By Kim Rittberg
In the hospital, at a bar, in a Bronx elementary school: that’s where the “aha moment” happened for these founders who made massive career pivots.
The delivery room was the backdrop to my ‘aha moment.’ As I looked down at my vibrating iPhone, just inches away from my IV drip, I thought Why am I working right now? Can’t I be present for this monumental moment in my life?
I had the clarity that I wanted to leave my job as a digital video executive to launch my own video strategy business. While the destination was clear, the path to get there was an overgrown jungle. Over the next several years, I hacked my way through with lots of research, a few trials by fire, and a ton of social media marketing.
Since that delivery room ‘aha moment,’ I’ve won six awards and spoken from coast-to-coast teaching entrepreneurs and professionals how to become thought leaders through video and podcasts. I also host a podcast called Mom’s Exit Interview focused on people crafting careers that work for their life, often including huge pivots or business launches. Along this uncharted path, with an unknown destination, when I wasn’t looking, I’ve found my purpose: helping other business owners find and use their voice.
Here are three other founders on the moments that led to a massive career change.
While recovering from an injury: A pivot from professional soccer player to broadcaster and beauty founder
Right after making the Olympic team in 2008, professional soccer player Leslie Osborne tore her ACL and ligaments in her ankle. She underwent surgery and the doctors told her she’d never play professional soccer again. Osborne says the 18-month recovery period was a “dark and difficult time,” but it also forced her to figure out what else she was passionate about. She began to work in sports broadcasting and explored different companies and nonprofits. Eventually she still ended up playing soccer for another five years before retiring. She said while for many athletes, retiring leads to a very real “identity crisis,” she avoided that and “actually was looking forward to my next steps in my second career.” Osborne has remained in sports broadcasting and has become an UPPAbaby brand ambassador and a cofounder of Bay Football Club and Hustle Beauty.
Osborne now coaches other athletes on their career path. To push through the identity crisis of retirement or shifting, she encourages people to ask themselves “If money wasn’t a thing, what would you be doing?” She recommends finding multiple passions and having a “backup plan” if your interests or plans change. While her examination began in the hospital, it’s something we can all do at our own pace proactively.
Seeing the same issues repeat: A pivot from a school social worker to funding underrepresented founders
An elementary school in the Bronx, NY, was the location for Himalaya Rao-Potlapally’s life lesson. As a social worker, she realized that every year “it’s the same issues that come up over and over again with different students” and she felt discouraged when she felt like she was “on a hamster wheel.”
She asked herself “what is the impact here?” and made her first self-described ‘mini-pivot’ into nonprofit work. And after getting rejected for management consulting jobs, she decided to get her MBA and got a job in venture capital. There she asked, “What are we doing to ensure that many more people, and particularly diverse and underrepresented people, can be in a space where they can have scalable ventures?” and is now the Managing Director and Solo GP of The BFM Fund, a seed-stage fund focused on Black and diverse-led US companies across a variety of industries.
Rao-Potlapally says, “It’s scary because no one’s telling you what to do. No one’s telling you how to succeed,” but she feels driven by her purpose and says “we’re making awesome impact.”
Sometimes finding that purpose is as simple as asking yourself, what change do you want to see in the world?
While tending bar: Pivot from odd jobs to canned cocktail entrepreneur
Bronya Shillo’s aha moment came while she was bartending at her family’s hotel bar at the Pequot Inn in Fishers Island, NY, which is just a few miles off the Connecticut coast. They served a drink called Fishers Island Lemonade, which was a blend of whiskey, vodka, lemon and honey. Over the years, Shillo tended bar in the summers, did odd jobs including in masonry and as a librarian, and worked in marketing at UnderArmour.
Shillo still thought about their family’s cocktail and noticed, “We’re running out of this lemonade constantly,” and, channeling her family’s entrepreneurial spirit, thought “I wonder if I should just try to give this a go.”
Shillo felt there was a void in the market—canned cocktails wouldn’t become a thing for several more years. After two full years of development, Bronya launched Fishers Island Lemonade in 2014, pioneering the ready-to-drink craft cocktail category. The company was acquired by Spirit of Gallo in 2023.
Shillo said “the confidence was definitely there” for her to launch, as she felt she knew the audience well and believed in the product.
Finding your Aha moment
Leslie Osborne turned an unplanned athletic career pause as an opportunity to delve deeply into what the next stage of her career could be. Himalaya Rao-Potlapally stepped out of an unfulfilling professional cycle to work with purpose (and impact). Bronya Shillo realized that her family had the recipe for success inside her family’s bar.
For me, my confidence has certainly wavered, my path has wandered, and I certainly couldn’t see all of the steps on that journey. But clarity of purpose guided me. Despite being worried about what my business would look like and how I would find clients, I knew the life I wanted was not compatible with my corporate career. I wasn’t sure how to get where I was going, but I knew I had skills and determination to pick my way through the underbrush. And I used my “zone of genius” as a compass. Most of the time I see the sun peeking through, and am living the work-life experience I was hoping for.
Whether it’s impact, passion, or entrepreneurial spirit that drives you, that aha moment could come when you least expect it, and the secret is to listen to yourself.
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Kim Rittberg is an award-winning Digital Marketer who specializes in helping professionals and business owners become thought leaders through video and podcast content. You can grab her free download 10 Tips To Improve Your Video to Grow Your Revenue and “How to Sell Yourself in 30 Seconds” here.
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