https://www.listennotes.com/e/f2681435f41d4ef5a9af41404690b669
30 Jun 2025 · 31 min
Susan Drumm talks with Sterling Hawkins about leadership and growth. They discuss how discomfort drives personal development, handling change, and building accountability in organizations.
Foreign Hi, I'm Susan Drummond. Welcome to the Enlightened Executive where your personal evolution sparks your leadership evolution. Each episode we feature groundbreaking techniques and strategies to help you get the edge in personal and leadership effectiveness. This episode is brought to you by Meritage Leadership. At Meritage, we strengthen leaders and empower teams to achieve high performance. Go to meritageleadership.com to learn more. Are you curious about your own development path to enlightened leadership? Take our free 5 minute quiz at susanjum.com to discover your superpower and the roadblocks so that could get in the way of effective leadership. Today we're focusing on the power of embracing discomfort to create true change. And I'm excited to introduce my guest, Sterling Hawkins. Sterling is an author, investor, entrepreneur, keynote speaker, and founder of the no Matter what movement. Sterling shows people how to practice trust to achieve the results they want, regardless of the obstacles. Sterling developed his trust powered success system to learn from a painful collapse of his multi billion dollar startup involvement. He's since combined his business background, research and practice to launch and invest and grow more than 100 companies. So welcome Sterling.
Susan, excited to be with you. Thanks for having me on.
Absolutely. So, wow, discomfort. We've got to embrace it.
We do. You know, it's funny, we're all experiencing discomfort these days, personally, professionally. And the first thing I hear from people oftentimes is, Sterling, I don't need to go find more discomfort. Look at my business, my relationship, family, my bank account, like, like all the things, like I've, I' got enough. And my answer is always the same. Oftentimes we're placating and living with that discomfort versus truly using it and embracing it to create a breakthrough result for ourselves, our business, our community, and even family.
Well, let's talk about that distinction then. What is required to lead in today's incredible pace of change?
Yeah, I think the biggest thing is our capacity to change. It's no secret change is only accelerating the world. And we see it everywhere. From the pandemic fallout a couple of years ago to the AI conversation that seems to be prevalent just about anywhere and everywhere. The political, the economic, the global instability. It really is everywhere. And a lot of those things we have no control over. There are things that are going to happen in the world that are just going to happen with little or potentially no influence from us. And so the question to me is, how can we grow and change and adjust ourselves and our teams to be able to keep up with that change? What exactly does that look like? And the Deeper question which I think leads us into our whole conversation today is it's unknown, it's uncomfortable. And instead of avoiding that discomfort or denying it or pretending it's not there, we start to face some of those really hard realities for ourselves as individuals and for organizations and use them as pathways to growth instead of just surviving until the next day.
Well, tell us a little bit about your experience with dealing with discomfort and some of the stories that led you to the topics that you talk about now in your speaking.
Yeah, well, sometimes people look at me and they're like, sterling, you're a thrill seeker. Like you love the unknown and the uncomfortable. And honestly, I, I did not come out of the womb that way. If anything, it was the opposite. You know, if it's comfortable, that sounds good to me. And you know, things went relatively well for me early on. You know, I grew up a fifth generation retailer in my family supermarket, which was fantastic. And it was hard work though. It was one of those families where if you're part of the family that owns the store, you've got to work harder than everybody else. And I didn't love that at the time, but looking back on it, I'm like, what a fantastic experience. And right out of college I got together with my dad and we started a retail software company. You can probably guess who our first customer was. Our family store, of course.
Right, right.
And we end up growing and selling and becoming part of this multi billion dollar startup. It was kind of like the Apple pay before Apple Pay. And let's transport ourselves back to 2004, 2005 when we were starting this thing up. There wasn't an iPhone, there wasn't Apple pay. People looked at this as like, wow, this is the future. And I totally bought into it. We raised hundreds of millions of dollars, multibillion dollar valuation as you said. And I thought it's just a matter of time until we're going to go public, cash in. And I'm clearly the next Steve Jobs. You know, I was super humble in those days, but the housing market collapse, what was that? 2008, 2009?
Yeah, yeah.
Our funding dried up and the infrastructure we had built, 700 people, offices all over the world. It was bigger than our revenue would support. And so when the housing market collapsed, we couldn't raise more money. All thing went bankrupt and I was thrown into the deep end of the unknown and the uncomfortable. And honestly, I bottomed out for a while. I, I was scared, I was kind of embarrassed because I felt like we'd raised all this money, and we failed. Like, how. How is that possible with that much money? And it wasn't until I started, like, really confronting some of those things and looking at, well, what went wrong with the organization from a culture perspective and how did I personally contribute to that, did it start me on this pathway of engaging with discomfort. I thought, okay, well, if how I was doing things previously didn't work, what if we go the other direction? And I started to do the things that scared me the most. So skydiving, shark diving, ultra endurance races. And funny enough, given what I do today, also, public speaking was very high on that list. Absolutely. It was debilitating for me. I think I was always shy, Susan.
Yeah.
But after that company collapsed, it was debilitating for me. And I found that the more that I was engaging with the unknown and the uncomfortable, the more that I put myself in situations that demanded growth, the more I was able to deal with them. And, you know, since I found all sorts of research and work with all sorts of people in different organizations, and I found that that's really the defining factor. The better we get at handling what's uncomfortable for us, the better we get at truly stepping into the unknown, the better we can lead ourselves and our organizations.
And it requires this, I think, over time. Noticing what's working, what's not, and then what scares you and going for it totally, but also taking some measured risk, I would imagine, as part of the process.
Yeah. And I think there's. There's a difference between real danger, not just physical danger, but professional danger, and discomfort. And oftentimes our internal compass around those things isn't properly calibrated. We build up something as so terrifying, and it could be something as simple as a conversation, a difficult conversation, or raising money for our startup, or having a conversation with our team, or launching a new product or starting a new business. And it was those things that. That really made the difference for people as they were able to step into it.
Yeah, we're hardwired to perceive danger and threat right from, you know, surviving in the savannah. And so. So our whole subconscious is geared to look for that, look for anything that looks like that. If it's a squiggly line, it could be a snake. Right. And. And so how do we work against this evolutionary process that's built into that amygdala part of our brain and make the proper assessment. Danger versus discomfort.
Yeah, originally, discomfort drove behavior. So if we were cold, we needed to find a shelter back in caveman days, or if we were hungry, we had to sort out, well, how are we going to forage or hunt for our food? But these days, at least for most of us, in this beautiful modernity we've created, we don't have to engage with discomfort. We no longer let it really guide our behavior. And we tend just automatically as human beings to steer away from it. And we will survive that way. But survival, I don't think, is any way to live. And it's certainly not a way to create breakthrough results. I think the first step is that we've got to start to see and acknowledge the things that we've been avoiding, where maybe we're half in or half out, where we've been putting things off for days and weeks and months and maybe even years. The things that are just easier to sweep under the rug and pretend are not there. It's really acknowledging those things that are there is the first step, and then coming up with some kind of game plan to actually address them, to do something about them. And I found this research out of University of Michigan, and they were studying our favorite topic here, discomfort. And they were looking at physical discomfort, like you've stubbed your toe, or emotional discomfort, like maybe there was a shift with your work or in your relationships. And they found that the brain and body process that discomfort almost identically. So much so you can take Tylenol and it will help you with emotional pain. Now, all the disclaimers about that, I'm not a doctor, that's not a biohack. I don't suggest you have like a bowl of Tylenol on your desk and pop a couple every time you get a little bit anxious. But what I do suggest is that if where we meet discomfort is the same anywhere, we can grow our capacity to deal with it everywhere. It's a muscle we can build. So oftentimes what I've seen with people, let's just take a difficult conversation for sake of an example here. Sometimes that conversation is too difficult to confront head on. Initially, we haven't built that discomfort muscle. So anywhere you meet discomfort is going to help you build the capacity for that. And it could be something as simple as getting out of bed when the alarm goes off, or going to the gym, or taking a dance class or running a marathon or running a 5k doing something uncomfortable anywhere, that's going to translate into this belief, or I think of it as like trust in self to be able to bridge some of those gaps so that maybe you're a little more prepared for that difficult conversation and you feel a little More confident about stepping into it.
Yeah, yeah. And so if you're going to do really embrace the discomfort of change, or let's say making it very practical, having a difficult conversation.
Yeah.
How do you like, what does that look like? And what's a leader truly doing that and what's an example of one that's not?
Yeah, well, I think leaders that don't embrace discomfort are typically avoiding it or denying it or just surviving. And that looks like getting up and going through the motions and not knowing the things that deep down you really know you probably should be doing, you need to address. But the leaders that are embracing discomfort, they're not merely putting themselves in uncomfortable situations. I think that's a little bit of a pitfall for many, like, oh, I'm going to put myself in these difficult situations and I'm going to run a marathon and take a cold bath and start my business and launch the new division, like all the things. But the leaders that really start to transcend that discomfort, come to terms with, maybe a better word is, have an acceptance of that discomfort and acceptance even of pain. And it's that acceptance of those things that makes the formerly uncomfortable comfortable, which to me is the definition of growth. When we're making what was formerly uncomfortable comfortable, that is growth. And it will manifest not only in the results that we have, but in all the people around us.
And so you've got, I think, something like a five step process to think about how leaders should embrace discomfort and move through it. Can you share what that is?
Of course, yeah. The first step we talked a little bit about is acknowledging it, like starting to notice, even in small ways, where you're avoiding discomfort. And it might be like the alarm thing we talked about getting out of bed when the alarm goes off. That's a big one for me. I don't know how it is for you, but I start avoiding discomfort first thing in the morning when I hit the snooze button two or three times, I'm like, I don't need it today. And then a little while later, maybe I'm feeling a little tired and I grab a cup of coffee because I don't want to feel the discomfort of feeling a little tired. Then I get to wherever I'm going and without even thinking about taking the stairs, I step into that elevator and I hit the button of where I'm going. And I think, if, if we're avoiding discomfort even in these small, trivial, seemingly insignificant ways, what are we doing with the big things that actually matter? And so when we start to notice it. It gives us a little bit different perspective to move through the world. Now once we notice it, then we have to do something about it. And with that I think commitment is a really important piece. When we commit it actually reframes our brain to look for new opportunities, new openings for action that are invisible to us from where we sit prior. So we've got to make that commitment in a really big meaningful way, meaningful to us. I think about it as the commitment has to be bigger, stronger than the discomfort. You're almost forced, self forced to have to deal with it.
Do you think that what's important in doing that is really have a vision of what could be on the other side of that discomfort? Because I imagine the possibility like to get so committed to making that change. What I've seen be required is to think about and imagine you're through this circumstance and what would be possible from this end. And usually that could be that driving commitment force, but maybe not all the time.
Love to hear, yeah, I, I think envisioning what's on the other side is very helpful but not necessary because oftentimes what's on the other side is, is far better than what we can even imagine sometimes, at least in the realistic sense through what we're looking at something. And in, in lieu of, or in addition to that vision, it's surrounding yourself with accountability that's going to support, support us to move through whatever that, that commitment is. And not like soft, low level commitment. I'm not saying like get with your accountability partner and they say oh no problem, you didn't do it, you'll do it next time. But really somebody that's going to dig in with you and it's easy, especially as high performing leaders to think, well I don't need that piece, right, we're high performing, we have results and it feels sometimes beneath us in some ways. But the research doesn't lie. When we're held personally accountable to something, we are 95% more likely to achieve it. 95%. By the way, as you bring this into your team, into your organization, we're nearly four times as likely to achieve those things. And importantly, it's not accountability out of making somebody look bad and wrong, but it's accountability in terms of true love and support of I want this for you and so how can I support you in achieving that? Does that make sense?
That makes sense. And I think the word accountability is used a lot in organizations right now. It's like the number one thing I hear leaders complain about like, I just, how do I have my team feel more accountable? Be accountable.
Yeah.
And how would you, how would you approach that?
Yeah, I, I hear the same thing. I mean, it's prevalent everywhere. I. And you know, it almost seems like something a lot of leaders complain about. Like, my team's not accountable.
Yes, yes.
And I, I'd offer this idea that accountability is not only up the ladder, but how you inspire it in terms of your team is by having accountability down the ladder as well. So sharing with your team some of the things that you're committed to and asking them to hold you accountable. And as you have this two way accountability, that's what makes it okay for the rest of the team to really start to take it on where they see, oh, it's not just some leader telling me to do these things and I've got to show up and do it.
You need to be accountable who is.
Built into the fabric of the culture. And that can be incredibly powerful.
Yeah. Yeah. Well, I love it's leading through modeling the behaviors that you want to see. But also as a leader, perhaps, you know, acknowledging, hey, I tend to shut down conversation too soon and dialogue and I want you to hold me accountable. Let's have a code word if you see me doing that. If you think we're shutting things down too soon, I want to hear about it. Right. And you have full permission to do that. Now, I think for a lot of leaders that would, that would feel like a very scary ask.
Yes. Yeah. And I feel like, you know, as a leader, we can't ask other people to do things that we're not ourselves willing to do. And as we can confront or embrace that discomfort, that's what starts to manifest it within our teams and our organizations and communities. Like when people can see, oh, this is how this person's showing up, they're open and even asking for accountability. To your point, that makes it okay for everybody. And that's where you get those big bumps in performance where it's like, yeah, people are going to fail sometimes. They're going to mess up. And that's okay because we're committed to growth, period. And we're willing to navigate some of those failures or missteps for the greater good.
Yeah, yeah. Because they're not going to be able to step into their discomfort if there's also a prerequisite that there's no failure. Right. Like, why would I want to do that? Right.
Exactly. And the fourth piece is, you know, we all run into problems. There's not enough budget there's not enough time that you're everywhere. Right. Like I just don't have the resources to do it. And usually we're looking at those problems through the lens of diminishment. So if I can't hit 100% of my goal, well, how about 90%? Right, about 80% or 70%. And depending on how difficult things are, that 70% starts to look pretty, pretty good. You know, like all of a sudden that's the benchmark we're striving for. Whereas mathematically we leave out the entire other side of the equation, which we are just as likely to be able to achieve again from a mathematics standpoint. So if not 100%, why not 110%, 150%, 200%? And by having that, that shift in mindset to say, well, if I can't hit my goal, what if we make it a bigger goal? It gives us a new way to look at problems that can help us navigate those things to not only hit 100%, but maybe even better than we originally expected.
Well, that's an interesting point. I'm wondering if you have an example of where you've seen a leader do that and how it worked out for them.
Yeah, many. But I think maybe my favorite example is actually Richard Branson back in the early 90s when he was running Virgin Atlantic, the airline company. Now back in the early 90s, it was a difficult economic time globally, and he wanted to retrofit all of his planes with the latest and greatest entertainment system. I think there was like a 10 million pound proposition. But given the economy, the banks wouldn't lend him money, his partners wouldn't lend him money. He couldn't even call in favors. And he did exactly what we're talking about here. He created a bigger problem and said, well, if I can't retrofit these planes, why don't I buy an entirely new fleet of planes, which is a 4 billion pound proposition right now most of us would look at that and say, well, if I can't retrofit all the planes, well, maybe we'll start with one and then we'll do two, and in the next decade we'll have them all. But he reframed it and he calls up the CEO of Boeing and Airbus and have the exact same conversation, which is, if I buy a new fleet of jets, which they were willing to finance, will you throw in the entertainment system for free? And they did. So they wound up with the latest, greatest, best equipped jets they ever had in the company's history. And it came from actually creating a bigger problem, giving him and his team a new lens to look at that problem through.
And I bet he's even creating a new opportunity for the, the people that are that at Boeing. Like, well, maybe we should offer this as an opportunity for people to do. And how could we do that? Like, does everyone have to buy a fleet of planes in order to make that happen? Or is another way to do it so by them thinking big, they actually are so pushing, mowing to think bigger.
Totally. Yeah. And that's my favorite thing about this work is it creates this ripple effect of growth where you look at those things in new ways. Not only is it the people around us and our teams that start to look at things new ways and navigate these problems in new ways, but it, but it's our partners as well. And so we share this growth in a ripple effect that we will never see the end the of.
And what about. Is there a fifth one? Did you hit that one?
The fifth piece we touched on briefly is the acceptance of that discomfort, or I call it in my book, surrender. The disclaimer here is not surrender in terms of give up. Like, this isn't your get out of jail free card and sit on the couch and eat.
Yeah, you've got no matter what in the Microsoft. Yeah.
What I mean is accepting things exactly as they are and exactly as they're not. And this is where we truly grow from discomfort. Because discomfort alone is not enough. When we open our mind to new ideas, new perspectives, and just as important, if not more important, we soften our heart to some of those uncomfortable feelings and let them pass through us. We start to transcend them. And through those five steps, we have growth regardless of the circumstances. In other words, no matter what.
Yeah. Yeah. And so what would you say would be a good way that a leader could begin to make some changes? Like right here, right now, tomorrow, what's one thing that we can do to accelerate the acceptance of the discomfort?
Number one is socializing. Share it. Open yourself up about it. And where we meet, discomfort is the same anywhere, and we grow our capacity for it everywhere. So I don't care if you're sharing with your teams about a new athletic thing that you're doing or conversations you're having in your personal life or things you're doing professionally, but as we can share those conversations from a place of trust and vulnerability and saying, yeah, I'm setting out to do this thing, I don't know if I can do it, but I am committed to it. Then that starts to make it okay for those people around us as well. One of the things we did with one of the largest dairy companies in the world is we put together an internal podcast because they've got people all over the place, distributed all over the world. Right. And they said, well, how can we socialize discomfort when we have people all over the place? And so we put this podcast together. It's not on the Internet. You can't go find it. It's just. Just for team members. And we brought in their leadership, their team members, people throughout the organization to come onto the podcast and just for 20 minutes or so share about something that they're working through from a really vulnerable way. And that had the same effect of people can socialize it. They can see, oh, my team members, my boss, the people around me are doing this. So it's okay for me to step into some of that discomfort myself.
Yeah, yeah. And I see the opportunity for a lot of leaders to also do this around. AI yes. Just having this discussion yesterday that, you know, you can see, gosh, that might, you know, as an attorney, that might impact what I'm able to do if chatbots can come up with the contract on its own. Right. When. When are my clients going to be able to. To use this methodology? And at the same time, okay, putting your head in the sand isn't going to do it, but you might find some really unique opportunities if you go through that acceptance and recognizing this is. This landscape is changing how we're going to do business.
Yeah.
Therefore, what is the new opportunity? And I just saw this happen with an attorney who puts together their prenuptial agreements and therefore they're. They're able to. Rather than they could do something that's more done online, but it's that people trust him. It's not just like, to some degree, can you trust ChatGPT? Sometimes you can, sometimes you can't. Like, but he's. He. Because he knows that work, but he could create something out of it that's more turnkey then he's. Then he's found some opportunities there for himself in a. In a more custom, custom way. So that, that's, that's an example of what I've seen where people are embracing and going with the changes that are going to happen. But how can they still provide value from their, from their expertise and knowledge.
Yeah. Resistance to change or the unknown or the uncomfortable things never works. All it does is it prolongs the pain. And oftentimes, I know, especially as high performers, we get into this like work harder, work smarter mindset and I'm all for that, but working harder means probably more hours. Smarter is doing the same things, but more efficiently. But when we can do what I think of as like the real work, the real work of making the uncomfortable comfortable, we address some of the things with AI. We look at new pathways forward, even if seemingly in the short term we, we might be taking ourselves out of the equation or invalidating some of the work that we did in the past. When we can summon the courage for some of those things and take those steps forward, we create these, these step changes in performance and breakthrough results that you cannot see otherwise. Wise.
Yeah. Does it ever get comfortable? Does your skydiving get comfortable?
No. No, but. But you grow your capacity for it. It's funny, I, I bungee jumping in, in New Zealand a couple of weeks ago and I posted a video of it and a friend of mine commented, sterling, how do you look so calm? And the truth of the matter is I was not. But I've been in enough uncomfortable situations that I, I've built the capacity for, for it where yeah, I can still feel the fear. I know it's there, but I built a relationship with that fear. Those uncomfortable feelings and thoughts that I have that give me a better capacity to move through some of those things wherever I meet them.
Absolutely. I just, it just highlights that phrase. You know, courage isn't the absence of fear, it's taking action in the face of fear.
Absolutely.
That's what I see you doing and that's what I see your messaging about. Where can people learn more about you and your work?
Well, it's all@sterlinghawkins.com I'm pretty searchable on social media as well and I'd love to hear from anybody that is working on this stuff or wants to dig into it more, even share some of the uncomfortable things that you're working through as an individual in your company or in your team. I'm always responsive there.
Well, great. Thank you so much for being on the show today and definitely, I think a message that is quite timely.
Susan, it's an honor and a pleasure. Thank you. I look forward to picking up the conversation again soon.
Yes. And if you like this episode, you're not going to want to miss my interview with Daniel McCollum, a CEO who shares how self awareness, vulnerability and intentional growth drive high performing teams and resilient cultures. Let's lead the way. Hope you enjoyed today's episode and I'd like to point you to the next important step. Hit the subscribe button to get notified when we release new content. I'll see you on the next episode of the Enlightened Executive.
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