We had the good fortune of connecting with Stephanie Benedetto and we’ve shared our conversation below.
Hi Stephanie, we’d love to hear about how you approach risk and risk-taking
I don’t often think about “risk” or the cost of doing something. If I want to do something, it seems silly not to try, especially when a simple version can be tested easily before jumping in. I also give myself full permission to stop doing something or change direction if it doesn’t suit.
My main stance is, “What have I got to lose?”
Our ideas about risk are entirely made up. There’s simply no way to know whether something will work or not, no matter how much research and thought you put into it. I’m not suggesting that you don’t do due diligence in evaluating ideas; that would be foolish. However, the best choices come from your inner guidance, not from a logical analysis alone.
When faced with something I’d like to create or do, I recognize that I can never know how it’s going to work out, or even if I’ll enjoy it if it does. Instead of trying to solve this impossible quandary, I ask myself, “Would I like to find out?” If my answer is yes, I’ll do it.
My willingness to take risks has allowed me take advantage of opportunities and do things before I felt ready for them. It’s taught me that what you need shows up when you need it, when you say yes, and not before.
Begin and the path will open before you.
I left my marriage of 17 years, my home in New York and the business owned with my ex-husband that made us over $1 million in online sales, to travel the world pet sitting. Some might see that as risky, but it ushered in a whole new era of my life. I’m happier than I’ve ever been and doing work that fulfills me. I had to let go of the familiar to reinvent myself. I didn’t know what it would be like, but I knew that I wanted to see.
I run my business the same way. I’m constantly doing experiments and trying things. Sometimes it works out, sometimes it doesn’t, but by making sure I enjoy the process, it’s always a win. Living that way doesn’t feel like a risk; it feels like really being alive.
What should our readers know about your business?
I help coaches and change-making entrepreneurs unleash their irresistible message and attract soulmate clients with playful (un)marketing, no hype or hustle required. Where mainstream marketing tells you to work hard, I help you take the pressure off and let business be play. Rather than following the so-called rules of marketing, I help you (un)market your business by throwing out the shoulds and musts, instead letting it be as simple as doing what you love and sharing it joyfully. I help entrepreneurs learn to trust their intuition in making aligned choices, rather than following someone else’s “proven” system or strategy. The result is a joyful, authentic business (and life!) they absolutely love that’s fun every step of the way.
The path to my current business has been long and winding. I never could have predicted it. Learning how to do internet marketing was one of the most challenging things I’d ever done. It was a crash course in sales copywriting, content creation, email marketing. landing page building, ecommerce, advertising and more. I worked extremely hard during that time, and loved it until I got burnt out from the launch grind.
Now, I bend and break the rules of marketing as it suits me. I lead with my intuition, create with playfulness and let the path unfold easily. I’m not sure I’d be quite so good at breaking the rules if I hadn’t been so good at following them first!
What I’ve learned is that you can’t find happiness playing by someone else’s rules. Fulfillment didn’t come until I asked what I wanted, and then dared to follow that path, regardless of what other people might say. Following my intuition always takes me to beautiful places, even when it doesn’t seem to make sense. It’s through following my inner guidance that I’ve discovered the teachers, clients, partners and new opportunities that I didn’t know I was looking for.
Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
I live in Sarasota, Florida, apparently the #1 city for retiring. It’s beautiful year round.
My favorite things to do are either in nature, music or learning experiences. Since I haven’t had many in person events in my time here in Sarasota due to the pandemic, I haven’t explored those, yet. I would take them to see the manatees in Crystal River; if you’re here in winter there are dozens of gentle giants lumbering in Three Sisters Springs, and it’s a sight to behold. We’d go kayaking and swimming in the springs ourselves if the manatees aren’t present.
We’d go to Siesta Key Beach, one of the most beautiful beaches in the world, known for its white sands. I’d also take them hunting for shark teeth on Caspersen Beach, and we’d grab craft tacos at the Screaming Goat. Downtown Sarasota and nearby Lido Key are full of great restaurants and charming shops.
Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
Michael Neill and his work have changed my life. I stumbled onto his Advanced Course six years ago, and have been following him ever since.
I’ve learned how to live with lightness, express my voice, tell stories that inspire me. He models being a top performer and master of his craft who is also a loveable mess of a human being. His work as a coach, teacher and writer is simply amazing, and his business model is one I’d like to emulate in my own way.