SDH 436: Overcoming Fear and Making The Ultimate Leap From Corporate to Entrepreneur with Rose Mills

Hello, She Did It Her Way listeners! Welcome back to another episode of the She Did It Her Way podcast. Today we are joined by guest, Rose Mills. Rose is just a gem and I’m excited to share how we met and how our paths crossed. Rose is a corporate executive turned entrepreneur, now a social media strategist helping female solo-entrepreneurs and small business owners get clear on their social media strategy, a strategic roadmap that helps to elevate brands from ordinary to extraordinary.

I met Rose two years ago at the 2019 She Did It Her Way Summit and it’s just been such a joy and an honor to be able to see her journey unfold. She is a true social media strategy ‘Queen’, and I thought, let’s bring her on and talk about social media planning and all that good stuff. But before we do that, Rose shares her journey of going from corporate to going out on her own.

Rose remembers the day that she made the decision to really start investigating how she could go from corporate career to entrepreneur, it was something that she had been wanting to do, but just wasn’t really at that point ready to make the leap quite yet. On an early morning flight to San Francisco she found herself in a window seat in the clouds, looking out and realizing that it was her wedding anniversary that day! She realized she was actually missing her wedding anniversary since she was traveling again for work. She sat there recounting how she had sacrificed so much time with her family for her corporate travels and finally thought to herself:

“I don’t want to do this anymore.”

She wanted to be home celebrating family events with her loved ones and not feel like she needed to sacrifice her family time for her career. With that, she began to pray. She prayed to be shown the path of what she could possibly do. She was looking for guidance and began to see signs that all pointed in the direction of ‘strategy’ – one of my strengths and something she was already successfully doing with corporate clients. She helped very large brands create strong and strategic brand partnerships, along with digital strategies and social media. 

It clicked. If she could do that for a very large client, why couldn’t she do it out on her own? 

She determined that small, female business owners likely felt these same struggles that she was experiencing, and her niche was born. Rose decided to leverage her strategy with her love of social media, and turn that into a business in helping female entrepreneurs, leverage the organic nature of social media to grow their businesses to elevate their brands and and support their businesses.

In April 2019 Rose attended the She Did It Her Way Summit and she considers this one of her big ‘A-Ha’ moments. She could do this. Make the leap. Do it on her own. Successfully.

With so many people claiming to be social media experts, Rose took a different approach. She took her experience, love and personal success on social media and leveraged that to build her business and set herself apart.

That feeling of ‘not feeling worthy’, Rose had those exact feelings. She had to really step back and think about what it was that she is good at, and what other people were saying that she was good at as well. To do this, Rose had a lot of discussions with her current clients and accountant, asking them what they thought her strengths were.

Their response was overwhelming and always this;

“Rose, you have helped us so much with our corporate strategy. Why would you not think this isn’t something that you could do on your own?”

Her first client was one of those classic ‘right place, right time’ coincidences… She and her husband are members of the Chicago Yacht Club and they were looking for engagement strategies. She gave a short presentation on social media and someone at that meeting approached her after the meeting. They had a sit down and talked about his goals for social media, thus he became her first client.

Despite social media being a crowded space Rose has truly left her mark on the industry while allowing it to bring her so much fulfillment and joy personally and professionally. 

While Rose was rocking at social media, she decided to make another major pivot to continue doing something that brought her a lot of joy: coaching. After helping dozens of women gain their own clarity on their social media strategy and brand presence, she realized that is what made her truly happy.

To honor her late father, Rose lives by the rule, ‘Always do the right thing’.

You can connect with Rose (personally) on Instagram. There she shares all of her best tips, tools, and strategies on social media. You’ll always walk away with a good strategy for social media that you can implement for your business, but you’ll also walk away knowing her personally.

Until next week, keep doing it your way!



  • “Always have your 15-second pitch ready.”
  • “People can open doors, but it’s always up to the individual to walk through that door.” 
  • “There’s no cheating involved, there’s no tricks, no hacks; it’s always about doing the right thing, never taking the easy way out no matter what.”
  • “If you’re the smartest person in the room, you’re in the wrong room.”



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