No Matter What with Sterling Hawkins

Judd Shaw: [00:00:00] Driving, you know, exotic cars, total wolf of Wall Street life, and some of the loneliest and darkest and most disconnected times of my life. Welcome to Behind the Armor, where we deep dive into the heart of what matters. I’m your host, Judd Shaw, adventurer, storyteller, agent of change, and speaker on authenticity and human connection.

Join me as we explore the complexities of human connection featuring theorists, scientists, and speakers. Our mission is simple, to inspire you to reclaim your true self and create genuine connections with others. Join me as we lay down our armor and live Hey, you beautiful people, and thanks for tuning in.

Today, we’re speaking with Sterling Hawkins. Sterling is an author. Investor, entrepreneur, keynote speaker, and founder of the hashtag no matter what movement. Sterling strives to teach people how to achieve the results they want regardless of their circumstances. From [00:01:00] creating a multi billion dollar startup to collapsing And coming back to launch, invest, and grow over 50 companies, Sterling has taken his experience to work with C level teams and speak on stages around the world.

Let’s uncover what’s behind the armor. Well, my friend, you and I have a lot of connections that I am so looking forward to talking about since I saw you in San Diego. Sterling, welcome to the show. Great to be here, John. Honored to be here. I’ve been hearing about you from many places and it feels like this conversation is a long time coming.

So here we are finally. I do too. Yeah. I do too. And I wanted to first, um, get right in to the hashtag. No matter what. Yeah. Um, you know, for me, I’m not [00:02:00] so sure what’s gotten me through all my darkest moments. I haven’t taken the time to find if there’s a common pattern, not that got me there. That I know, but got me out of there.

And sometimes I just think it’s no matter what. Candidly, this was not like some marketing ploy. Um, I didn’t hire a branding team to be like, Hey, come up with some really smart positioning for me. This was a mantra I used to get out of bed in the morning, um, to get myself going, to make the phone calls I didn’t want to make, to have the uncomfortable conversations that I knew I needed to have, but really didn’t want to.

Um, And it turns out that that mantra as it’s worked for me, works for many people in many companies. And that’s really how it started. It was, you know, me telling myself to get out of bed. And then my sister kind of caught onto it and working through something. She’s my business partner, by the way, I wouldn’t be doing any of this without her.[00:03:00]

And then some friends and then their friends. And then all of a sudden we were like, I think something started here. So it was very organic. It’s, You know, it’s a personal and professional for you, you, um, by nature, you know, you, you design, develop and build a startup that ultimately is worth billions and that disappeared in like a cloud of smoke.

Yeah. And. You know, can rock us not only personally, but rock us professionally. Is that where this came out of? It did. Yeah. I think I got kind of lucky right out of college admittedly. So I started this retail software company with my dad and we actually owned a grocery store as a family. So we had a place to trial it and test it out and learn things.

And we ended up getting acquired pretty quickly by this group in Silicon [00:04:00] Valley. And, you know, as you said, raised hundreds of millions of dollars, multi billion dollar valuation. It was, you know, the story is like a scene out of Wolf of Wall Street, you know? And in actuality, the whole thing came falling apart across probably nine months to a year, but it felt like that, it felt like it was overnight.

And I didn’t know it at the time. I would talk about this differently at the time, but my whole identity was wrapped up in it. My identity was wrapped up in the money and the success and the penthouse and the startup, the unicorn nature of the whole thing. I can call whoever, do whatever, go wherever. And when it fell apart, who I was felt like it fell apart.

Does that make sense? Does it make sense? You know, Uh, as a personal injury lawyer, when I got to the point where I’m driving, you know, exotic cars and flying private [00:05:00] and, and, and yachts and crude things and total wolf of Wall Street life. Right. Um, and some of the loneliest and darkest and most disconnected times of my life.

I couldn’t get out of it because I just, it was my identity. Well, who would I be if I wasn’t this and so sometimes I got so sucked down that I think the universe had to, had to pull that in a different direction or otherwise that would have been how I died helping that identity. Yeah, I, I think about it similarly, like I wouldn’t have been happy with who I was like, yeah, I had all the superficial things and it looked great, but underneath there was no fulfillment.

There was no purpose. There was no connection. There was no authenticity. It was all this like facade that got created. And from the outside looking in, you’d be like, wow, that guy’s living the dream. Right. I [00:06:00] really look back on it now as one of the biggest blessings of my life. Certainly some of the hardest years I’ve been through and so grateful for that because it’s connected me with what I think matters most in the work that I’m doing now.

Let’s call, let’s call this version, excuse me. Let’s call this version of us. Yeah. Our 1. 0s. But our 1. 0 is we’re, we’re developed narratives and beliefs, and we all had different, Upbringing, some people have trauma like me, others don’t have the trauma, but still meet a dark night for, for a number of reasons.

So our 1. 0s are, are, are Wolf of Wall Street days, right? They are, we will use people if we need to, to get what we need because more than anything is the validation, uh, we are being heard. [00:07:00] In a big way, we are being seen in a big way, not for the right reasons, but you know, they, they, they serve all the right needs and, uh, and, and suddenly none of that, you know, feels right.

And, and, and serves us the way it may have protected us earlier. What for you, Sterling, what was your zero to 1. 0? Tell me about like just your upbringing before you get to the point. Where you develop a company that becomes your identity. Yeah, I, I had a pretty good life. I grew up in upstate New York, pretty close family, really close family.

I should say, especially my immediate family. Uh, we had this family business. So I remember growing up and going into the grocery store when I was a little kid and passing out cookies and chopping celery and, uh, I thought it was the coolest thing in the world until I turned 15 and my dad put me on night crew.

And all of a sudden I was like, Oh, this is, [00:08:00] this is real work. You know, it was this totally like 180, like, wait a minute. You mean I can’t just eat whatever I want, do whatever I want and have fun. And, It was, you know, some really hard work. I was waking up at 4 a. m. and filling the ice coolers for the different departments and stocking shelves in the middle of the night.

I mean, it was kind of gritty stuff. I didn’t like it at the time, but again, another one of those things that I’m grateful for because it really put me in touch with work. It wasn’t one of these like, Oh, you’re part of the family that owns the store. Here’s your, you know, success card. It was, you’ve got to work harder than everybody else.

You’ve got to do the jobs that nobody wants to do. And if you’re not cut out to lead this organization, You will not, um, which I have a lot of respect for. And, you know, I think that’s why the team and the culture really respected my father and what he was doing there. And [00:09:00] frankly, why that business was as successful as it was.

And I knew the store like the back of my hand, you know, I spent my entire life there. So like I knew the people and I knew our suppliers and I knew the operations and I knew our pricing strategy and like, I knew the store so well. When I graduated college, I thought, you know what, it’s, it’s time to spread my wings a little bit, you know, my vision’s a little bit bigger than this store in central New York.

So I started this retail software company with my dad and it was pretty straightforward to integrate it into our point of sale system and bring some of the technology forward into that store. Cause we controlled everything. And, um, it was interesting to watch how some of the team members and customers engaged with it at the time, especially in those early days.

And really before we went very far, very far, excuse me, we ended up selling it. So it was, it was pretty quick. [00:10:00] What’s, um, really important for the listeners and a good reminder for myself is that. We both come from different childhoods. We have different childhood experiences. I was not close with my father.

In fact, it was a very tortured relationship. It was the cause of a lot of my trauma. And, uh, and so that relationship was, was lacking. And there’s these other, you know, things that go on that made me feel at early 11 suicidal. But What, what it goes to show and validate for everyone else who’s maybe have a difficult time Feeling not heard and seen because they didn’t have childhood trauma, right?

Everybody sounds like so many of us is a every child more people have [00:11:00] more trauma and trauma We’re calling trauma different things big T’s and little t’s and what’s important in validating Is that you didn’t have to have a terrible childhood or a different experience, uh, uh, you don’t have to have a difficult childhood or terrible experience growing up to have gotten to a point where you are lonely and disconnected to.

Totally. It took me a long time to realize exactly that it’s not what happened to you. It’s what you’ve made it mean. And I did have a pretty good childhood and, you know, certainly like everybody else, some little T trauma stuff. But what I was left with Judd is I didn’t have anything to point to. I was like, well, what’s wrong with me?

Nothing major happened to me, at least that I could recall. And so it almost created this, this trap door that took me even lower because I didn’t have a reason for all of these self doubt and worry and negative self [00:12:00] talk that I dove into. Right? That’s, it’s, it’s a part of my framework is getting behind why we wear the mask.

And sometimes when you get masked up, it’s like, What’s worse is having a problem that you can’t get a diagnosis of. Totally. Because the first thing you can do to attack a problem is you have to be, you have to know of the problem. And so to your point and to so many people out there who don’t have these things to point to, don’t say, ah, I can blame it or point it to this.

Where I can say this is the root or cause of it. It’s sometimes even more isolating in your own head to say, where is this coming? Why do I, and then tell me if I’m wrong. And then you start to say, I don’t have a right to complain. Yeah, right. You know, who’s going to listen to me? You know what they’re going to say if I complain and that [00:13:00] isolates us more.

Yeah. You know, the, the business breakdown was one thing, but I think how I reacted to it was even worse because I kept up the facade. I, um, kept going to the fancy dinners and the expensive trips that I couldn’t really afford. And people would ask me, cause they knew the company fell apart. It was public news.

It was on TV and, you know, newspapers and everywhere else. And they’d say, Sterling, are you, are you okay? Do you need help? And I’d say, Oh, I’m fine. I was not fine. I was embarrassed that the pain of that breakdown, not just of the business, but all the personal pain that it connected me to was, was more than I could confront at that time.

And that’s actually what started me looking for. Well, if I don’t have something to point to, if I don’t have this thing in my childhood of my life that I can quote unquote solve. What can [00:14:00] orient me to the human growth work that I know I need to do? And that’s where I started getting obsessed with this comfort.

Right? Like anywhere, I maybe couldn’t see this thing in childhood that happened to me, or the decision that I made, or this thing that I told myself, or this lie that I believed from when I was 6 years old, somewhere in there. But I could find where I was uncomfortable now and use that as an orienting factor to say, okay, well, here are the areas that you need to grow.

The first of which was, you know, consistent with some of the things you’re sharing here. is acknowledging to other people, Hey, I do need help. Yeah. I love that. And thanks for your sharing and your vulnerability about that. I, I wonder, uh, you know, for you, what, what do you think was the root of [00:15:00] the need to keep up the persona, the need to keep the mask on so more of us can learn how to take it off?

So I’ve thought a lot about this in, through different modalities, through conversations, through therapy, through plant medicine. Like I’ve explored it through just about every angle I possibly can. And I don’t know if I can point to like a singular event, but I can point to at some point I thought. That I needed to keep up this facade of who I was, you know, maybe it was something small, like my mom said, don’t don’t laugh so loud.

Or my dad said, hey, don’t scream when we have company over. Like, it could have been something small like that. But all of a sudden there was this disconnect between who I am authentically. And who I think I need to be in the world. So [00:16:00] there was this facade who thought, well, if I just go through the best practices and do things that people tell me and do everything by the book and check the boxes, well, then that will lead to success.

Like how can best practices not lead to some sort of success. But I realized is they’ll get you somewhere, but they leave you hollow. And so it’s, for me, the work has been bringing back that authenticity of self with how I show up in the world and conversations with others, how I present on the stage, how I work period.

Did you trace some of your stuff back to a particular event or is it similar? Yeah, it’s a great question. I appreciate it. You asking, you know, when I came on the other side of my healing journey and when I say the other side, the starting of being healed, right? It’s one of those mountains with a top, you know, like we’re always [00:17:00] continuing to heal.

There is so true. So true. And, uh, CBT and DBT and a lot of therapy and land medicine and, um, I thought, could I reverse engineer my own healing where I came out with this framework called the connection cure and it stands for cure stands for C U R E conscious awareness. So being able to understand that we are not showing up as our most genuine selves, that we’re not being authentic, at least not consistently with.

All the places we’re showing up in the world and then understanding what is the root cause. Of those masks, and they may be different. Maybe childhood trauma like it is for me, it may be loss of a loved one. It may be because society or your caregivers told you you’re not permitted or not, you know, to do something could be many, many things, but understanding the root of why [00:18:00] we wear them so that we can take that mask off and maybe layers of mass.

Sometimes we’re not even aware we’re wearing them. And then be able to first connect authentically with myself and then with others. And then once I’m able to show up that way by renewing, that’s the R in cure, I can now expand those connections with myself deeper and with others to create a ripple effect with within their own organizations, communities, relationships, and friends.

And so I did a lot of thinking. And for me, my story actually. Is riddled with dark nights and, you know, traumas, small and big because I, what I realized is that I have the 11 year old, the 18 to 23 of a 32 year old inner child. I never stopped stopping the behavior. So I didn’t have this, you [00:19:00] know, moment of root cause.

I had the whole life of, ah, you are the problem. Mm hmm. You know, and how do I forces itself? That’s right. But then I had to stop demonizing and I had to stop telling myself I’m broken. I was telling myself that Sterling, I was like, you are broken. And when I tell myself that, that’s what told me that after work, I could go in a meth den and do drugs all night.

Mm hmm. Kids and a wife at home. I’m broken. Yeah. That’s, that’s where I belong. That’s my, those are my people. I didn’t even know them an hour before 12 midnight. You know what I mean? And so, yeah, so for me. It was a huge task, but in an important one to be able to understand the root cause of all of this was the, was the same.

[00:20:00] It was this desperate need to be heard, seen and feel valued. And then, so now I’m doing it in the most unhealthy, the most steroid megaphone way. Because I don’t know now to throttle. I don’t know that just because I’m on every billboard in New Jersey, and I want to keep going, it’s because I just want to be seen.

They’re not, the ROI isn’t there for the business anymore, so what’s it about? Yeah, yeah, I think many of us, most all of us, end up living a life of compensation and not even realizing. Compensating for, you know, something that happened with a parent, or feeling like we’re not smart in a certain grade, or we’re not good at certain tasks, or we’re not lovable, or we’re not good enough, or we’re not acceptable.

And then we spend the remainder of our adult life [00:21:00] Compensating for that, trying to make up for it in the way, in the ways best that we can. I think what you said is a necessity of this kind of work, which is, there’s no band aid for that. There’s no like superficial approach of like, Oh, well, if, if I just make more money, if I have the right relationship, uh, if I live in the right place, like we tend to look to solve that gap with superficial things.

And it doesn’t work. It becomes this treadmill of more, better, faster, cheaper, like, whatever it is, it’s only by doing what I would say is like the real work, the hard work of getting to the source of where some of those inadequacies started, can you actually shift them? And when we’re doing that kind of work.

In our personal or professional lives, it’s all the same, but the impact of that is transformative, literally impossible to see the possibilities of from where we sit today. And to me, that’s [00:22:00] the thing that’s incredibly inspiring about it and scary at the same time. Sterling, this is such a message for our brothers and our sons, for young men who are Uh, in a dangerous space.

They are not feeling heard. They are not feeling seen. And they go online to find out what it’s like to be a man. Where is their place in society? And that’s when they’re exposed. To people who say, Hey, life sucks. And I know the way out. And this is the way to do it. And that breeds toxic masculinity that we see today.

Masculinity isn’t toxic. That’s the toxic part of it. And, and, and, and, and, and that message has to be repeated. I had the Ferrari, that smell of the leather wears off and people are going to, who care? You don’t know. I know I, I, I deprived you, I still curled up in a corner of a [00:23:00] concrete floor and cried owning all of that.

Thinking about ending my life. Yeah. Okay. So pursue that, take it at least if not from me and not from Sterling, from anybody else who can tell you that it’s, there’s not a pot of gold at that end of that rainbow, it’s lonely and sad and disconnected because all of those material things, they’re not sustainable for me, Sterling, like service.

I, that is for any of us. Yeah. Yeah. And it’s tempting. It’s this tempting trap to think like, if only, if only I had the money, if only I had the Ferrari, if only I had the yacht, if only I had a, you know, whatever it is, but if you’re going down that line of thinking, it’s, it’s a dead end because, you know, you’re a great example of it.

You acquire those things, but it doesn’t [00:24:00] solve anything. So. So can’t this is amazing and here it is, where’s, where’s the hack for us who are living with insecurities and we’re pursuing our success because of those insecurities. As a result of those insecurities, I’m working harder and harder as a lawyer, not enjoying it, but because I was driven on insecurity and needing more and more and more and more.

Right. How do you know, how do you know how to stop? How do you stop? Yeah. Well, I think that’s why discomfort is so important. You know, I called my book hunting discomfort, not because I wish it on anybody. I’m not like out here, fear mongering or pain mongering, or, you know, wishing ill on any person or any company.

I’m really not, um, but most [00:25:00] people will come to me. and say, well, Sterling, look at my business, my bank account, my relationships. I don’t need to hunt discomfort. I’m surrounded by it. And my answer is always the same, which is you’re not hunting discomfort. You’re living with it and you’re probably placating why you have it.

And so I think the first step or the hack to break us out of these toxic cycles is to start identifying that discomfort, the things you’re avoiding. The things you’re denying, the things you’re like buckling down just to try and survive and get through the next day. That discomfort holds the keys to our breakthrough as an individual.

And then that translates into more healthy relationships and more organic business growth. Therein lies the power, the superpower of authenticity. Because in my opinion. That’s when [00:26:00] you can say, I’m struggling. Um, uh, I’m fighting a battle. I’m not talking about, uh, and know that everybody else likely is too.

And the more authentic, genuine human connections we have, the more likely we will thrive in the world around us, because that’s, that’s what, that’s the power of the human connection. authentic connection, right? There are so many people showing the best parts of their life. There are so many, uh, great people curating a perfect life on social, making what they want their great life to appear even greater.

We’re, you know, and, and I think what happens is the more we recognize that we all struggle, that life is a challenge. I think the more we can lift each other up, [00:27:00] then bring each other down. Yeah, I mean, there are discomforts that we all deal with, but I think it’s that fear of exposure. How I refer to it, that’s, that’s the fear of being seen as your authentic self.

Typically people don’t have any problem showing the best sides of things and their successes and their wins and all those things, but it’s the shortfalls. It’s the misses. It’s the things you’re embarrassed about or the things that you wished hadn’t happened to you or wished were another way. That’s where that true authenticity comes through.

And what was important for me is that, that fear, that discomfort of exposure was so strong for me. I couldn’t confront that barrier directly. There was nobody in my life. There wasn’t therapy. Like I was so resistant to those things. I actually had to start in another place, which was finding things that I was uncomfortable with, but [00:28:00] not so uncomfortable that I couldn’t actually.

Do it. So I started taking, uh, you’ll laugh at this, all the different kinds of dance classes that I could find. I’m, I’m not a, I didn’t like grow up a dancer or anything, so I was finding like ballet and tango and all these things super uncomfortable. But it started to break down some of that ego, some of that barrier.

And later on I found this research outta University of Michigan and they were studying discomfort. They were looking at physical discomfort, like somebody stubs their toe, and they were looking at emotional discomfort, like maybe somebody going through a bad breakup. And they found that physical, mental, emotional, the body and brain process discomfort almost identically.

So much so you can take acetaminophen, like Tylenol, and it will help you with emotional pain. Now, all the disclaimers about that for everybody listening, right? I’m not a doctor, that’s not a biohack, I don’t suggest you do that, that’s not the latest Instagram trend, like, do [00:29:00] not do that. Um, I think the insight there is that if where we meet discomfort anywhere is the same, We can grow our capacity to deal with it everywhere.

It’s a muscle you can build. If you want to grow your bicep, well, you go to the gym. If you want to grow your resiliency, your authenticity, your depth of connection with others, and maybe even your, your business results or your financial performance, you hunt discomfort no matter what form it’s in. Um, that was really the power that I tapped into early on.

And I didn’t even know it. It was just kind of this. Automatic thing of, I know I need to make my uncomfortable. I need to break something in myself. And you know, I just found out later, there’s some research that backs it up. I was going to ask you, did you go right to sharing? Like did you start opening yourself up with maybe a loved one or a therapist or somebody?

Cause for me, I, I couldn’t, [00:30:00] that was unthinkable for me. I think in renewing connections, um, and turning your authentic self outward, there are risks. And, you know, some relationships you have to shed, some will shed you, they won’t like that version, but it’s important to do this first with those you feel really safe with.

And, um, and for me, one of those first relationships was actually my chief operating officer. No kidding. I had known for a while that I had tormented, you know, 10 years of her life with me because she knew that 1. 0 she helped build a company and I was just chaotic. You know, I go in and if I fired five people at once, it was to make a scene, you know, and she would say, well, who’s going to do their job and I’ll do their job.

[00:31:00] Meanwhile, I don’t know any of their jobs. You know, I was just making things worse because, um, I’m not authentic. I’m not, you know, Leading with authenticity. And so it’s just a different version that comes on. That’s reactive to situations in, in business. You know, I always felt under attack and so it’s always someone else’s fault.

Um, and you know, I really, um, I, I, I created. A very difficult place for her to try to operate in. And so, after I had gone on this healing journey, I thought that she would be one of the first persons that I needed to reconnect with. We needed a, a new start. And speaking of new starts, I even needed one for myself.

Where are you in upstate, where did you grow up in upstate New York? Outside Syracuse, a town called Skinny Atlas. It’s one of the Finger Lakes. Do you know it? I, well I know the area well because I [00:32:00] spend a lot of time up by Ithaca. Uh, New York. Beautiful. Yeah. Well, certain times of the year, it’s beautiful.

Very true. Uh, and, and, you know, so I had to step away from New Jersey, go all the way to California, 3000 miles away and step away from myself and my life to literally say, like, what does Judd want? Who is Judd? You know, and, uh, and so once I was able to really answer that and work on myself and when I turned to working with others, I called Chrissy and I told her, let’s take an executive retreat.

But this time we met at the San Juan islands out in Washington. And instead of talking about KPIs and processes and systems and oversights and targets and goals and financials, I just, you know, Talked about us. I learned that she was getting a dog at the time and she was learning about my healing journey.

And, you know, we sat on the, uh, edge of the, uh, of, you know, in Washington, you know, with Orca whales in the [00:33:00] background and, and, and Canada just beyond sight. Right. And, uh, and sat there and, and shared a moment on a log where, you know, We were human. And at that point, I realized that still after all that time, she had my back and I had hers.

And so, going back to it now, I realized, wow. Now, I was able to ask for help. Now I was able to say, I can’t even come home, come in today in this office right now. I just got some bad news going on in my life and I’m, I’m just, I’m not in the, you know, I got you, judge. No problem. I can, she can lean on me. She now, she now in one meeting teared up and shared with me that she could never, ever cry in front of me before that moment.

She said, you have no idea how long I would prepare all night. Knowing that you were on my calendar the next day, terrified to tell you. And so now she, she now [00:34:00] can lean on real advice because she’s telling me when she really has a problem, before everything was perfect, right? She doesn’t have to be. And so, so yes, I, I renewed that connection with her safely, effectively, and it led to me feeling empowered, those kind of connections with others.

Yeah, and I would bet that not only did you create this deeper, more authentic connection, but I bet performance went up in the organization as well. Like, that’s, that’s the really interesting thing to me because I’ve worked with a lot of, uh, leadership and companies and they always want to do the same thing.

Talk about goals and KPIs and metrics and technologies and innovation and tools and what are the numbers and where are we going and how are we getting there and I think we need to have those things. But if you want to break through in performance, it’s some of those tough conversations, vulnerable, authentic conversations like you had with your COO that I think are the critical missing piece in a lot of these places.

Yeah. We were working, [00:35:00] you know, six days a week, many hours. There were no weekends or nights when I would talk to my team or managers and leaders. And now this 2. 0 or even 3000 version of me, uh, leading authentically, we work four and a half. Days at 12 o’clock on Fridays our office shuts down because now we have moms who say they can spend You know an afternoon doing Errands that they wanted to do so they could spend the time with their kids on the weekends And and dads too and then you know others saying, you know, I don’t have to now do Things and chores and blah, blah, blah.

I can enjoy my weekend. I can enjoy my time. I can recharge my battery. We are more productive, more efficient, more profitable than we were ever before. And we’re working less time. And that’s what authentic leadership did because it gave Chrissy then permission to lead that way with others. And now people are not questioning our direction.

They’re not questioning leadership. They’re raising problems and surfacing those [00:36:00] giving feedback, opinions, and, uh, it’s a highly much more efficient and healthier way Workplace. Amazing. Yeah. And I think the takeaway is, is not just professional. Like, yeah, we, we can do this in organizations and we should, but we can do it in our friend groups and our families and our communities.

We can literally do it everywhere. And all the research will say the same thing that, you know, You actually saw in your business, which is when you have authentic, deeper, more trust center, more human centered conversation. Every single performance metric goes through the roof. Burnout goes down, retention goes up.

You know, people are just happier. They’re more productive. They’re more engaged. They start to align themselves as an individual human with the organization. And when we’re working as real, authentic human beings, I think that’s when we get our best work done, whether it’s in the household or in the office, [00:37:00] Sterling, what do you say to the question?

What is bring your most authentic or bring your genuine version? To work look like so it can’t be, you know, someone, for instance, I mean, I have tattoos, but there are workplaces that would like you to cover them up. Or if you have a nose ring, take it out. It doesn’t mean that you’re inauthentic because you’re complying with company standards or some policies.

I think it’s in the core values of yourself. And that organization, but what, what does that mean to you when, when, when you’re telling people or business or using the terminology about bringing your authentic self to work, what does that look like? Yeah, to me, it’s, it’s not how it physically manifests at all.

It’s not about showing the tattoos or whether you have a tie or not. It’s literally the personal intention of being seen. All the good things, all the bad things, and everything in between. When you [00:38:00] have that willingness to be seen, it doesn’t mean you have to share what happened last night, or, you know, you gotta show somebody the tattoo on your back.

But you’ve got that vulnerability. And now ability to connect with others in really profound and meaningful ways Bottom to top right? Uh, my job is front line and I I get the mail Uh, and I bring the mail, uh to the office and I sort the mail and I give it to the different departments Well, you know that can mean uh, I i’m valued for my job.

I understand that it’s important. I feel valued Seen for the value that I bring. Uh, I, I, I take my time to make sure I get there on, on time when the mail comes and, and on time when all the departments need it, you know, and I don’t make light of it because these jobs are needed. Every job, whatever that position, it’s the person who’s doing it.

They feel that they’re bringing value to the organization and the organization sees that. [00:39:00] So, so now they’re, they, they, they’re finding purpose in the work. They’re bringing the energy to the work. They’re protecting the work and, and they’re pushing the work forward. Yeah. Absolutely. I think the, the purpose in all of our lives, this is not like Sterling’s thought.

This is research driven. The purpose in all of our lives is not the tactics. It’s literally how we’re showing up. I have gotten into the German American theologian and philosopher Paul Tillich’s work in the last several years. And he says, as human beings, we’re all concerned with these, these finite goals.

What am I wearing? What’s my performance at work? How much money do I have? How many locations have we opened? How many people have I hired? Finite things that either happen or don’t happen. And we do need those things. We need to be measuring those things, working towards that growth. Absolutely. But at the end of the day, at the end of our lives, those are not the most [00:40:00] important things.

What’s most important to all of us are the infinite things like love. Joy, connection, peace, gratitude, courage. And when we connect with those things, we orient to the things that are ultimately important, the real purpose in our lives from like a deathbed standpoint. And we bring that version of us every day to the office, into our relationships, especially into the unknown and the uncomfortable, we start to transform some of those finite things.

And I think for me that had been an incredible shift of like, Oh, I was looking for success. in all these finite places. What did my bank account look like? What was my car? Uh, who was I dating? How great was my penthouse? And wondering why I felt empty. Well, it was because I was paying no attention to the things that from a human standpoint mattered most.

And when we can orient ourselves to those things, it’s, it’s transformative. [00:41:00] Both personally and professionally. Yeah, they, they go together. Yeah, they do. You know, um, It’s, it’s the hunting discomfort, though, that’s still Even acknowledged today that I struggle with because, you know, it’s like, God, I’ve had so much discomfort.

I don’t want any more. I don’t want any more pain. I’ve been through so much pain. But when I think about what you’re saying, it sounds cliche, but it’s also where I grew most. I didn’t grow from all the success. It’s, it was this pain, this, the, the, the, the resiliency and the validation That I’m going to be okay and I can get through anything.

No matter what. Totally. Yeah. And I, I respond similarly, you know, when it comes to something uncomfortable, my immediate reaction, oftentimes without even thinking about it is I [00:42:00] don’t want to do it because It’s by definition, uncomfortable. Why would we want to do those things? It’s almost like built into our psychology to move away from the uncomfortable.

Yeah. Um, but it is important to catch those things because I worked with a lot of people talking about wanting to realize their potential in their lives and their relationships and work or in their organization, right? Like, how do I realize my potential? And they’re happy to take on all the happy emotions like love and celebration and peace.

And they want all of those things, but they don’t want the pain. They don’t want the suffering. They don’t want the embarrassment. They don’t want the self doubt and they don’t even want the potential of failure. And it’s like, well, how can you realize your potential? If you’re effectively denying at least half of your human experience, you need all of those things to bring all of yourself forward.

That is so good. That is so good. Falling [00:43:00] forward. I, I, I, I love that. I, I think we need it. And, and it’s something that, you know, I’m not one of these guys that gets up on the podium and is like, oh, do this. Like, I’m taking my own medicine every single day. Yeah. You know, it’s the work, it’s the practice. I, I know you’re doing the same thing.

It’s not, you’re on, not on the top of a mountain and telling people how to get there. Yeah. You’re on the climb and you invite people to join you. Uh, for me, I, I, I, I was at the mountain and I, I fell all the way down and I was trying to tell people what it’s like to, to get back up there in a healthier, um, safer way, you know, speaking, um, Some of the therapies you explored.

So, you know, you and I have this just such an interesting thing in our universe. I keep running into the Sterling world, you know, in different places. And, uh, one of those places for me was plant medicine. Uh, you know, out in Colorado, um, [00:44:00] uh, we have a, a mutual, Well, a person we know choo choo that we, Oh yeah, she’s fantastic, right?

Isn’t she? And so like, tell me what, what’s your experience with that? What’s your experience with plant medicine that’s, that’s helped you in this particular your journey? Yeah. Well, first I think it’s important to note, I’ve never been a drug person. I drank quite a bit during those successful years that I had, but drugs always scared me.

I thought no matter what drug it was that I would take it and I was going to die at, you know, that’s probably something from my childhood. We know that’s not true, but I was just always scared to dabble in any of those things. But it was first something about ayahuasca. That just called me for years. I didn’t know what it was, but I would research it online and talk to people that have experimented with it.

Terrifying beyond terrifying for me. But eventually I got to this place where I said, you know what? [00:45:00] I’ve, I’ve got to try this. I’ve got to dive into the unknown and experiment with this in a, in a safe way. And I found this place in Costa Rica that had doctors on staff and it was first class. It was, it felt safe enough for me to try it.

And I remember standing in line for those people that don’t know, usually you take ayahuasca in ceremonies and there’s a number of people there and you line up and you take a little shot of this. Root, basically, it tastes like dirt, but I’ve been lying to take my first glass And i’m having all the crazy self conversations about it.

Like what are you doing here? This is insane You’re definitely gonna die in this crazy place in costa rica. Your mom was right You’re gonna be a drug addict like all all these things Good. I kid you not. I was so scared. Tears. Tears were coming down my face. And I realized now why I was so scared is because ayahuasca and a lot of these plant medicines gives you access to the unknown, [00:46:00] the profundity of the unknown in your unconscious, which for decades, I was avoiding.

So no wonder I was scared. And that first night was one of the most transcendent, incredible experiences I’ve ever had in my life. And, you know, it started using some of these modalities as part of my growth. Still scares me to death every time, but I get so much from it. You know, again, an important message of the distinction between you and I that actually brings us together, which is a shared experience.

But for a different reason, I’m the opposite, you know, young, you gave me a pill in my teenage years. I took it in the NAS. What did I take? I had more fear because I, I perhaps went about that with my approach to life. And so then when I valued both myself and my life, I too questioned, [00:47:00] you know, anything that I would now ingest in my body.

But like you, that experience. Opened up a channel of compassion and forgiveness and harmony that it could not have tapped into alone. or in any other method, at least that I have tried thus far. Agreed. I, I think in theory, you can get there if you want to meditate on a mountaintop for 40 years, but no way for most of us to reach those levels and to access those parts of ourselves without some kind of facilitating mechanism.

And I think the, experiences can and often are transcendent. They were for me, sounds like they were for you. Um, but at the same time, it’s not like a silver bullet. It’s not a magic wand that says, okay, now, now you’re healed. No, [00:48:00] you know, there’s, Months and years of hard work after some of these plant medicine ceremonies, you could probably attest to yourself that is bringing the authenticity, the depth, the pain, the suffering, like you bring those things into the world.

And that is just as challenging, if not more so. Um, That’s a great point. At least in my experience. That’s a great point. You know, you’re addressing those blind spots, those, those things that you get triggered about that are taking you either to your knees or resulting in bad business decisions that you regretted.

You know, they, they open those things up and they bring them. And so, you, you know, after that, you’re walking away now just dealing with that. You got to integrate. And yeah. And so, uh, yeah, definitely do it, in my opinion, professionally, uh, you know, and, and, and because. You know, there’s a lot out there about that psychedelics and things like that, but, you know, at least in my experience for this purpose, you know, in that kind of setting, um, yeah.

[00:49:00] So, okay. So if we’re going to, we’re going to, you know, I love that we can draw on distinction for commonality, right. Which is, uh, we’re telling, you know, let’s tell, telling anybody, you know, get uncomfortable, find discomfort, right. Uh, you know, go out in nature. Eat some plants, , um, you know, yeah. Feel to, uh, you know, to, to lower that nervous system, to regulate and be able to repair, uh, yourself, excuse me, and, uh, to repair yourself and, and, and show up authentically, right?

Yeah. And, and, and connect. And connect with another human. Yeah. So another thing there. Uh, maybe that we can draw both on is, uh, I just was just before you came on, I was talking to another shared friend, James, uh, who, uh, you know, out in, uh, Oregon, [00:50:00] um, who’s making some great video content and, uh, you know, he, he says to say, hi, by the way, nice.

So low back and, uh, that’s all related to our keynote today. You know careers tell me about what’s going on on your keynote. Yeah Well public speaking being seen was actually my biggest fear and maybe this is another contrast point with us Like you wanted to be seen right? I was terrified to be seen And I think that was the case throughout my whole life.

I remember being in like lower school and college and having to give presentations. And I just wouldn’t melt down. Like my face would turn bright red and my hands would get sweaty. I’m sweating through my shirt and the room starts to spin. Like it was beyond terrifying for me. And when my whole life fell apart after this business collapse, uh, I, I lost, Not only did I lose everything, but I drove myself into [00:51:00] debt.

My girlfriend broke up with me and I had to move into my parents house in my 30s. Like I literally had less than nothing and starting to understand that discomfort wasn’t something to be avoided. It wasn’t something to be denied. It was literally the pathway to my own breakthroughs and kind of putting this to the test.

I decided one of the first things I would do is I would start speaking in public because I was, I was so scared. I thought, okay, this, this is how I’m going to break myself. I’m going to do the thing that I am most scared to do. And it’s really crazy how it happened. I can’t remember if I mentioned the story to you or not, but as I’m having this epiphany living in my parents basement, I get this junk mail from a conference in Singapore.

And it was just literally junk mail, inviting thousands, tens of thousands of people to join them at their event. And I thought, okay, well, if discomfort’s the way I’m going to put this thing to the [00:52:00] test and I wrote, or I hit reply and I wrote, why don’t you have me speak best Sterling, and I still have this email, by the way, and I don’t know if it was a situation where I got lucky or, you know, something greater smiled upon me or I.

Didn’t have anything to lose literally, but somehow I ended up getting on the phone with the conference director, talk him into being not like a breakup speaker, but the keynote speaker of his entire event, like now that I’m in the business, I’m like, that was insane. And I cannot believe I sold him on that.

Like, and it, and it felt like, uh, a game. It didn’t feel real. It, at least it didn’t feel real until he sent me the legal agreement and I’m looking at it in my email box thinking. Well, I’m a huge failure. I don’t know what I’m going to talk about, and I’m terrified to do this. But in that moment, I did what I think we all [00:53:00] need to do in those moments of discomfort.

Before self doubt stops us, is I sign that agreement and I sent it back to him. I was locked in to do it. It, you know, you could probably say the same or I’d be interested in what you have to say about it. But like you need sometimes the external accountability to force you through some of these things because it’s so easy to turn back, especially when you get into that precipice of fear.

Definitely. Definitely. Definitely. What are the, what are some of the takeaways that you want from your audience after they hear you? Well, the biggest thing is that discomfort is not a problem. It’s not something to get rid of. It’s not the thing that’s in the way it literally is the way that is the opportunity.

The unknown and the uncomfortable are where all the results [00:54:00] are for us personally, for us professionally, for our connections, for authenticity, for literally everything is on the other side of discomfort. And when we can start to understand it as not something to move away from or to avoid or deny, that gives us an ability to move through life in a different way.

a way that’s not responsive or compensating for our pains or doubts or insecurities of the past, but literally gives us access to our own human growth and access to our greater potential. That’s probably the most important thing. Oh, and, and by the way, I gave that talk in Singapore. I thought I was going to pass out.

I don’t remember giving the talk, but it was that conference director that put me in touch with all of his conference director friends. And that was actually the beginning of my career. And I was like, well, not only is discomfort holding us back, but oftentimes it’s the pathway to some of the things that can mean the most to us.

Very stoic, a [00:55:00] kind of principle. Very stoic. Exactly. That, that, you know, that difficulty, that uncomfortableness is the path, right? Uh, I love that. I love that. And you know, yes, for me, I, you know, as a, as an attorney, I, I think I went to be an attorney cause I didn’t think I was going to be an actor. And then they have this jury and they have, they can’t not listen to you.

They have to listen to you. And so, you know, I’ve like a, I have an audience of 12 that don’t have a choice, but, uh, and so you’re right. I mean, I sought that attention, but for those reasons, but you know, here’s a commonality again for the different reasons that we came here. Your fear, my, my desire to get up there for all the attention in the world, the different, the similarity there is owning your story, owning your story, that we all have a story and, and the story is, is like anything else afterwards.

The, the [00:56:00] binding is coming across the, the papers. Sometimes they’re coming out, the cover doesn’t even, you know, but. But it’s your story and own it and be a great writer of your story and author it in a way that you take agency and ownership in how that story moves from chapter to chapter. I love that.

And accepting what your story is right now I think is our access because I spent So many years, like wishing things were a different way. And if only that business didn’t collapse, and if only I had this conversation, uh, a different direction, if only I was a different person, well, then everything would be okay.

Uh, Carl Jung, who I’m sure most everybody listening is familiar with, arguably the father of modern psychology. She said, we cannot change anything. Condemnation about our business past, our personality, who we are, our failures, our successes, condemnation about anything [00:57:00] does not liberate. It oppresses, makes it very hard.

I would say impossible to do much else. It’s only once we accept our story, embrace our story, all the successes, all the failures, everything in between. Can we actually move forward in a meaningful way and develop those deeper connections with others and find that authenticity of self? I love it. You know, we’re also, uh, authors.

Um, you’ve written for adults. I’ve written for kids. I have a children’s picture book series called Sterling the night. It’s a good name. It’s a good day. I’ve got to get these books for my, uh, my nieces. I got four nieces and I haven’t got it. Share it with them for sure. Percent, you know, and, uh, and, and tell me a little, you know, the book hunting discomfort.

Tell me about. What led up, you know, to the book itself. Yeah. Well, you know, what’s interesting for me is [00:58:00] even though we can talk about these things and I’m really loving this conversation, by the way, we could talk about these things. It doesn’t make going through it any easier sometimes. Like pain is pain.

Grief is grief, avoidance is avoidance, and people have been telling me to write a book for years, and I always was like, oh, well, I’m busy, I’m speaking, I don’t need to, it’s coming, you know, I was just putting it off until tomorrow and tomorrow and tomorrow, and all of a sudden, I’m writing a page out of Shakespeare, and I didn’t even know it, you know.

And it wasn’t until the world shut down in 2020 when the pandemic struck and every stage, every workshop, every event I was scheduled for canceled in about a week. And I went to this place of, I cannot believe this is happening to me again. My, my life’s falling apart. Everything that I’ve worked so hard for, I’ve, you know, climbed this next mountain after being in the [00:59:00] pit of failure and sorrow.

And it’s falling apart again. And it was in that moment that I realized, wait a minute, I’ve been avoiding writing this book. I’ve been scared to write this book. And as soon as I noticed that, I started getting ahold of publishers and saying, okay, what does it take to write a book? What does it look like?

How do we structure those things? What are the business deals? And I started, I think it was about three months later and it was, Something that I had thought about for probably a decade at the time, had, had done research and case study, you know, I was speaking and teaching and talking about this stuff.

So I had so much material, but the process of going through it took about a year and it was filled with heartbreak and love and excitement and a little bit of terror, especially when I released it because it felt so vulnerable and I had to come back to that. Oh, that, that is the [01:00:00] way. Yeah, I can appreciate all of it.

Uh, and having experienced that and also doing that during the pandemic. And my reason for me was that was a way that I started the connection with myself, getting creative, getting playful, getting childlike, you know, coming up with little characters and it just felt good for my system and healthy for me.

And, you know, maybe, um, for others, but you know, that’s what drove me. I, I just wanted to get creative. Um, you know, Yeah, I was going to say, I think we all have these like limitless reserves of creativity and ingenuity. Yes. And when we’re operating from the facade of best practices and checking boxes, oftentimes we don’t even know that it’s there.

I can just speak for myself. You know, [01:01:00] people are talking about authenticity and connection and all that stuff. But honestly, back in those days, I looked in the mirror and I’m like, I’m not sure there’s anything there. Right. I don’t know if there’s anything within me. And it took going through this discomfort, going through the courage to kind of share some of these things and show up authentically that I, and I think we all can tap into this just innate human creativity that’s within all of us.

You know, at that moment in my dark moment, I actually felt like a shell of a human. Like just walking out and, and now just filled with so much more, you know, let, let’s try to get this wrap up and it’s some tips because I absolutely love this actually. So the conversation starts with, uh, you are unique, but you’re not special.

You’re not alone. You can have Sterling’s, uh, childhood. You could have mine and something in between. You still may meet a dark night, right? We all are fighting different types of small and [01:02:00] big struggles. Let’s be honest about that with each other and be vulnerable about that. Right? Uh, find, find discomfort, hunt it, find challenges, out will come, get to the root of it, get to the root of it, get, you know, uh, get authentic, get connected.

You know, you and I are a member of a community together, which is a beautiful group of human, amazing people, just really incredible humans. And, uh, and so get, get connected. Right. Um, I love what you said is, you know, is, is. Is fill, fill yourself with endlessly, endless possibility. Yeah. Yeah. The things that make you happy, that bring you some element of joy.

And [01:03:00] uh, I might add one more, which is, yeah, please accept the story, like do, do the hard work of coming into acceptance with everything that you’ve been through. Yeah. You know, I’m, I’m of the, Belief that there are no mistakes. There’s not something that’s happened to you that makes you incurable or that has permanently broken you.

There’s opportunity there. There’s possibility there. There’s authenticity there that just takes some courage to dive into and really own, these are your words, own that story. Yeah, it’s not only, uh, thanks for the reminder of owning your story, um, but, you know, when I talk to you, Sterling, and I’ve said before, forgive yourself what you do in survival mode, but speaking to you, my friend, makes me feel green and connected and safe.

Because I don’t [01:04:00] feel judged, I don’t feel shamed, and I don’t feel alone. And that’s what speaking to you today felt like, and I really appreciate it. It’s the same for me. I mean, I’m listening to you sharing brought tears to my eyes, because like, I know what the depths of human pain feels like. And as we said before, pain, pain is pain.

Your circumstance is totally different than mine. But when we confront it, we can start to see it, and appreciate it, and really have. And compassion and empathy for people going through it. So thanks, thanks for the conversation. And thanks for sharing. It’s been amazing. And to make it, you know, full circle, it comes back to just for our listeners, no matter what, no matter what, no matter what Sterling, you are an author, uh, an incredible businessman.

Consult keynote speak. I mean, you’re just doing so much for so many others. And I’ve seen the impact that you are making on people’s [01:05:00] lives. I’ve, I’ve witnessed it. I’ve been at the table around people who are incredibly connected and feel your energy. Final question for all my guests. Who are, who are putting so much love and energy and resources out into the universe for good.

What does Sterling do for himself to authentically connect? So this has been many years in process, but a habit that I now have is I write, to me, it doesn’t really matter the format, call it writing blogs or content or journal, a journal. But it’s getting what’s in me out of me on a daily and consistent basis.

And that fills my cup, whether it’s good, whether it’s bad, it’s just the process of writing it down. [01:06:00] And maybe it’s something about being seen. Like I can finally see myself with when it’s on a sheet of paper. Wow. I love that. Wow. I love that. It’s cool. I just thought of that. Like maybe that’s what it is.

Oh, hold on. I love that because I need your help. Okay. Yeah. Probably so many others because there’s so many things about journal, journal, journal, journal, and I hear it and I have 20 different cool journals from leather bound. They all are on my shelf. I don’t journal because I struggle with the time, but you, my friend, my universe in you, there’s something about it.

So help me understand. How do you get into the commitment of the routine? And is there anything you go into? Is there a model? Three of these, three of these, um, for amount of time. Tell me what, what’s your routine look like? Yeah. Um, for me, it started from kind of an organic heart centered place. I would write when I felt compelled to write.

Or I was triggered by something, some problem, some [01:07:00] obstacle, like I was dealing with something and then I would just start writing. And I didn’t force myself with a commitment early on. It was like, okay, every morning at 5 a. m. I’m going to get out the pen. I’m going to write. It started from when I feel something, then I’m going to write.

And then it’s kind of evolved into a habit. And I have a loose framework. I like to look at what have I been avoiding? Denying or surviving, right? Like what’s the discomfort I’m dealing with at the moment. Yeah. And then what am I grateful for? What do I love? What has brought me inspiration and joy? But frankly, I still show up and while I have that as a loose framework, I just write what’s on my heart.

And it could be like, I hate all these things going on right now. I’ve been through kind of a tough, uh, quarter the last three months or so. And the other day I wrote down, like, here’s all the things that have sucked for me. In my life, in my professional life, in my personal life, in my health, like I’ve been going through a lot lately and it was getting those things out and then owning them that I think was really valuable [01:08:00] for me.

So I don’t know if that helps you or anybody else, but it works for me. The idea of hearing and seeing yourself right now is mind blowing. Like I want to go write in journal just to do it for me right now because that perspective just changed it. I love it. Yeah. I think it changed it for me. I didn’t even think about it until I said it.

I was like, wow, I think there’s some magic in this conversation, Judd, that has brought a lot of gems forward. And I’m excited about that one too. Sterling, please let me know how I can support you in your world. Uh, you are a gem, my friend of a human, and I am so grateful and so appreciative for your time today.

I cannot thank you enough. Thanks so much for being on the show. Thank you for having me. A lot of gratitude and look forward to supporting however I can. I want to extend my deepest gratitude to you. If you’ve enjoyed this episode, please follow us on your favorite platform or share this episode with a friend.[01:09:00]

You can also follow me on Instagram at Judge Shaw Official. A special thank you to personal injury law firm, Judge Shaw. Judge Shaw Injury Law for their support in helping us bring this podcast to life. Remember friends, authenticity isn’t about being perfect. It’s about being real. It’s about embracing our vulnerabilities, celebrating our strengths and owning our stories.

Until next time.