MGU 210 Gresham Harkless | Discovering Yourself


People are considered the most adaptable creatures that they can acclimate to various degrees. We were once in the “discovering yourself” stage but it seems we cannot go out of our prized comfort zones. Almost always you hear people saying that they are growing and yet, they are lost in the stagnant space. Sitting down in conversation with Whitney Lauritsen and Jason WrobelGresham Harkless Jr., Founder of CEO Blog Nation, imparts his insights and personal experience he used to get that aha moment despite the motionless growth circumstance. It’s not always the case that if you’re comfortable and satisfied, you’re developing. Listen in and learn the points we can try to improve on. 

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Key Points In Discovering Yourself With Gresham Harkless Jr. 

Life is full of unexpected surprises. I feel like that is almost rhetorical in that statement. We had some interesting challenges prior to starting this episode with our guest, Gresham. I didn’t know if this episode was going to happen, but through the grace of God and technical support, we are back on and doing our thing. I was telling Gresham that sometimes the pre-show banter is so good, then I’m like, “We got to stop. We got to save this.” We were flowing and getting into some interesting subject matters. 

I wanted to flip it back and start this episode by talking about some of those unexpected setbacks in life. Gresham and I were bonding over the fact that we’re huge sports fans and former basketball players. I’ve also experienced a litany of scary, challenging injuries through basketball. It’s interesting because I feel like in some ways, when we have setbacks in life, it can be easy to get down on ourselves and get into that depressive state like, “Why should I even bother? This is too hard. Am I ever going to be normal again?” 

We need to be resilient. Uncertainty, pain and suffering will inevitably find us all in life. Click To Tweet

I had mentioned to Gresham that sometimes, the mental side of a comeback and getting ourselves back into playing shape or getting ourselves back into a state of health and vitality is way harder than the physical effort. I wanted to kick this episode off in somewhat of a maybe unconventional way, Gresham, in touching on the idea of mental resilience when we are facing tough stuff in our life. You were telling me that you had a gnarly Achilles tendon tear. I want to kick it off by talking about you overcoming these injuries when you were in athletics and also, how that scenario in life sets you up for dealing with other challenges. Welcome to the show. It’s great to have you.  

I’m super excited to be here as well. You’re absolutely right where the tech snafus are like a micro chasm of everything that it can sometimes happen in life, and how to try to get through them and continue on. My love was always basketball. That was my go-to and that’s what I always did. You were asking if I had played any pick-up or anything like that and I was saying not as much anymore. It was largely because of the Achilles tendons here that I had before I even started my business and did all of those things.  

Fast forward a lot of years, I wanted to start a business. That was always my goal and I didn’t have everything set up in order to do that, but I was like, “There’s something that I want to do.” I left the job that I had that I didn’t feel like it was a great job and I said, “I’m going to start doing, at that time, freelance writing.” I wanted to make sure that I was mentally in shape, but also physically in shape, so I was like, “I haven’t played basketball in a while. Let me go shoot some hoops and play a pick-up game.” I went to this church and I was shooting.  

We were playing a pick-up game and I was telling Jason that I felt this hammer slammed into the back of my leg. I looked and there was nobody behind me. It was probably one of the most painful injuries I had, so I had to push myself with my legs off the court. Everybody went back and forth, but I ended up driving all the way back home and did all of that. I was probably about 45 or so days out of leaving that job that I had. I was about maybe two weeks or so away from the insurance that probably would have taken care of it.  

All of that happened and I was researching and doing MD to try to figure out what was going on. I eventually was like, “I might have torn my Achilles tendon.” I eventually went to the doctor and the doctor couldn’t even touch my leg. That’s what led me to being in what I call a dark place. I couldn’t get around, so my dark place was just in my bed. I wish I had to do something bold. I said, “I have entrepreneurial tendencies. I want to start something, so I want to take bold action.” It didn’t go according to plan at all. It was one of the darker moments that I’ve had.  

Now I can say, going years forward, that it was something that I needed to have happened. I say I’m hard-headed enough that probably if I didn’t tear my Achilles tendon, I would have been bounced around doing a bunch of different things. At that time, I wasn’t a happy camper. I was sad and I was embarrassed because I was trying to do something bold and it didn’t work out. In hindsight, it’s 2020 and it was something that led me there.  

I wish that I can say that I knew that I was going to build myself up from that. It was me, at that time, pouring myself into interviews, the blog that I have, and all of those things where I couldn’t do anything else. That was the light at the end of the tunnel. It was reminding me of where I wanted to be. It was still a dark time because you never know how those things are going to come out. For me, it was a gradual process. I can say now that definitely happened for a reason, but I didn’t know at that time. 

It’s interesting to talk about these moments in our lives. When we’re in a point of pain or suffering or depression or sadness as you’re talking about, Gresham, when I’m in those positions in my life, it feels like they’re never going to end. Intellectually, we know they’re going to end. “I’m not going to be at this level of pain and despair for the rest of my life.” In a way when we’re that deep in it and we’re that deep down the well, it sure feels that way, doesn’t it? It’s like, “When am I going to be out of this?” As you’re coming out of this injury and you’re getting your strength back, and I assume you’re going through physical therapy to get your function back, what’s that process of coming out of that darkness for you?  

Whitney and I talk extensively about mental health, depression, and suicidal ideation. We talk about people’s origin stories. Something we love to get into is to get those deep soulful personal stories. As you’re recovering and getting your strength back, how did that process inform you as an entrepreneur and as a man to face the uncertainty, pain, and suffering that is inevitably going to find us all in life? How did that set you up for being more resilient and trusting like, “I can make it through this darkness,” and find the light on the other side of it? 

I didn’t tear my Achilles completely, so I didn’t have to have surgery, but I still had to have the cast after cast, going through PT, learning how to walk again. I remember even figuring out how to take my toes and pick up marbles and move them from side to side. All those things you take for granted. You start to appreciate all the things that you’re able to do on a regular basis. I always bring myself back there to understand even the process of everything. Especially with starting a business or anything in life, I tell myself all this time it’s a marathon.  

You want to make sure you’re staying focused on the day-to-day, but you don’t want to get so caught up in where you’re going to be or trying to move too fast where you cheat yourself out of the process but also maybe even stir up a lot of that frustration on things not moving as fast as you want them to go. That time was me realizing that no matter how much I wanted to start walking again, I had to remove one cast to get another cast. I had to learn how to get to one crutch and another. It’s a whole entire process, so you can’t treat that process.  

MGU 210 Gresham Harkless | Discovering Yourself

Discovering Yourself: Don’t take things for granted just because you assume everything is going the way that you want them to go.


For me, it made me respect the process to do anything. Whether it be starting a business or learning a new skill or a hobby or whatever it might be, I have to get present with that. Of course, it’s always a process that I have to learn from. It’s something that I always go back to, that moment because I took a lot of things for granted because you assumed everything was going to go the way that you want them to go. When they didn’t go the way you want them to go, that’s when you find out who you are.  

That’s when you get to that resilience and that mental toughness because things will not go 100% how you want them to go. How are you going to react to that? That’s something that I challenged myself. If I ever get in that place, I’ll say, “You did the Achilles. You were able to get through that. You were able to get through the physical part, but also the mental part of being stuck in bed, not being able to get your food, and things like that, so you can get through a lot if you’re able to get through that.” 

I’ll bring up a couple of basketball analogies. Whitney’s laughing because she’s like, “Is this whole episode just going to be about basketball wisdom and analogies?” It might. I legit feel though, Gresham, what you reminded me of was right before the NBA finals with the Lakers and the Heat, they were talking to Jimmy Butler and Pat Riley about their philosophy as a team. We hear a lot about with sports teams and also companies that there’s a culture. What’s the culture of the team? What’s a culture of a company? 

He was saying that when you get tested by life and get these challenges, you find out who you are and what’s inside of you. Pat Riley and Jimmy Butler were talking about their whole team philosophy about a lemon. Pat said, “What happens when you squeeze a lemon?” Jimmy said, “You get lemon juice.” Pat Riley said to Jimmy, “Exactly. When you’re squeezed in life, what’s inside of you comes out for everyone to see.” This lemon juice analogy is like, “When you get squeezed in life and you face setbacks, challenges, suffering, pain, and confusion, what the hell am I going to do next?” 

It does start to reveal deeper parts of who we are. Maybe things that we’ve never even accessed before. I know certainly that there have been times in my life, and Whitney as well, we’ve been through a lot as friends and business partners, that times of strife, financial hardship we’ve all lived through. I got to see some sides of myself on a deeper level that I hadn’t acknowledged or fully seen yet. Your story, Gresham, is poignant in the sense that those are the moments in life. It’s not that there’s not value and happy moments or joyful moments or celebrating, but I don’t necessarily think those moments reveal as much about ourselves as the tough times do. 

It’s getting through the muck and the darkness that we’re like, “Not only did I survive that, but I learned a whole lot about myself.” The other thing, too, you talked about slowing down and you talked about taking time to appreciate the things that you took for granted. It is important to take this in when we’re in a moment with digital tech and social media. Whitney and I talk a lot about this go, hustle, grind all the time. This constant pressure where you see business leaders, entrepreneurs, thought leaders, authors, etc., always preaching the gospel of hustle and grind. 

Sometimes in life, it’s more important to play at your own pace, another basketball analogy, and then you make the game fit around you. I’m wondering if that mentality still translates into your business as an entrepreneur where you play at your own pace. You don’t get caught up in the stuff that you see on social media about people telling you how to run your business or how you should do your promotions. How do you find your lane and how did you find your lane amidst all that noise? It’s so easy to get caught up in the noise. 

That’s a valid point. When I tore my Achilles, one of the things that I wanted to remind myself of is I started to get hardened to some degree, even as I was recovering. My friend had a wedding and it was in New York. They were like, “You’re not going to come to the wedding because I know you tore your Achilles.” I said, “I’m coming to this wedding.” I’m on crutches on the bus taking that five-hour bus ride to do that. The lemon juice that was in me was like, “This hurt and this sucks, but I want to try to not have it dictate my life.” 

That’s what came out of me from that and that’s how I’ve tried to approach things in my life. Many times, especially when you’re younger, you start to believe that you should be X, Y, and Z or A, B and C because so-and-so says that or because everybody’s doing that. Whether we’re talking about being on social media channels like, “This is how you should run your businessYou need to be a speaker,” or whatever that might be, how that manifests itself. For me, I am a big believer of when you’re young, a lot of times, there are seeds planted of who you are and what makes you who you are, so I always go back to that.  

When you face setbacks and challenges, you will see a side of yourself on a deeper level than you haven't really acknowledged. Click To Tweet

I started a family newspaper when I was ten years old. My dad went TDY, who was in the military. I like creating, writing, and doing all those things, and that’s something I always went back to. When I was trying to figure out who I wanted to be and who I was, I went back to that story because for me, it was something that was unique. It was something that I did not do to get any popularity at that time. I was just trying to connect with my dad and of course, sell some subscriptions to make a little extra dollars and things like that. That’s something that made me who I was and what I feel like I always go back to is that creation of content piece. 

It was definitely a process. I tried to be other people. I tried to do what everybody else tried to do, but it didn’t feel right. I tried to try on those shoes, so to speak, and they didn’t fit. I didn’t feel genuine. I didn’t feel like I was authentic. I didn’t feel like I was running my own business. My goal was to start a business and hopefully make an impact and create change. If I have to do that by being somebody else, I might as well just get the 9:00 to 5:00 job and do the regular, whatever it is that I didn’t necessarily want to do. If I can’t do and run my life and approach my life in the way that is in alignment with who I am, then what’s the point of me even doing it? 

It’s tapping into that same mentality that I had when I tore my Achilles where I’m like, “I’m going to try to do it my way. If it doesn’t work out, then so be it, but I’m going to try.” There’s nothing worse than the pain of regret, so I try to tap into that, stay true to that in every aspect, and try to have that filter of, “Is this in alignment with who I am?” I’m not saying that I’m afraid to try things, but still, that’s happening to who I am and going forward from there. 

I’m curious, what is your process for tuning into yourself? That’s something that I’m constantly reflecting on. It’s a long process to understand ourselves and who we are because we have to brush away, chip away, and dig away at all these different elements of ourselves and all these layers that we’ve accumulated over time. I find that many of those layers are other people’s influences or society’s influences.  

We have many things at play. Each of us has some story we have in our head, and then, of course, there’s a lot of timely and cultural messaging out there that can get in the way and cause us to think that we’re less than. That we’re never going to make it because of who we are born as. I’m curious, what does that process been for you, Gresham, as you’ve tried to figure out who you are so that you can be in alignment? 

It’s an always-evolving process. I almost feel like you never truly feel like you understand all the different aspects of yourself. For me, a lot of it is trying different things and seeing what works and what doesn’t work. It has been absolutely huge, but I’m maniacal about understanding myself, taking the Myers-Briggs test, and all of these different kinds of personality set to try to get an idea of who you are. What makes it probably a little bit more difficult is we’re evolving.  

It’s like businesses and life itself. We’re changing and evolving, too. Something that I might not have liked ten years ago, I might love now, so it’s drilling down and working. For me, it’s absolutely trying things and seeing what works and what doesn’t work. It’s what helps me to understand that. I always try to get alone in a quiet space to question myself and meditate on different things that I’m trying or different things that might be certain ideas because when I do that, it gets a little less noisy.  

You don’t take away the history or the culture or all of those aspects, but when you get quiet by yourself to some degree, you have only yourself to answer to. When you’re able to do that, it allows that to happen, so that’s usually what I go through. It’s not structured, but I feel like it’s something that has helped guide me to where I am now. It doesn’t mean that everything I do is completely in alignment, but I’m always trying to get more in alignment in trying to fulfill my goals, aspirations, and gifts on an even deeper level. 

It’s interesting that you touched upon the personality tests because that’s something that I’ve been drawn to over time and we’ve talked about some of them. I started watching a documentary that I haven’t finished yet, so I can only speak on maybe the first half of it. Have you heard of the HBO documentary called Persona?  

MGU 210 Gresham Harkless | Discovering Yourself

Discovering Yourself: When things don’t go the way you want them, that’s when you find out who you are. That’s when you get to resilience and mental toughness.


I haven’t.  

It’s interesting because the subtitle is The Dark Truth Behind Personality Tests and that’s what intrigued me. I have to say it wasn’t captivating enough. It felt a little drawn out and that was part of the reason I haven’t finished it yet. I don’t get the point of the documentary at this time. However, it isn’t an investigation into our cultural infatuation with personality testing and the origins behind them. They go deep into Myers-Briggs, which I found fascinating. Some people believe that it has a bit of a troubled past. 

In fact, a lot of these quizzes are used in workplaces to discriminate against others, whether it’s racially, around sex gender, or mental capabilities. There is a guy in this documentary in the part that I’ve seen thus far who’s had a lot of mental health challenges. He found that he was being rejected from jobs because they were forcing him to take tests like Myers-Briggs, and then based on his results, they would decide if he was qualified or not. 

He felt like, “You’re not going to hire me because I’m an introvert. You’re not going to hire me because there’s one part of my personality that you think means that I’m going to show up in a certain way.” I’m interested in what you drew from Myers-Briggs and how it plays a role in your life. As part of this conversation for each of us, reflecting on the reasons we’re drawn to personality tests. Are they telling us the truth or are they giving us another label that might even not be something that benefits us? That’s a big question I’m asking myself. 

I haven’t heard of that, but I’m definitely going to check it out. I almost feel like, for me, the personality tests have been a way that I use and understand myself to know where my zone of genius is, so to speak. I use it more so as a tool, not as a box. We can talk about tests and we can talk about educational tests. There’s a lot of biases that go into the people that create those and we have to look at those things. A lot of times, people use tests in order to place people in boxes or say somebody can’t do X, Y, and Z. They don’t have a holistic look at what it takes to build a team or maybe run a business or to do it on an impactful level. Many times, people will manipulate things in order to have what they consider to be their goal, personal prerogative, or whatever that might be.  

They’re going to use a test. They’re saying, “This person is an introvert. I don’t want to hire an introvert, so I’m going to use that as a reason for not hiring that person without drilling down and getting to know that person.” Personality test is not just one. Myers-Brigg was one. There’s another one called True Colors. There’s a lot of different ones. I personally have used it as a way to see myself and understand my tendencies. Not to put myself in a box, but more so understand like, “How can I respect my strengths and my understandings but know how somebody else who’s completely different wouldn’t jive with me but could compliment me and it can create a more holistic and stronger team?”  

I am almost attracted to people who are different more so because that provides an opportunity for us to grow strong together, which is often what happens in a lot of businesses and organizations. I see it a lot in sports as well. We get this, “I want to be around people that look like me, talk like me, and think like me because I want to be comfortable.” Rather than, “I want to grow and be better and make a bigger impact.” I use these tests to get around people who are not like me so that I can grow as a person where iron sharpens iron. That’s what I feel overall. That’s interesting. I definitely want to check that out for sure. 

It’s interesting because I feel like maybe in certain circumstances, Gresham, people might surround themselves with people who look like them, act like them, talk like them, and have similar backgrounds because it is comfortable. Maybe people are looking for a certain level of ego validation. “If I have people who think like me and have the same life perception, then they’re constantly reaffirming my belief system. My belief system never gets challenged. My prejudices never get challenged. My short-sightedness never gets challenged.”  

Just try to do things your way. If it doesn't work out, then so be it. There's nothing worse than the pain of regret. Click To Tweet

To your point, we don’t ever get the kind of growth we would get by iron sharpens iron, the friction. What I thought of when you said that is the friction of like, “I want to put myself in conversation with a person who might not have the same political beliefs, religious beliefs, or worldview, but if I can come to it with a level of respect, love, and openness, I don’t have to agree with that person.” One big thing in our society is realizing, “Even if I don’t agree with you, I can still respect, love, and care for you as a human being.”  

Maybe not even love. Maybe that’s going a little too far, but at least the base level of respect and be open to your perspectives and your worldview, even if I disagree with it. Whitney and I talk a lot about cancel culture. There are many gradations of whether or not we see it as malicious or we see it as a mistake. Endemically, we’re not coming together and having the type of discourses you’re talking about where it’s like, “I know this is going to make me uncomfortable. I’m going to head right into this conversation or this situation or invite certain types of people into my business, sphere, and team because it’s about the collective good. It’s not necessarily about me being comfortable and what I want, but through this experience, it’s hopefully going to help everybody grow.”  

That comes down to leadership. It seems to me that you, as an entrepreneur, having that growth mentality means you are willfully putting yourself. I don’t want to assume, Gresham, but you are willfully choosing to put yourself in uncomfortable circumstances. You’re a dude who’s wired like that. You seek that out. Is that accurate? Do you seek out those uncomfortable types of situations because you know it’s going to help you grow?  

Yeah. That’s part of it. Definitely, I do know that’s where growth happens, but often, it’s because I have been the other in many situations throughout my life. If we go all the way back to me growing up, I was in gifted classes. Often, I was the only kid that looked like me in a lot of those classes, so I always felt different. I always didn’t feel like I belong to some degree. It’s not something that I always seek out. That’s who I am. That’s the comfort. That’s how I grew up. It’s all the things that I saw. Many times, especially with leaders, you have to want to get outside of your comfort zone in order for that to happen.  

Many times, we get caught up in like, “This is our comfort zone. This is what’s good.” We don’t realize or even try to see if something on the other side is potentially even better. Nobody tries those things because people are so stuck into like, “This is how I feel comfortable. This is a validation for my belief systems, so I don’t have to have those other conversations.” For me, I’m often not filled up with a room of people, even though I went to an HBCU. Once you start to drill down, you start to realize that people think differently. They have different viewpoints, feelings, and so on and so forth. 

I do constantly seek that out and I don’t feel as comfortable when I am in a room, sometimes virtually or in person. When everybody’s thinking the same things or I’m getting validated to feel like I’m great or I have the best ideas, I almost push back against that and I don’t necessarily want to be around that. I don’t know exactly why, but that is something that I don’t want because I know I can always be better. I don’t get better by someone patting me on the back and saying, “You’re great. You’re doing everything perfectly and you don’t have any room to grow.” That’s not the case. 

We had a previous guest, a psychotherapist named Dr. Kathleen Smith. One of my favorite quotable that you reminded me of from that episode, Gresham, was she said to paraphrase, “There’s no amount of praise that’s going to help you grow.” We don’t grow through praise. That hit me. I remember when she said that in real-time, I was thinking back to my childhood or sports and a coach or my parents are like, “Good job. You did great. You’re awesome. You’re the best center who’s going to be a point guard before you know it.” That’s a little backstory.  

Gresham and I both had early growth spurts and we were both centers on the basketball team power forwards. All of a sudden, everybody else grew and we’re like, “We’re not the tallest anymore,” as a side note. It’s interesting to think about praise doesn’t help us grow. If we think about it, for me at least, there was a belief system that it did. If I got the right amount of encouragement or encouraged others that would help with growth. Maybe it affirms your sense of self. Maybe it’s a confidence booster.  

Sense of who you are and confidence is not the same as growth. These are all different things. I’ve been tripping on that because since her episode came out, I’ve been thinking about that like, “I’ve been trying to grow through praise for a long time and realizing that hasn’t been the key.” It’s like, “What if I put myself in a situation where I’m not being patted on the back all the time?” It’s like on Clubhouse, which hopefully we’ll do a room with you, Gresham. When Elon Musk was on there, people were asking him about entrepreneurship and I can’t remember exactly what the question was, but his response was, “If you need reassurance or praise, you shouldn’t be an entrepreneur.” 

I was like, “That was cold, but that was real.” I feel like whether it’s us as artists or entrepreneurs or the melding of those worlds. You talked about your writing, Gresham, and your creativity. There’s a lot of solitude in that process. The three of us can agree that in any creative endeavors we’ve done from video to podcasting to writing, there’s a lot of alone time. Oftentimes, in that solitude of creation, there isn’t someone coming up in our office going, “You’re doing a great job. Here’s a cookie.” We’re alone doing our thing for hours.  

It begs the question if perhaps we’re used to getting that praise and we jump into a solo endeavor or entrepreneurship, which can be sometimes crazy as hell and it can be tough to run your own business. I suppose this is for both of you, Gresham and Whitney. Without getting that praise from external sources, how do we keep ourselves moving forward and growing with all of that alone time and all of that doubt that creeps and all of that, “What the hell am I even doing anymore?” I have so many moments like that where I’m like, “What in the hell am I doing?” I lose my faith in what I’m doing. Without that pat on the back and the cookie, how do both of you keep yourselves going? 

It’s funny that the guest said that because I’ve been looking a lot for this. There’s this concept called the dark side. It all taps into how and what motivates you. Sometimes, people get motivated and I don’t think there’s enough, at least I couldn’t google and find enough, about the dark side and sometimes, getting motivated from negative things. You hear it a lot in sports. You definitely hear Tom Brady. He’s 198 or whatever number pick he was. He always has that chip on his shoulder to try to show people that he’s better. That’s something that I don’t think necessarily works for everybody, but I find that works for me. 

It’s a balanced being because you don’t want to get too much in the dark side where you’re filling yourself out with such negativity that you start to believe in. You start to go off the deep end and don’t focus on what you’re ultimately trying to do. For me, tapping into that to try to prove to other people, which you don’t want to be so outwardly focused that you’re losing sight of why you’re doing what you’re doing. If you can tap into like who you are, what you do, what your goal is, what your gift is, and you can revert that energy, frustration, pain, or whatever it is into those positive things, and you can show to people.  

Maybe not face-to-face, but doing it for validation like, “I did this,” has helped me out tremendously. I started to read about a lot of people that were successful and how I consider them successful. I realized that it wasn’t a straight line and it didn’t happen overnight. Even though when I first started, I said, “It didn’t happen for them, but it’s going to happen for me. I’m going to do it overnight.” I didn’t do it overnight and I’m still working on it. Understand the process and the grind of what it takes to get there, the marathon as I always say. It’s something that I try to remind myself of and if I ever get in that dark space and I don’t know what to do, I also try to look at people that have been successful and what that process is like. 

MGU 210 Gresham Harkless | Discovering Yourself

Discovering Yourself: Try to be alone or in a quiet space, question yourself and meditate on things. To some degree, you will only have yourself to answer to.


On my show, many times, I’ll ask people to hop in a time machine and talk to their younger business self. The answer I would always have is like, “Let yourself know that it’s not a straight line.” Many times, you quit before things can get good because you think that it’s a straight line. As soon as you hit some type of turbulence or adversity, you think that you failed but you haven’t failed. You can still keep going as so-and-so did. If we don’t hear those stories and we don’t know about that, then a lot of times, we think that we should throw in the towel before we are even just getting started. 

I was thinking about this during my yoga practice. One of the most important things I ever heard about yoga is that it’s called a practice for a reason. Yoga is not something that you perfect necessarily. I’ve been doing yoga since 2006, so it’s been a long time and it’s been a journey. I don’t do yoga to try to become some perfect yogi. I do it because it makes me feel good each time I do it. That in itself is reward enough and that’s incredibly important in this conversation, too. We need to focus on what we’re enjoying.  

However, there are times where we don’t enjoy it, and this also ties into yoga because sometimes, I don’t want to do it. Sometimes, I’m bored as Jason has talked about. I remember when Jason told me he found your yoga boring. I was like, “What does he mean?” I kept reflecting on it and realized, “I could totally relate to this. Sometimes, it does feel boring.” I have to ask myself, “Why am I doing it?” I’m doing it for that enjoyable experience as some or most of my yoga classes provide, but I also do it despite any discomfort and boredom because I know that over time, it has a long-term effect on my body and my mind.  

When I’m consistent with yoga, that’s when I feel my best. Sometimes, the consistency doesn’t pay off for months. For example, I’ve done yoga every single day of 2021. I’m not positive. I might’ve skipped a few days, but I have been consistent. Only after about 2 or 2.5 months did I start to start to see results in my strength and my flexibility, but also in my mind. A lot of people will do something like a yoga practice and expect results faster. What I was reflecting on is it’s too bad that when it comes to our health, businesses, and relationships, many of us have been conditioned to think that if you don’t get results fast, then it probably isn’t right for you.  

If you’re not getting results from the way you’re eating, you’re probably eating the wrong foods. If you’re not getting results from the way that you’re working out, you’re probably doing the wrong workout. If you don’t feel like this relationship is perfect after a short amount of time, it’s probably the wrong relationship. Also, if you don’t get results from your business, you must be doing it wrong. We have this mentality where we want results within 30 days. How many times are we framed in all these different elements of our life to get something within 21 days, 30 days, sometimes even less?  

It’s rare that results happen that fast. How could you possibly judge whether something’s right for you or whether something’s going to lead to success in such a short amount of time? What you’re saying, Gresham is incredibly important to this conversation. We have to remind ourselves of this constantly. Even though we might know it on a logical level, emotionally, we need the reminder. Jason and I have conversations about this show about our brand, Wellevatr.  

It can be frustrating when you’ve been working on something for a while and you don’t see the results that you expected, but that’s another great time to examine. Nobody’s guaranteeing you results. If they are, you should be running in the other direction because how could anyone possibly tell you what results you’re going to get with your specific case? That’s been something I’ve had to learn the hard way. I’ve been promised all sorts of things romantically, physically with my health and with my business, even mentally.  

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A lot of people want to frame things as, “You’re guaranteed to get results or your money backFollow my guidelines. If you do it exactly as I say, you’re going to get those results.” What I would do is try to follow those strategies to a tee and when I didn’t get the results that I was promised, I thought I was doing something wrong. I thought there was something wrong with me because they said it was going to work. Now I’m of this mentality of, “I don’t believe that anymore. That’s just a lot of marketing and speak.” 

What comes up for me in this conversation, too, Whitney of consistency and doing the same things over and over again is Winston Churchill. He said, “Success is moving from failure to failure with no loss of enthusiasm.” How many times is it like, “Pick yourself up, dust yourself off, and try again.” I can’t believe I’m quoting Aaliyah and Winston Churchill in the same sentence, but I just did. It is that mentality of we look at social media and we see certain people that might be labeled an overnight success, and then we realize an overnight success has 10, 15, or 20 years behind them.  

When we dig under the hood, we get to the truth of their story. As you said, Gresham, it’s not a straight line. It’s a double decahedron. It’s something crazy. It’s definitely not linear. To me, whether or not it’s the Churchill thing of moving from perceived failure to failure or it’s just doing the unglamorous things. To go back to social media, there’s a big misnomer. I’ve seen a lot of young people get into entrepreneurship because they’ll see the Lambos, Ferraris, the mansion, hot girls, hot guys, watches, and all the material, external trappings of what it means to make it. I was that dude for sure.  

You get into your business and you realize that a lot of business in entrepreneurship is that consistency. It’s doing the “boring” routine things over and over. “Every week, I’m going to write my newsletter. I can do three episodes a week. I got to do my SEO. I got to do my meta tags. I got to follow up on the emails. I got to eat right. I got to take care of myself.” The routines can be “boring” but legit, it is the unglamorous parts that are going to separate the people who hang in there and have longevity in this business versus the people who get in because they think after two years, they’re going to get the Lambo, house, watch, and the hot partner. A lot of people give up because they realize a lot of this process is not glamorous at all. In some ways, I find it, at times, excruciatingly rote, banal, and repetitive, but that is the stuff that builds brick-by-brick. That’s what builds the house.  

Gresham, without throwing anyone under the bus, I’m curious, with you doing so many podcast episodes with people in the CEO space, do you hear a lot of cliché statements? How often do you, for lack of a better term, disagree with somebody but you’re respectful because they have a different perspective than you? You must attract a lot of people that are conditioned to say a lot of these statements about success that maybe they heard from somebody and they feel like that’s the right thing to say on a podcast, or is it completely different? Do you find that people are self-aware and saying unique things and not those clichés? 

It depends. I won’t throw anybody under the bus for sure. I’m a marketing guy, so hearing a lot of other marketing people, often, you’ll hear a lot of those things as well. I usually try to do my part, granted it’s a laser-focused interview to try to drill down a little bit more. I try to bring the lightweight. Even somebody that says that they’ve been successful in two years in their business, I try to bring back that they worked for seven years before that so that people can understand that. I try to help out with that because many times, we forget the journey and ourselves, even if it’s not in the same business of what it takes to go there. 

People, sometimes, say things that will attract people. I understand that from a marketing perspective, but I feel like it is doing such a disservice to people that are starting businesses that have great ideas that think that they’re going to be successful in a year or in 30 minutes. I try to redirect that as much as possible when I hear it or I try to pull as much information that I can so that people can understand that it isn’t a marathon. People don’t say it. As already said by Jason, I was that person as well where I have different things that I tried. 

Going back to the question you asked about what made me understand what was in alignment, sometimes, it was for me trying so many different things because I thought it was easy. I thought I could do these hundred businesses and I would be successful. I would have the Lambo and all of those things. In reality, I had to understand, “This is my lane. This is who I am. This is what I’m willing to work at for twenty years and maybe just get close to success.” When I answered that question, it made me adjust and filter what I do and don’t do on a different level. I try to redirect it on the podcast where people say that or drill down more to understand that. Sometimes, you get people to say more, but you can only do so much. You can’t answer the questions for them. 

Thank you for doing that. That shows a lot of integrity. It’s, also to your point, helpful because I’ve certainly talked in marketing soundbites, too. A lot of us feel like we need to. I was refreshed when I watched the Oprah interview with Meghan Markle and Prince Harry because hearing Meghan Markle speaks so honestly and not in soundbites, made me emotional. Just thinking about it, it brought up so many emotions for me. Did you watch that, Gresham? I’m assuming Jason has not watched it.  

I haven’t watched it. My girlfriend told me that I need to watch it. There are some big things that were being said there about her experience. It is on my list and she’ll definitely make me watch it for sure.  

I recommend it. I was blown away by it because it feels different than most of those conversations. That’s the other thing that is so important about that interview because certainly, there was racism, sexism, and leadism at play. There are a lot of isms going on in that experience that Meghan Markle had and Prince Harry as well. He talked about his own experiences and it’s semi-shocking but also not surprising in a lot of ways. I was so grateful for them being open because we need to hear that type of open dialogue. One of the big themes is that there’s a lot going on that we do not see in the media.  

MGU 210 Gresham Harkless | Discovering Yourself

Discovering Yourself: Ego validation is when you prefer people who share your belief system. Your belief system never gets challenged and you don’t get growth.


On a logical level, we know that what we see on social media, magazines, and television does not represent the whole of a person. Meghan Markle said this. The people with the biggest smiles might be going through some of the hardest times in their life. In fact, she gives an example of a media appearance that she had to do when she was on the verge of committing suicide. First of all, to share that publicly was remarkable. She had to go to this public appearance when she was considering that and she had told her husband what she was thinking about and the mental challenges she was having. 

Yet, what we see as the public is her looking perfect and beautiful and smiling. She said when the camera lights came on, she was a completely different person, but when the lights were off and when the cameras weren’t on her, she was sobbing. What an important thing for her to share with the world. I wish that more people would speak up about that. To your point, Gresham, I don’t want to hear these stories of overnight success. They do not serve us. To your point, it’s doing truly a disservice for us because as emotional human beings, we see these things, take them, and internalize them. 

I know for most of my life, I was seeing those messages of the quick fixes. “Buy this thing. Get this result.” “Buy this program, get results within X amount of time.” For me, a lot of the health side comes up. I think about how as a little girl, I would see magazine articles about how to get flat abs. It was always about like, “Just work out for five minutes a day for this amount of time and you’ll get flat abs.” I have never had flat abs in my entire life despite everything I’ve tried. If I added up all those perceived failures, I would think that I’m doing something wrong because I tried all of those other things and none of them worked. 

Something must be wrong with me because marketing’s telling me that they worked for others, but the truth is that a lot of these things don’t work. It’s just false advertising. It’s completely true in business as well and it’s sad. To your point, too, Jason, people are saying that to boost up their egos and get validation because they believe that if they can convince somebody that their success was either easy or special or formulaic, then maybe they’ll get that pat on the back that they want. If we step back, each of us and anyone else reading as entrepreneurs, we are doing ourselves and others a disservice by positioning ourselves like that to get that momentary benefit from that marketing. 

The terminology that comes up to that I suppose I hear a lot from “successful” entrepreneurs and business leaders is the idea of being self-made. That seems to be a thing that people are like, “I’m self-made. I bootstrapped it.” Whitney and I do this Clubhouse room and we hear these terms a lot come up like bootstrapping, grew from 0 to 9 figures, self-made. What it comes up for me when I hear that terminology, specifically self-made, is it’s like we live in a completely intimate interwoven tapestry of fellow human beings on this planet. What does self-made even mean? Does that mean nobody helped you on your journey? Didn’t you have a mentor? Didn’t you have a coach? You didn’t have anybody, proverbially speaking, patting you on the back and pushing you forward? 

Nobody creates in a vacuum completely, whether that’s our partners, girlfriends, a mentor, or coach. Everybody I know has somebody in their corner, at least one person in their corner. When I hear self-made, it bothers me because it distorts this idea of what it means to be an entrepreneur that you’re just working in a vacuum with no help and no support from anybody ever. Know at a certain point, you scale. You get a VP, creative director, and COO. At some point, you scale and you’ll be successful. You got people on your team helping.  

Maybe I’m misinterpreting the term self-made but I take umbrage with it because I feel it’s used in a misleading way often to purport an idea that someone has been locked away in a bubble somewhere, and then just pooped out $10 million. It’s like, “Fifteen years later, here’s $10 million. I did it all in this plastic bubble with no help from anyone.” That’s not reality. That’s my impression of it. Gresham, I’m curious about all the CEOs and the people that you work with, is that something that comes up? Do you see people talking about being self-made? Do they use that terminology and position in a way to pump themselves up a little bit? Does that ever come up for you in your interviews?  

Yes. You hear it sometimes in people’s bios. “I’m self-made millionaire or billionaire,” or whatever that might be or whatever status they make it to. As you Whitney said, a lot of times, I feel like we all have tools that we can use in our lives and in our business. We talked about the personality test, for example, and how that tool could potentially use to create a bad culture and a bad environment. I feel like the same thing could be said for using a phrase like self-made. It has an opportunity to build somebody else up, but at the same time, you can say self-made as, “I’m better than you,” because you’ve taken ten years in order to build your business. 

“You’re somehow incomplete. You’re somehow haven’t done enough. Let me sell you my $999 coaching program,” or whatever it might be. That’s where it comes down to the morals of us as individuals. We’re stewards in many different ways where you have been able to reach that success but you don’t necessarily go into exactly what it took to get there. You don’t talk about the failures, the mistakes, and things that you didn’t do well in order to get to that level. That’s something that I feel like to some degree, sometimes, it’s the person, but I also feel like, from a society standpoint, it’s a lot more soundbite headline rather than a deep dive type of conversations and content that we’re taking. It is why I love what you both have been able to do and building. 

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As Jason said, entrepreneurship is hard as hell. There are so many different things that you have to juggle and worry about. If you don’t get an idea of the totality of what it is to run a business, if you see self-made, nine figures, three years, you’re going to say, “In three years, then I’m going to be able to do the same thing,” but you don’t see the ten years or you don’t see that person is 75 years old. It took them that much time to build up all of those things in order to start a business. It’s so important for us to be stewards in so many different shapes or fashions and forms. It’s difficult because of the media, the soundbites, and the information that’s available to us. 

We all should be reminded of doing more of a deep dive and reading more about those specific people that we look up to. I talked about personality tests. There are not just one personality tests I try to do. I try to do multiple things and try to measure all those things up. We should do that in so many different aspects because if we don’t, we don’t get the reality of what it takes to be successful, and it doesn’t happen overnight. It’s a shame and I feel bad for anybody who thinks that because I feel like it caps what could be created and what could be done in this world. That’s what I hopefully try to do in the interviews. 

I want to talk about nature versus nurture in terms of when a person chooses to start a new creative endeavor, a new business, or whatever it may be. When I say this, I’m not saying there’s anything wrong with being an employee or a traditional 9:00 to 5:00 office job or remote work. I’ve always been curious because I had a conversation with my mom about the temptation I sometimes feel to go back to the illusion of security, the benefits, salary, and 9:00 to 5:00 job.  

In my previous life, I started off in the marketing and advertising world. I was a copywriter for advertising agencies and marketing agencies. I did that for about a decade right out of college. Sometimes, I do. I get tempted. The little guy on my shoulder is like, “There are benefits and security and it’ll be easier. You’ll be able to sleep better. Go back to it.” Not that there’s anything wrong with that choice. I do not want to besmirch anyone who chooses to have that as their income model at all.  

In the nature versus nurture conversation, I remember when I left my last gig over eleven years ago before I became a full-time entrepreneur. “I don’t think I can do this again,” I remember saying that to myself and saying that to my mom and some other friends. There was something in me that was like, “I don’t think I can take orders from someone else. I don’t think I can help someone else become rich.” There’s something in me that wants to be born. There’s something in me that wants to be expressed.  

Even if it’s hard as hell and even if I feel ground down and destroyed by life, I have to somehow express this thing in me and bring it to the world. I’m curious, do you both think that’s something that’s almost like a genetic impulse of that level of independence, freedom, and drive? Is it something that might happen through a series of events over our life where we’re conditioned and nurtured to maybe head down that path? It’s not for everyone. 

I’m not saying that to separate the three of us and say we’re better than everyone, but it is not for everyone. As you said, Gresham, it’s hard. It’s wonderful, rewarding, creative, and exciting, but it’s tough. Do you guys believe it is a nature-nurture thing or a combination of both that would drive someone to be an artist or an entrepreneur and start their own thing and go through all the beauty and hellishness that comes with it? 

From my perspective, Jason, it is more of a nurture. After reading books like Selfie, which you brought up initially and we talked about a while back on the show, one of my bigger takeaways from Selfie is that it’s a generational thing that is happening with social media. Each generation has its own set of perspectives on life and also trauma. Another book I’m listening to, which is completely blowing my mind when it comes to trauma and parenting is called Adult Children of Emotionally Immature Parents. 

It’s also interesting to read books about different generations and how parents believed they should parent. A lot of the parents around our parents’ age didn’t have a lot of emotional tools. They didn’t necessarily get a lot of support from their parents and that could either lead them to be harsh and intense with us. Maybe they have high expectations and they want us to be high achievers. That’s why a lot of people that are in their mid-forties or younger may have this big obsession with being self-made, making a lot of money, and being successful. Parenting has a huge influence on that. 

The even younger generations growing up with all these examples, they’ve been marketed this. They have been drawn to careers as influencers. In fact, for teens, being a social media influencer is one of the top career paths. I don’t quote me on it because I don’t know the statistics, but I’ve seen this in multiple places and articles that I’ve read that teens want to be YouTubers, Instagrammers, and TikTokers. They want to do that full time. They want to be their own bosses. They don’t want to make money from others. 

The pandemic has probably influenced a lot of that, too. That desire to not have to depend on somebody else to make money is another element here and it’s something worth examining for you and me, Jason. I’m curious, Gresham, about your experiences, too. Why are we drawn to working for ourselves? Is it that we’re destined for greatness or is it that we don’t have the patience to deal with rules and we know we don’t have to?  

We have the tools to start our own businesses at home in our pajamas truly. We have many abilities to make money online. Why would we bother going to work if we can make as much money, if not more, from home? Of course, to your point, Jason, it’s not as easy as it looks and it’s not going to be for everybody. I’m super curious what’s going to happen for the younger generations and their experiences of this because just as not everybody can be a CEO, not everybody wants to be their own CEO. It’ll be interesting to me.  

What is going to happen for the job force when people are getting so fed up working in these traditional 9:00 to 5:00s or working retail or all of these different career paths that are more structured? If a lot of people abandon those jobs, how does our society even function? We need people to work at grocery stores, drive Ubers, and service food at restaurants. CEOs need employees. We can’t do it all on our own or we don’t want to. What’s going to happen with the percentages of people increasing wanting to work for themselves and start their own businesses? 

What could it potentially happen with many people that are thinking about starting the businesses and feel like they have it in them? I feel like it’s a combination of both the nurture and the nature. With what we’ve been talking about, I feel like it’s okay to want to be an employee and want to move up the corporate ladder or whatever success means to you. Most of the disservices people don’t know what it means or what it doesn’t mean. There’s a trade-off for everything. To start a business, you have a trade-off. A lot of times, if you’re going to do it and you’re going to do it well at least, you’re going to potentially not be able to do a lot of the personal things.  

Some of those things have to go by the wayside. You have to balance and see, “This is my vision. This is what I want to do. This is what I’m deciding to do. This is what may be the trade-off,” whether that be an employee or you’re starting a business. You’re absolutely right, Whitney. If we drill down, people are unhappy and that’s what we have to look at. A lot of times, people think that they see an Instagram clip and they believe that will make them happy, but they do not understand what happiness is and how to find that in their lives. 

They’re chasing this thing or that thing in order to happen. That manifests itself in jobs or relationships. It can manifest itself in so many different ways. If we don’t understand that happiness and fulfillment and look into ourselves and understand our gifts, understand that maybe we do have tendencies to be more entrepreneurial and if we cultivate that, we can be better. If we understand, “Maybe I’m a great artist and I did that since I was five years old. Let me cultivate that a little bit more. I could potentially be great at that.” You get to make the decision on what you do or what you don’t do, but we do have that nature, which is our natural tendency and gifts, but that nurture comes in and how that’s cultivated into who we’re going to end up being. 

Many times, when we make those decisions of, “I’m going to take this path,” we don’t realize the real journey that it takes to get there and that’s where we end up having people bounce back and forth. I was that person as well, so I was the person that bounced around to different jobs. It wasn’t until I realized that I wasn’t being fulfilled no matter where I went, that I had to do some introspective thought into like, “What do I want to do?”  

For me, I felt like I had some fear around starting a business and I had to face that and look at my environment as well. That’s what led me to feel more fulfillment and I don’t think that fulfillment is necessarily a Lambo or things like that. It’s the fulfillment that comes internally, not externally. That is always a process that I go through and it’s something that I continue to have to fight through. If I can stay true to that, then that’ll help me not get caught up in what I should be doing, if that makes sense. 

It resonates big time. It comes back to, Gresham, to encapsulate how I feel about what you just said, defining and getting clear. This can be an evolving definition of what success and fulfillment mean to us. Not what it means to you or Whitney or our parents or clergy or society or partners because all of that can be influential. One of the most courageous things, to your point, is to do the difficult work to look inside of ourselves and ask, “What is it I’m doing this for?” We hear start with why. It’s high-quality questions and cracking ourselves open and going, “What am I doing this for? Why am I doing this? On those hard nights or weeks or months, why am I putting myself through this? What is the greater good of all this?”  

To your point, maybe it’s not the Lambo anymore. Maybe it’s not the giant mansion. Maybe it’s not the watch and the followers on Instagram because, on some level, external validation is not a sustainable thing. It’s almost like a drug. We just want more and more of it. This journey of starting a business, being an entrepreneur, being your own CEO, or doing the creative work. Whether or not anyone has necessarily like a spiritual practice or a spiritual belief, I feel like, for me, my journey into entrepreneurship and conversations like this are part of my spiritual practice. In the sense of I get to know more about who I am as a being.  

MGU 210 Gresham Harkless | Discovering Yourself

Discovering Yourself: Let yourself know that it’s not a straight line. You quit before things start to get good because you think it’s a straight line.


When I say spiritual, yes, I meditate because it helps me with my mental health, but my point is in encapsulating this episode that this journey of business, entrepreneurship, artistry, creativity is deep down, we can know ourselves better. That’s a never-ending journey. That has no endpoint. This has been a deep, beautiful, and soulful episode with you, Gresham. It’s been a wonderful exploration with you. Thank you for taking the time. Thank you for riding the waves of the technical difficulties, being with us, and sharing your story and who you are. It’s been delightful.  

We loved having you and thank you for being such a positive influence in this space. When I was on your podcast, it resonated with me. It was one of the best podcasts I’ve ever been on because you have such a positive presence and you do it in an intentionally polished way. You’ve created a great structure and you know how to approach this without it being too transactional, which is a special thing that you’ve done. Given how many episodes you’ve recorded and how many people you’ve had, it can be easy to get into a rhythm where you fall out of alignment with why you’re doing it. You’ve made a big impact on me and now Jason, and hopefully, our readers. We appreciate you being here and all the work that you’re doing. 

I appreciate getting the opportunity to be on as well. You guys are doing phenomenal things. This is something that’s not talked about enough. I appreciate you for being stewards in that way. We were definitely resilient, so we got a chance to do this. I appreciate you for the opportunity!


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About Gresham Harkless Jr.

MGU 210 Gresham Harkless | Discovering YourselfGresham “Gresh” W. Harkless Jr. is the founder of CBNation and Blue 16 Media. CBNation is a Business to Business (B2B) Brand focusing on increasing the business success rate by providing visibility and resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs (, podcasts ( and videos (
Blue 16 Media is a digital marketing agency providing digital marketing services including web design & SEO to small to medium-sized businesses and organizations. Central to his marketing philosophy is that You Are a Media Company: Developing a Marketing Strategy to Connect with Your Target and Reach Your Goals. Gresham is proud a graduate of Howard University & Georgetown University. He also is a graduate of the 2020 Leadership Center for Excellence Young Professionals Program ’16 and recognized by the Alexandria Virginia Chamber of Commerce’s 40 Under 40.


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