Daphne Pinkney, Exuberant Leader of The Pinkney Realty Team

Daphne Pinkney is ranked by the Mainstreet Organization of Realtors as a top 1% Chicago real estate professional in both sales and transaction units. Pinkney has over three decades of experience in the finance and mortgage industry. In September 2021 alone, she closed over 4 million dollars in transactions. She leads the Pinkney Team, which extends throughout the U.S. and 17 countries worldwide. Pinkney embodies the true essence of a dynamic and passionate leader. Her exuberant and warm presence is both contagious and uplifting to those she encounters. Alongside her partner, Jennifer Hernandez, she has co-created an initiative called the “Do-Over.” Their movement encourages people to start over at any point in their life if their circumstances are no longer serving their higher purpose. Together, they help people overcome hardships, acquire financial freedom through home ownership and find purpose in life. 


Daphne Pinkney: I’m the oldest of two children. I never knew who my biological father was which led to a chaotic life cycle for me. My mother worked two jobs, one of which was with the Chicago police force. I took advantage of her absence by running the streets and doing whatever I wanted. From this, I got mixed up in the wrong crowd. 

The absence of my biological father led to rebellion and resentment. Although my mother gave me everything, I still felt a deep void. The death of my grandma when I was 15 sent me into a crisis. I lashed out by hanging with the wrong people. I was a good student and maintained good grades, graduating as salutatorian in eighth grade and in the top 10% of my high school. But I turned to the streets and bad company for two years, experiencing shootouts and a world of violence and chaos. I knew in my heart that I didn’t belong there. I knew that at the pace I was going, nothing good could come from it and I was going to self-destruct in becoming a product of my environment. 

As a way of escape, I asked my mother, two weeks before the start of the college semester, to allow me to go away to Southern Illinois University. I got pregnant and had to return home after the first semester. I went back to college after I gave birth, but knowing what it was like to have an absent parent, I withdrew after two short months and went back home to my baby. 

Thankfully, I came across Jobs For Youth, which opened amazing doors for me and changed the trajectory of my life. My first career job was as an engineering assistant for Harza Engineering located inside the Sears Tower at one of the largest engineering firms at the time. Prior to this, I didn’t have any work experience, except for McDonald’s. This is how it all started.

Later in 1993, I had a boyfriend at the time whose cousin, Wanda Smith, told me they had a job fair. I was hired on the spot at a mortgage company for a customer service team position. I quickly worked my way up the ladder in Corporate America and was able to financially support my family. But I still felt an emptiness and disappointment from dropping out of college. After going into leadership and ministry, I started reading self-improvement books and led a small group. Then I came across Rick Warren’s book, “The Purpose Driven Life,” and realized that God was my Father and that I was not an accident. From this experience, I decided I would live a purpose driven life.

Fast forward from age 22 to 26, I worked as an operations manager and was overseeing dozens of people. Then I started producing the mortgages, processing underwriting originations for HSBC from 1993 to 2006. Later, I went through different positions in some of the major mortgage companies, where I was either a processing manager, closing manager or funding manager. 


Daphne Pinkney: I began my career in the mortgage industry three decades ago and then in real estate 10 years later during a pivotal time in my life. My father, one of two people that accepted me as their daughter, became ill and passed away while I was experiencing a midlife crisis. After his death, I grew to hate my job and the people there. 

I was traveling like crazy, and my boss didn’t appreciate me. It was not a good environment. 

For five years, my husband kept telling me to do real estate. I kept telling him no. His entire family consisted of entrepreneurs. They don’t believe in working for people because they value their freedom. My husband said to me one day, “What are you waiting for? I don’t know what’s more disappointing—the fact that you don’t believe in your God, your husband, or yourself!” Ouch. The seed was planted. I didn’t know why I was so scared. He was so tired of me coming home complaining every day. 

Then my father was diagnosed with cancer and my mother was very sick. Prior to passing, my father told me to do something that would make me happy, he said “Life is too short. Don’t just exist, live.” 

My boss was the least empathetic over the loss of my father. I remember crying in my car before I went home, and telling my husband, “I’m not going back to work tomorrow.” He said, “Good.” 

I tried to figure out what I wanted and what my purpose was. I thought, what if I got cancer tomorrow and had six months left to live? Would I be satisfied with the life I had, just working in Corporate America, giving my all with nothing to show? 

Without my knowledge, he had already purchased a 10-month real estate class for me. I only had four weeks left to complete it or we’d have to pay for it again. I took a 12-week leave of absence for mental health to gather myself. I pushed myself during that time, even under that pressure. I woke up every day to attend real estate classes from nine o’clock to six-thirty without fail. I passed my real estate class in four weeks and on the first try, leaving me eight weeks to decide if this real estate career was that missing link––and it was!

When I started selling houses, I made a lot of money quickly. I was a people pleaser my entire life, but real estate was just for me. It gave me freedom and a purpose. It allowed me to help people obtain homeownership and financial freedom. 


Daphne Pinkney: My mother was 15 when she became pregnant, yet she succeeded in life. She worked hard to get to where she was. Now me, on the other hand, I became pregnant at 18. I decided I couldn’t just work at McDonald’s––I had to do a “Do-Over.” 

There was a period of time where I received Medicaid and food stamps. I used to be so embarrassed to go into the store with those paper stamps. I didn’t like how they made me feel when I received them. I dropped out of college while all of my friends graduated, but I had opportunities they didn’t have, like building a professional work history while they were collecting degrees. Now today, I’m in the top 1% of realtors in Chicago.

My “Do-Over” was to start my own company and in order to do so I had to recondition my mindset. I tell my children all the time, life is like a blank canvas: use watercolors, erase it and start over as many times as you like. 

There is no definite number of times you can start over, so keep doing it until you get it right. And if it feels right, do more, go stronger, harder, faster and longer. You too can be a success and rise like a phoenix out of the ashes of your life.

Interview by Tricia Love Vargas
Photography: Aaron Lacy
Wardrobe Stylist: Jamar Hart
Hair & Makeup Stylist: Gabby Cardenas
Read Next: It’s Never Too Late To Start Your “Do-Over”


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