Tips From A Former Server: An Inside Look Behind The Scenes Of An Industry

Restaurant & Night Life Industry in Downtown Chicago

Veronica Montes
5 min readApr 27, 2021
Clavada En Un Bar

Dim lighting, from elegant fixtures that dangle looking like long sexy legs with contemporary chandelier heels, invites you to walk into an elegant dining room while you’re guided to your booth by a gorgeously chic hostess. You’re gagged by the hostess’s impeccable bone structure and posh outfit. It’s a leeewk!

Sultry electronic beats vibrate across the room and you quickly Shazam the song so you can listen to it later. After the song is stored, you scan the room and see a diverse crowd of guests but mostly affluent people in suits. But what you do for a living is not who you are.

You are completely bigger than what you do and your reservation is under a name with weight. Not only are you dining with an expert on the menu, but you’re also about to greet the vibrant cast who amp the ratings of the entire production. You’re welcomed with love, joy, and excitement by servers, bartenders, and managers. You’re happy and grateful to be surrounded by so many talented friends and colleagues.

The Beautiful People

With my cinched waist, petite body, long luscious black hair, high cheekbones, plump lips, and chic fashion, I easily landed a spot in the highest-grossing neighborhoods as a server in the restaurant and bar scene of downtown Chicago. Well, not quite. My introduction to this world was thanks to two fun-loving socialite friends who had been working in The Industry throughout college. One opened my eyes to the possibilities of exploring the scene not limited to thrilling nights out living on the edge, but luxurious dining experiences with key relationships. My other friend connected me to her manager at the legendary Boss Bar on Clark Street. Thanks to these talented boss women, I have these wonderful stories to tell.

My love for bars, restaurants, and dining is complex. As a daughter of two Mexican immigrant parents who worked in the restaurant industry for several years and owned a restaurant for nearly 15 years in Pilsen, I dedicate this story in honor of all they lived through in this industry including the hard work in their sacrifice, stressfully dangerous nights, the kindness they demonstrated to their employees, and discrimination they have faced.

I grew up in the apartment above the restaurant my parents owned throughout the middle of high school and resented the lack of privacy, fear for my safety, and the constant smell of tacos on my clothes. Life, fortunately, allowed me to see my parents’ hardships from the window of my personal healing experience during the years I worked in the Industry. I am so grateful to share these insights with you to enhance your future dining experiences and offer you to see more than meets the common eye.

The Knowledge

Hustle hard in the Industry means being knowledgeable of extensive menus and upselling items for high check averages for a higher wage. Confidence is the key to selling anything to anyone. This was very challenging for me at first. At the time I started working in restaurants in downtown Chicago, I was personally experiencing what others might call an existential crisis but I identify it as a beautiful spiritual awakening. While I navigated the earth realm, I was solely focused on graciously accepting my sole existence by simply being. I channeled peace by simply observing and appreciating the beauty in other people and honoring their unique paths.

With time and experience, describing the food I loved to suggest came naturally and, depending on my mood, I even ensured my guests had a blast with my fun and playful attitude. Fortunately, numerous tastings and rigorous training at various venues sophisticated my palate and developed my ability to know what I love and don’t in my dining experiences.

Network’s Networth

I worked with hospitality groups like Lettuce Entertain You and DineAmic Hospitality. As an employee perk, restaurant groups offer you employee discounts and comp tabs at their other venues. Even better, most of my industry friends shared our discounts across hospitality groups and most importantly, our insights. Navigating the menu at the best spots in River North, Gold Coast, and West Loop along with several experts of this industry elevates your dining experience to another level. You learn about unique and creative ingredients in food and cocktails but also cherish the sense of comradery.

I am happy to have found myself and my true path along with other creative individuals in this industry. For so long, I struggled with my self-confidence. I feel I barely fostered my creative gifts and talents before. I worked with such amazing talent for several years whom I observed working hard to achieve their personal and professional goals in a chaotic and stressful environment that is sometimes structured to demean them. They did so while simultaneously creating memorable experiences for those escaping their day-to-day reality. They were, in my eyes, orchestrating the success of most of the venues with their talents. Appreciating their commitment, knowledge, and drive inspired me to channel that energy towards my passion for writing.

The Industry

I learned so much from the contributing roles of servers, bartenders, barbacks, managers, maître d’s, security personnel, food runners, bussers, mixologists, wine directors, event managers, chefs, hospitality directors, and operating partners. This industry fosters creativity beyond their food and crafted cocktails. I witnessed many colleagues finish college after years of struggling to finance their degrees, found non-profits, thrive in acting and modeling careers, evolve into successful comedians, create beautiful art, innovate the nightlife scenes, and generate several avenues of revenue. But like most misunderstood industries, we’ve endured discrimination, sexual harassment, and belittlement by guests and employers. On the upside, my experience trained me to have a strong spine and know who I truly am to be able to advocate for myself, protect my spiritual energy, and keep cashing money flow.

Read more on understanding empathy and healing with creativity in this industry.

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Veronica Montes

Writer & Content Strategist, Mexican American Woman, Poderosa, Spiritual Warrior