7 Self-Made Lady Boss Stories to Inspire You (When the Going Gets Tough)

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Self-made Lady Boss Stories

We have all been there! Uninspired, unmotivated, and afraid to try something new. 

It’s easy to not believe we can ever make a difference or pursue our dreams because we don’t think we could leave the security of our 9-5.

We have people who think our ideas are silly and unattainable. It’s also scary to invest money into something, even something we love. 

We all struggle with mindset and imposter syndrome, comparing ourselves with someone else who has already found success.

Guess what? 

They started right where you are. 

They struggled and worked hard for what they have now, they had to face imposter syndrome head-on, they had naysayers and failed attempts to get where they are today too. 

We want you to know that even when things look impossible and out of reach, you still have what it takes. You can try and fail and get back up again. Girl, the world needs what you have!

We have compiled a list of some lady bosses that inspire us and we hope they inspire you too. 

1. Jenna Kutcher 

Goal Digger Podcast

Jenna Kutcher grew up in small-town Minnesota. When she was 22 she decided to invest in a used $300 camera. At the time she was stuck in a corporate office job working for Target. 

Knowing nothing about photography or entrepreneurship, for once she felt a passion for something! Jenna started a side hustle as a wedding photographer.

3 years later she had built a very successful photography business but was battling burnout and knew she needed to cut back her hours and enjoy life.

Spending less time shooting weddings Jenna started thinking about how she could take what she had learned starting her photography business and teach it to others so they could do the same.

This led her to grow a 7-figure empire! 

Today, Jenna’s main goal is running the Goal Digger podcast. She teaches four different courses to entrepreneurs and does social media influencing and speaking engagements. She even works as a #AerieReal Role Model for Aerie. 

You need to imagine the life that you want 10 years from now because overnight success does not exist. The decisions you’re making and the things you’re doing today will directly influence what will happen in your future. Build the life that you want to live. 

Fun Fact: Jenna’s first real job was cleaning limousines.

Laptop on bed table

2. Joy Mangano

Serial Inventor

Joy Mangano was born on Long Island, New York. She has a BA in business administration.

Joy was always inventing as a child and during her first job at an animal hospital she invented a fluorescent collar for cats and dogs to be easily seen at night. Shortly after, another company launched this idea to the public. 

Joy went on to hold a variety of jobs while getting married and having three children. After her divorce, she struggled to make ends meet. She worked as a waitress and an airline-reservations manager while raising 3 children.

Joy was inspired by the day to day grind of housework and at 34 years old the Miracle Mop was born! 

It took a couple of years to develop and a big investment that she borrowed and saved for. In an effort to take her product to the next level she pitched it to QVC. Her first efforts were a flop but it didn’t stop her.

Joy decided to go on QVC again and pitch her product herself to her audience. She went on to sell 18,000 mops during her first-hour long appearance on the network, proving that she could connect with her audience and make them see the need for her product. 

Joy did not let her first rejections stop her from trying again.

What encouragement can we take from Joy’s story? 

It takes time to be successful. The people who don’t take no for an answer and continue to believe in what they have to offer, are the people that become successful!

Fun Fact: Housework inspired her big break.

3. Bethany Hamilton 

Professional Surfer

Bethany Hamilton grew up on Kauai’s north shore. At 13, rising surf star Bethany lost her left arm to a 14-foot tiger shark. To many, this was the end of her dream career.

However, one month after the attack, she returned to surfing and within two years she won her first national surfing title. 

One of the biggest comeback stories of our era, Bethany Hamilton is undoubtedly an inspiration for us all. She defied the odds with her story of determination, faith, and hope.

Today, Bethany is still a professional surfer! She is also an author and motivational speaker. She currently has her own blog and online course where she helps others work through the nitty-gritty of life’s challenges. 

Bethany is a true example of going for your dreams and putting in the work to do it. She shows us all that the right mindset will set us apart. 

Fun Fact: Bethany has written several poems, and also a few songs.

Laptop on desk with green plants

4. Lori Greiner

QVC Queen

Lori Greiner grew up in Chicago. She majored in communications, focusing on journalism, television, and film. She was briefly a playwright and also designed and sold her own jewelry on the side.

While making jewelry was a side hustle, one day Lori had an idea that would help her keep all her jewelry organized in the same place.

This was the start of a multi-million dollar idea. 

Lori created and patented a plastic earring organizer with sliding rods that could neatly store 100 pairs of earrings. Using borrowed money, she created a prototype of the product which was picked up by J. C. Penney.

She took out a $300,000 loan and paid it back in eighteen months. All the success she gained selling her product on HSN quickly led her to become a serial inventor.

Lori joined the TV series Shark Tank and went on to invest in “Scrub Daddy” which is Shark Tank’s most successful product yet, with $100 million in sales. 

It’s encouraging to know that through Lori’s side hustle she went on to launch a wildly successful business career. 

Fun Fact: Lori drinks her coffee with Swiss mocha flavoring.

5. Sara Treleaven Blakely

Inventor of Spanx

Sara Treleaven Blakely was born in Clearwater, Florida. She is a powerful female entrepreneur who started the multimillion-dollar shapewear company, Spanx. 

Did you know Sara failed the LSAT’s TWICE while studying law?

She then decided to go work at Disney World. When things didn’t work out the way she had planned (her hope was to audition for the role of Goofy), she decided to go home and live with her mother.

Sara got a job at a local company selling fax machines door-to-door for 7 years. She had doors slammed in her face and her business card was torn up in front of her multiple times.

This constant rejection made her stronger and immune to the word “no”. 

During this time she knew she had become a good salesperson, but she really wanted to sell something she had created herself.

Sarah’s success started completely out of the blue when one day she wanted to look slimmer in her fitted white jeans. She cut out the feet of a pair of pantyhose and couldn’t believe how good her butt looked! 

That moment was the birth of Spanx, Sarah’s multi-million dollar company! 

We can all be encouraged by this story of perseverance and not being afraid to try something new. 

Fun Fact: Sarah paid $250 to trademark the word Spanx in 2000, she changed Spanks to Spanx at the very last minute.

Laptop on desk with orange and red details

6. Natalie Elizabeth Ellis

Serial Entrepreneur

Natalie Elizabeth Ellis was born in England. If you are a female entrepreneur, you have probably come across BossBabe Inc.’s many quotes and motivations on Facebook and Instagram.

Natalie is the mind behind this inspiring female brand. 

She is a serial entrepreneur who, at just 26 years old, has successfully scaled multiple businesses across a variety of industries.

BossBabe’s mission is to help other women get out of places where they feel stuck and teach them how to empower themselves to build freedom through entrepreneurship. We can totally get behind this! 

Natalie’s journey of entrepreneurship came with its portion of loneliness, trials, and constant hard work. 

Natalie knows a thing or two about building an empire online, never giving up, and taking an idea and turning it into a money-making reality. 

Fun Fact: Sara Blakely is one of her role models. She loves seeing women crush it at work and still find time to have a great family life. 

7. Marie Forleo

Multi-Passionate Entrepreneur

Marie Forleo was born and raised in Jersey, with nothing more than passion, a laptop, and a dream. A self-proclaimed “Multi-passionate Entrepreneur.” 

When Marie graduated college, she went straight to work on the floor of the New York Stock Exchange. A nagging voice inside her head told her this was the wrong path, that she was meant to do something more with her life.

She had many interests in many unrelated things. 

After her many failed attempts in the corporate world, Marie began to realize her multitude of interests was a strength.

She started waiting tables and doing all kinds of odd jobs to keep a roof over her head while she began building her coaching business from the ground up.

She calls herself a “multi-passionate entrepreneur” and has found success in many areas of her life and helped others do the same.

From the NY Stock exchange to choreographing for MTV, publishing two international bestsellers, and creating a digital education company, she’s done it all!

Marie believes you don’t have to fit into the traditional “box” of success. No matter what obstacles you face, you have the power to change your life and even change the lives of others. 

Fun Fact: When Marie was young, she dreamed of becoming a Disney animator or a fashion designer.

Feeling Inspired? 

If you are ready to become your own badass boss lady and take a step towards the career of your dreams, sign up for Esther’s FREE Masterclass on how to work from anywhere as a virtual assistant. Esther answers all of your questions about how to work from anywhere as a VA.

Esther has helped over 2,000 women to date start their careers as virtual assistants using The 90 Day VA Virtual Assistant Internship Program

And the good news is that Esther’s signature course 90 Day VA is opening for enrollment on May 1st!

90 Day VA takes you through all the virtual skills you need as a Virtual Assistant…AND supplies you with 10-20 legit job leads every week!

Are you ready to be that boss babe you were born to be?



Chelsea James headshot

Chelsea James is originally from South Africa and works as a virtual assistant to creative entrepreneurs. She specializes in Content repurposing, Social Media and Podcast Management as well as many backend organizational tasks that help simplify the workload for her clients, so they can focus on building their businesses. 

She is a content intern for Virtual Assistant Internship and a student of 90 Day VA. Chelsea and her New Yorker husband currently live between South Africa and New York. When she is not working you can find her doing yoga, paddle boarding and enjoying a good cup of coffee with her precious family.  

For more information about Chelsea’s virtual assistant services, click HERE. To follow Chelsea’s travels through Instagram, click HERE.


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