Dr. Trisha Bailey

Unbroken: The Triumphant Story of a Woman’s Journey

MONARCH: I’m so excited to be speaking with you. I apologize in advance, but I’m going to want to know everything because you have so many positive and amazing things that are going on. Let’s start from the beginning. You are from the lovely island of Jamaica. Tell us what your childhood was like and about your beginnings.

DR. TRISHA BAILEY: Oh yes, my childhood was extremely happy. I was raised by my grandmother along with my aunt and my sister. I cherish my grandmother; she was the most amazing woman ever. We didn’t have much, but at the time, I didn’t know it because we were happy children. There was no TV, electricity, or running water. We walked three and a half miles to school each way. But everyone around us had the same life, so we didn’t know we were missing anything. Our family bond was to care for each other in every aspect of our lives. Being in that space built character and resilience; it taught me the meaning of hard work but also how to be kind and loving to the people that surround me. My life was that way until the age of 13.

MONARCH: That’s beautiful. What was your role in the family?

DR. TRISHA BAILEY: I was a fighter and everyone came to me. Whether it was my sister, my cousins, the boys, the girls, whoever got themselves into a pickle, they always came and got me. MONARCH: Although it came out in fighting, you really were showing signs that you were a natural-born leader, someone people ran to for whatever it was. You are a solution provider. As a child, what did you want to become?

DR. TRISHA BAILEY: My plan was to become a teacher. I was going to get an undergraduate degree in human development and family relations with a concentration in early childhood education because I love, love, love children. Then my mom told me that I wasn’t patient enough be a teacher—so I had to find another career.

MONARCH: How did you feel about your mom’s comment? Did it discourage you?

DR. TRISHA BAILEY: No, it actually didn’t. Very rarely am I ever discouraged. So when she told me, “No, you can’t be a teacher,” I just said, “Oh, okay, I can’t be a teacher. Let me find another career.” Then I started looking into the financial space because I love numbers, they’re constant. I worked as a stockbroker at a wealth management, which was a natural transition after college. I thank God that my mom redirected me, not because I look down on the teaching profession but because I’m in a space now where I can thrive naturally.

MONARCH: Let’s fast forward. You have 16 businesses and an enormous amount of success. How much work did you have to put in to achieve this level of success, and where did that drive come from?

DR. TRISHA BAILEY: I had to work my knuckles and my kneecaps off, but that drive comes from my grandmother. Every week I watched my grandmother and my aunt start at 2 a.m. They would load a donkey with all the farming we produced, then they would walk 25 miles to the market, work all day selling the produce and various other items, then walk 25 miles back to home. So that work ethic was always ingrained in me. When you work hard, everything else becomes easier. As I transitioned into corporate America, I carried that work ethic with me.

MONARCH: Having that strong family background and that foundation…and then you came to the U.S. alone. How did you handle that?

DR. TRISHA BAILEY: When you live in Jamaica, especially rural Jamaica, the goal is always to go to America. So going to America is like a big deal, a huge deal. Also, they tell you the streets are paved with gold. With that said, when I got off the plane in New York, I didn’t see any gold streets. It was dirty and smelly; it was a complete culture shock. However, I knew that I needed to adapt to a new way of life to become successful. Now that I’ve been in the United States for some time, I understand that the meaning of “streets paved with gold” means that you can create your own opportunities, wealth and riches.

MONARCH: Tell us about your career in finance.

DR. TRISHA BAILEY: I was married in college, and my husband at the time said, “Apply to Solomon Smith Barney.” It was the largest brokerage firm in the world and In in my mind, I thought, “There’s no way that this company is going to call little old me,” so I sent resumés to all these different places, Aand it just so happened, they were the only company that called me. This career move gave birth to my becoming a financial advisor and stockbroker. I was the youngest stockbroker in the history of the company, and the only Black woman in New England with Solomon Smith Barney. once they hired me.

MONARCH: I would imagine having this understanding of money was extremely helpful in building your empire.

DR. TRISHA BAILEY: Absolutely. The two top things that I tell people to do are to be is be disciplined and have financial literacy. If I did not have that financial literacy, I wouldn’t have been able to grow to the space I’m in. I already had the work ethic and discipline. But financial literacy has been central to the development of every component of my business. If you don’t know the information, there is no way that you’re going to be able to strategize and know if someone is giving you sound advice or telling you a whole bunch of crap or not.

MONARCH: I wholeheartedly agree. It sounds like you have good judgment and a spirit of discernment. Has that extended to all areas of your life?

DR. TRISHA BAILEY: Oh, I definitely have the spirit of discernment when it comes to business. Now, in my personal life, I didn’t always make great judgments.

MONARCH: Give me an example of your business discernment.

DR. TRISHA BAILEY: Here is an example of how my spiritual discernment plays out: Let’s say we have a surprise visit from an organization to check our accreditation or licenses; I always know when they’re going to come. The day before they arrive, I’ll say, “Make sure you guys are following all the rules, have X Y Z in place, etc.” You know this organization might be showing up. You might get inspections soon, and for some reason, it happens. My staff, they always jokingly say I have this ESP. I’ve always had that on the business side. I have never had a single time that I’ve made a wrong business decision. I’ve never lost money, ever, in business. The reason why is because of that discernment when it comes to business, and I am a strategic thinker. I think extremely fast and can evaluate most things within a few minutes of presentation. And know that this is a great direction or it’s not. Now, on the personal side of things, I did not have the same discernment, so I went through a lot and, finally talk therapy and EMDR therapy helped me get healthy and strong.

MONARCH: So is this what made you write the book, Unbroken?

DR. TRISHA BAILEY: Well, I went into a coma, and when I came out of it, I knew what my purpose was.

MONARCH: How long were you in the coma?

DR. TRISHA BAILEY: For eight days. While in the coma, I was a little girl with a flowered dress on, and when I would turn, I would see beautiful flowers just radiate the entire world. There were no buildings, no manmade things; everything was natural. Then I would turn again, and the scene would change to water; it was so peaceful and surreal. When I came out of the coma, I was in so much pain that I wanted to go back.

MONARCH: I want to interject here. When you say pain, are you saying physically or emotionally?

DR. TRISHA BAILEY: Both physical and emotional pain. Coming out of the coma, my face was completely swollen, probably three times the size of what it usually is, and I was in physical pain and in emotional pain.

MONARCH: Wow. God said, “You know what, I have to keep you here to do my work,” and that’s exactly what you’re doing.

DR. TRISHA BAILEY: Yes, so that’s the reason why I decided to write Unbroken—knowing that my purpose in life is to help others. I am using the book to show the world what the formula looks like coming from dirt poor to becoming a billionaire….and coming from emotionally damaged to healthy and whole. I wanted everybody to have that formula because I shouldn’t be one of the few. I should be among many people who look like me, who are in these financial spaces and healthy emotional places. I know a lot of women go through a lot of the things that I went through, so as they read the book, they will be able to see themselves within my experiences. Men will also be able to relate. The book also provides the business side of what I did in order to become the business person I am today.

MONARCH: That is beautiful. You recognize that God spared your life, so now you are being obedient.

DR. TRISHA BAILEY: Yes, absolutely.

MONARCH: I want to know more about your healing and mental health development through therapy.

DR. TRISHA BAILEY: I started doing talk therapy in 2010 because after the relationship with my oldest son’s father, I said to myself, “I’m doing something wrong here. I mean, I need to really care for myself.” So I did that therapy for ten years and then I would take a break in between therapy and date another not-so-great person. Then in 2020, I had to go back into full-fledged therapy because I dated another not-so-great person who was an amazing father but a horrible person to me as a husband. I said, “Something’s got to give because I know who I am over here in the business side. I’m growing. I’m making all these great decisions, but my personal side is a mess. What is going on here?” So my therapist recommended EMDR therapy—eye movement desensitization reprocessing. I did eight sessions of EMDR. In those sessions, it was explained to me that trauma is like ice cubes within your subconscious. The trauma is frozen there. And what you think you’re running from, your subconscious is actually having you run directly to. So I’m running toward the wrong men because my past trauma is making decisions for me talking for me versus my healthy mind, which is what my business mind draws its decisions from. In doing the EMDR therapy, I was able to melt my ice cubes (the trauma) so that I can process information and evaluate people the way that I should, especially men. As a result, I started dating and having healthy relationships and I ended up meeting the absolute love of my life. I did not know men like him existed. And I believe that is because I was able to release the trauma and replace it with the love and kindness in my heart that I give out now and receive back. It’s amazing!

MONARCH: That is absolutely wonderful. So we got Unbroken. We know what the readers are going to take from the book. Now tell us, what does it mean to create your own yes?

DR. TRISHA BAILEY: It means to create your own opportunity. It gives you a sense of freedom to be able to develop yourself, to be able to tap into your own talent. I know a lot of people are trying to figure out what their purpose is, but there are different ways of figuring that out. You can ask yourself “what do I love to do?” “what am I good at and what brings me joy?” You can also ask two or three friends that you know for sure will answer that call at 3 a.m. in the morning. You ask those friends, not a spouse because they’re biased. It has to be friends. Why are we friends? What is it about me that is unique or special or that you treasure most? You may get the same answer from every person that you talk to. And whatever those answers are, you’ve got to almost peel the onion. But why? Why are you answering my call at 3 a.m.? And then whatever it is that they tell you, more likely than not, that’s your purpose. As long as you hone in on and develop that purpose, you’ll be able to create your own yes and move into the area in which you are happiest.

MONARCH: Creating your own yes equals happiness. I absolutely love that. Now what do you think is the number one reason that women—or men—do not achieve success?

DR. TRISHA BAILEY: Discipline and a lack of financial literacy. A lot of people are not disciplined and are unable to be critiqued. One of the things about me, I lead in a communal space. One brain is not better than 20. One brain is not better than five.

MONARCH: Now, what is your process for growing a business? What do those steps look like?

DR. TRISHA BAILEY: I always tell people, “Don’t do anything that you don’t know anything about.” I believe in staying in your lane. For example, once medical equipment and supplies started supporting itself, I added my second brand, which were my pharmacies. And medical equipment company is feeding my pharmacy businesses. My pharmacies feed the medical equipment businesses because they function in the same space. They’re different suites but function in the same space. So whenever you are expanding the business, make sure they are feeding each other. Don’t jump from medicine to financial management, because they are two very, very different fields. Or medicine into hair dressing—they are very different fields. So if you’re a hairstylist, create your own product line. Do lashes; do nails. Expand within your lane because everything is feeding each other. Therefore it’s going to grow so much faster with one effort versus multiple efforts.

MONARCH: Like they say, this has to make sense.

DR. TRISHA BAILEY: Yes, make it make sense.

MONARCH: Dr. Bailey, this has been such a great pleasure. I have learned a lot. I am leaving this conversation inspired. Are there any words of wisdom that you would like to leave us with?

DR. TRISHA BAILEY: Absolutely. Be disciplined with your money. No matter how much you’re making, no matter how small it is, pay yourself first, even if it’s $50 that you’re saving. Fix your credit if your credit is not good. Pick up these two books: The Bond Market and The Stock Market. Those are two of the first books financial management books that I read. The Bond Market teaches you about the debt market, and The Stock Market teaches you about the equity market. They teach you about the economy, what works when and what works other times. So those are the things that I’d share with young people and other people in the world: understand the world of finance, be discipline in saving, and become financially literate. Real estate was my first investment, and it should be most everyone’s first investment if they’re looking for financial freedom in the future. And it doesn’t happen immediately by the way. It takes time, it takes work, and it takes patience. But it can and will happen if you believe in yourself and stay the course.

MONARCH: Thank you so much. This has been an amazing conversation.