
Careers, Kids, and Kicking Ass: Lisa’s Story
“Being a mom is the absolute hardest job I've ever had in my life and I feel like, sometimes, I need steel-toe boots just being a mother,” says Lisa Proeber. Lisa is the owner of The Middle Six, a sales and business development firm, a serial entrepreneur, the author of the new children’s book “Mama Cow,” and a mother of two young boys. But her journey to get to this point wasn’t simple.
Starting her career
Lisa was born and raised in Milwaukee, Wisconsin. In her 20s, she met a guy and followed him to Arizona where she stumbled into a job in sales. At the time, she knew nothing about sales, but the company trained her, and she discovered she was a natural. Her relationship didn’t work out, but she found her calling in sales. She stayed at that job for 11 years until she eventually moved back to Milwaukee to be closer to family.

Becoming a mother
She was always driven in her career, but what she truly wanted was to be a mom. At 34 years old, she wasn’t in a relationship, but decided it was time to talk to a doctor about options for getting pregnant on her own.
Lisa’s friend Kate recommended a doctor who could help her navigate the process of finding a sperm donor and trying intrauterine insemination (IUI). Finally, on her 35th birthday, she ordered sperm and threw herself a giant party to celebrate. After her second try, Lisa was pregnant with her son, who was born in March of 2020.
“One of my favorite parts of being a mother is that there’s this unconditional love,” says Lisa. “My little boys cling to me like spider monkeys and I just love it. I soak it up.”
Bumps in the road
When her first son was born, Lisa worked in business development at a commercial furniture manufacturer. The pandemic hit the company hard, and Lisa was let go from her job when her son was only a few months old. It was certainly a shock and wasn’t easy, but it gave her the opportunity to search for her dream job.
Eventually, she landed a job at a company where she was tasked with creating a business development program. While searching for the job, she was also going through the process of having her second baby. Again, she used a sperm donor and with luck, got pregnant on her first try. The day she started her new job, she found out she was pregnant.
When she told the owner of the company she was expecting, he was less than thrilled. In fact, they denied her maternity leave and told Lisa they didn’t owe her anything. Unfortunately, limited or no maternity leave is an all-too-common challenge that many women in our country face.
But Lisa knew her rights and was going to advocate for them. A few months later, she came back to ask for maternity leave with an attorney at her side. The company responded by firing her – two weeks before she had her second son. Once again, she found herself with a new baby and no job.
Lisa successfully asserted her legal rights and had a positive outcome, but the experience proved eye-opening. It led her to reevaluate her career path and ultimately inspired her to become her own boss.

A new start
As a mom of two, Lisa began talking with various businesses and explaining her sales expertise. Multiple companies asked if she would consult for them, so finally, in April 2022, she started her own business called The Middle Six. From there, she took off running.
In her first year, she had 27 clients – Xena Workwear being her first. She is now the sales executive for Xena and has helped them build out a new sales channel. The Middle Six has grown to have three full-time employees, two part-time employees, and contractors. On top of that, she now owns two board and brush franchises, wrote her first book, and is starting a bar in Milwaukee.
Discovering her love for Xena steel-toe boots
Lisa is passionate about her work with Xena and believes in the brand because she loves wearing her boots. In fact, she became one of their first customers when she met Ana, the founder of Xena, at her table at Women of Influence event.
Having worked in sales at a construction company at the time, Lisa knew stylish steel-toe boots were absolutely necessary. “I immediately said, ‘I need those because I want to walk on a site and demand respect,’” says Lisa. She would regularly meet with clients and hold photo shoots at construction sites, do building walk-throughs, and hosts event with clients – all of which required steel-toe boots.
“One thing I teach about the art of sales is the flair in your outfit. The outfit is so important in how you represent yourself. Your outfit is your interview,” says Lisa. “That’s one of the things that's so powerful about Xena. They're empowering women to show up like they would for an interview. That’s your one chance to impress people."

Mama Cow
Lisa’s latest project is her children’s book, “Mama Cow” which just launched this month. She wanted to write a book that would explain her story of being a single mom by choice to her children and other kids.
When she realized there weren’t children’s books that told the story of nontraditional families, she decided to write her own. “I want to make this book that helps introduce those concepts to kids earlier,” she says.
You can back the book now on Kickstarter to help get it in bookstores and in the hands of families.
Advice to women who want to be mothers
Choosing to become a mother can be a hard decision for many women, even if they have always known they wanted children. Lisa understands that everyone’s life circumstances are different, and knows that questions around timing and work-life balance can feel like barriers
But her advice is this: “If you want to be a mother, be a fucking mother. There's nothing standing in your way and there's a million different ways to do it. There’s never a good time to have a baby – just have the baby. You can do it all.”

