Cassandra D Freeman of Thoughtful Inspirations: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

by Christina Gvaliant

Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur  we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Cassandra D Freeman.

Cassandra D Freeman is known as the “#1 Dream Builder” — as a wife, award-winning speaker, four-time author endorsed by Brian Tracy, mother of four boys, and founder of Thoughtful Inspirations; she is driven to help women leaders and their families achieve their dreams. Her goal-oriented tools such as ‘The Little White Lie’ book and motivational e-courses within Never Give Up Academy are a few resources she offers to help you maximize your fullest potential. Seeing others become their best selves and pursue their wildest dreams is what motivates her — allow her to help you create the life you dream of too!

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Cassandra D Freeman: Well, my back story begins with the fact that ever since I can remember, I have always been an entrepreneur. The earliest memory I have is making yarn jewelry and selling it down my street. It was my first business partnership with my friend Sharell. We were in 2nd grade. Then there was the candy business. Followed by the nail technician business. Even with all of this evidence of entrepreneurial giftings, I did not actually realize it was a gift until later on. I ended up going to college to become a pediatrician. I realized later on down the line that medicine was not a good fit for me because all I could think of was helping people to never give up and build their dreams. So, I left all of my medical training behind after 10 years to build my dream. Now I teach others how to do the same. There was a time in college where I was encouraging another student. I don’t even remember the class or what I was saying to him. All I remember is him saying, “Are you like a motivational speaker or something?” At the time I just smiled and looked confused. I told him no, that I was headed to medical school and I laughed at how ridiculous it sounded. Now when I tell my childhood or old college friends what I do, they are never surprised. They always say, “Cassandra, you have always been that way lol.” That is why it’s good to ask others what gifts and talents they see in you…many times they can see things in you before you do.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Cassandra D Freeman: My “aha moment” was realizing that I might have to live without my dream. You have probably heard someone say that when you go into business it should be something you love to do. They usually mean that when things get hard you need to love what you do because it makes you keep fighting for it. Well, I had the opposite happen. I felt like I had lost the thing I loved, and it caused me to have the revelation that I couldn’t be without it.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

Cassandra D Freeman: I was definitely a natural-born entrepreneur. Since I can remember I have had several businesses from making yarn jewelry at 7 years old (which I was terrible at lol) to have a candy store in middle school, and finally a nail salon in high school and college. Being an entrepreneur was always my instinct. I had parents that always supported my entrepreneurial pursuits. They would buy supplies and get me any training I needed. When I wanted to learn how to be a nail technician, my mom found me at a school nearby, and my dad cleared out a room in the house for me to run my own nail salon. Looking back, it amazes me how much they trusted and supported me. They never told me, “No you can’t do that.” I just remember finding so much joy in creating and selling. Creating and selling came as naturally as breathing.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

Cassandra D Freeman: I would have to definitely say, my parents. I remember with every business their support was amazing. For my yarn business, I asked my mom, if my friend Sharell and I could go down the street to sell our yarn jewelry. I can just imagine a little me asking that question lol. My mom happily said sure. There was one other person I recall in the story. It was an elderly woman. I had walked up and down the street and I hadn’t sold many pieces of jewelry, but I was always determined. Hearing the words ‘no’ never deterred me, I just kept right on knocking on doors. But there was this one older woman who opened the door and said, “Sure, I’d love to buy a piece of jewelry from you.” I think they were like 25 cents, but she gave me way more than that. I just remember being the happiest little girl. That older woman taught me a lot in that one moment. One of the lessons that I take from her even now is that I always support kid businesses. I will sometimes hear parents tell their kids that their product is not good enough to sell yet. I always find a way to go and buy several. I could not imagine myself at that age and my mother telling me that my jewelry wasn’t good enough. Or any one of my customers echoing the same. I also learned that no matter what happens or how many no’s you get…your ‘yes’ is coming.

What do you think makes your company stand out? Can you share a story?

Cassandra D Freeman: What makes my company stand out is how thoughtful we aim to be. I have the gift to remember what people’s dreams and goals are. So, when it comes to my audience; I know what and who they aspire to be. I have had countless stories of helping my clients and anyone really in extraordinary ways. I had one client who wanted to learn to fly but their own excuses kept getting in the way. For their birthday I purchased a pilot trial flight where my client got to fly a plane in the air with an instructor. He was so moved in so many ways. That forever changed his perspective and now he is a pilot.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Cassandra D Freeman: The three character traits that were most instrumental to my success would be being a student of life, risk-taker, and being resilient. There are really so many examples of all these characteristics but the best way to explain them would be to describe my process for marketing my book the Little White Lie. I had written several books before the Little White Lie but this one was different. Because I was a student of life, which means I love to learn and read; I took a course on book marketing. I believe in being my own competition and keeping that in mind keeps me resilient. One thing I learned in the course was how to get people to endorse your book. Armed with that information, I decided to take a huge risk. I decided to seek out endorsements from the top people in my industry. I was so nervous to do it, but I did it! A few weeks later I received a personal handwritten letter from Brian Tracy along with his endorsement. I was in shock but so amazed and thankful! I took a risk and the most amazing thing happened for me. I was thrilled and still am to this today. And it was the combination of all of those successful business leader traits that lead me through.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

Cassandra D Freeman: Oh yes. Back in 2012 when I first started my business, it was the advice that if you aren’t making six figures in your business then you are doing something wrong and you should listen to “this expert” and they will show you the magic formula on getting those beautiful six-figure numbers. The truth is that it’s hard for everyone starting out and you have to find what works for you and your business. Just because someone else uses a different system does not mean your customers will respond in the same way. After I went down a wormhole of experts, I finally got back to what was a fit for myself and my business. Then I got expert help based on the needs of my own businessmodel.

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

Cassandra D Freeman: To have the mindset that we are all in this together. I would also say to work your hardest to get things done well ahead of time and take all the breaks you need. Delegating work to a trustworthy source is important as well.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Cassandra D Freeman: Show up. Show up in person, show up online, and show up live. The more you show up, the more you can connect with your audience and industry. Show up consistently so people trust you to always be there. Every time you show up, share something of value.

Can you help articulate why doing that is essential today?

Cassandra D Freeman: Lots of people are inconsistent. They do not show up or they do so halfheartedly. Most people do not realize that one of the truest keys to success is staying consistent. When you are consistent people see that you are reliable, trustworthy, and a real leader.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Cassandra D Freeman: They want to make everything so perfect. But nothing is ever perfect because there is always room for improvement. You have to realize that your business evolves as you do. It is okay to put a lean product out. It actually gives your audience the ability to suggest changes for you to make it better. You get to hear feedback and decide how you want to take your product/service to the next level.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

Cassandra D Freeman: The highs and lows are different than a regular job because there is a personal growth requirement in entrepreneurship. I have yet to speak with an entrepreneur who did not emphasize how much entrepreneurship has helped them grow in all areas of their lives. Within entrepreneurship things are ever-changing. All types of challenges come at you and you have to become exceptionally creative. In a regular job, there are typically other people in place to handle major company issues and a person usually has a focused role. As an entrepreneur, you can be doing every single job yourself, especially if you are a solopreneur. Within every single role, you have the associated problems, but you also get to enjoy the rewards.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

Cassandra D Freeman: Every time I create a new product or course, I am unusually excited. I love every part of my business, but the creating is what just amazes me. I love to get an idea and make it real. My latest creation that I have not even launched yet is my own inspirational jewelry line shhh. I also get super excited every time I hear a success story from my audience. They are so good at making me cry tears of joy. My client Caretta has written several books now. When I first took her on as a client, she had a finished typed book, but she was stuck. By the end of her coaching, she was doing her own book party, launches, and tours. She even made a dedication to me in her 1st book. That was special. Speaking of books, I had a former neighbor/friend whose husband followed me online. I had no idea he followed me on social media. A few years later my friend shared with me that as a result of following me, he wrote a children’s book. I immediately went to purchase a copy. I was so blown away. That just goes to show you that you may think no one is listening to you, watching you, or reading your posts…but someone is always watching. You never know who you are helping. So, keep going.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

Cassandra D Freeman: Anytime I begin to compare myself to other people I feel very unsettled and low. I have to remind myself of who my real competition is and that is me. I do not know anyone else the way I know me. So, it’s only fair that I compare myself to the one person I know the full story on and that’s always me.

Based on your experience can you tell us what you did to bounce back?

Cassandra D Freeman: I take a mental step back and a moment away to refocus. I sit a few minutes in front of my vision board to remind myself of what my goals are and what I am trying to achieve. I go look at my Successful Journey Chart and see all of the actions I have taken to get to where I am today. Then I realize the only person I need to be winning against is the one looking at me in the mirror.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

Cassandra D Freeman: I would say the five things you need to successfully ride the emotional highs and lows of being an entrepreneur are a support system, proof that progress is happening, a flexible plan, a hard work ethic, and rest. Throughout the entirety of me being an entrepreneur, there were so many highs and lows to choose from. The best example would be during early covid. Since we all had stay-at-home orders without any vaccine at the time and covid was new; everything got canceled including all of my speaking engagements. But being an entrepreneur is all about being resourceful. So, I had to adjust my business strategy. I have never been a stranger to hard work, so I threw my whole self into working my new plan. Then I got exhausted and burnt out. That taught me (and it took me years to learn this) that rest is work too. It is the time when your body is working to heal and rejuvenate. Over the years that was a common trend with me. I would work until I was just burnt out. This time I had really burnt myself out though, not to mention I was also experiencing many deaths in my family and in the community. I had to take three months off from my business because I didn’t rest properly. Another thing I learned was that every strategy and every big life event needs some sort of scheduled rest or reflection time. As I started getting back on the upswing, I listened to a few of my mentors share with me how they plan their time off. I listened to entrepreneurs who I looked up to, share how they were taking a step away from their businesses to help their children academically get through covid. And of course, they kept their businesses running so that not even their clients knew they were taking a break to refocus their family lives. After I took in all of that information, I went back to my vision board and my Successful Journey chart to remind myself of where my business has to come from and to remind myself where it’s headed. I adjusted my plan again to include rest. And not just for my body…for my mind, emotions, my family, and my friends because we are all in this together. After that low, I returned with so much impact that my business strategy returned more profits to me than with my pre-covid plan. That is why it’s important to not get stuck on one plan, be flexible.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Cassandra D Freeman: Resilience is a person’s ability to bounce back or get back up. It’s their ability to fall down, get back up, and dust themselves off. Resilient people fight the urge to give up. They understand that it is all a journey. That every journey has detours, bumps, stoplights that take forever, beautiful views, fun sites, and everything in between. But they also understand that it is in getting back up that you learn the most amazing lessons life has to offer.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

Cassandra D Freeman: My family, namely my parents and my Uncle JC always encouraged me in everything that I did. I used to play basketball. After one game where we lost, I remember my Uncle JC sitting down with me. I loved his breakfast and his milkshakes. After the game, he made me a chocolate milkshake and turned on this hilarious movie. When the movie was over, he said, “Let’s schedule a date tomorrow. Maybe we can watch some professional women’s basketball games and discuss what we see.” He taught me countless lessons but, at that moment, he taught me about what it means to be aware of how you feel but also create a game plan to be better.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

Cassandra D Freeman: Yes. I always aim to do that. Ever since I can remember people have told me I always have a peacefulness about me. What helps me keep a positive attitude are two things: my habits and recognizing what I need at the moment. When it comes to habits, I have a few things that keep me optimistic: reading, listening to motivational audios and videos, praying, listening to music, exercising, and eating healthy. On stressful days I have also taken the time to identify what I need, which can vary depending on the situation. Usually, those needs are either reading, walking, running, having a homemade smoothie, or watching something that will make me laugh.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

Cassandra D Freeman: When you have a positive attitude, you are more grounded, and your clients learn that they can rely on you. Being positive makes you more inviting to all people. It also helps your family to love entrepreneurship as much as you do. Being an entrepreneur can make the work and life balance a bit rocky but with a positive attitude, it gets easier to focus on what’s important at the moment. There was an occasion very early in my business where I had an event and my photographer told me at the last minute that they could not attend. Instead of getting upset, I asked one of my sons to do it. I had seen a gift of photography in them anyway so I thought maybe I could teach him what I know (I got certified in film and photography development in college and that was also one of my businesses.) Well, he did it! We all had the most amazing time. And after the event, I spoke with a few other speakers who had their children taking photos for them that day too! It was really a great experience with a great takeaway. To keep a positive attitude and have fun with your solutions. Also, my son still takes some business photos for me to this day.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

Cassandra D Freeman: I have a quote that I wrote years ago in my first book. I remember it vividly because any time I am not handling a bad day well (which is rare) my closest friends always remind me of what I wrote (Cue the eye roll and laughter). “The words never give up are more than just a phrase. It’s in your thoughts, it’s in your actions, and it’s a way of life.”-Cassandra D Freeman

How can our readers further follow you online?

Cassandra D Freeman: My username is @thecassandraf. You can find me on social media on all platforms. You can also find me anytime on

This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!

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