“I feel like me facing that (skydiving), to me, was more symbolic than anything else.”

In this episode, Nick speaks with Gresham Harkless Jr. “Gresh” shares his journey from childhood experiences that shaped his entrepreneurial spirit to facing fears through skydiving. The conversation delves into the impact of military life on Gresh’s upbringing, his transition into entrepreneurship, and the lessons learned from failures.

What to listen for:

• Facing fears can lead to personal growth and confidence
• Skydiving was a pivotal experience for Gresh in overcoming his fear of heights
• Childhood experiences can shape your personality and adaptability
• Entrepreneurship was a natural path for Gresh, influenced by his family’s background.
• The importance of taking calculated risks in career transitions
• Failures can lead to valuable lessons and resilience in entrepreneurship
• Self-mastery is a journey that requires daily commitment and self-reflection
• It’s essential to listen to your inner calling, even when faced with external doubts

“You did something you were afraid to do, which I think is probably, I think the most powerful thing for me.”

• Facing fear and taking action is an empowering experience.
• Overcoming fear often leads to personal breakthroughs and self-discovery.
• Every small victory over fear builds a stronger sense of self.
• Your bravery can motivate others to face their own fears.
• True power comes from stepping outside your comfort zone.

“If there’s something that you’re afraid of, it doesn’t have to stop you, it doesn’t have to paralyze you, you can still continue to do it.”

• Fear is natural but doesn’t have to be a barrier.
• Taking steps despite fear reduces its hold on you.
• Facing fears strengthens mental and emotional resilience.
• Continuing to act shows fear doesn’t control your choices.
• Fear can coexist with progress—you don’t have to wait for it to disappear.

About Gresham “Gresh” W. Harkless Jr.

Gresham “Gresh” W. Harkless Jr. is the founder of Blue16 Media and CBNation. Blue16 Media uses media & technology to change lives. These media properties include Blue16 Marketing, a digital marketing agency providing digital marketing services including web design, website support & SEO services. CBNation consists of media properties (blogs, podcasts, and videos) helping the business community succeed. Central to Blue16’s marketing philosophy is that You Are a Media Company and that every organization is in the media business and can strategically leverage marketing tools, platforms, and “ingredients” to reach their goals. He has recorded over 1600 podcast episodes of the I AM CEO Podcast and shared the 100+ business lessons he has learned from recording the episodes in the I AM CEO Handbook Volume 3.

• http://iamgresh.com
• http://iamgresh.com/linkedin
• http://iamgresh.com/instagram

Resources:

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Your Friends at “The Mindset & Self-Mastery Show”

Nick McGowan (00:02.264)
Hello and welcome to the Mindset and Self Mastery Show. I’m your host, Nick McGowan. Today on the show we have Gresham Harkless Jr., Gresh , how you doing today, man?

Gresham Harkless Jr. (00:14.222)
I’m doing awesome Nick, excited to be here.

Nick McGowan (00:16.332)
Yeah, I’m excited too. We’ve met a couple of different times. We’ve talked about different things and I know we’ve been both looking forward to this podcast interview for a little bit now. So why don’t you kick us off? Tell us what you do for a living and what’s one thing most people don’t know about you that’s maybe a little odd or bizarre.

Gresham Harkless Jr. (00:32.588)
Yeah, well, for me, I always say like I’m very much so a busybody. Some people call that entrepreneur. But I am somebody that’s like to be involved in a lot of different things from the DC area. Been here since I was like five years old. I was a military brat. So my dad was in the military. He lived and I lived and we lived in different places. But I spent most of my time here in the Northern Virginia area. Went to school here, went to Howard for undergrad, Georgetown for my master’s. Had some.

not ideal ways that I went into the working world, but needless to say, it led me here. One of the reasons I really kind of fell into entrepreneurship, I would say, or entrepreneurship maybe even chose me, is I was the kid that sold potato chips on the playground. When my dad actually went, he got reassigned when I was 10 years old to go to a different country, I started what was then a family newspaper. So,

wasn’t anything huge. was just me in front of a Microsoft Word document with some clip art, figuring out all the things that were going on in our family. And I would put it in there and we would send them because we didn’t have instant opportunity to connect with people online like we do now. At that time, it was just literally send to him those newspapers. And as a true entrepreneur, I guess you can say, I sold the subscriptions to family members, too. So I was covering all the things from

Nick McGowan (01:42.786)
Mm-hmm.

Gresham Harkless Jr. (01:53.902)
squirrel getting into my grandma’s house to a wedding that didn’t happen, that was supposed to happen. But yeah, those are all the things that kind of planted the seeds. So like when I started to go through the journey and figure out who I was and what I wanted to do, I went back to those, I call it 10 year old Gresham, you know, stories. So for me that, you know, planted a lot of seeds and, know, that’s what led me here to eventually start what I have a bunch of different things I’m involved in, a digital marketing business.

do a lot of content around entrepreneurship and business myself, and then also like starting a franchise brokerage business. But that’s a little bit about me. something fun and interesting is that I had a fear of heights for a long time. So one of the things that I did was I went skydiving to try to face that fear. And every time I’m like kind of a little bit nervous about anything, I got the pictures, I got the video to make sure I hold onto it.

I always look at that picture to say if I could do that, I could do hopefully just about anything.

Nick McGowan (02:50.698)
I mean, you probably could have just ended with the, the newspaper being the interesting thing. Like that’s such a cool thing. And I think one as an entrepreneur, like you can learn that, I’ve been an entrepreneur all the way since I was a little kid, selling little things or doing this, doing that. So it may have been manipulation as a kid, like, yo, you need to give me 10 bucks for this newspaper. What do you mean that for you? Or like, whatever, you know, but for you to go through that and

Gresham Harkless Jr. (03:09.486)
Please.

Nick McGowan (03:18.716)
where you’re at. It makes sense because you’ve gone through those things. I want to touch on the military movement and all of that. But before we get to that, I do want to talk about the fear of heights and you stepping out. mean, that’s like an actual psychological theory of getting yourself locked in a room with that thing. Like people that are afraid of spiders, they’ll be locked in a space with the spiders and have to come face to face with it. There’s a part of me that thinks, yo, that’s real fucked up.

people are terrified of clowns. It’s like, well, great, here’s a bunch of clowns. But I can also understand where some of it is just a psychological perspective of if you shape the way you think about it or look at it, then you can shape that story. I’ve often brought up to people if I told you there was a bear a bear in the other room, and told you to go in there, you’d probably like get the hell out of here. No. But if you walk in, it’s a little teddy bear, he probably tell me to screw off or whatever and laugh about it.

Gresham Harkless Jr. (04:13.88)
You

Nick McGowan (04:15.404)
But if it’s this giant grizzly bear, it’s a whole different story because the story that we tell ourselves with that. So break that down a little bit of you knowing that you had that fear of heights and actually getting to the, to the part where you were strapping yourself up, getting on the plane, getting off the plane at what 15,000 feet up or whatever. like all of that, I haven’t done that yet. I can imagine that must’ve been, you must’ve been shaking through most of that, but like talk to us about it.

Gresham Harkless Jr. (04:45.326)
Yeah, absolutely. And you know, so funny, like I don’t know where that fear actually came from. But I think I think that I think my cousin, who’s a little bit older, have one older cousin, had a big fear of heights. I remember as a kid going to Carowinds, which is kind of like Kings of Mania we have here. So big amusement park. And she didn’t want to ride any of the rides. And I feel like at that time I was so sure I couldn’t get on any of the rides. But I don’t know where exactly I picked that up from. But I wonder if that was like part of those kind of memories that kind of stick with you. But

Nick McGowan (05:01.144)
Hmm.

Nick McGowan (05:13.912)
Yeah.

Gresham Harkless Jr. (05:14.894)
I was really big on facing fears because I started to do a lot of reading myself and understanding around fear and what is it. You have the acronym, false evidence appearing real and those things. And you start asking yourself, and I literally cannot tell you, that’s the only thing I think as to why I was afraid of heights. I didn’t have a traumatic story. was just literally I had this fear. So I’m not really sure exactly where it came from. So when you start to inspect it and start to look at it say, why am I afraid of it?

you start to like really question that to some degree. like when I was in college, for example, I knew that I had, I wasn’t comfortable, I don’t know if fear is the right word, but might be fear of public speaking. So that was one of the things I took a public speaking class my freshman year. So I just tried to really attack those things as much as possible. So I was kind of looking at what is the next thing. And one of my buddies from college said that he wanted to do skydiving and said, Hey, I would love to do that as well.

Nick McGowan (05:58.264)
Hmm.

Gresham Harkless Jr. (06:10.636)
So we both decided to do that. We drove down, I think it was about two hours from where I was, maybe about two and a half hours. I remember I told my mom that I was gonna do it and she was like, okay. And then I think I remember her calling me like right before I was about to like get ready to go inside of the building. And she’s like, hey, just trying to make conversation. Hey, how are you doing? What are you up to? Are you really thinking you’re gonna do this? So you go through all of that. You step into the building and

Nick McGowan (06:33.013)
the

Gresham Harkless Jr. (06:39.79)
You pretty much see all the things, so you’re already kind of exhilarated and ready to go and jump out of the plane and do all the things, but you sit down and you have to sign away your life. So there’s about, I think, 10 to maybe 20 pages of paper that you have to sign, basically saying that if you die, that it’s not on us, you can’t sue us. Watch a video, and I think the worst part of probably that whole experience is like, you’re ready to go when you get there. You have to sit.

Nick McGowan (06:57.592)
Cheers.

Nick McGowan (07:04.44)
Hmm.

Gresham Harkless Jr. (07:05.452)
You literally have to just sit and wait. You’re seeing people come in, they go up, they come back, and you’re just sitting and thinking about like, am I really doing, is this really like, why would I do this? And so you’re going through that whole process and those things. And I think as we got closer, they called us to go out. We went in a small plane with maybe, I want to say maybe about six of us or so. And because I got the video and the photos,

Nick McGowan (07:13.825)
you

Gresham Harkless Jr. (07:32.95)
I was in the back, so I think they had the cameraman and everyone in the front, you know, closer to the front. So you’re sitting there again, more and more time. You’re sitting there watching one person lean forward, go, they’re gone. And you’re watching it over and over again. So during training, they’re telling you that, you know, what you’re going to do. So they say, basically when you’re ready to go out, you put your hands up in the air and you’re going to lean back three times and then you’re going to go out. So of course the three times is not the three times, it’s actually two times. So.

Nick McGowan (07:43.956)
the

Gresham Harkless Jr. (08:01.004)
By the time I do that, you can see in the video, I’m putting my hands up and I’m leaning back one, two, and I’m trying to go back a third time, we’re already gone. We’re out in the air and literally, I feel like my face is still kind of up there because you’re just falling flat into the sky. yeah, was just, it’s that first 10 seconds that I think is the most exhilarating part. after that, they, because I’m going in tandem, so I’m with the person.

they pull the parachute and you can literally see the views. I don’t think that there is any comparison to be able to see what I saw then. And yeah, I mean, that was a little bit of like what happened at that time.

Nick McGowan (08:38.474)
It’s different than base jumping, you know, but I’ve heard the same thing about base jumping where it’s like that initial bit. And then as you get further down, like the, I’m glad that you said the tandem, because whenever I do that, the first handful of times or whatever it’s going to be, I would like to have another person who’s done it several hundred times attached to me as a redundancy and a fail safe. if I can’t pull it, make sure we both survive and we’re not pancakes.

Gresham Harkless Jr. (09:00.067)
Yes, smart move.

Nick McGowan (09:07.062)
I could imagine that’s probably just so peaceful and serene when you’re just kind of cruising along, looking at all of the world from a bird’s eye perspective and like nothing else matters at that point. Like you’re not, you may be worrying about different things or thinking like what’s going to happen and how are my legs going to buckle or whatever, but probably not even, you know, just kind of moving through it. So when you landed, maybe it didn’t happen that day.

Gresham Harkless Jr. (09:17.313)
Mm-hmm.

Nick McGowan (09:35.33)
Maybe it happened a few days later or weeks later or whatever, but when was that moment when you started to go, cool. Well, I’ve done that. like, semantically you felt it where you were like, I no longer have that fear anymore. And that probably checked off different boxes for other things as well. But can you recall when that was?

Gresham Harkless Jr. (09:55.68)
Yeah, you know what? I think it’s, so me and my buddy afterwards, I can’t remember if we went to McDonald’s or something like that. I think it’s that when it kind of sunk in a little bit. It wasn’t like after we landed on the ground. was just like, we just jumped out of a plane. Like, and it just like, you start to really believe that. But you know what’s so funny that I found out? I don’t think that it ever got rid of that fear, if that makes sense. Like I still am like, I wouldn’t jump out of an airplane.

Nick McGowan (10:06.071)
Hmm.

Nick McGowan (10:09.954)
Yeah.

Nick McGowan (10:21.11)
Hmm.

Gresham Harkless Jr. (10:25.326)
But I think that it gave me more of that you did something you were afraid to do, which I think is probably, I think the most powerful thing for me. It’s like, if there’s something that you’re afraid of, it doesn’t have to stop you. It doesn’t have to paralyze you. You can still continue to do it. So I think that’s what happened for me. Granted, have not, I still not going on roller coasters. I’m still not jumping out of a planes on a regular basis, but I feel like me facing that to me was more symbolic than anything else. So I still feel like I probably have that fear, but

I don’t even know if fear is the right word. It’s just something that I’m not as comfortable with and I would do it again, but I am not jumping to do it again, if that makes sense.

Nick McGowan (11:03.0)
full pun intended. Yeah, that makes total sense, man. And I don’t expect like, we as people want that instant gratification of like, I did the thing and everything’s solved. And then at that point, I did all these other things. It’s like, that’s not really how life works. It may with some things, like there may be certain things where go, well, I’ve done that. I can do other things similar or, but even just to be able to have that little bit of a

Gresham Harkless Jr. (11:04.923)
Exactly.

Nick McGowan (11:32.448)
a stronger bond with yourself of like, I did this thing. It also makes sense why you’re not like, cool, I’m going to go jump out of 15,000 planes because I did it one time. Some people, maybe there may be some people that do that and they’re like, this is what I want to do for the rest of my life. And like, that’s cool. But I don’t always, I don’t expect that to be how it is. Cause life isn’t really black and white. It’s often gray and colored and there’s so many different pieces to it. so man, first off, I think that’s cool that you did that.

And I haven’t done it yet. I want to be able to do it, but I kind of expect that the same thing will happen. Like I won’t jump out of like 18,000 planes after that, but just that little bit of extra confidence that I’ve done this thing. You can do it. think a lot of people can relate to that too. And sometimes probably more so than we actually give ourselves credit for. So for you and I, for the people that are listening, I mean, if we really think about it, there are different situations that have happened in life where you

If you look back at it and you go, well, damn, I didn’t really give myself enough credit and not to like lather it on, but to go, I’ve done this. Like you said about public speaking, there’s a part of me that could understand if you were kind of a shy kid, because I could sort of see some of that or at least like theorize some of that. But knowing what I’ve know of you, it’s like, no, that’s not a thing. That’s not the Gresham that I know. It’s not who you are. It’s not how you go about things. But that’s

Not a thing that happened like you, you were really afraid to talk to people and Tuesday you went to a meeting and Thursday afternoon you were talking your ass off. Like, I don’t think that that’s really how, again, life works. but I want to tie this back to the childhood that you have. Being able to bounce around, having the opportunity, but also I guess, kind of the detriment in the sense of like having to change schools, losing friends, starting at a new school.

Gresham Harkless Jr. (13:08.43)
You

Nick McGowan (13:28.906)
starting to make new friends. What was that like? And did you find yourself becoming a bit more introverted? Or were you easily extroverted of like, well, you dropped my ass here, and I’m going to make friends with people. And when we move, you drop my ass there, I’m going to make friends with other people. Like, what did that look like?

Gresham Harkless Jr. (13:45.046)
Yeah, you know, it’s so funny. Like I was a military brat, but I feel like I really wasn’t a military brat because I only moved four times, I think, in my life. And most of those times were before I was five. I did move when I was 10. Like we moved, but we moved in the same city. So it was just moving from a townhouse to a house. And I went to a different school. I think that might have also led me. probably one of the I think I think one of the big reasons is probably more of my

Nick McGowan (13:57.079)
Okay.

Gresham Harkless Jr. (14:13.55)
parents, which is why I was a little bit more quote unquote introverted. And I think it was just that safety because, you know, we look at, you know, I think it generally generationally, you my, my, my dad was in the military after he retired from the military. He went and worked for the government. These are very stable positions. My mom worked for a utility. So those were things where I think that there was just a lot of safety where I didn’t really go outside of my comfort zone to do things that I was uncomfortable with. So

Nick McGowan (14:30.456)
Hmm.

Gresham Harkless Jr. (14:40.302)
That’s why I say I don’t know if I should say that I have a fear of speaking as much as it’s like I’m comfortable here I don’t want to do anything else that is not what I already know and I think that was probably a lot of what it was so But you know, my first job was, you know retail so I was working and selling, know CDs and things like that So I talked with people and did those things But I think that you just build things up in your head and sometimes it may or may not be real which is where a lot of that

Nick McGowan (14:59.97)
Thanks.

Gresham Harkless Jr. (15:07.63)
Fears like it do am I really actually fear to fearful of this? Am I scared like you start to inspect those things? So but for me, I think that’s probably where a lot of that came from is that I was just very comfortable, which is a blessing, but can also be somewhat of a curse because when you’re comfortable, you don’t really grow because you’re always kind of doing the same things. But I didn’t move when I was 10. Like that was around the same time that my dad, that was actually a very transformational time. Now I think about it for probably about eight to around 10.

Nick McGowan (15:11.448)
Hmm.

Gresham Harkless Jr. (15:37.386)
We moved when I was in fourth grade. My dad got his assignment to go away for a year. So it was kind of just me and my mom and we talked to my dad online and things like that. But I think I went to a new school, just all those things happen around that same time. So I think that was maybe the most kind of transformational time. But no, I mean, for me, like after I got kind of settled in, kind of, you know, I was comfortable. So I just kind of stayed in where I was more than anything else.

Nick McGowan (16:05.72)
Well, so I’m right there with you with the comfort where there’s like creature comforts, you know, I joke at different times, like everybody needs like that time with like a bag of chips and fucking Netflix, like just veg. You don’t have to be go go go like I am total anti hustle culture bullshit, where people are like, I work 9 billion hours a day. It’s like, fucking why? What trauma are you putting yourself through?

Gresham Harkless Jr. (16:18.126)
Yes

Nick McGowan (16:33.058)
but I do find it interesting how your parents both had stable, secure positions and you became a sadist and you were like, fuck it, I’m gonna be an entrepreneur. Let’s just inject pain as often as possible and try to figure out my way through it. Were there other entrepreneurs in your family or was this kind of your stepping out and kind of being rebellious?

Gresham Harkless Jr. (16:43.15)
You

Gresham Harkless Jr. (16:58.414)
I guess it was my rebellious. So I feel like my mom does, she had an embroidery business she did on the side. So everybody had like their side things, not everybody, but you always hear things. But I think one of the things that kind of stuck with me more than anything else is I remember my dad, they were thinking about starting a business, starting like a car wash or something like that. They were always talking about that.

Nick McGowan (17:07.64)
That’s cool.

Gresham Harkless Jr. (17:20.482)
Both my parents got their degrees in business management. So I felt like that was always there. And I feel like, again, me being a young kid, I did a lot of the entrepreneurial things. that wasn’t really cultivated. It was, like he said, kind of a nice thing. Billy’s doing this. So let’s get him a little bit extra money so that he can buy some candy. It’s kind of like that kind of feeling. But when I started to get older and I started to say that, I I feel like I have entrepreneurial tendencies.

really know exactly what that is. But I feel like that’s like, it’s not me trying to be on a podcast. It’s not me trying to get an accolade. It’s just like, this is just me being me. I love to create stuff. I love to build stuff. I love to tinker with stuff. That’s just me. So when I started to like say that and started to express that and say, Hey, I think I might want to start a business and things like that. I got a lot of you shouldn’t do that. Or you should wait, or this is a better time. I got a lot of that. And I think a lot of that was from that comfort. So

Nick McGowan (18:13.132)
Yeah.

Gresham Harkless Jr. (18:18.306)
To your point, like when that’s happening, I’m like, you know, and I’m a man of faith. So I prayed on it. I did all the things. And I said, I feel like this is like just who I am. Like I don’t even want to be this person, but I feel like I have to be this person because this is who I was created to kind of be. So it wasn’t like a rebellious, like, you know, I’m burning the boats and I’m taking the island. It was just more like, Hey, this is just me. Like, I don’t know how else to be. I tried to be the other guy.

Nick McGowan (18:39.711)
Sure.

Gresham Harkless Jr. (18:45.832)
I experienced layoff and I was gonna get laid off again. Just all these things happen where it was like, I did all the things I was supposed to do and look how this is working out. So, I might as well do things my way and see what happens.

Nick McGowan (18:49.112)
Mm.

Nick McGowan (18:56.952)
Those are two critical pieces that I think sometimes we can jump past, maybe three. So one being the people that I think get into business just to make money. I can understand if you’re like the goal and the game is money, but that doesn’t ever really sit right with me. That was one of the things when you and I first connected, then we played in a similar playground and like sandbox of things. And I was like, there’s so much different stuff we can do and all these different things. like,

Either one of us are like, but we need to make billions of dollars for the fucking love of just billions of dollars. It’s like, how do we use it as art and just create and what do we do and being able to go from there, but also being able to understand that when you feel led by your faith and no matter what we call God, the energy universe, whatever any of us call it, there’s that like,

deep knowing at times where you just feel I need to go in this direction. And sometimes, I guess sometimes is probably a pretty soft way to put it. Oftentimes people can say, well, I don’t want to listen to it. I don’t want to go down that path because they start to think about it. They start to get logical with it. Like, well, I have this and I have the security and I have this Morgan, I have these kids and there’s this spouse and there are these things. And like they start to stack stuff in front of it.

But no matter what you call God, the energy universe, whatever it is, if you get an, I think of them as God nods where God’s like, yo, you should go do this. And it’s like, the fuck am I to say no? Like, okay, moving along and then figuring out like, how do you go about that? But also that authentic side of it. And I know that that’s somewhat buzzwordy at times and like the authenticity of it, but being you, like there’s only one Gresh.

Gresham Harkless Jr. (20:36.119)
you

Nick McGowan (20:50.978)
There are other people that may have similar paths, have done some similar things, but we’re all uniquely us. And we, as people, will sometimes go, well, I want to be so unique. I want to be like that person. That doesn’t really make any sense. And just being you and doing the things like you experienced, some people will say, that’s not a good idea because they’re putting their shit on you. They’re projecting onto you. And that can be difficult for somebody to not take that. I’ve had different conversations with people.

not so much on the podcast, but just throughout life. know, people bars or restaurants or parties or whatever, where they’re like, man, I thought about doing this thing, but, and they either have this story that there’s these other things like why I needed to go to school or at a family or my so-and-so told me I shouldn’t. And they listened to it. And I think there’s a fine line with that where like, you got to be mindful, but you also have to walk your own path.

Like if somebody told me, I’m just going to quit my job and go start a band and do all these things. Like there’s a part of me, it’s like, yeah, go do it. And there’s another part of me. It’s like, cool. But let’s also think about it. Like let’s plan these things out a little bit so that you can move about it in kind of a smoother and smarter way and not just add frustration to yourself. So I’m looking for some advice for the people that are going through that stuff now.

Gresham Harkless Jr. (21:55.606)
Yeah

Nick McGowan (22:14.614)
people that are either a leader in their business and they’re like, you know, I don’t feel like this is the right thing for me to do because I feel called to go do this other thing. Either God’s calling them to do it. They feel led to go do something else. But they’re battling these different stories from people telling them what to do, what not to do, but also the shit that’s within themselves saying like, I want to go do this thing. But how do I do it in a smart way? What advice would you give them?

Gresham Harkless Jr. (22:40.59)
Yeah, well, I’ll tell you my unsmart way. How about that, So I was feeling that call and I was that person where, you know, I had gone skydiving a few years ago and I said, hey, you know, I can tackle the world. I’m going to go skydiving, quote unquote, again. You know, I’m going to I’m going to do that. And I felt unsettled like this is right after school. I was like, this is not where I’m supposed to be. I had an outside sales job with the post office that wasn’t really outside sales because I knew I wanted to start a business. I said, hey, if I want to start a business, what’s the best thing that I

Nick McGowan (22:43.18)
Good, there we go.

Nick McGowan (23:00.493)
Hmm.

Gresham Harkless Jr. (23:11.134)
and get good at and that was sales. So I took an outside sales position, but it wasn’t a sales position actually. was just, it was the title as we were kind of talking about before, not actually the actual work. So I was very unsettled there. didn’t feel like it was the right place, but this was like a place, this is actually the perfect place that I think was in alignment with my dad and my mom. And the reason I say that is not necessarily because they were like, you should work there, but it was, if you don’t know about the post office, very great benefits.

Nick McGowan (23:12.61)
Sales.

Gresham Harkless Jr. (23:39.608)
people don’t leave the post office. People stay at the post office, especially the position that I had. And I was not where I felt like I should be. So when I say it was the unsmart way is because I got advice of like waiting to see, but my thing was always like, when is the right time to leave? Because after you have the wife, the kids, the three and a half dogs, the mortgage, all those things, it becomes harder and you also are less likely to want to do that. So

Nick McGowan (23:57.9)
Hmm.

Nick McGowan (24:03.746)
have.

Gresham Harkless Jr. (24:08.77)
For me, I just really wrestled with it. You know, again, I prayed on it and tried to figure out what exactly I should do. And so I decided to put in my resignation and I left that position. And when I left that position, I was already in the mindset of I was going to do a lot of freelance writing because I love to write. I love just like creating and writing has always been my thing that I love doing. So I said, I did a lot of freelance writing and I was going to try to do some other things. But the main thing I was going to focus on is freelance writing. So I had

a couple of regular clients that I would freelance for and write and do those things. But I said, one of the big things you want to do is make sure that you’re mentally where you’re supposed to be, but also physically. So I want to get as in best shape as I can as possible. So I used to play basketball in high school. So said, let me get back to playing basketball, doing all the things. So I went to this church. They had an open gym. My buddy told me about and I was shooting basketball, doing all the things.

And so I go up and I think I’m getting a rebound or something. I feel like somebody takes a hammer, slams it in the back of my leg. I look behind me, there’s nobody there, torn Achilles. Not all the way torn, but torn. Not only that, Nick, it was literally 45 days after I had left my position. So 30 days I had insurance, 45 days I did not. So the reason I bring all that up is because that’s probably the unsmart way to do it. But…

Nick McGowan (25:21.174)
Ha!

Gresham Harkless Jr. (25:31.67)
In the same breath, I would say, in hindsight, I feel like had I not taken those steps that I had taken, I probably wouldn’t be here talking to you today. it’s kind of like one of those things where do you want to, I think Elon Musk has this quote where he says, a startup is kind of like chewing on glass and staring into the abyss. You don’t want to chew on glass and stare into the abyss, but you want to start something up. So it’s hard to of like divorce the two of those things.

Nick McGowan (25:40.408)
Hmm.

Gresham Harkless Jr. (25:58.06)
So that’s the experience that I had. And I was in a really dark place when I was kind of going through that because I made a bold move and it did not work out. going through that, I think that I would tell people that if you can realize that if you want to start a thing, whatever it is, whatever your goal is,

more than likely it’s a journey. It’s not just one step. It’s probably multiple steps along that journey to get to where you want to be. And even if you are quote unquote where you want to be, you’re going to continue to kind of want to cultivate that, get better at that. So what I say is that maybe I would tell Gresh before he left and tore his Achilles that maybe you can start something a little bit more on the side that’s sustainable. But in the same breath, I feel like I did have those things in place. It just didn’t work out. So.

Nick McGowan (26:39.544)
Yeah.

Gresham Harkless Jr. (26:41.806)
I don’t know if that’s a really great piece of advice, but that’s just what I’m feeling at the time. It’s like, you can’t always know all the steps. You try to put as many things in place, but don’t feel like you have to make a leap. Try to do it as strategically as you can. You can have a side hustle. You can have a thing. And most of the people that are successful, it doesn’t happen overnight. It happens because you take step after step after step.

Nick McGowan (26:47.319)
Thank

Nick McGowan (26:53.506)
Hmm.

Nick McGowan (27:02.06)
Hmm. Yeah, there’s a lot into that. Like it can be easy to look back and be like, damn, 15 days ago, I would have had a different story or whatever. But at the same point, years and years later, to be able to look and go, well, it worked out the way that it did. There’s no should, there’s no shouldn’t. Like you can always look at things and go, well, maybe I could have done it differently or maybe not. Like whatever, it’s all how it is, but your path has been your path.

and you’ve turned it into what you’ve turned it into. Some people at that point would have turned back and been like, nope, I can’t do it. And they’d put the tail between their legs and that would be the end of it. Other people may have gone the extreme opposite where they’re like, cool, break my other one and whatever, know, like give it all. Yeah, whatever. But I guess kind of what I get from that even is being able to understand where you’re at in each moment to then make what moves you feel.

Gresham Harkless Jr. (27:44.75)
It’s like my heart.

Nick McGowan (28:00.49)
is right in those moments with the information that you have. Just like for the most part, think most everybody does the best that they can in each moment, but there may be times where there’s some things that are holding them back. There’s some trauma that has held them back or some limiting beliefs or things of that sort and being able to understand and see that stuff and then do the work with it. Like, yeah, it sucked that that happened to you, but you got through it and you’re in a better spot.

And now this is just a story you tell on a podcast or just to friends at different times. That’s not like a thing where everything detrimentally went downhill because you didn’t allow it to, because that’s not the person you are. But I’m sure there were dark moments throughout all that stuff and for everybody to be able to take from that and go, well, you just kind of keep moving along without allowing the abuse to abuse you, you know? So I, I appreciate that, that you started off like that of like, well, let me tell you the way not to or whatever.

shit, even I think about that at times where when I started this podcast, I talked to a couple of consultants and I was like, my first questions are, how did you fuck up? And I talked to some people who started their podcasts and I was like, how did you screw it up? Because I want to know what you did so I can try to be smarter about it knowing that we’re all going to fail in different ways. But, so along all of that, what’s your advice for somebody that’s on their path towards self mastery?

Gresham Harkless Jr. (29:04.461)
Yeah.

Gresham Harkless Jr. (29:20.462)
Yeah, I would definitely say that understand first of all, it’s a path and in and of itself is a journey. And the only way you can go on that path and journey is to take that step and the first step and the step after that and the step after that. I think that we sometimes build it up to where self mastery has to be this destination, but I truly feel like it’s something you never ever reach. And if you’re on that path, it’s more like a mentality.

So I feel like if you start to understand that you can always sharpen the saw to get better, sometimes things are gonna work out the way you want them to work out, sometimes they’re not. And I think if you balance between the two things, as you said so well, you make the best steps with the information that you have and understand that you can still move. Like even if you get knocked down, you can move backwards, you can get back up, you can do whatever it is that you need to do. I think that we have to continue to kind of understand who we are and what lights us up.

And that’s gonna be one of our best guides to ultimately where we wanna be. So if you continue on that path, then I think that’s gonna get you there. But remember, it’s a path, it’s a journey. It’s not a straight path. It’s not something that you just check off a box and get done. It’s not a to-do list. It’s actually something that you have to do on a daily basis. And you’re gonna be drawn and driven to do that as well.

Nick McGowan (30:33.676)
Yeah, great points, man. Look, Gresham Harkless Jr. , it’s been great having you on. I appreciate you being on with us today. Before I let you go, where can people find you and where can they connect with you?

Gresham Harkless Jr. (30:43.392)
Absolutely. You can head over to I am GreshThat’s I-A-M-G-R-E-S-H.com. I have a podcast as well too, so you can find links to the podcast. I have lots of, I call them hacks, which are like productivity and efficiency hacks that you can find there just to make entrepreneurs and business owners more effective and efficient. But Nick, truly appreciate you. Appreciate you holding the space and the time as well too, because people don’t have these conversations. So I commend you for kind of giving space for that. So thank you so much for allowing me to be a little bit of a part of it.

Nick McGowan (31:10.872)
Absolutely, thanks again, man, I appreciate your time.