Dr Toscha Dickerson of Dickerson Management & Associates: Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life

An Interview With Pirie Jones Grossman

Pirie Jones Grossman
Authority Magazine


I struggled a lot with believing in myself and thinking that I could live life on my own terms. I overcame this thinking by attending training that taught me about neuroscience and getting rid of limiting beliefs. I studied the mind and how the brain operated. I wanted to know how I could motivate myself and be positive. I begin writing affirmations to myself and repeating them, believing them, and memorizing them. I started hiring business and life coaches to help me level up and think differently. I knew that I had to do things differently than how they were done in the past if I wanted a different result.

Many successful people reinvented themselves in a later period in their lives. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Kroc was a milkshake-device salesman before starting the McDonalds franchise in his 50's.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Dr. Toscha Dickerson.

Dr. Toscha Dickerson is the CEO and Founder of Dickerson Management & Associates. She spent over 20 years in the supply chain management industry until 2018, when she decided to take a leap of faith and leave her corporate job to pursue entrepreneurship. She is a best- selling author, certified professional life coach, and an international speaker.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I am thrilled to share my story!! I was born in New York and stayed there with both of my parents until the age of 4. My mother decided to leave, and we moved to Louisiana, where I grew up in a single parent household. My mother was a hard worker, and she made sure we had everything that we needed. I don’t recall us ever going without anything that we needed. I am the youngest of my siblings. My grandmother would have all the young girls in the neighborhood come over to her house on a Sunday and cook dinner. We would sit around the table while she told stories of how women should act and carry themselves. I will always remember those talks and her wisdom she passed down to us.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

One of my favorite quotes about life is “To Whom Much is Given, much is Required”. This quote is relevant to me because after I found out what my talents and gifts were and what I was truly meant to do in life, I felt compelled to share with others. This quote reminds me to never forget that I am blessed, so I am required to bless others.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much?

If you can, please share a story or example for each. My top 3 qualities that I possess that have allowed me to accomplish so much would be my leadership skills, communication skills, and my resiliency. I have always been a leader as far back as I can remember. I have always been the one to start groups, community service projects, protests, etc. I was that girl in school who would take up for those who didn’t have a voice. I am still that person, who believes in doing the right thing and bringing out the best qualities in others. I love networking and communicating with different people. I enjoy reading and learning new cultures and hearing different perspectives on certain topics. I also believe in following your dreams and never giving up. It doesn’t matter how many times I have received a “no” or a “rejection letter”, I will always keep going because I know there will be a “yes” around the corner. Let’s just say that I don’t throw in the towel easily without a fight.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

My career in supply chain management has been a great career. I have been blessed to work for some very respectable companies and municipalities during my tenure in Corporate America. I have met some lifelong friends along the way, and I have always given 110% of myself in every position that I have held. The career path wasn’t easy and if you look at the percentage of women in the industry, there aren’t that many. I can recall being the only woman traveling with a team of men to different supplier locations to have meetings and complete site visits. I can also remember being the only black woman sitting around the table during team meetings and often wondered, why wasn’t there more of us in this field.

And how did you “reinvent yourself” in your Second Chapter?

I reinvented myself because I wanted something more in life. I wanted a sense of purposeful work that didn’t focus solely on money. I wanted to make a difference in people’s lives and wanted to see change in mine as well. I wrote my first book while still employed and I thought this would be a great way to end a career and start a new one. I wanted people to hear my story and understand that I was evolving and now was the time for me to take my leap of faith. After my book was published, I resigned from my job and began my new career as an Author and open my own consulting and coaching business. I am so proud of myself, and I am so glad that I made the decision to do it.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

The trigger that forced me to resign was the unrealistic metrics and goals that given to me and my team. I explained to the Director that this was not going to work, and nothing was done about changing it. I knew in that moment that it was time for me to leave. I didn’t bother looking for another job within the industry because it would have been the same thing at a different company. I realized it was time for me to believe in myself and be my own boss. I was done dealing with unrealistic goals, ridiculous metrics, and tedious projects.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing?

As I was writing my book, I realized that I was interested in helping others transform their lives because I was going through a transformation as well. I realized that I wanted to help people find their authentic self as I had to find myself after all those years. How did you find that and how did you ultimately overcome the barriers to help manifest those powers? I found my niche in telling my story. I didn’t understand that people wanted to know about my struggles, my pain, my opinion so they can avoid the things I had gone through. I had concluded that there was value in my story and sharing it with others was my way of helping them overcome fear and obstacles. I took courses and became certified as a professional life coach and begin working with women and teen girls. I decided to continue studying and learning as much as I can to help myself and others in transformation.

How are things going with this new initiative? We would love to hear some specific examples or stories.

My new career is everything that I had hoped it would be. Since leaving my corporate job, I have written a total of 5 books, I have been asked to speak on many platforms including sharing the stage with Les Brown and Dr. George Fraser. I am fortunate to work with Lisa Nichols of whom I admire so much. I have been sought after to coach teenage girls, created a coaching program to help women explore self-discovery and reduce stress. I have been busy building my brand and loving every minute of it.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There is not a particular person, but several people who influenced me to start my new career. I remember after writing my first book, I was asked to be a guest on a podcast called Brave Files. This was my first interview about my book, and it was so empowering. I didn’t know how much I had gone through in life until I heard someone else quote me and take me through my own events. It was in that moment that I felt that I needed to keep going because this was something much bigger than me. I had to reach other women and share my story and give them a voice. Can you share a story about that?

Can you share the most interesting story that happened to you since you started in this new direction?

The most interesting thing that has happened to me so far is being featured in Speakers Magazine. I was new and upcoming author and speaker, and I didn’t know what I was doing. I remember submitting my information to be featured and by surprise they accepted my information. I was featured in the same magazine as Les Brown on the cover. I ordered about 20 copies to give to others and framed it. It was 3 years later; I was sharing a stage with Les Brown and wrote a book anthology with him. I knew that anything was possible after this happened.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

I struggled a lot with believing in myself and thinking that I could live life on my own terms. I overcame this thinking by attending training that taught me about neuroscience and getting rid of limiting beliefs. I studied the mind and how the brain operated. I wanted to know how I could motivate myself and be positive. I begin writing affirmations to myself and repeating them, believing them, and memorizing them. I started hiring business and life coaches to help me level up and think differently. I knew that I had to do things differently than how they were done in the past if I wanted a different result.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

It was hard in the beginning stages of my new career. It was scary because now I was unsure of the people supporting me and who was waiting for my downfall. I started surrounding myself with people that I wanted to be like, people I admired, and those that I felt was doing extremely well in the areas that I wanted to work in. I changed my mind set and how I viewed situations. My family was always supportive in everything that I did. I recall when my first book was published, my mom announced in church one Sunday I came home to visit that I had copies of my book in the car, so everyone needed to purchase a copy.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

I had to get comfortable with public speaking which makes many people nervous. One thing that helped was writing my first book and being a guest on different platforms to discuss it. This helped me to get out of my comfort zone and share my story publicly. I was able to overcome fear by doing this and it prepared me for so much more later in my career.

What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

A few things that I wish someone would have told me in the beginning was not everyone will support you including friends. I used to think that if my friends didn’t support me by purchasing a book or course that they weren’t truly my friends. I had to learn that they supported me, but it was in other ways. I had to understand that my products and services are not for everyone and that I needed to find my target audience to sell too. I wish someone would have told me that it is okay to fail and redo it as many times as you need to. I always thought that I needed to get it right the first time. I wish someone would have told me to have a financial strategy written before starting my business. I started out spending more than I was bringing in and I didn’t have a budget. I also wish someone would have told me that success takes time, and it is defined differently by each person. I stopped allowing society to tell me what success is, and I began to write down and go after what success is for me.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

If I had to start a movement, it would be a self-care movement. I would teach women about the importance of self-care and self-discovery. There are so many women who are confused about what they want to do in life or who they are in life. I would challenge every woman to focus on herself for an entire day, to show how important it is to put us first and not feel bad when doing so. Our mental, physical, emotional, and spiritual well-being are so important to us that if we don’t focus on us, how can we be any good to others.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. :-)

If I had to choose a person to meet with in private, it would be Tyra Banks. I think she is a smart businesswoman and I love her story and how she persevered through so many obstacles. I would love to sit with her and talk business strategies and being a serial entrepreneur.

How can our readers further follow your work online?

Of course, readers can find me on social media platforms Instagram @drtoschadickerson. I’m also on LinkedIn at Dr. Toscha L. Dickerson and my website is www.dickersonmanagement.com

Thank you so much for sharing these important insights. We wish you continued success and good health!



Pirie Jones Grossman
Authority Magazine

TedX Speaker, Influencer, Bestselling Author and former TV host for E! Entertainment Television, Fox Television, NBC, CBS and ABC.