Ossa CommunityPodcaster Interviews

From Corporate to Creative: Interview with Amanda Boleyn, Podcaster & Founder of “She Did It Her Way”

Do you have a career dream that seems too good to be true? Or an awesome business idea, but no clue how to actually get it off the ground? Have you ever felt stuck at your 9-to-5, feeling like sometimes you’re not seeing sunlight for days on end?

Amanda Boleyn can help. She is the founder and host of She Did It Her Way, a popular podcast that focuses on empowering women entrepreneurs to leave their comfortable corporate positions in the name of following their dreams. She knows firsthand that it can be a scary — but worthwhile — leap of faith.

Amanda is passionate about helping other women escape their unhappy careers because she’s been there herself. Amanda created She Did It Her Way to offer women access to resources like networking events, coaching services, and educational materials that can help them discover the freedom and fulfillment they are looking for in their career.

At first, Amanda started her podcast as a hobby. However, by connecting with fellow female entrepreneurs and building a strong community, she was eventually able to turn her She Did It Her Way podcast into a thriving full-time business.

We talked to Amanda to find out more about her background, her mission, and her podcasting journey.

Name: Amanda Boleyn

Company: She Did It Her Way

Podcast: She Did It Her Way

Job Title: Founder/CEO

Current home base: Chicago, IL

Originally from: Dubuque, IA

Helping people create clarity by getting them into action.

One thing on your bucket list:
Take my parents on an international vacation.

Quote/piece of advice that you live by:
“When you change the way you look at things, the things you look at change.” – Wayne Dyer

Personal Anthem:
Imagine Dragons – “Whatever It Takes”

A book or article you read in the past year that you recommend:
Atomic Habits by James Clear or Breaking the Habit of Being Yourself by Joe Dispenza

A woman in history you admire & why:
Ruth Bader Gingsburg, because of her willingness to continue to pave the way.

A present-day woman you admire & why:
My 92-year-old grandma. She taught me that the secret to life is just keep going.

What inspired you to start or join your current company/line of work?
I was a traveling freelancer and wanted to carve out something of my own.

How do you feel yourself making an impact and generating positive change through your work?
I love what I do everyday. I love the process of building a business.

What is one thing you have accomplished through your work that you are most proud of?
I’m most proud of the fact that we’re helping women see the world differently and showing them what is possible — to live a life of abundance.

What is one major work milestone that you would like to accomplish in the next year?
To launch our signature online course within the next 6 months.

What is one new project/endeavor you are currently working on that you are most excited about?
Next year’s She Did It Her Way Summit.

What do you see as one of the biggest challenges facing your industry today?
There are far more podcasts out there than there were when I launched my show in 2015!

What is one of the greatest challenges you have personally faced in your podcasting experience?
I failed to manage the podcasting process correctly. We uploaded the incorrect audio for a podcast episode, and it was live for 5 days before I found out. My mistake was that I only checked the episode’s audio on my website (where it was correct), and not on the iTunes app (where the wrong audio had been uploaded).

What were you doing before your current role?
I was a full-time freelance consultant working with large organizations around the world implementing sales, marketing, leadership development, and employee engagement training programs. I was working with employees, managers, and directors to create clarity in their organization and to figure out how to shift behavior and create work environments that facilitated success.

What is one of the best pieces of advice you’ve ever received & why?
To not major in minor things. It is only 20% of your efforts that drive 80% of the business. Make sure you’re focusing on the right activities.

What is one of the worst pieces of advice you have ever received & why?
I was told that in order to have a successful business you must work extremely hard and grind it out.

Can you tell us about a time when you took a huge risk/did something you were scared to do, and it totally paid off?
Hosting my first in-person event — the She Did It Her Way Summit. I remember the Thursday before the event, I was in total panic mode. I told myself I’d never do another in person event again. It was a big leap. We ended up having 35 women from 11 different states sign up and attend within a 3 months span. 2020 will be our fourth year hosting the event!

Are there any great personal or professional resources you love that you would like to share?
My favorite software is Asana (I have a free Asana training guide that you can download: (shediditherwaypodcast.com/asanaguide), Manifestation Babe Podcast, and Tony Robbins programs.

Fun fact about yourself:
My two favorite sports are soccer and tennis. I was in theatre all four years in high school. I’m a one on the enneagram personality model. I make my bed every single day, even when I’m traveling 🙂

For more from Amanda Boleyn and She Did It Her Way:

Website // Instagram // Twitter // Facebook

Back To Top