Welcome to the Design Your Dream Life Series!

If you’re new here, this is a series where I interview people who have designed their dream life. You can find all the interviews here on the Design Your Dream Life Page.

I’m so jazzed to have Amanda Boleyn share her story today! Amanda is the founder of She Did It Her Way, which was named 1 of 12 Best Podcasts for Entrepreneurs by Forbes.

To give you some context, Amanda’s bio reads: Amanda Boleyn made the leap from Corporate America to Entrepreneurship at the age of 24 where she started out as a freelance consultant working with large organizations across the globe implementing sales, leadership and behavior change trainings. In 2015 Amanda knew that she wanted to create a lifestyle and business that was location independent that focused on helping other women make the transition from Corporate to full-time business owner. She launched She Did It Her Way Podcast and since then created an annual event and a monthly membership program. Amanda has been mentioned in Forbes, Inc.com, Huffington Post, Entrepreneur.com and others.

Here’s my interview with Amanda…

Amanda Boleyn

Finish the sentence “I knew I was living my dream life when…”

The first time I knew I was living my dream life was when I made the leap from Corporate America to freelance consultant. I had the opportunity to travel the globe and facilitate content on topics I loved, I got to interact with people every single day and absolutely loved what I was doing. It didn’t feel like work.

Since then, what I consider my dream life has shifted and transformed.

With She Did It Her Way, I’m no longer location dependent, I can work from anywhere. I get to spend more time at home, I don’t live out of a suitcase, I get to create a routine because of the business I’ve created.

The best part is even though my definition of what my dream life is, changes over time, I have designed my life so that I always get to live it. My corporate job is no longer a factor.

What was your life like before all this that led you to make a change?

My life wasn’t my life – it belonged to the company I worked for. I gave up holidays, weekends and a life for a job that I didn’t love. It felt like I was letting life pass me by, every moment, everyday I was there.

It was my first job out of college and at the time I was lucky enough to have a mentor in my life that told me I could live and have anything in life I wanted. It was completely different than what I was constantly told, “You’re not supposed to love what you do, that’s just how life is.”

I was in a complete state of emotional turmoil about should I stay or quit? What will I do? What will people think if I quit?

Then one day I made the decision that I was done. No more. From that decision, opportunities started to pop up in which I found what I call my bridge job (the job that creates space and margin in your life that leads to what you ultimately want to do), which later allowed me to make the ultimate transition into the world of entrepreneurship.

Within a week of making the decision to leave, I found my new bridge job and put in my two weeks.

What’s your lifestyle like now?

While I can work from anywhere, I’ve found that being at home, working from my desk produces the best results when I need to get stuff done. Otherwise on days when I need to create content I’ve found being at a coffee shop is the best environment for that.

I have a pretty ritual morning routine. The first thing I do when I wake up is head to the bathroom to brush my teeth and wash my face, change out of my pj’s into regular or workout clothes, drink at least 8oz of water, spend 5 minutes using my theracane and stretching, meditate for 15 mins, make my coffee, my 5 Minute Journal, then I either dive into a book or straight longform journalling. The whole ritual takes about an hour.

I also love to travel and enjoy having the flexibility and freedom to do so.

She Did It Her Way

How many hours per week do you work?

How many hours I work a week really varies. I pay more attention to the work I produce and create rather than making sure I put in a certain number of hours for the sake of putting in hours. Typically it ranges between 35-40 hours of focused work. Right now I’m in massive action mode so I will continue to work as many hours as it takes me to produce the products I’m working on.

How do you make money?

She Did It Her Way makes money through podcast sponsors, live event sponsors, ticket sales to the live event, and affiliates.

Over the next 6 months I’ll be creating targeted funnels and adding online courses based on my segmented personas.

How did you get started?

How I got started really stems from when I left Corporate America completely in May 2012 at the age of 24 as a freelance consultant. It was there I got my first experience of what entrepreneurship life could look like.

I was doing work that I loved, traveling the globe, facilitating meaningful and impactful content in addition to working alongside other consultants who were a joy to work with.

About 4 years in, I started to feel lonely and living out of a suitcase was no longer enjoyable.

In 2015 I launched the She Did It Her Way Podcast. I’ve since added an annual event — She Did It Her Way Summit and a monthly membership program, Her Way Society.

I’m very excited about what the next 12 months will bring!

She Did It Her Way Summit

How long did it take for you to make $1k per month?

I didn’t start monetizing She Did It Her Way until August 2017, when I signed on the first sponsor for the first ever She Did It Her Way Summit event in October 2017.

To be honest, I hesitated monetizing She Did It Her Way in the beginning. I felt guilty about it, mainly because I viewed it as a hobby, not a business and how dare I try to make money from my hobby, right?

Once I changed the way I looked at She Did It Her Way from hobby to business, I shifted my mindset to that of a business owner.

I started asking myself, “How can I provide even more value to those who are showing up every single week to tune in?” This has had a huge impact on how I serve my audience. They get more value, and I’m able to make money, too.

How long did it take for you to make six figures per year?

This year is the first year She Did It Her Way is on track to do around six figures, so that’s a little under a year and a half after I started monetizing it.

Amanda Boleyn

What do you wish you knew when you were starting out that you know now?

I wish I knew better how to transition out of being self-employed to being a business owner. When I first started out I knew the difference but I ignored it.

Until I realized that I no longer wanted to be in a reactive state when it came to getting projects, rather I wanted to influence and have control over my life and business.

I also wish I had a better understanding of my relationship with money and how it impacted my ability to build a business whether it be an abundant or scarcity mindset, how our childhood experiences impact our adult life or how to remove money mindset blocks.

What advice would you give to someone who is starting out and wants to design her dream life?

  1. Know the outcome you want. Ask yourself, “what do you want your life to look like? What type of business do you want to create? What type of lifestyle do you want?”
  2. Find someone who is already successful at what you want to do. People who are successful are not lucky, they are doing something different than anyone else. They have a strategy that works. Success leaves clues.
  3. Model the person you want to be like. There’s no reason to reinvent the wheel. Learn from the person who has the results you want. Figure out what strategies she uses and use them in your life.
  4. Master your mindset. Entrepreneurship is 75% mental, 25% tactics. Do as much work on your mindset (how you think and feel) as you do focusing on tactical strategies to implement. The pay off is huge and shouldn’t be underestimated.

Where can people find you if they want more?

A Final Note!

A HUGE thank you to Amanda for being part of the Design Your Dream Life series!

I love Amanda’s experience having a mentor who told her she could live and have anything in life she wanted. This belief alone can improve your life exponentially. Amanda is proof of that.

I also really admire Amanda for sharing her experience feeling hesitant to monetize her hobby. So many new entrepreneurs go through this.

When Amanda talks about transitioning from being self employed to being a business owner, I have so much admiration. I’m totally still in self employment mode, and I intend to be until my business is beyond seven figures. I love that she did this right away. It’s going to make growth very seamless for her.

Finally, I looooove Amanda’s advice about mastering your mindset. This is why I created Design Your Dream Life Academy and talk so much about mindset work. It’s the foundation for everything else.

Amanda’s community is amazing. She interviewed me on her podcast, and I’ve never had so many people reach out to me after an interview. (You can listen here.)

Are you inspired by Amanda?! Let her know in the comments!

P.s. If you want to start an online business, join me in Online Business For Her!