigham Young University, Magna Cum Laude, BA, Music.
First job: On Wall Street as a “sales assistant” (but it was really a secretary).
A surprising thing to know about you: I was born in Spain.
Favorite TV show? The Good Wife. Fairly Legal. Smash.
Background: No one ever told Whitney Johnson there was a time limit on dreams. But looking at her career path, you might have thought it an impossible one. A married woman starting her professional life at 30—with a music degree and a few years of secretarial experience—she was an unlikely candidate to be launching her own investment firm and her own nationally-anticipated book.
After spending two years as a missionary in Uruguay and another year earning money during college, Johnson graduated at 27 and moved to NYC with her husband. He was working on a PhD, and she got an administrative job to pay their bills.
But two decades later, by virtue of night school, determination, and daring to dream, she rose to become a double-ranked institutional investor, a contributor for the Harvard Business Review blog, and president of Rose Park Advisors, the investment advisory she co-founded with Clayton Christensen—all by her 40s.
When Whitney left Wall Street after 15 years, she had achieved the dream that began when she dared to go for the brass ring. And she thought achieving your dream was a rite of passage for everyone. Yet she soon discovered that many women don’t know what their dreams are. After hearing these women’s stories and dreams, she was inspired to write Dare, Dream, Do, a three-step guide that encourages women of any age to pursue their passions.
Read on for Whitney’s story on how she found her path—and how she’s now helping others do the same.
Did you always know what your dream was?
No. I majored in music at college because I was talented and my parents expected me to. By the time I came to New York City, I didn't want anything to do with music. My parents were the gatekeepers for my dreams until then. As the oldest, I always felt I had to get their approval, implicitly or explicitly. Because it was my parents’ expectation, they kind of inadvertently took the dream away from me, so it couldn't be my dream anymore. I think it’s really important that we let our children have their own dreams.
Was there an upside to these expectations?
I’ve thought about this a lot. On one hand, it was tremendously debilitating. But on the other hand, it gave me tremendous drive. I'm always trying to prove myself.
What was your first job?
Moving to New York was a catalyst. I had a music degree, I didn't know anybody, and I had to put food on the table. All I knew was that I wanted to be a professional and I wanted to use my Spanish skills.
I found a job working for a retail broker who did business in Latin America. I did that for three years, but there was something inside me that drove me to strive for the brass ring and get into the investment banking game.
It was a huge step for a woman at that time. What motivated you?
I sat next to a bullpen of 20-something guys—total testosterone. It’s basically a locker room with suits. They would yell, “If you don't open this account, you're such a girl." And I thought, just as I had in elementary school, “I'm just as good as these boys. I can play dodge ball just as well as they can. I want this!” That was the turning point for me. I think it was a combination of knowing I was smart (although lacking confidence), and being married to someone who believed in me.
What was the first moment that you felt you had made it?
I'd been an analyst for just one year when I was ranked #3 in Institutional Investor [a publication that recognizes financial analysts for their performance], which was really good. That was when I hit my stride, in terms of drawing on everything that I did well and finding my sweet spot.
Then I proceeded to be #1 for eight years straight, except for the year after I had a baby, when I was ranked #2. I thought, “Okay—I'm good at this.”
What did you learn on Wall Street that helps you now at Rose Park Advisors?
What seems like a step back may actually afford opportunities that aren’t stereotypical, and thus bigger. After having a child, I was asked if I wanted to move into equity research. At the time, equity research was looked down upon. Investment banking was the “real deal.” But the more I thought about it and talked to people, it felt like the right decision. As a research analyst, you have your own franchise and you’re backed by these huge firms. I ended up in a better position to intercept market conditions. It also was very entrepreneurial, so I learned that you have to wear different hats and you have to be willing to scramble.
What made you leave Wall Street?
By 2005, I reached a glass ceiling. I wasn’t going up, so I wasn’t going to learn more. I “retired” and began exploring entrepreneurial activities. I wrote a children’s book, a ton of business plans, backed a magazine, and did volunteer work with Clayton Christensen, with whom I eventually went on to found Rose Park Advisors, along with his oldest son, Matthew.
What was the inspiration for the idea behind Dare, Dream, Do?
Once I left Wall Street, I started interacting with the mothers in my community more frequently. These were well-educated women who had often chosen to be at home. I naively thought that everyone had a dream and went for it, but many of these women didn’t know what their dream was. There was this unspoken sense that it wasn't their privilege to dream. Dreaming was for their spouse or their children, but not for them.
Through this, and through my own process of embracing my mothering side, I came to believe that we achieve greater happiness when focusing both on our dreams and on other people in our lives. I think we lose an important piece of ourselves when we only do one or the other.
How did you actually get the book done while also building Rose Park Advisors?
At first, I started blogging to encourage women to dream and invite them to tell their stories. I didn’t think I could write a book, but then I realized that if I could pull their dreams out of them and edit them into a book, we would all have these marvelous stories. It’s my dream because it’s a combination of knowing how important it is to dream and being the encouraging voice that I always wanted to hear. Whenever I can actually help someone along with their dream, it makes me really, really happy.
What is the one lesson you would want to impart to 20-something women?
It is all very circuitous. Big decisions in life are not about conventional planning. They're discovery driven. If you don't know exactly what you want to be when you're 21, it’s okay. When you see these “30 Under 30” lists, you might be discouraged for a few minutes. But, in fact, many people don’t get where they are going early on. And if you are determined, you will eventually get there.
To quote C.S. Lewis, I would say, “Do not dare not to dare.” Make decisions that prop the doors of possibility open. When you have two paths and you're largely indifferent, pick the harder one. Your 20s is a time of getting doors opened. In your 20s you want to be broadening. Then in your 30s, you can start going down a path of narrowing.
Check out more from the Finding Your Path series at The Daily Muse!
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