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Episode 26: The Fearless Chase with Madison Anaya

Madison Anaya shares how she chooses to fearlessly chase after who she was created to be by helping women creatives live with purpose, love their work, and make an impact. She shares hot tips on imposter syndrome, building her Fearless Chase community and what she did for her 20 seconds of courage challenge!

About Madison

Host of the Fearless Chase Community where there is a podcast, Facebook group, and events for millennial creative entrepreneurs She was on a path to living her suburban

dream, going to college, getting married to her middle school sweetheart. Between personal and family crisis Madison quickly realized that wasn’t what she wanted and set out to fearlessly chase who she was created to be on this journey whatever it was supposed to be. Now she brings together the best parts of business school and best friend sleepover brunch style and helps creative women build a life and business with purpose.

Who I Am is good enough

Knowing this comes up every couple of months. She can pinpoint pretty much the exact moment when she knew she wanted to finally take that leap of faith. MadisonI married her middle school sweetheart, doing the thing that she thought she was supposed to be doing. She didn't love it and had two very hard years of being and newlywed. A couple months after she got married, she totaled her car, and then a few months after that they lost her father-in-law to stage 4 cancer, and then a few months after that her house flooded in hurricane Harvey, and few months after that her mother-in-law got diagnosed with cancer, and a few months after that my parents got divorced and it was just like one thing after another. It felt like every two or three months something tragic was about to happen. She felt like everything happening to her right now most people deal with in lifetime and it’s smashing all together back-to-back within like 2 years for her. At this point, she was ready to do her own thing, but she wasn’t sure what her own thing was.

She came across Rachel Hollis on Facebook, read Girl Wash Your face and attended her Rise conference in LAX. She realized there was a space for personal development and hosting events, she was intrigued and wanted to go for it. She stopped going to school, and started a podcast called The Fearless Chase because she wanted to learn how other people had fearlessly chased after their own dreams and see if there's a common thread.

Routine of Courage

Madison’s definition of courage is seeing the fear and doing it anyways. She named her podcast The Fearless Chase not because she thought you will ever be without fear, but it’s choosing to move past it anyways on a daily basis. She doesn’t believe that we were created to live in fear, Different times when courage showed up for her Madison include choosing to leave school. She was a little nervous and chose to do it anyways. In order to kind of get in this routine of courage, she decided to take on this 20 seconds of Courage challenge that derived from a quote in the movie We Bought a Zoo. It’s something along the lines of “Sometimes all you need is need is 20 seconds of insane courage.” Madison decided if her dreams were outside of her comfort zone, she needed to get out of her comfort zone on a regular basis to get comfortable with being uncomfortable.

Imposter Syndrome

Madison has struggled with imposter syndrome since the beginning of her entrepreneur journey. Reframing in her head as being in training has helped her a lot with imposter syndrome. If you can look at it whatever you’re starting with you’re not an imposter, you're just in training then you will always be in training of your value and growth

One Way to Leverage Energy

Trusting and Letting Go

Interviewing Dave Hollis

Interviewing Dave was actually very early on when the podcast just started. She wasn't really struggling with imposter syndrome so much, she was just so nervous to mess up. It's not stemmed from ‘I'm not enough’ for ‘I'm not big enough for them’ to come onto the show, it's more so she wants to make sure that she asks all the right questions and serves her audience.

Hosting 1st Entrepreneur Event

It was not successful in the way Madison called it out to be. She decided she would really open up and see in a real time view of what it looked like. She called her shot and she was going to get 50 paid tickets. Each time someone bought a paid ticket, she would write their name on a sticky note and put it on a wall. She had 50 people in the room, but she didn’t hurt her goal. She thought it would crush her. She came out feeling successful even though that wasn’t what she initially thought success would be because she served her audience genuinely and authentically.


Choose to fearlessly chase after who you were created to be


“Comparison is the Thief of Joy”

Courage Song:

“Whole Lotta Woman” by Kelly Clarkson

Listen to songs on the Courage Up Playlist!


Fierce, Free, and Full of Fire by Jen Hatmaker


Connect With Madison


Connect With Ming:

Instagram: @mingshelby

Facebook: Ming Shelby

Listen to songs on the Courage Up Playlist!

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