Does Fortune Truly Favor the Bold? Listen to Find Out

Jenna Kutcher 

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January 9, 2023


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Fortune favors the bold. Have you heard that phrase? Do you believe it? Jen Cohen has seen the evidence of this concept in action. In order to really benefit from it though, you need to discover your own form of boldness, and Jen can help.

She is the speaker behind the viral TED Talk, “The Secret to Getting Anything You Want in Life”. Jen Cohen has made an impressive career as an authority in health and fitness, a motivational speaker, a chart-topping podcast host and more… And there’s one common theme throughout all of these career milestones: Choosing boldness and going after the life she wanted, not the life she was given. 

In this conversation, Jen and I will explore what it means to be bold – because it’s not just taking risks – and how you can level up your failures and turn them into your greatest strengths. We talk about mediocrity and the big, bold move she made that got Keanu Reeves to call her back… You have to hear this story!

Average and Mediocre

Earlier in Jen Cohen’s career, she identified herself as, “average, even mediocre,” she told me. “I really kind of failed a ton and so I got kind of immune to it. It didn’t really affect me or bother me as much.”

But being average and failing frequently actually proved to be a benefit to Jen. She explained, “When you are average and when you are mediocre, you have to learn to be resourceful and that’s a blessing and it’s served me very well in my life. A lot of times if you’re great at everything, you can just rest on those laurels and I didn’t have that luxury and most of us don’t have that luxury.”

Mediocrity can be your biggest asset. Jen said, “If you are someone who, if you feel that you are just average and not special or great in something, or not talented in one particular area, great. That’s amazing because that’s how you’re gonna flourish and that’s how you’re gonna shine.”

Ditch Self Doubt

Jen and I talked a lot about self doubt and how it can tank our biggest dreams before we even go for them. She said, “The self-doubt that we all fear and feel is what holds everyone back. That’s the number one reason why we don’t go for the job that we want, we don’t go for the guy or the girl that we wanna date, and we end up living a life that’s ‘good enough’ and and acquiesce to what’s in front of us as opposed to chasing what we really want.”

Jen says we need to reframe how we think about ourselves. She shared, “You may not be good enough at anything yet, but I really believe, and I’m an example of this, you don’t have to be the best. The people who are the best aren’t the ones who actually win at the end of the day. It’s the people that try.”

“It’s about acting, practice and movement. There’s something about momentum, right? Something in motion stays in motion, but you have to start doing it,” Jen continued, “And like anything else, start small.”

She put that into context, saying, “The boldness that I’m constantly preaching is about stop overthinking, stop thinking that you’re not good enough. You just have to think, ‘let me just try it. Let me just go after it. Let me just do a little bit here. If you’re someone who needs to be bold, you can start by doing little things, so you can get comfortable doing the big things.”

Press play to hear the example about calling your cell phone company and how it makes for great practice at being bold.

What’s the Worst That Could Happen?

When Jen was 17-years old she dreamed of becoming a personality on Much Music (kind of like the Canadian version of MTV). Press play on this episode to hear about the big, bold move she made that involved writing her phone number on a gum wrapper for Keanu Reeves… And how it actually helped her get close to this big dream. 

Though she didn’t ultimately get the job, she did get the audition and was a runner up. Jen said, “And the reason why I’m saying this is because you miss a one-hundred percent of the shots that you don’t take, and you don’t know what you don’t know.”

That bold move, handing over her phone number to a big celebrity who thought she just wanted an autograph, was a pivotal moment for Jen. She shared, “It proved to me that boldness is a much stronger indicator of success than being smart, than being talented. If I had too much experience and I was too seasoned and I knew too much, I would never have even made that shot.”

Think of it this way the next time you’re on the verge of making a bold move: What’s the worst that could happen? The worst thing that would happen is you would be no better or no worse off and could go back to doing what you were doing before the big bold move. That’s not so bad, is it?

More from Jen Cohen

Pick up her new book Bigger, Better, Bolder wherever books are sold and tune into her podcast Habits & Hustle for more from Jen Cohen.

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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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