SDH 188: Following Your Fears and Feeling all the Feels with Jen Sincero

How many times have you heard us and other entrepreneurs on this podcast rave about Jen Sincero'sbook, You Are a Badass? Isn't it about time you guys heard from her yourselves?

Well today's the day She Did it Her Way listeners! We've gotten Jen, author of You Are a Badass and You Are a Badass at Making Money, on the podcast today! We are so jazzed, to quote Amanda, to share with you her journey towards becoming a successful author and a life coach!

Jen's entrepreneurial story started when she was in her 40s, and after living a good life for a while as a writer and a musician, she was still broke and living in a garage. She knew she had ample amount of talent, but could not understand why money just seemed to evade her. She didn't really have a wake-up call or epiphany moment, she just got really tired of living below her potential. She knew that she was capable of more, and couldn't watch herself waste her gifts anymore.

She decided to swallow her pride and look for some financial guidance. She started reading self-help books, going to coaching seminars, started her online coaching business, and writing books. However, it was a life coach that she met at a coaching seminar that had the greatest impact. With her fee being a quarter of Jen's annual income at the time, she took a huge risk by hiring her. But Jen connected with her story, because she too had lived the life of an experienced broke person, and was now making six figures by just helping people. Terrified, she took out another credit card, despite her debt, and was all in. She did everything she told her to do and soaked up as much guidance as she could as she helped her with coaching business for writers.

Through the process, she learned to get over the negative stigma involved with focusing on monetary gain. One exercise she repeats in both of her books is writing a letter to money as if it were a person. This helps people get over their fears of being judged for focusing on money, and bring money into a relatable mental space which makes it easier to obtain. For her, the letters revealed that she felt like money wasn't available to her, and was the root of a lifestyle she could never see herself being a part of.

As she grew her business and projects, she also found that her fears around making money stemmed from losing a source of affection from her father. One way her dad would show his support and love for her was throwing her $20 or $100 dollars every now and then. If she made a lot of money, she felt that they would no longer have that connection, and outshine her father.

What led her to this notion was when she wanted to work with a life coach she really respected, and that cost $85,000. To even be in the head space to consider spending that much money made her think about her father, who was an Italian immigrant.  She pictured him in his yellow vee neck sweater, with his hands in his pockets, staring sadly at his feet because he felt he couldn't take care of her anymore. But she had to move past that thought, allow herself to prosper, and realize that her dad would always see her as his little girl who needs $100 bucks once and a while.

Through it all, she has learned to disprove her excuses and learn to love the thrill of living outside of her comfort zone. She has also learned to love herself and help others learn to love themselves as well, by reminding readers at the end of every chapter of her book. She knows how easy it is to be hard on yourself and feel as though success is equated to perfection. So she reminds readers, and herself, that there is beauty in our flaws and we have to be okay with things not being perfect; whatever the hell that means, as Jen would say.

Hear more from Jen in this week's inspiring episode!

In this episode you will...

  • Learn to become savvy about making money and live up to your potential
  • Get over negative connotations revolving around money
  • Find out where your fear of money lies and stems from
  • Remember to love yourself
  • Live outside of your comfort zone, and do things that scare you
  • Begin to realize your excuses aren't true


"I just got so freakin' sick of hearing myself talk about being broke...and not just sick of struggling, and scraping by...but more importantly...I knew in my soul that I could do better. And the fact that I wasn' just got too excruciating... And that's when I made the decision to get some freakin' help. To do whatever it took to learn about money...and really go for it in a way I had never gone for it before." -Jen Sincero

"We're all struggling, we're all doing our best, and the most important thing is to just get in the game and go, and not wait until everything's perfect [and] you're 100% ready...just do it who cares." -Jen Sincero

"Do something that scares the living crap out of you every day, and that moves you in the direction of where you want to be...if you really want to change your life, you had better be scared. If you're not scared you're doing something wrong." -Jen Sincero
"That commitment to our excuses as opposed to that commitment to really gotta be open if you want to grow. You gotta be available to be wrong, which is what we hate...but to be right about our excuses is very important to us. And when we'd rather be happy than right, then we open up a whole new world of possibility." -Jen Sincero


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Amanda Boleyn