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Something utterly unexpected and delightful happens every time I check into the Iron Horse Hotel. So much so that I refuse to make plans beyond simply arriving. All I know is that it will be luxurious and the place makes me feel like scattering slow sideways smiles to strangers, like I have a secret they should really know about. This trip, I arrived to a blue cocktail garnished with fizzy Pop Rocks, along with a directive to drink up, freshen up and appear in the lobby in 20 minutes. My reward for following instructions? A male model and photographer waiting for me in the bar. Well, hello. It’s tough being a part-time model, I tell you what. Especially when the photographer encourages you to “get closer” to a tall, handsome Midwestern man with a sexy brain. We finished our photo shoot and were immediately surrounded by the magical Alice in Wonderland party, complete with both Tweedles (Dee & Dum), toppling teacups and tremendous top hats. The rest of the weekend was punctuated by mimosas, excellent company and my first taste of blueberry-chocolate-venison chili.

On to Chicago, still sideways smiling. We were graciously hosted by a friend’s brother, who happens to be an entrepreneur. I’m not sure if I’ve been paying attention more, or if I keep running across people who are just inherently interesting. In any case, I find my path strewn with entrepreneurs, people doing their own thing and loving it. I’m inspired. And scared that I might sort of have the potential to be one. I’ve been fighting it for years, working for a Fortune 50 company, enjoying the perks of good health insurance, banking holidays and a predictable, generic cubicle to call my own. But I’ve long been compelled by the drive, ambition, creativity and accountability of entrepreneurship. There’s something about people who take what they’re good at and what they love, their ideas and their passion, then smoosh them together and go for it. Despite what most people think of MBAs (corporate life, Wall Street), it turns out there’s a vibrant culture of people who pursue MBAs in order to be better entrepreneurs. It’s something I’ve not yet explored at Darden, although it’s a top-ranked entrepreneurship program (another example of Darden being what I need, before I know I need it).

On Friday, an entrepreneur friend asked me: given the choice to participate in an entrepreneurial venture, would I choose to be President or Partner? President, he implied, manages, moderates, channels and fixes things ahead, around and behind the Partners. Enables, if you will. Partner, however, is in the thick of things making messes and money right and left. Almost splitting who has the vision, and who enables the vision. Of course, the lines aren’t often so crisply drawn, and choosing one or the other seems a luxury. For me, I’m more comfortable in the enabling role. Yet I’m pretty sure I can do the vision thing too. I’ve just never taken the chance to really try either. Should I?