In Conversation with Alpana Singh: The Highs and Lows of Restaurateurship

Almost two months ago, I made the decision to quit my 9-to-5 job in favor of setting out on the entrepreneurial path. With a $60 Ikea desk and an old bamboo plant I had bought long ago in the desperate attempt to bring positive vibes to a negative office experience, I converted my closet into my new workspace. The first item that went up on the wall was an article ripped out of the pages of Chicago Woman March/April 2017 issue on Alpana Singh.

Perhaps you know her as the youngest woman ever to achieve the status of Master Sommelier. Perhaps you know her as the former host of the popular TV show Check, Please. Perhaps you’ve dined at her restaurants in Chicago—The Boarding House, Seven Lions, or the newly opened Terra and Vine. I know her as the woman who unknowingly persuaded me to “dare greatly.” I had already made the scary choice to start my own business. Alpana Singh showed me the beauty in the fear.

“When you first jump in, you’re given every reason not to. And yet, you do it anyways.” Alpana regards me over a glass of water across a table in a darkened back corner of Seven Lions. “And then your worst fears become realized. You have regret.” I sit quietly, knowing her words to be true.

“And then you have these moments where you do win and it feels good. It’s a back and forth of highs and lows…you’ll get addicted. The highs are just enough to make the lows worth it. What keeps you going is seeking that high, that adrenaline, and that anxiety.” Her expression softens. “Achievement,” she continues, “becomes more like a crash. Because it’s always ‘Now What?’”

I had to restrain my relief at hearing someone speak of this messy path so frankly. As if she senses my emotions, she continues. “Entrepreneurship is very lonely and that doesn’t get talked about a lot,” Alpana says, all traces of humor gone. “There’s always the fear of missing out. There’s always guilt and shame. There will be spikes.”

Throughout this reflection on the business of entrepreneurship, Alpana’s tone is almost reverential. Having built her life on chasing the “highs” in the food industry, Alpana sees the self-made achievement story with everything she does. For example, “I always like to remind people that wine is the story of an entrepreneur. And, just like any entrepreneur, they’re going to have a fantastic tale of trials and hits and misses. It’s also the added element of uncertainty.” Here, her eyes shine with excitement. “Think of the vineyard cycle—what if it rains or hails? What if Mother Nature doesn’t cooperate with you? What if there’s a fire? It’s like you’re on pins and needles.” She smiles widely. “And yet, they persevere.”

Alpana’s jump from the Alice-in-Wonderland-like world of wine to the restaurant business in general wasn’t just an example of achievement leading to the “what’s next” syndrome. “Growing up,” she explains, “Food always represented the happiest times of my life.” Being raised as a first generation Indian immigrant in America, Alpana felt the cultural clash that all those in her position, myself included, experience. “Restaurants were the one place I could just be myself,” she said, almost wistfully. “There was an element of sameness…of normalcy. I don’t think I’ve ever lost that magic.”

That craving for “normalcy” ties in to the importance of seeing diversity. Looking back on her time hosting Check, Please, Alpana never intended to ‘make an impact’ from a diversity standpoint. “I don’t consider myself to be brown, I just consider myself to be American. So, I didn’t take into consideration that I look different. It wasn’t until after I did it that I really understood the impact that I had.”

One of Alpana’s customers once recounted that her daughter saw Alpana on television and said, “Oh my god, Mom, that woman looks like me!” It served as a source of reinforcing inspiration. “Seeing diversity tells you that you have a place and that you belong,” Alpana emphasizes. “It tells you that you deserve a seat at the table.”

Today, Alpana has more than just a seat at the table. She has a powerful voice that speaks out for the advancement of women, the solidarity and madness of entrepreneurs, and even for the sense of community that any restaurant brings to a neighborhood.

“Restaurants have bad days,” she states, as she scans her own restaurant to make sure everything is running smoothly. “You’d have to punch me to get me to complain about something at a restaurant. I understand how hard it is and the pressures that they face. People can really get beat up in this business.”

The conversation, naturally, turns to restaurant reviews via Yelp and bloggers/influencers. “Sometimes people don’t pause and understand how their words affect a community. Restaurants add a lot of value to a community. When you hurt a person who dared to Dare Greatly, the restaurant gets affected. The jobs go away. The storefront gets boarded up.” She takes a reflective pause. “I welcome feedback. I have yet to disagree with anything a reviewer has said about any of my restaurants (except for a mention about one of the chandeliers at The Boarding House). I just want people to be aware that there is a lot of power behind that keystroke.”

With all the talk of highs and lows of the business, Alpana’s greatest joy revolves around two aspects—her employees and delivering “the magic”.

“I wouldn’t do this if I wasn’t experiencing joy,” she laughs. “It’s the great love of my life. I know what it’s like to sit down and feel special and taken care of. Everyone should feel that. As for my employees, I love hiring someone and watching them grow and win. I don’t save lives. But I help people.”


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