How Leaders Keep Success From Turning Into Complacency

You have a team that’s hitting its numbers. Winning contracts. Meeting goals. No major fires to put out.

And somehow, that’s the problem.

Somewhere between good enough and great, something quietly disappears: the hunger, the edge, the willingness to go after something harder than what the team already knows it can close.

This is not a motivational problem. It’s a drift problem.

And drift rarely announces itself. It shows up later—in next quarter’s missed opportunities, next year’s pipeline, or the client relationship you assumed was safe until it wasn’t.

In my conversation with Jake Thompson, founder of Compete Every Day, we explored why success can become one of the most dangerous moments for a high-performing team. Jake works with organizations that already know how to win. And that’s exactly where the risk begins. After repeated success, teams can start to relax the very standards that created it.

The question for leaders is not, “How do I motivate my team?”

The better question is: “Where have we started to drift?”

The Three Types of Drift Leaders Need to Watch

Jake named three patterns that show up often in successful organizations: victory drift, busy drift, and comfort drift.

Victory drift happens when success causes a team to take its foot off the gas. You win the big deal. You assume the client will renew because they always have. But while you’re coasting, the client is still deciding whether you are earning the relationship.

Busy drift is the illusion of productivity. You answer emails, sit in meetings, respond to requests, and end the day exhausted—but the truly strategic work never moved forward.

Comfort drift happens when the team becomes accustomed to a certain level of performance and stops stretching. The numbers may still look fine, but the standard has subtly dropped.

A team can be busy and still not be effective. A team can be successful and still be losing its edge.

Why Goals Alone Won’t Keep You Sharp

High performers need targets. Without a clear target, people drift.

But there’s a trap in becoming overly attached to the finish line. Leaders often tell themselves, “Once we hit this revenue number,” or “once we land this client,” everything will feel different.

Then the goal is achieved—and the satisfaction fades.

That does not mean goals are useless. It means goals are mile markers, not the source of fulfillment. They give direction and focus. But leaders and teams that sustain excellence are not simply obsessed with being the best. They are committed to being their best.

That distinction matters.

When you are trying to be “the best,” you are measuring yourself against someone else’s game. When you are trying to be your best, you are measuring yourself against your own standard.

And standards are what keep a team from drifting.

Play to Your Standard, Not the Scoreboard

Jake shared a powerful frame from sports: great teams play to their standard, not the scoreboard.

The scoreboard is a lagging indicator. If you’re ahead, you may relax. If you’re behind, you may give up. If it’s close, you may only then bring your full energy.

Standards ask something different:

How do we show up every day?

What behaviors do we hold ourselves accountable to?

What do we do consistently, whether we are winning or losing?

Your team’s culture is built through the standards you reinforce, not the slogans you repeat.

If you used to hold people accountable to a certain level of preparation, responsiveness, or client care—and now you let it slide because the results still look good—that is drift.

If your calendar is packed but your strategic priorities keep getting postponed—that is drift.

If your team is comparing itself to competitors, peers, or other departments instead of playing its own game—that is drift.

The Comparison Trap

One of the most honest parts of my conversation with Jake was his reflection on comparison.

It’s easy to measure your business, career, or leadership against someone else’s visible success. This is especially common in executive networks, entrepreneurial circles, and platforms like LinkedIn, where everyone appears to be winning.

But comparison often means you are measuring yourself against someone playing a completely different game.

Jake named three comparison traps:

The “why bother?” trap, where someone appears so far ahead that you talk yourself out of trying.

The “always behind” trap, where you feel you can never rest because you are chasing an invisible finish line.

The inferiority trap, where someone else’s success makes you feel smaller instead of more inspired.

Leaders are not immune to this. When leaders operate from insecurity, teams feel it. Trust erodes. Collaboration turns into internal competition. People start protecting their image instead of pursuing the mission.

The best teams compete externally, collaborate internally, and measure themselves honestly.

A Simple Practice to Interrupt Drift

One of the most actionable tools Jake shared is a weekly Start, Stop, Continue review.

At the end of each week, ask yourself:

What is one thing I did not do this week that would make me more effective next week?

What is one thing I did this week that I should stop doing?

What is one thing I did well that I should continue?

The value is not in doing it once. The value is in creating a rhythm of reflection. Over time, you start to see patterns. You notice what keeps appearing on your “stop” list. You see where your stated priorities and actual behaviors are misaligned.

This is leadership self-awareness in practice: reflection followed by a different choice.

You can also use this practice with your team. Instead of only reviewing outcomes, review the habits that created—or undermined—the outcomes.

Where did we play to our standard?

Where did we coast?

Where did activity replace progress?

What will we do differently next week?

Start Tomorrow Tonight

Another practical shift: decide tomorrow’s top three priorities before the day begins.

At the end of the workday, write down the three most important outcomes for tomorrow. Put them somewhere visible before you open email, Slack, or your phone.

When you start your day in response mode, your agenda is shaped by everyone else’s urgency. You may feel productive, but you are not necessarily leading.

Your attention is one of your greatest leadership assets. Where it goes determines what grows.

The Bigger Game

The most fulfilled leaders I work with are not only chasing personal achievement. They are connected to a bigger game.

They are asking:

What am I building beyond myself?

Who becomes better because of my leadership?

What kind of culture am I creating through my daily choices?

That bigger mission creates a more sustainable source of motivation. It also helps leaders move beyond ego-driven comparison and into contribution-driven performance.

Because your greatest strength can also be your biggest blind spot. The drive that helped you win can become the pressure that disconnects you from your team. The ambition that built the business can become the comparison trap that keeps you from enjoying it.

Transformational leadership starts with self-awareness.

So this week, look for drift before it becomes costly.

Where has success made you comfortable?

Where has busyness replaced progress?

Where are you measuring yourself against someone else’s game?

Then choose one standard to recommit to—not someday, not next quarter, but this week.

That is how high-performing teams stay hungry.

That is how leaders unlock their potential.

Episode Transcript

Susan Drumm: You have a team that’s hitting their numbers, winning contracts, no fires to put out, and somehow that’s the problem. Because somewhere between good enough and great, something quietly disappeared. The hunger, the edge, the willingness to go after something harder than what they know they can close.

This isn’t a motivational problem, it’s a drift problem. And drift doesn’t announce itself, it shows up in next year’s pipeline when it’s too late to do anything about it. Today’s conversation is about how to spot it before it costs you, and what the best leaders do to pull a high-performing team back from comfortable into hungry.

I’m Susan Drumm, and this is The Enlightened Executive, where your personal evolution sparks your leadership revolution. Each week we spotlight cutting-edge strategies to help executives and entrepreneurs grow in leadership and in life.

My guest today is Jake Thompson, founder of Compete Every Day. He’s a speaker and a four-time author with 500 programs delivered for organizations like Deloitte, Pfizer, and Titleist Golf. Jake started his brand in 2011 by first selling t-shirts out of the trunk of his car, which are now worn by leaders in over 62 countries.

Jake’s work has been featured in Forbes and Inc. Magazine, and his Compete Every Day podcast has been downloaded over 2 million times. Jake, welcome to the show.

Jake Thompson: Excited to hang out, Susan. Thanks for having me today.

Susan Drumm: Yeah, so tell us a bit about your work and who it’s for.

Jake Thompson: Yeah, so I am the founder at a company called Compete Every Day. We work with leaders a lot in sales teams and sales-adjacent organizations, and then trade organizations, on how we battle drift. However drift shows up—a lot of our trade, construction, and manufacturing clients tend to have more challenges on the leadership side, so we typically refer to that as busy drift or comfort drift. And on the sales side, it’s victory drift.

We typically don’t work with newer organizations, but with organizations that have had success. And we know that the most dangerous thing for a lot of teams and leaders is success, because we tend to take our foot off the gas, we tend to relax on our standards, and all of the things that made us successful in the first place, we kind of feel like we’re past that.

And then we get to a point where we look up and think, “Crap, what happened? What happened to our organization? We were so far ahead,” because we got so comfortable that we eventually drifted off course. And so, we do a lot of work around helping those teams and organizations from a keynote standpoint as well as from a coaching and training standpoint.

Susan Drumm: Got it. So, what is driving that phenomenon that happens? Because it doesn’t happen to every leader. I know I work with some leaders who always keep raising the bar, and they’re so impressive, and yet others don’t. So, what is the distinction?

Jake Thompson: There’s a few things, right? Biologically, we are hardwired so that if we don’t have a target, we’re naturally going to drift. And as you talk about high performers, what I love about it—and it sounds like the people you work with, and a lot of the clients I’ve had to work with—is there’s not really a finish line that they’re pursuing.

Simon Sinek famously talked about playing the infinite game or the finite game. The finite game is one we typically get caught in from a business standpoint: if we can just get this funding, if we can just reach this sales number, if we can just get this distribution, we tend to think that’s going to be a tipping point that changes everything. So we put, metaphorically, all of our eggs in that basket.

And then we reach it, and we’re not very fulfilled. We find out that that wasn’t more than just a mile marker along the way. Naturally, the way our brains work, a lot of us are looking for a point where we feel like we’ve made it—we feel like our company’s made it, we’ve gotten there. And there’s no real point.

What we find is, in the people you work with, the ones that are constantly growing are really obsessed with being their best over the best. And there’s a small distinction in that. We’re raised and taught the idea of being the best—we want the biggest business, we want to dominate our industry, we want all these things—but then we reach it and we reset back to zero.

Or we never get there, we compare ourselves, and we consider ourselves a failure for not having gotten to some point we think we should. The idea of being your best is backed by all the research: when you’re consumed with constant growth and improvement instead of a finish line, you’re just asking how do I get a little bit better today than I did yesterday, how do I help my team. We experience far more resilience and grit, and we find more fulfillment in our work, because it’s not hoping that a magic finish line somehow changes everything for us.

This dopamine high is going to get there, but we actually fall in love with the chase, the growth, and the curiosity of what we can learn. What happens to a lot of leaders is we just get caught up in benchmarks and finish lines and looking at someone else’s game, more than anything else, because of what we see on social media and in our networking organizations. The ones who continue to keep showing up, who don’t get caught off course, just keep setting markers: okay, how do we improve this? How do I get a little bit better?

And they’ve got those systems, targets, and standards. That’s what we would essentially say. If you think about it in sports, legendary football coach Nick Saban always said that you play to your standard, not the scoreboard.

The scoreboard is the lagging indicator. If you’re up a lot, typically people take their foot off the gas. If they’re down a lot, they think, we can’t win, what’s the point? They only play well when it’s close.

But when you play to your standard, you ask, what are the standards and expectations I’m going to hold myself to every day as a leader? How am I going to carry myself? How am I going to show up? How am I going to pour into my team? Then you find that that person is consistently growing in the long term.

Susan Drumm: So that focus on the journey versus the end goal—there’s a paradox there, right? We want to have goals, because, as you said, if you don’t have those targets or goals, you start to drift. And at the same time, if you’re solely focused on the goal and not the journey, you won’t actually have the sense of fulfillment you think you’re going to have when you hit that goal.

Jake Thompson: Yeah, the researchers call it the hedonic treadmill. All of the research on happiness and fulfillment shows that no matter how high the achievement, you reset. Sometimes it’s a couple of days—you talk to Super Bowl champions, they’ve won the biggest game of their entire lives, and within 48 hours the high is gone. It’s out the window.

On the other side, it can take up to six months, but we eventually always reset. The difference isn’t between people who have goals and people who don’t. We consider goals more like North Stars—they give you a direction, they’re the things we’re aiming for, but we’re not expecting them to fulfill us.

We’re expecting them to be, “Oh, that’s great, what else am I capable of?” I look at them more as mile markers, like you’re running a marathon. Goals are mile markers moving me in the right direction toward an ultimate goal—a career goal, a thing I want to have, places I want to go—but I’m not expecting them to be more than that. I’m just grateful to have gotten there, versus expecting them to fulfill me.

Susan Drumm: Interesting. So, tell us a little bit about how you came to this. Like this work and why this topic?

Jake Thompson: Yeah, so it’s really interesting—my journey is very different from a lot of people. I started my company selling t-shirts out of the trunk of my car 15 years ago, last month, honestly. I was a marketing consultant living in Dallas. I thought I wanted to be Jerry Maguire, a sports agent—spent a few years in that industry, realized that’s not what I wanted to do.

It was 2008, couldn’t get a job. I had an MBA, I had non-traditional work experience in the sports industry. So I built a consulting practice through word of mouth and referrals. I got to a point where it was going really well, but I was incredibly unfulfilled.

I’ve always been a junkie for learning—my mom is a teacher, so I credit, or blame, her for that. I’m always reading: psychology, leadership, human behavior, all the things I wish I’d known when I was young. So in 2011 I started Compete Every Day with the simple message of what happens when we stop comparing ourselves constantly to everyone else and start competing with ourselves.

At the time it was just t-shirts. Then, over the next five to six years, as the brand grew into customers in 62 countries, people would ask me to come speak. They’d say, “Talk to us about how we actually compete—it sounds really cool, it’s a cool philosophy, but how do we get our people to show up and compete every day?”

So, working with clients, doing continued research, testing things with teams, we started to build frameworks that actually worked with organizations. Now, here’s where it gets interesting. Over the last year, the speaking space has become incredibly crowded, as we’ve kind of laughed about off air—there’s a ton of people who speak in sales and organizations around leadership and high performance.

So I wanted to dive into the data of what gets us booked and rebooked so often, but more importantly, what our clients say about us that’s different from anybody we might go up against for gigs. You’re trying to find your competitive advantage. So we went through every one of our sales conversations that led to gigs and the ones that didn’t, to see why they found us. We went through testimonials post-event, and we went through post-event interviews.

The thing that kept coming back in all of the research was twofold. One, you helped our team bridge the gap between knowing and doing—we knew we shouldn’t take our foot off the gas, but we still did, and you helped us figure out how to battle it. The second is, when our team was really comfortable, you gave us frameworks to keep everybody accountable and still moving.

What that signaled to us is: most of our work is with teams that already do really well. They already know how to win. But we’re all guilty of drifting at some point. And drift is where we started to put language—we’ve all heard the phrase, we all talk about it, it’s a slow decline into a place you don’t want to be. But when we started to name the different types, that’s really where the IP started to take a life of its own.

So victory drift is the idea that you win, you take your foot off the gas, and then suddenly you lose. We do it all the time—say we’ve had a client for the last three years, why wouldn’t they rebook with us? Well, they’re deciding, do I still want to do business with them, or have they taken me for granted?

Busy drift is one that’s dangerous for a lot of leaders, because it feels really good to get into our inbox first thing in the day, or to scroll LinkedIn, and we check boxes and delete emails and do all this stuff that feels productive. But then we look at our goals, we look at the priorities we need to be working on, and we did none of it. Busy drift is that day where you wake up, you hit the ground running, and by the end of it you’re exhausted but you didn’t get anything done that you needed to, because we were distracted.

And busy drift is that one that catches us, and what we—

Susan Drumm: —to pause on that, the idea that actions equal output, not all the time, right? I know so many leaders who are so exhausted, so busy, and I’m like, well, where’s the tracking of the outcomes, though? We’re tracking activities, not outcomes—instead of…

Jake Thompson: —emails did you answer? That’s a terrible activity to respond to, right?

So let me give your audience something really helpful right now. What we say is, the way you fight busy drift is with great review. If we think about it, the definition of insanity is doing the same thing over and over again and expecting a different result—yet how often do our workweeks mirror that definition?

The way we turn effort into progress, instead of a broken record, is with a healthy review system. So for us, we teach our teams to do an exercise every Friday called start, stop, continue. It’s very basic—I learned it years ago in a mental performance program—but you just ask yourself three questions.

What’s one thing I did not do this week that, if I did next week, would make me more productive, a better leader, more present? What’s one thing I did this week that, if I’m honest, I probably should stop doing to be more productive next week? And what’s one thing I’m doing well that I should continue doing? One to start, one to stop, one to continue.

What I love about this is it’s three little bitty targets. It’s super simple—you do it once, no big deal. You do it every week, and now every week you’re competing against the previous week. Our brand is Compete Every Day—it’s always about competing with yourself, so how am I competing to get better?

But it also makes sure you’re checking whether you’re working on the right activities. And if you’re not, well, next week you need to start time-blocking an hour a day where you don’t have meetings, where you’re not on calls, where you’re working on key things—versus hoping you find the time, or just repeating week after week after week, never really making progress, and then wondering, “Where did my year go?”

Susan Drumm: Yeah, and you know what I love about that is you could really use AI now to enhance that process, and I’m sure some of your clients do—if you just start a thread with these three questions, answering them every week and going back to it, and then start to look at the themes and patterns. Because everything we talk about is around the patterns that follow you. It gives you the ability to zoom out and see exactly, “What do I notice over time? I keep doing the same thing,” where normally, when we’re on autopilot, we don’t notice that.

And I think asking these three questions and leveraging a tool to be able to see and show you your patterns can be really powerful.

Jake Thompson: Super powerful, and it also takes it up a level. One of the things we used to do, before AI got to the point it’s at now, is when friends in the industry would just need accountability, I’d say, “Listen, I can’t get on a call with you every week, but here’s what we can do. On Monday, you text me what are the three targets you need to get done this week. And on Friday, I want you to text me your score—three for three, one for three, whatever the case may be—and I’ll hold you accountable and follow up with you.”

But it’s very simple. You can now automate some of that with AI, right? Because you can have a task scheduled every week: “Hey, Monday morning, what are your three priorities for the week?” On Friday afternoon, it’s scheduled, “Hey, what’s our score for these?” And then you add your start, stop, continue.

Now you’re getting a snapshot week over week, and every month, if you’ve built it correctly—if you’ve built that custom GPT to be your thought challenger—it can say, “Hey, identify where the holes in my game are. Help me see: I put this in my stop every week, but I keep going back and doing it.”

Susan Drumm: Mhm.

Jake Thompson: “What could it be? Ask me questions that’ll help me uncover, or pull at the thread to figure out, what in my behaviors, my environment, my habits are leading me to continue failing at this.” And so, I think that’s where leaders can be really helpful, because the change we want to see is the result of little bitty choices. The decision to not start your day in your inbox is a small choice with massive repercussions for your productivity in the long run.

Susan Drumm: And so, where should you start your day?

Jake Thompson: So, I’m always big on priorities. I’m big on planning tomorrow tonight. One of the things I always recommend is—building this habit is difficult, because our first inclination when we wake up is to reach over, grab our phone, check notifications, check email, and get into a defensive, responsive mode all day. It’s really hard to go from playing defense to playing offense.

So it’s something as simple as taking a sticky note, and at the end of today, as you’re listening to this, just writing, “What are my three priorities for tomorrow?” You know them—they’re probably on your computer right now, on your desk, unfinished. So you put them right on your computer screen. We’ll literally take a sticky note and put it on the computer screen.

Or right now, I have this thing called a desk board buddy—it’s got a big whiteboard on the front that I can write on right here on my desk, so I see it. The first thing I do when I sit down is look and say, “What are my three priorities for today? How do I start working on number one?” Some days, number one for me is diving into my CRM and doing follow-up with certain clients—it’s outreach in that regard.

But I’m not getting into my inbox to say, “Ooh, let me delete these ten emails so I feel super productive in how I start my day,” when I really haven’t done anything that actually helps me. So I’ve found that process—planning tomorrow tonight, writing your three priorities for the next day, and putting it somewhere super visible before you get into your inbox—helps with that.

Susan Drumm: Well, I like the structures you put in place with the whiteboard, and how you keep using it and see it happen. What about the fact that priorities change during the day? Something comes in—I’d better check my email first thing, because it might actually set my priorities for the day based on what’s coming in. How do you think about that?

Jake Thompson: Yeah, so, everyone’s different, right? There’s no one-size-fits-all on anything. However, I would argue that maybe 1% of the emails we get actually set our direction for the day. Now, there are emergencies, and things happen, but part of that is also communicating with our teams: if it’s a crisis or emergency, you need to call or text, don’t send an email. Here’s my response time based on email versus everything else.

So there are instances, but what I’d say is it’s almost like getting on social media. Have you ever gone on social media to make a post, but then started scrolling, and looked up and it was 25 minutes later and you’d watched 15,000 reels, and thought, I really need to get off here—how did I spend this much time? You went to do one thing and got sucked in.

Versus what happens if I set an alarm for two minutes—I go on social media, I make a post, I start to scroll, and the alarm goes off in two minutes to jog my attention. You’re setting a boundary, an accountability, to make sure you don’t go down the rabbit hole. The same has to apply to your inbox. You need to set up structures to do it.

It’s one reason they recommend that if you work from home, you don’t have your phone in your office with you—you’re going to get notifications that will distract you, or just the fact that it’s sitting next to you still has this pull, like, oh, I need to check my phone, versus what’s the task at hand I should be working on. You’re looking for little ways to set yourself up for success, and it’s not big moves. That’s the thing—it’s little bitty adjustments where you think, ah, that’s so stupid, I didn’t put my phone in the other room. Try it for a week and see what happens.

It’s not telling you not to check your phone. But there are people I know who understand their own behavior with email, so they have auto-responders that say, “Hey, I check my email at 11:00 a.m. and 4:00 p.m. Central Standard Time—I’ll get back to you during those periods. If it’s an emergency and you need an immediate response, please text or call.” That’s how they approach it very intentionally, because our attention is one of the most important things we have as leaders. Our time, and where it goes, determines how productive and effective we are at leading our teams.

Susan Drumm: Yeah, I think the same is true of team meetings. There are so many team meetings where I don’t see time bound to topics, and I also don’t see what’s the question of essence—what are you actually here for, and do you keep coming back to that, or do you end up going off on tangents? I call them outcome-based agendas versus topic-driven agendas, but it’s the same idea: you might get sucked into a rabbit hole, and if you do, more likely than not, where has your productivity gone?

Jake Thompson: Very much—the joke is, how many meetings could just be an email? It’s true. There’s also a habit where the larger our teams get, the more we have meetings with people who don’t need to be there. There’s no relevance to them, to the outcome, but we feel like, well, we’ve got to have everybody in this meeting, versus, “Hey, here’s what I need from you, here’s our goal, here’s the outcome for the meeting,” versus, “Oh, we just have a standing Monday meeting and everybody brings whatever and kind of goes with the flow.”

One of our coaching clients was trying to do a really good job of making emotional, relational deposits with her team in their team meetings—what was good over the weekend, what’s going on—but she felt like the meetings were just dragging on. I said, I’m all for making relational deposits with your team, I think you have to know your people, get to their head through their heart. But what if we structure that on a Thursday, and then Monday morning meetings have a clear agenda: here’s the outcome, here’s what we’re going through, everybody knows what they’re responsible for, what they need help with, here’s our goal for the week?

It was so much more effective. About two weeks in, she said our meetings are like 25 minutes, everybody starts the week strong, we’re ready. It’s a whole different attitude versus walking in for a 60- or sometimes 90-minute Monday morning meeting, where you just feel like you have to do something to feel productive. So those little shifts, to your point, the outcome-based agendas, are so helpful in getting us moving in the right direction.

Susan Drumm: Yeah, so much. Well, every person doing meaningful work has had to confront something in themselves along the way. So I’m curious—what was the old pattern in how you were leading, how you were showing up, and what needed to shift?

Jake Thompson: Yeah, you know, the biggest one I always go back to is kind of an ongoing battle, which is why the crux of my latest book is around it—it’s just the unhealthy relationship with comparison, and living in this state of trying to placate my ego: oh, we’re doing better than them, oh, how does it look, oh, we’re not as good as that person. It was funny, because for one, it got me into trouble growing our apparel business, because I tried to make us look bigger than we actually were.

We took on financial capital and debt because I worried more about the appearance than the actual growth. I think we all fall into that trap in some regards. We join networking groups—we’re in EO or YPO—and we walk into a room, and it’s all about how we measure up with everyone else.

Oh my gosh, that group got funding, and I’m in a business where we don’t really need funding, but we compare ourselves anyway, even though they’re building a different business. It’s like the single mom who’s raising three kids, holding down a full-time job, who works out twice a week for her own mental health and sanity, going on Instagram and comparing herself to a 24-year-old with no kids, who works from home and works out seven days a week. You’re going to lose that battle, because you’re playing two very different games.

But we do it in so many senses, and I did it. I have to be very mindful to check myself on it. Also, the more I’ve been in business, similar to you, Susan, the more I realize how much of what we see online is not reality. The people who look like they’re thriving are, a lot of times, struggling. The person who suddenly got 400,000 followers on Instagram bought a bunch of them. There’s so much fakeness out there.

The more we get caught in the comparison trap—we call it, there’s three of them. The first is the why bother. Psychologists call this the what-the-hell effect, which is one of my favorite things about it: when you see somebody who’s so far ahead of you, or appears to be, you think, why bother, what’s the point, I can never do what they do.

The second trap in comparison is the always behind. When I finished grad school and started Compete Every Day, I was doing the consulting, selling t-shirts out of the trunk of my car, hustling, driving across the country in my truck. I’ve got friends who are doctors and lawyers—they had real jobs, they had mortgages, they were married. And if you grew up in the South and you’re single in your 30s, everybody thinks something’s wrong with you.

So you feel like you’re always behind. For me, I could never take a day off—I’d be on vacation in a beautiful setting, feet in the sand, with my work laptop, because I felt like I couldn’t take a day off. I’m always behind, I’ve got to catch up to some mysterious finish line I think is out there.

And then the last is the inferiority trap. This is the one where, especially with social media, we just feel like we’re less than because we don’t have what someone else has, or appears to have. We tend to talk ourselves out of starting altogether.

For me, it’s learning how that shows up, especially in the workplace—we become insecure leaders. And when we’re insecure leaders, our teams don’t feel connected to us, our teams don’t trust us. Our teams then start competing against each other, because they’re playing the ego game like we are, instead of being a collaborative culture, we become a competitive one.

I’m all for competition, but the best teams collaborate together, compete with themselves, and then are more competitive externally. But it doesn’t happen if a leader is so consumed by their ego and insecurities.

Susan Drumm: Well, going back to when you got—I mean, this is fascinating. I love the different types of comparison, and absolutely, as I’m listening to you, I’m seeing it in a couple of leaders I’m coaching right now, how that’s showing up. But for you, was there a specific moment or experience that really cracked that pattern open for you, that allowed you to see it?

Jake Thompson: I mean, it’s funny, because I feel like a lot of our struggles are constant—you’re constantly battling, you just build better frameworks and barriers. I always think back to when I started speaking. When I started shifting our business in early 2017, I was working with a coach who’d worked with some of the biggest names in the industry, and I was talking to him one day because I felt like I could be pretty good at this, but I was comparing myself to these household names.

I was like, I’ve never been homeless, never had a drug addiction, didn’t go to jail, didn’t lose a limb—I don’t have any of these crazy stories. I’m a pretty regular guy who just started a t-shirt company and likes to encourage people.

Susan Drumm: Yeah.

Jake Thompson: He said to me one day, “I have very high expectations for you.” But he said, all of these things you’re talking about that you don’t have—how many people in your audience do you think have them? I said, I don’t know, a few. He said, maybe. Maybe. Most people are trying to figure out how to lead a team, how to not get a divorce, how to raise healthy kids, how to deal with stress. They’re dealing with the stuff you’ve dealt with.

So worry less about what you don’t have and how you compare to these other people with these crazy stories, because the audience can’t directly relate to those stories either. They can’t imagine what it’s like to be a pro athlete. They can’t imagine what it’s like dealing with credit card debt because you tried to grow a business the wrong way, and now you’re embarrassed and struggling, having to let people go and have tough conversations—but they can relate to that. So let them relate to that.

I remember thinking, I need to play my own game. That really started the journey, as we were growing this space, of asking: what’s the game I want to play? What are the rules? And then how do I just play it to the best of my ability, instead of worrying about what everybody else is doing.

Susan Drumm: Oh, I love that. So now, what would you say the edge of that pattern is? What are you still actively working on in yourself today?

Jake Thompson: You know, I think it’s just catching myself, catching the internal dialogue. It’s hard not to be engaged—as a speaker, a lot of my friends are speakers. You go on LinkedIn, we post about our business, we post about where we spoke, and it’s super easy to see somebody post and think, oh my god, I’m not speaking today, they’re speaking today.

It’s a very visible business, yeah. And I laugh, because I was telling a friend this the other day—I said, June is always my slowest month. One year out of the last seven have I had multiple gigs; typically June is the month I vacation. We know it, we plan for it. This year we didn’t plan a trip because I’m doing a big mountain challenge this weekend, but I know that’s just how it is—January, February, I’m always booked.

And I laughed, like, man, I see these people always booked, what’s wrong with me? I have to catch myself in that dialogue. I’ve got a mutual friend who’s just blown up this year and done a lot of gigs, and I see her post everywhere, and I think, man, she’s just crushing it. And a friend said, well, she should be at X fee. And I thought, oh, we’re playing different games—I’m comparing myself in a different game.

So for me it’s just constantly catching it, reminding myself. Every day I write—got to give a shout-out to Charlie Smith, who’s a mental performance coach—my identity statement. I got into that habit earlier this year, just reminding myself that my measuring stick is in the mirror, not my feed. Here’s who I am, here’s what I’m trying to do.

It’s really helpful for me, because when I do get off track, I can catch myself with my identity statement. I’ve got friends and coaches who remind me too. I’ve realized how much of a waste of energy and effort it is, because we don’t see the real picture, the full picture.

Some leaders listening to this want to build a great business, but they also never want to miss one of their kid’s soccer games. Other people listening don’t really care about that—they want to build a game-changing company. That’s okay, both ways. But the problem is, when we try to play someone else’s game, or compare ourselves to someone playing a different game, we start to limit ourselves.

So for me, it’s having the frameworks mentally to catch myself and ask: why am I comparing myself? Is this really reality? Is my ego being threatened, or am I inspired by it, and what can I learn from it? Once you reflect back and catch that, it’s like, okay, move on—what’s the game, what am I doing today, what am I doing to grow toward my goal, versus stewing on this?

Susan Drumm: Yeah. I love the phrase “compare to despair”—the more you look externally and compare yourself, the more you’re probably going to get off track from what you really need to do. And those things can get in your way and stop you from moving forward, like you mentioned before—the why bother, or the I’m always behind, so I have to be in frenetic activity.

I’m working with a leader right now who’s doing that—always in frenetic activity, because he always feels behind. But he’s not actually doing the right strategic work that he needs to do.

Jake Thompson: Yeah.

Susan Drumm: It’s just being in action and hopefully I’ll catch up one day, right? But there’ll never be a day he catches up. That’s the thing. That’s the—

Jake Thompson: —finish line. There is no magic. Everybody listening: you will die with your to-do list. I hate to tell you, you will die with a to-do list undone.

Susan Drumm: So, what’s a frame or a tool or something that you want leaders to take away or something they could do tomorrow that would help them get out of the drift trap or the comparison trap?

Jake Thompson: Yeah. So, on the drift side, I’d say this: if you’re having success and you feel yourself starting to pull back—I’m all for taking breaks, but think about an athlete. An athlete has an off-season, but there’s a start of the off-season and an end of the off-season—there’s a deadline. Drift happens when we don’t set a deadline.

“Hey, we’re going to celebrate this week that we just had our best quarter ever, but next week we’re back at it.” So if you notice yourself justifying taking your foot off the gas, or relaxing on standards—“I used to hold them accountable on this one activity, but you know, they’re doing really well, so I don’t need to as much anymore”—you’re really starting to be susceptible to drift, especially victory drift.

Now, busy drift we talked about—just implement a simple start, stop, continue on a Friday, so you start reflecting on your activities. That’s a huge piece of the puzzle. With comparison, there are a few things you want to do. The first step doesn’t even have to do with comparison—it has to do with the person you see in the mirror.

That’s getting ultra clear on: what game am I actually playing? You want to understand what’s the game you want to play, because here’s where that becomes valuable—when you’re confident in what you’re trying to do, everything else becomes data to learn from, instead of a measuring stick of where you fall short.

I say this very specifically. Glen Powell, who’s a famous actor, was in Top Gun 2, The Running Man—he’s been in a lot of stuff. He went out for the main role in the latest Top Gun: Maverick. He wanted to be the lead, and he didn’t get it—they gave it to Miles Teller. Tom Cruise and Bruckheimer, the director, still wanted Glen in the movie, but Glen was like, “I went out for the main role, I wanted the main part, I didn’t get it, so no.”

And they said, “Come sit and meet with us.” Glen goes and sits with them. They sit him down, and Tom Cruise—a superstar whose movies have done $12 billion around the world—says, “Glen, what do you want for your career?” Glen says, “You. I want to be you.” Tom Cruise smiled and said, “How do you think I did it?” Glen said, “You took leading roles in great movies, that’s what you did.”

And Cruise laughed and said, “No. I joined great movies and made my role great, regardless of what it was. I controlled what I could and did the best in that moment.” Glen said it changed his perspective on how he approached work, because it no longer was, “I have to have this perfect opportunity if I want to be at the level Tom Cruise is at.” His input, his behavior—the thing that’s 100% in his control—was to make every role great. And I need to do the same.

The beauty of that is, Glen Powell understood the game he wanted to play was to be a movie star, but he was comparing himself to the wrong point—he had the wrong data. Once he got clear on “what do I need to do, I need to be great at this,” that’s all he started focusing on.

So when we think about our leaders—if you know the game you want to play, “Hey, I want to build a thriving culture where everybody in my organization is personally and professionally fulfilled, and I get home to see my kids play soccer every week,” then you put that in your calendar, and you block off every one of those soccer practices. And then you block off time every week to have face time with the people on your team, to make emotional deposits into them, to get to know them. That’s how you play the game. And then it doesn’t—

Susan Drumm: —matter, because it’s your scorecard, too.

Jake Thompson: And that’s your scorecard. Then you’re not worried about what the CEO down the street, or your friend in EO or YPO, or anyone else is doing, because they’re playing a different game. Now, if they’re playing your same game, you can ask them, “Hey, how do you do this? How do you manage to retain your top talent? I’m looking for ways to better build connection.” You start asking questions, versus, “Oh my god, Susan, you’re so much better at that than me, I can never be what you do, so I’m just not even going to try.”

That’s what I tell everybody—most of us have never sat down and asked ourselves, what’s the game I actually want to play, what’s the future I want to create? We just see what other people are doing, and I think we chase their game partly because a lot of us have crossed finish lines and reached goals and it didn’t fulfill us. We see someone else, and they seem happy, they look happy on LinkedIn—maybe if I reach their goal, it’ll fulfill me in a way mine didn’t. And all we’re doing is playing on that hedonic treadmill.

Susan Drumm: Yeah. And also, there can be a bigger game, too—what is it that you want to create for others in the world, not just yourself? That’s what I’ve also seen: those who have a vision that’s a little more expansive, that goes beyond themselves, are more fulfilled in the end, or along the way in the journey, because it’s not just about, “What do I get out of it?”

Jake Thompson: Absolutely. Well, you’ve got a more sustainable source of motivation—that intrinsic motivation for something bigger than yourself is always so powerful. I always reference back to a book I read when I was building my consulting practice, overweight, just hated life—a book by Donald Miller called A Million Miles in a Thousand Years.

It was a memoir, but Donald talked about making a movie after his first book, and he said, “What I learned is great movies and great stories mirror great lives.” He said, “You think about Star Wars, Harry Potter, whatever your movie choice or book choice—it has a main character who has a mission or purpose bigger than themselves. They’re willing to engage discomfort and conflict, and they invite others to join alongside them.” He said, “Those are the components that make for a great story, and they make for a great life.”

That book rocked my world, but it applies to our leaders. If you want to be truly impactful, you have a mission and purpose bigger than just filling your own pockets. You’re willing to do things other people won’t do—it’s uncomfortable to have one-on-one conversations, it’s uncomfortable to put your team above your ego. And you invite other people to join you. When you do that, magic happens.

Susan Drumm: I love it. Well, where can people find out more about you and your work?

Jake Thompson: Yeah, best place is our website jakethompson.com. And if you’re on social media, I’m active on LinkedIn and would love to connect with you there.

Susan Drumm: Well, thank you so much. If you liked this episode, you’re not going to want to miss my interview with Jason Miller, who says that in the age of AI, leaders need creativity, judgment, and reinvention. Let’s all 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 and the bell to get notified when we release new content. I’ll see you on the next episode of The Enlightened Executive.