A few years ago, over one of those casual weekday dinner parties where the wine and candlelight combine to almost make you believe it’s the wee hours of Saturday, my friends and I chanced upon a trail of discussion: What should our “Word of the Year” be for the upcoming year? The idea was part intention, part focus point, part goal-setting, and we went around the table each sharing our one word and the meaning behind it. I scrawled down the picks (words and phrases like “partnerships” and “outside the box”) so they wouldn’t be lost in the glitter of good cheer, and tucked the note into a box by my desk.
And there it sat, hidden under a mess of chargers and pens and USB drives, lost and (almost) forgotten. And yet, in a sort of voodoo, self-fulfilling prophecy, our words slowly worked their magic. I had no idea how my word choice would untangle itself and work its way into the very core of my world. When another dinner party with the same friends this January prompted me to dig and find the paper, it felt like a piece of fortune-telling from the past. My word?
How perfectly fitting.
You might call me an accidental entrepreneur. Today, I run a company called guesterly with my husband, but being an entrepreneur was never (ever) in my plan. It was only by being wide open to clues — and complete life changes — that I charted this path. Here’s how being open to little clues set me on the path to business success.
1. Be open to things outside of your flywheel. For years, I considered myself the luckiest girl in the world. I was a food editor at places like O, the Oprah Magazine, where I spent my days interviewing chefs, testing recipes and playing with delicious food. I could wax poetic about Point Reyes Original Blue Cheese and spend hours philosophizing on the best pasta shape for a particular sauce. And I also liked my sane life: a run in the morning, yoga at lunch, drinks with friends post-work, good-girl (Daily Worth-approved) contributions to my 401(k) and savings accounts. So when I parlayed an article I wrote for O on food entrepreneurs into a book deal, I knew just how it would fit into my life: I’d conduct interviews with top entrepreneurs after work, write in the early mornings, learn a ton more about the food industry and end the year more informed about the big picture of food in America. The end goal: be a better (and in-demand) food editor.
But as I wrote “Cooking Up a Business,” I realized it wasn’t just the food aspect, per se, that excited me — it was the business savvy and inspirational startup stories I wrote about! And whenever someone suggested I think about consulting or writing full time about the business of food, I got a pit in my stomach. Why? I realized I didn’t just want to write about entrepreneurs — I wanted to be one.
Takeaway: We all have an area of expertise — mine was all things culinary. But by diving into the world of business for my book (through food) I found a new love. What can you try that’s adjacent to your expertise area — or completely outside of your flywheel? You never know what might spark a deep interest.
2. Be open to solving your own “problems.” At the same time I was writing the book, I was also planning my wedding. My husband and I had guests coming in from all over the country — all of our favorite people in the world would be together for one epic weekend. We came back to our wedding’s focus — inclusive — again and again. How could we connect the dots amongst our guests and make everyone feel like part of our inner circle? We turned the problem over in our heads for almost six months. Finally, inspired by a college freshman lookbook, we created a mini-booklet with photos and fun facts about each guest. We printed them on our home printer and mailed the booklets out a week before the wedding, a special little welcome present. And that’s all it was supposed to be.
Then friends who had attended our wedding started to call (yes, call — not even text!). Could we do the same mini-books for their upcoming weddings? We quickly turned into weekend bookmakers and enjoyed going to weddings that had our so-called “guesterly books” — they were just more fun, and our friends loved their unique present. And then a friend-of-a-friend called. He’d loved the guesterly book at a recent wedding; could he pay us to do one for his?
Takeaway: Put something out there in the world, whether it’s your to-die-for jam, that blog you’ve always wanted to read or that dress that’s as comfy as yoga pants. Share it, let people try it, talk about it. And if the world wants it, you’ll quickly know.
3. Be open to embracing the same animal — in a different costume. My husband and I had been creating a dream trip for years: our Travel Around the World fantasy. I imagined rappelling down cliffs in Patagonia and wandering through vineyards in France and biking through crazed Southeast Asia streets.
But it turned out that at the core, I was looking for adventure. And when it came cloaked in a startup cape, I realized that it was the same concept — go big, experience the world in a new fresh way. (Good thing it scratches the same itch because we proceeded to pour our “travel-the-world” money into guesterly!)
Takeaway: Whatever you’re looking for — recognition, autonomy, adventure, flexibility, creativity — might come disguised as something else (like entrepreneurship!). Being open will help you see when an unexpected opportunity or path fills the same desires.
4. Be open to the wake-up call. I had three big clues staring me in the face: Writing my book had made me catch the entrepreneurial itch; we had stumbled upon a new product concept that people were already willing to pay for; and I was actively looking for a grand adventure. And yet… Maybe, just maybe, there was something interesting at the confluence of these rivers of clues. But I had such a nice life.
Then someone I was close to unexpectedly passed away. Caught up in a whirl of memorial services, I started to hear a story whispering through conversations. I doubt anyone else in the room walked away with the same story, but to me it was loud and clear: He had been an extremely devoted family man. So devoted, that sometimes he didn’t take big (albeit risky!) opportunities that came his way.
I was stunned. I had a big, risky opportunity staring me in the face. I had learned about the skills I’d need to build something and had a product concept that people loved and even a small stash of money set aside for an adventure. The clues clicked together like a puzzle. After months of tossing the guesterly idea around like a misbegotten ball, I suddenly had fire in my belly.
In the summer of 2013 we finally embarked on the rollercoaster ride of building a business. In retrospect, the clues seemed so obvious, but I know it’s only by luck that they rang loud and clear. Luck, or, as you might call it, being open.
Rachel Hofstetter is the author of “Cooking Up a Business” (Penguin, 2013). She was so inspired by the entrepreneurs she wrote about that she left her food editor career to launch guesterly, a software platform that enables anyone to create a playbill for life’s special events. Today, you can find her sharing guesterly with the world by day — and recipe testing at night!