I’m Amanda Boleyn and I want to share my story with you. 

The short version is I spent two years in Corporate America before becoming a full-time freelancer turned into a full-time business owner.

I turned my hobby into a full-time business.

When I started She Did It Her Way it was just a podcast.  

Now because of what She Did It Her Way has grown into I get to coach women who are starting businesses and who left their corporate job to pursue their business full-time. 

Okay, now for the more in-depth version… 🙂 


I went to the University of Iowa (I was born and raised - Dubuque, IA), majored in finance and got my entrepreneurial management certificate (it was like having a second major but without the title). Between graduates and undergrads, there were on average about 30,000 students at any given time. I LOVED going to a BIG 10 school.


College wasn’t difficult for me but it wasn’t easy. I was a terrible test taker, didn’t know how to study and my skillset was always learned through doing, which I do believe has helped me be a better entrepreneur because I’m less afraid to make mistakes, but it didn’t always help with my gpa 😉 

Upon graduation I received a handful of job offers but accepted the one from Target to work in one of their stores. (NOTHQ in Minneapolis). I accepted the position and started 3 weeks after graduating. I moved two hours west of Iowa City to West Des Moines, Iowa where I’d begin life post college.

Um, and let me just say, there should be a school dedicated to helping students transition to real life. Can I get an amen?!



I started out as an Executive Team Leader in a Super Target (65 million dollars in volume) and I was in charge of the soft-lines department (Ready-to-wear, men’s baby, girls, boys, shoes, and accessories).

I had 4 direct reports (team leaders) and my role was to ensure all operations ran smoothly (easier said than done).

That’s me (to the left) with the other three new Executive Team Leaders! Meg, the second one in from the left, has become one of my best friends! She stood up at my wedding last August and I get to stand up in hers this December.

Working at Target was no joke. The four of were selected out of an applicant pool of 1,250+. I don’t think I quite knew at the time when I started what was in store for the next year (no pun intended).


At the time it was a pretty cushy job for a recent graduate, Target offered great salary, benefits, and upward opportunity within the company. Within the first 6 months I was considered on what was called the HIPO track (high-potential) where they intentionally groom you to have your own store within 2-eighteen month rotations.

I was on track to be running my own store by the age of 25 making a six-figure salary.

Nine months in I increased my initial salary by 20% through a bonus and passing my pay grade interviews due to my performance and ability to manage talent. More on that in a moment. But you can imagine how proud I was, excited, and determined.


Yet… I was majorly conflicted. When I started I was placed in a bottom performing store and my department was the bottom performing department out of all departments within the 11 district stores.

It was the most challenged I had ever been in my short 23-year life at that point. I started coaching and performance managing 3 out of my 4 direct reports immediately when I started. I was working easily 60 hours a week if not more depending on the time of season, working every other weekend and every other holiday. I’d go days without ever seeing the sunlight. I’d arrive to open the store before the sun came up and left after the sun when down. Shutting the door to my office and having a good cry became the norm. 

I found myself countlessly with one foot on the boat and one foot on the dock, should I stay or should I go. Until one day, after working 13 days out of 14 days, on a Monday, I found myself at my kitchen table listening to a sermon from the previous weekend because I couldn’t make it in person. Tears started streaming down my face. I broke. I had hit the breaking point of no more. It was then that I knew it was time to move on.


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The month of June was occupied with finding another job, one that would help me create margin in my days that would allow me to explore what it was I really wanted to do with my life. 

In July I went to Succeed Faster, a conference my mentor Adam Carroll had put on at the time in Chicago. Succeed Faster couldn’t have come at a better time. It was the weekend in between me ending my career at Target and starting my new one at Wells Fargo. 

I feel like this would be a great time to include that when I worked at Wells Fargo, it was actually through a third-party agency. When I left Target, I took at 20% pay cut, lost all benefits including retirement and PTO. I supplemented my income by working at a local gym which allowed me downtime to read, get a free gym membership and make money.

That leap (from Target to Wells Fargo) was actually scarier than leaving corporate altogether because it was the first step in truly pursuing my dreams and getting uncomfortable.

Okay back to Succeed Faster. While there I met a gentleman by the name of Chad Carden who’s whole business is employing 1099 contractors to fulfill his client projects. His projects consisted of facilitating and coaching sales, leadership development and employee engagement training within large organizations across the country.


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Chad and I had stayed in contact since we met at Succeed Faster. I had expressed interest in learning his business and being a potential resource for him.

The big moment came at the end of April 2012, when I got a call from Chad and he told me about a project he had working with att inside their call centers. Without hesitation I accepted the opportunity to fly out to San Diego and be part of the Train the Trainer (this is where facilitators and trainers learn the material to then go out into the field and roll it out). 

Over the course of the following 6 years I had the opportunity to work alongside brilliant minds, engage with fantastic clients and travel the globe.

I’ve facilitated sales and communications training for JP Morgan, “Analyst to Associate” program, leadership development for health care facilities, new program training for Weight Watchers. I’ve emcee’d and facilitated breakouts for Intel’s sales executive event in Barcelona, worked with Intel’s product marketing team to demonstrate how artificial intelligence works and more.


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I want to take a step back for a moment and share why I started the podcast. Leading up to this point I had been traveling quite a bit and living life out of a suitcase. The dazzle of traveling to a new location every single week slowly started to wear off. I felt alone. I started the podcast as a way to connect with other female entrepreneurs and build relationships. I honestly had no grand plan on what I wanted for She Did It Her Way. It started out as a hobby. 

As the year went on She Did It Her Way quickly got recognized as one of the top-rated podcasts to listen to from multiple media outlets:

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Huffington Post

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“12 Best Podcasts for Entrepreneurs”


Because I was still doing a tremendous amount of freelance work for companies like Chad’s and others, it wasn’t until a few years later that I took the next step with She Did It Her Way. If you’re wanting to make the leap and transition out of corporate America you must listen to the podcast!


In less than three months (right after I got married at the beginning of August 2017) I pulled together my first one-day event, hosted in Chicago, “Basics of Building a Business.” We had over 35 women from 11 different states at our first event. I was absolutely blown away and inspired by every single attendee. 

The success of that event gave me the confidence to continue growing She Did It Her Way into what it is today. 

Basics of Building a Business


Six months later I hosted the second She Did It Her Way Summit, only this time it was two days long and focused on “Creating a Profitable Business in the Digital Age.” We had almost double the number of attendees and it was absolutely amazing to meet all the women who attended. 

I can’t wait for next years She Did It Her Way Summit! For next year we created two different ticket types - which I’m so excited for this! I did this because as I started listening more and more to my audience I realized that there were two slightly different camps. Those who were newly full-time business owners and those who were still side-hustling. And depending upon which phase of the journey you’re in, there are different focuses for each.

She Did It Her Way Summit
She Did It Her Way Summit
Welcome Party
Closing Celebration


Her Way Society is a monthly membership program that brings together women from all across the world dedicated to launching their own business. Every month we host a set of coaching and guest expert training calls. Enrollment opens 2-3 times a year. This is definitely a new baby for me and running a monthly membership program. I’m excited for all the success thus far and can’t wait to see what it continues to bring!



This past September I launched my first officially course! I had 14 amazing women sign up to participate. The BYOB ACCELERATOR was a culmination of everything that I have taught about being a freelancer through podcasts, coffee dates, and speaking put together in one central course. My favorite part about running this course live was that we had weekly coaching calls! I absolutely love coaching and working with women who are motivated and have the courage to step outside of their comfort zone.



2018 has been a full year of testing and tweaking, seeing what works, and what doesn’t.

In addition, it has been a year of taking massive action and not letting my mind get in the way.

I’ve slowly started to shift my time and energy from freelance work into building She Did It Her Way.

It has also been the most uncomfortable I’ve ever been as a business owner but that tells me I’m on the right path because I’m continuing to stretch myself every day.

The Current

After 2018 and having a full year of running She Did It Her Way as a business I can definitely say I’ve learned a lot.

Here are some of the things I took away in 2018:

  • I am stronger than I know

  • Everything is neutral until I give it meaning

  • Always provide more value and delivery results ahead of time

  • Staying committed to the goal but being okay with changing the plan

  • Knowing my target market makes everything else in my business easier

  • Start an email list asap

  • Start with ONE thing before introducing many things

My vision for 2019 is…

  • Continue to provide more value to my listeners

  • Get to know my target market even more so than now! Really dive into what are their challenges and frustrations

  • Integrate weekly blogging

  • Grow my email list by creating more opt-ins that provide more value for you!

  • Clean up my systems from landing pages/email marketing

  • Optimize my website but better SEO

  • Launch my signature program to help women make their ultimate leap from corporate to running their own service based business in Fall 2019 - stay tuned.

If you want to quit your job and start your own business from scratch, download my checklist and starter kit below! (The checklist I wish I had when I started!)


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