A Game Plan for Adding Chutzpah to Your Life

In Jennifer Cohen’s latest book, “Bigger, Better, Bolder: Live the Life You Want, Not the Life You Get,” you can replace every incidence of the word “bold” with “chutzpah.” The “Habits and Hustle Podcast” host’s new book is a trove of anecdotes and actions you can take to add more chutzpah to your everyday life. Over its 16 chapters (among them “Discover Your Bold Type,” “Mediocrity is a Superpower” and “Fix It, Farm It Out, Forget It”), “Bigger, Better Bolder” follows Cohen from rural Canada to Los Angeles, through her many career pivots: personal trainer, entrepreneur, author, podcaster. 

The book begins during the early ’90s, when Cohen was a student at a Jewish grade school in Winnipeg, Manitoba, where she was belittled by a teacher who called her “average at best.” She takes up fitness as a career after unsuccessfully auditioning for an Israeli folk dance troupe in high school. The rejection and mischaracterizations as a youth led Cohen to a life of calculated risk-taking and self-affirmation. Some of the book’s most inspiring moments involve Cohen crashing the Montreal Just for Laughs comedy festival, working at the Olive Garden and her chance encounter with Keanu Reeves. They’re entertaining, reflective and comforting for anyone who has ever been stung by rejection.

The Journal spoke with Cohen about “Bigger, Better, Bolder” and her tips on creating an authentic and bold life:

Jewish Journal: How does being called “average at best” by a teacher as a kid fuel your boldness?

Jennifer Cohen: I would say that we were all fueled by whatever trauma or impression or limiting belief that we had as a child and react accordingly. We can either react in a positive way that helps push us towards success and greatness, hopefully. Or it could take us down a bad rabbit hole of negativity, unworthiness. I chose to use things that I thought were negatives as fuel to push me and propel me. And because of that, I think I have a little chip on my shoulder for myself where I have to prove to myself that I am worthy or better than, and not let self-doubt dictate my destiny. 

JJ: What’s a phrase you want your readers to stop saying today?

JC: ‘I can’t’ or ‘I’m not good at …’ As you get older, you say to yourself, ‘well, I’m so bad at technology. I’m terrible. I can’t do it.’ It’s a self-fulfilling prophecy. The more you say it, the more that’s what you actually become, right? You can get better at anything, but if you start with ‘I can’t’ or ‘I’m not good at,’ there’s nowhere to go. 

JJ: Who are some of the boldest people you’ve ever collaborated with?

JC: Jesse Itzler [the co-founder of Marquis Jet, which sold seats on private jets] is super bold. He keeps on recreating. He’s a serial entrepreneur— he has an idea and he just goes for it. He’s very positive and he always thinks of how things can work out. He never rests on his laurels. He’s failed a lot, but he doesn’t let those failures keep him down. He just keeps on creating new things and he brings such enthusiasm. And so it’s such an infectious enthusiasm that it gets people to want to be around it and elevate and help and to be a part of something. 

JJ:  Can the average person be bold on a budget? 

JC: You don’t need money to chase a job or the company that you have interest in working in, instead of just checking LinkedIn for what jobs are available. Most bold moves don’t require money. What requires money is very different. What also happens a lot of times is people who have made a lot of money end up being less bold because they feel like they don’t put the effort as much into certain things.

JJ: What are the most common early roadblocks when setting out to live boldly?

“I don’t see failure as failing. It’s just something I tried and it didn’t work out. And then I will either try again or pick myself up and try something else.” – Jennifer Cohen

JC: We ourselves are our worst roadblock. We tend to hold ourselves back more than anything or anyone. Failure is such a part of life that you have to learn to become immune and desensitized to what failure is and reframe what failure means to you. To me, failure is just an attempt. It’s one attempt at trying something. It’s two attempts at trying something. It’s three attempts at trying something. I don’t see failure as failing. It’s just something I tried and it didn’t work out. And then I will either try again or pick myself up and try something else. But people get really stuck on the word and the idea of what it is, and then they let themselves spiral out of control.

JJ: How do you tune out the noise?

JC: Other people are too busy worrying about themselves — they’re not paying any attention to you. It’s your own self, your self-esteem and self-doubt. When people don’t want to go to the gym because they’re intimidated by other people, do you think those people are paying attention or looking at you? They are looking at themselves. They’re taking selfies of themselves. They’re lifting up their shirts, trying to see if they have abs. They are so not even remotely interested or curious or even looking in your direction. And that’s really with anything in life. When people have these big catastrophes in the media, people pay attention for a day, two days, and eventually it goes away because people’s memories are very, very short.

JJ: How does social media get in the way of boldness?

JC: So social media has amplified the comparison game where we compare our success based on somebody else’s success, we end up feeling worse for ourselves. There’s a lot of that happening in the world today. So you have to be very cognizant and curate the people in your life that you know personally— a board of directors who want to see you succeed, who are like-minded. Who do you look up to? Where do you get your information from? How are you building your self-worth? Are you looking at people that are making you feel good about yourself or making you feel bad about yourself?

JJ: What (besides buying your book) are three bold things our readers can do today after reading this interview?

JC: People think that you’re either born being bold or not, and that’s simply not the case. Boldness is a skill that anybody can get better at. And this can be as small and minute as when they go to a restaurant asking for salad dressing on the side. If you are not comfortable asking for a little thing in life, then you’re never going to be comfortable asking for a big thing. Another thing is you can call your cell service provider and ask for a better package than you have right now. Don’t just acquiesce to whatever is in front of you and let other people make your decisions. If you don’t create a routine, you will be assigned one. If you don’t create a purpose, you’ll be assigned one. If you don’t create a career, you’ll be assigned one. So people are too quick to adopt the structure that somebody else created to ease life’s uncertainty. 

You can buy “Bigger, Better, Bolder” and listen to the “Hustle and Habits Podcast” on her website, www.jennifercohen.com