The Art of Boldness with Jennifer Cohen

The adage that great success requires a dash of boldness is true. Achieving anything significant often requires stepping outside your comfort zone. 

But for many, boldness feels like an elusive personality trait, something you're either born with or not. “Not so fast,” says Jennifer Cohen. 

The speaker, entrepreneur, and bestselling of Bigger, Better, Bolder argues that boldness is a tangible skill that can be developed through practice. 

“You don't need to be born bold,” Cohen says. “It’s like any other muscle: the more you work on it, the stronger it becomes. If you don’t work on it, it atrophies.” 

The idea behind building your boldness idea lies at the heart of her “10% Target,” a philosophy featured in her book Bigger, Better, Bolder. 

“The concept is to chase what you want, not just take what you get,” she says. “It's about making ten attempts at whatever you want most.” 

In other words, if you take ten shots at your goal, you only need one yes to accomplish it. That’s only a 10% success rate that stands between you and what you want. Even if you fail at each attempt, learning from each one will open the door to something new. 

“It’s exposure therapy,” Cohen says. “You’re teaching yourself to be desensitized or immune to the feeling of failure because you’re doing it so much.” 

Failure and rejection are scary at first, so few people go out on a limb to strengthen their ability to be bold. Cohen sees this as a good thing, as the mere willingness to show up and push through the discomfort ten times is an easy way to stand out (in a world where many don’t even take one attempt at the things they dream of).  

So, as you set out to try ten times to get one yes, how should you go about things? What’s the right way to be bold? 

“People often have this idea that boldness is about being brass, abrasive, and aggressive,” Cohen says. “There are many negative connotations attached to the concept, but I don't see it that way. A bold person is just someone who stands up tall and is deliberate about how they’re living their life.” 

Being bold means asking people to help you achieve your goals. Whether it's the hiring manager at a company you really want to work for, a boss you want a pay raise from, or that special someone you want a date with, boldness means explicitly asking for something you want. In her teenage years, Cohen even found herself asking Keanu Reeves to be in her demo tape for MuchMusic. Believe it or not, the movie star said yes, a story she recalls in her viral TedX Talk.   

There’s a right way to do this and a wrong way (hence why some may associate boldness with being brass and abrasive).  

“I'm not just saying, ‘Give me this’ or ‘I want that,’” Cohen explains. “Boldness requires an ability to read a room, understand others, and be curious. Don’t try to be interesting; instead, be interested in others. Learn what drives the people you’re talking to and course-correct your goals to align with theirs. That way, you’re not a bull in a china shop—you’re someone ready to provide value.” 

To illustrate this, Cohen recalls a time when she made a major career pivot. 

“I had a great job in marketing for a big record label,” she says, “but I was passionate about health, wellness, and fitness and wanted to become a personal trainer.” 

After quitting her job, Cohen turned to her former employer with an exciting idea. 

“I told him that even though I'm not going to be doing marketing, I'd like to now come into the label as a personal trainer to get celebrities and artists ready for tours and music videos.” 

Cohen aligned what she wanted with what she knew the label needed—and even offered to work for free the first month. 

“People ended up talking to me and liking me. One label turned into two, which turned into three—and I was able to create my own opportunity out of it.” 

Boldness is all about creating opportunity in places they once didn’t exist, standing tall as someone ready to provide value for others in pursuit of new goals. It’s a skill that’s allowed Cohen’s career to see massive success across a wide variety of industries—and it can have the same transformative impact on your own life. 

“If I had something I was interested in, I went for it instead of stagnating and taking what was in front of me,” she says. “Being bold is about not letting other people define what your destiny should be.” 

When you see an opportunity you want, Cohen invites you to ask, “Why not me?” There’s an urgency to this message because you only have so much time on this earth to pursue your biggest desires. 

“When people are interviewed on their deathbeds,” Cohen says, “nobody ever says or thinks about all the things that they did. Instead, they regret the things that they didn’t do. Rejection hurts, but you can move on. Regret is something that you feel in your gut forever. I’d rather have a feeling of rejection than regret. If you walk into every situation with that mindset, you will be bold.” 

Jennifer Cohen is available for speaking engagements. Her book, Bigger, Better, Bolder: Live the Life You Want, Not the Life You Get, is available here.