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How Two Lists Led Me to my Dream Job

“Dream big.”

“Do what you love.”

“Ask for what you want.”

Sounds like a series of inspirational quotes found in a wall calendar or Facebook post, right? These tidbits of wisdom might seem generic, but they were actually the backbone of my journey to my dream career. It took me some time—a decade or so, in fact—but I finally figured out how to put these expressions into practice.

At the age of 27, I was living in Chicago, and my postgrad life was very different than I had expected. My dream of working at a renowned advertising agency was not what I had hoped—I hated the lack of creativity and absent upward mobility in my job as an assistant account executive. I tried switching to a new job at a catering company, but the company politics were overwhelming, and ultimately I was let go.

In that jobless and frustrated moment, I needed a change. So I packed up my chic downtown apartment, said goodbye to friends, and celebrated a last night out at my favorite club. I moved 2,000 miles cross-country to “temporarily” live with my sister, her husband, and their newborn baby (they will henceforth be referred to as “the Levs.”)

I thought making this move would help me find a sense of direction—and with the help of family, a very talented therapist, and endless career guidebooks, it did.

Most effective, however, were the following two simple exercises:

  1. Make a list of all the characteristics of your dream job—and be relentless.
  • What do I wear to the office? (A suit? Flip flops? A space suit?)
  • Who are my colleagues & clients? Do I call them? Text them? Write to them?
  • Do I travel for work? (In a private plane? My company car?
  • What time of day do I work? (Early morning meetings? Late night parties? 9-5?
  • How do I get to the the office? (A 20-minute walk? The bus? A drive?)
  • And so on. . .

When writing your list, aim high and ask for what you truly want. Include everything from work culture to lifestyle preferences to anything in between.

  1. Make a list of what you love to do during the normal weekly schedule.
  • Are you one of those people that loves to fold laundry?
  • Do you wake up to a sun salutation?
  • Is baking bread or cookies your favorite pastime?
  • Do you constantly peruse the internet for good airfare?
  • Are you checking the stock market and following CNN?
  • You get the idea. . .

When writing this list, take a couple days and be attentive to what makes you excited during the week. Include both the mundane (sorting socks) and the fun (trying a new recipe.)

Using my list #2, I realized I was loving the role of “The Levs’ House Manager,” which mainly involved cooking. I loved menu planning, preparing a grocery list, doing the shopping, assembling the meal, and watching the Levs sigh in relief when they saw that dinner was ready. Considering I had never cooked in my life, it was the list that made me realize just how much I loved it. I realized that I could create a business around preparing dinner for people, be my own boss, and start to check off goals from list #1.

I used the Levs’ kitchen as my testing ground for what was later incorporated as Dinner At Your Door. Within a few months, I had a client base, preparing and assembling 30+ meals each week. I signed a kitchen lease and moved the growing business to a more professional space. After four years, my dreaming big finally paid off, and it was time to expand. So I boldly asked for my own kitchen property—which turned into so much more. I purchased a vintage building, moved my operations to the new location, and began conceptualizing a unique use for the building’s restaurant space. Five months later, I hosted a grand opening party for Opal 28: a boutique event space, vintage accommodations & commercial kitchen.

At 32, I proudly sold Dinner At Your Door to focus solely on Opal 28. Now I’m 35 and Opal 28 just turned four. My team is a trusted family bound together by loving what we do: working with blushing brides, bartending, cooking, preparing event contracts, and decorating for the next party. I’m literally living out my dream job—based on the attributes of the list that I created way back when.

So if you think making lists sounds boring, remember this: I recently came across both of my old lists, which I hadn’t looked at for six years. Nearly every item on both lists could now be checked off. That includes even my grander asks, such as “flexibility to work remotely”— I write this article after spending three months living on a beautiful Caribbean island.

Those lists were fuel for overcoming frustration and finding a new direction. So I challenge you to make your own two lists—and then dream big, ask for what you want, and do what you love.

Defining Success - Do What You Love

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