When Everyone Has AI, What Makes a Leader Stand Out?

When Everyone Has AI, What Makes a Leader Stand Out?

For years, leaders built their careers by becoming the expert. 

They earned trust because they had the answers. They knew the business, understood the market, and brought years of experience to every decision. 

Today, that advantage is changing. 

Artificial intelligence can generate ideas, summarize research, and analyze information in seconds. It has made expertise more accessible than ever before. 

So where does that leave leaders? 

That question sat at the heart of my conversation with Jay Baer. One idea kept resurfacing throughout our discussion. AI is not replacing leadership. It is revealing what leadership has always been about. 

When information becomes available to everyone, the leaders who create the greatest value are the ones who recognize patterns others overlook. They make thoughtful decisions when the path forward is unclear. They understand people as deeply as they understand the business. 

Technology is changing how we work. It is also reminding us what leadership has always required. 

Expertise is no longer enough 

Expertise still matters. Experience still matters. 

But neither is enough on its own. 

The leaders who will thrive in the years ahead will not be defined by how much they know. They will be defined by how well they think. 

AI can provide information. 

Leadership provides interpretation. 

It is knowing which questions to ask before searching for answers. 

It is understanding the context behind the data. 

It is balancing short-term results with long-term consequences. 

Most importantly, it is recognizing that every business decision is ultimately a human decision. 

That is something no technology can replace. 

The pattern beneath the problem 

One of the ideas Jay shared that resonated with me most was the importance of pattern recognition. 

The best leaders rarely solve problems by focusing on one isolated event. They step back and ask a different question. 

What keeps happening? 

In executive coaching, I see this every day. 

One executive came into coaching convinced she had a communication problem. As we explored what was happening, a different pattern emerged. She was not struggling to communicate. She was avoiding the conversations that mattered most. 

Another leader believed delegation was the issue. In reality, he had built his success on being the person with all the answers. Letting go felt like letting go of his value. 

The challenge leaders bring into coaching is rarely the challenge that needs to be solved. 

Your greatest strength can also be your biggest blind spot. 

Transformational leadership starts with self-awareness because self-awareness helps us recognize the patterns driving our behavior before those patterns begin driving our results. 

Why our brains miss what matters 

Our brains are designed to solve problems quickly. 

That serves us well in moments of urgency, but it can also lead us to focus on the most visible issue instead of the underlying pattern. We treat recurring symptoms as separate events rather than asking what connects them. 

Exceptional leaders slow that process down. 

They create space to reflect before reacting. 

They become curious instead of certain. 

That pause is often where the best decisions are made. 

Pattern recognition is not about having better instincts. It is about developing the discipline to look beneath the surface before deciding what action to take. 

Better patterns come from better perspectives 

Pattern recognition is not something we develop in isolation. 

Every leader has blind spots shaped by experience, assumptions, and success. The more successful we become, the easier it is to believe our perspective is the complete picture. 

It rarely is. 

This is why cognitive diversity is such a powerful leadership advantage. 

When people with different experiences and ways of thinking examine the same challenge, they notice different patterns. They ask different questions. They uncover risks and opportunities that a more uniform team might miss. 

The strongest leadership teams are not the ones who think alike. 

They are the ones who challenge each other’s thinking in ways that lead to better decisions. 

Curiosity keeps leaders relevant 

One of my favorite moments in the conversation had very little to do with technology. 

Jay talked about walking away from a successful chapter of his career to pursue work that aligned more closely with what energized him. 

That decision takes courage. 

Many leaders stay on a familiar path because success creates momentum. Walking away from something that works can feel uncomfortable, even when you know you have outgrown it. 

The most effective leaders continue asking themselves difficult questions. 

What am I learning? 

What assumptions am I still holding onto? 

What no longer serves me or my team? 

Curiosity is more than a personality trait. 

It is a leadership discipline. 

The leaders who remain curious are the ones who continue growing while others become anchored to yesterday’s success. 

What leaders can do this week 

If AI is becoming part of your daily work, focus less on what technology can do and more on what only you can do. 

Start here. 

Notice recurring patterns instead of reacting to individual problems. Ask yourself what keeps showing up. 

Question one assumption that has guided your leadership for years. It may still be true. It may also be limiting your perspective. 

Invite someone with a different point of view into your next important decision. Fresh perspectives often reveal patterns you cannot see on your own. 

Protect time for reflection. AI can generate options in seconds. Good judgment still requires thoughtful consideration. 

Continue investing in your self-awareness. The better you understand your own leadership patterns, the better equipped you are to lead others through change. 

The leadership advantage that will always matter 

AI will continue to evolve. 

The question is not whether technology will change leadership. It already has. 

The real question is whether we will continue developing the capabilities technology can never replace. 

Self-awareness. 

Judgment. 

Curiosity. 

The ability to recognize patterns before they become problems. 

These qualities have always defined exceptional leaders. AI simply makes them more valuable than ever. 

Unlocking your potential has never been about knowing everything. 

It has always been about seeing yourself clearly, understanding the people around you, and making decisions that create lasting impact. 

Because transformational leadership starts with self-awareness. And in a world where everyone has access to the same information, self-awareness may become your greatest competitive advantage. 

Episode Transcript

Susan Drumm: Every competitor in your industry is making the same move right now: more automation, more AI, faster, cheaper at scale. But that’s not a growth strategy anymore — that’s just the price of staying in the game. The ones pulling ahead aren’t doing it with better technology; they’re breaking a pattern no one else in their industry has noticed yet. If your growth has flattened and you can’t explain why, you’re about to find out.

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

Today we’re talking with Jay Baer. Jay is a business growth and customer experience author, researcher, and advisor. He’s a seventh-generation entrepreneur who’s written seven best-selling business books and created six multi-million-dollar companies.

He’s consulted for more than 700 brands, including Nike, Oracle, IBM, and the United Nations. He’s an inductee into the Professional Speakers Hall of Fame and was voted a global guru for internet marketing and customer experience for three years in a row. And in his spare time, he’s the second most popular tequila influencer and educator on the planet. Jay, welcome to the show.

Jay Baer: I’m delighted to be here. I want to try to not only enlighten, but be enlightened. So let’s do this thing.

Susan Drumm: Awesome, awesome. Well, let’s get into your work and the why. So tell me a little bit about what you’ve been doing — you know, we talked about how you’ve changed. So what have you been doing, what was the belief behind that, and what are you doing now?

Jay Baer: I’ve spent 30 years as a business strategist, advisor, coach, and professional speaker. I’ve written seven best-selling business books, so I’ve spent most of my career trying to help businesses run a better business. And recently I set that aside and now I’m focused exclusively on Tequila Report, tequilareport.com, which is our industry-leading tequila newsletter for tequila consumers in the United States.

So the big shift for me is going from trying to help businesses get better to trying to help consumers make better tequila buying decisions. And also, really leaning into writing again as a core content feature. I’ve done a lot of podcasts, done a lot of videos — it’s nice to be working on something that is primarily written again.

But it is interesting. People can’t believe I actually — you know, being in the Professional Speaking Hall of Fame — just drop the mic, literally. But I’ve got to tell you, when you have the opportunity to turn your passion into a business, it’s an extraordinary opportunity to build a life around that.

Susan Drumm: Yeah, that’s amazing. Well, that’s a pretty major pivot that you’re making after doing 30 years of speaking. So I definitely want to get into that — what had you make that pivot, and what mindset shift and pattern did you have to let go of in order to make that happen?

Jay Baer: Yeah.

Susan Drumm: Let’s back up a little bit, because let’s talk a little bit about what you’ve been speaking on up until this point, because I think your message is particularly relevant right now.

Jay Baer: That’s the hard part about leaving speaking behind, because it wasn’t as if I didn’t have any speeches to give. I’ve turned down a lot of speeches for the second half of this year, and that is an expensive email to send, I can tell you that. The first three of those, you’re like, “Damn it, maybe I can just take that back.” But you’ve got to stick to it.

But here’s the thing, and this is what I’ve been talking about for the last six to twelve months. It’s interesting, because I started in technology and marketing when domain names were still free — true story. I started that long ago, and my partners and I, in my very first internet company, registered some domain names. And one of those was Budweiser.com.

And we got a letter in the mail, because email wasn’t even used yet. And the letter said, “We’re Anheuser-Busch, famously the makers of Budweiser. We want to make the first-ever website for Budweiser beer.” And it says here that you children — because I was the senior partner at the age of 23 — that you guys had the domain name, we want it back now. And we’re not just going to give it to you. I mean, we’re young, but we’re not stupid.

So we negotiated forwards and backwards, backwards and forwards, and we sold Budweiser.com in 1993 for 50 cases of beer. That is a true story. And—

Susan Drumm: That’s a story.

Jay Baer: I know. It’s been a long time. But one of the things I learned from that experience, and in many subsequent experiences, is that every new technology begins as a true differentiator. I started in the business when having a website at all was literally a business differentiator. Now, of course, everybody has a website. And there’s been many other cycles of technology since then.

So every technology advance — including the flush toilet, right? If you had the first flush toilet in your town, that was amazing, and now that’s pretty common. So all technology begins as a differentiator, but then becomes commonplace.

What we’re finding right now is that everybody in business, including many listeners to the show, are trying to use AI as their new differentiator. They’re trying to use AI technology and automation as a moat that sets them apart from their competition. And that can work, but only in the very short term.

AI adoption is so quick, and its accessibility is so widespread, that you’re not going to be able to out-AI the other guys. We’re all going to have the same robots very quickly. So at the back end of that, when everybody has essentially the same technology, what wins?

And what I believe the answer is, is that in a world of robots, the human touch is the differentiator. All the kind of bespoke, high-touch, human, emotional, and resonant interactions that we have between people are going to stand out in business in a way that, frankly, they haven’t in the last 15 years, because all we’ve tried to do is get more and more efficient using more and more software.

Susan Drumm: And what is that? So I agree with you that, over time — and I love your example with the domain name. I even think about when we had a big satellite dish in our backyard, and we were one of the first families to get HBO, and—

Jay Baer: Big deal.

Susan Drumm: —and that was a big deal, you know, come over to our house for movies. Now that would be a joke, right? So there’s a very quick race to the bottom, and even more accelerated, I think, than we’ve experienced in the past with AI. So I agree with you on all of that.

So what will stand out — what you’re saying is this human touch differentiator. Can you go into a little bit more about examples of where companies are using that to their advantage, and how might someone use it? Because what I notice is people are trying to use AI to have that human touch. In other words—

Jay Baer: Right.

Susan Drumm: —they’ll give AI a little bit of, like, “oh yeah, this person has a four-year-old kid,” right? And it’ll be baked into the response back. And I have a sense that you’re not just talking about that kind of use.

Jay Baer: Well, no, because that is inherently not human. The way we look at it is not using AI to send a better auto-responder. Certainly you can use AI to examine data and create additional levels of personalization — sure, that’s not what I’m talking about.

The reality is this: your mileage may vary at some point based on your role in your company, but as a general rule, Susan, the projection is that AI, when fully effectuated, is going to give every business executive approximately 25% of their time back. You’re going to get 25% more time, because the things you spend time on now are going to be done by AI, going to be hyper-automated, etc.

That’s great. So the question then becomes, what do you do with that 25%? And the reason we haven’t historically done as many truly personal human touches as we might know work, or might feel resonant and relevant, is because we didn’t have time. But now we’re going to have time.

So give an example — I was doing some speaking last year in Rome with Otis Elevator, one of the biggest companies in the world. They’re in 162 countries, right? Elevators, moving sidewalks, escalators — they’re everywhere, everywhere, everywhere.

So I was on stage with one of their key customers, and he runs a very large, 35 billion dollar multinational conglomerate in India. Not a sexy business — they build roads and bridges and all kinds of other stuff. But I asked him, I said, “You have a lot of big customers, a lot of deals that have huge impact on your bottom line. How do you break through that kind of scenario?”

And I thought he would say — given how big the company is, they have a very large IT department, a huge customer experience department, a lot of voice-of-the-customer research. He said, “Jay, every time I’ve got a deal that really matters, I invite the customer — prospective customer — to my office, and we just have a personal one-on-one conversation. And at the end of that conversation, I do the same thing every time: I give them a box of mangoes.”

He has an orchard of prize-winning mangoes outside of his mansion home. And I’m like, “Okay, this guy’s running a 35 billion dollar business and his secret weapon is mangoes.” It’s just a person treating a person like a person. And we all know it works — it’s just we’ve convinced ourselves that we don’t have time to do it. And largely, we haven’t had time to do it.

But I’m telling you that we’re going to get time. And the answer with the 25% capacity that AI’s going to give you back is not to do more AI, right? The answer is to take that time and use it to delight your customers and prospective customers in a way they haven’t been delighted before.

Chewy.com, the pet supply company, is the very best at this, right? You may know the tale where, if you lose a pet, they might actually find out about that — because they have a whole department to do that — and then they will paint a portrait of your deceased pet, add a handwritten condolence note, and FedEx it to your house. The chances of you then buying pet supplies anywhere else in the world for the rest of your life is minus 100%, right? They have you for life.

And mathematically — because I did a whole interview with them — they’ve got, I think they told me, 25 million customers. Don’t quote me on that, but 25 million customers. And approximately half of those customers get a touch from the organization that transcends the transaction. It’s not about, “if you buy extra dog food, we send you a t-shirt.” It’s just, we do cool stuff for you because we think it’s the right thing to do. Now, they’ve been doing it before AI, but we can all do that now, because we’re going to have the money, the time, the capacity back that AI is going to give us.

Susan Drumm: I love the frame of push it towards that human interaction versus more AI.

Jay Baer: It’ll stand out.

Susan Drumm: More people — you know, AI is mostly to free up time, but particularly on the entrepreneur side, because I’m in EO, Entrepreneurs’ Organization, I see my peers working harder than ever with AI. It’s almost like there’s this love affair going on with AI right now. They’re not getting up to work out, they’re missing dinner, working because they’re just so — it’s almost like an addiction right now. And I was like, “But I thought AI was supposed to give us time.” Like, what is happening here? How would you describe what’s happening? Will we really free up 25% of the time, or are we just going to fill it with more work like that?

Jay Baer: I think we will get the time back, because we have to understand that we’re still on the upside of the adoption curve, right? The adoption curve in AI is foreshortened and quicker than any technology in human history. Obviously, ChatGPT was the fastest-adopted technology ever — faster than fire. So that means we’re going to get to the next stage quicker.

But I think what you are feeling, and I feel the same thing — like, I am heads-down in AI all the time. I don’t feel like I’ve gotten a ton of capacity back yet, but I think that’s because everybody who’s in that place, and it is very common amongst entrepreneurs, is still in the “how can I reconstruct my life and my business using these technologies” phase. They’re still exploring the possible, not, “okay, we’ve got that, now let’s figure out how to make it more efficient.” So I think the time is coming for sure.

Susan Drumm: Yeah, yeah. And so I’ve noticed several leaders talking about this idea that growth right now feels like it’s flattened, and they’re wanting to know what’s going on. Do you think it’s because everyone’s sort of distracted, in a way, by what we just talked about — heads down, building the systems, getting it out, and not responding to typical customer outreach or sales processes?

Jay Baer: There’s a couple of things. One, growth has to be captured operationally, and so many organizations of all sizes and in all categories are using AI and technology to fundamentally reconfigure their go-to-market. And that’s going to be less efficient before it’s more efficient. So that’s part of it — you’ve got to separate actual growth from customer demand.

And so, in some cases, I find organizations being worse at marketing, sales, and customer service now, because they’re trying to pinstripe a moving car. That’s a natural outgrowth of trying to change everything with AI.

The other thing I think is really true is there’s a lot of economic uncertainty, which clearly has to manifest in customer demand at some point — it’s going to differ from category to category, of course. And you have this crazy bifurcation in the economy, which we’ve never really seen in the Americas, where the rich don’t care, right? They’re like, “we’ll spend whatever to get whatever we want.” And then everybody else is actually really paying attention to budgets — let’s get the cheaper toilet paper kind of a situation. So it’s the tale of two economies right now.

And even in the tequila business, which grew 40% in two years during the pandemic, when everybody was sitting home drinking tequila, it has now flattened out, right? But the tequila business is flat, while beer and wine are down 15 to 20 points. So in the context of a 20-point decline, flat looks amazing.

Susan Drumm: Right, right. So what advice would you give leaders — now let’s get more tactical, more specific. What are things they could do? What else have you seen working in terms of this human touch?

Jay Baer: What you want to do is audit all of your existing or potential customer interaction points. Where do customers actually intersect with your business? So it’s essentially customer journey mapping, but putting on top of that map places where you can either double down on human interaction or insert human interaction where previously maybe you didn’t do it that way, or recontextualize the nature of that interaction.

So you may know the banking company TD Bank — they’re Canadian and American, both sides of the border, quite large in Canada, meaningfully large in the US. They used to have this program where, if you had a home mortgage with them and you paid off your home — pretty cool, right? Paid off your home, you own the house, amazing — they would send you an email that said, “Susan, you’ve just made the final payment on your home per the agreement that you signed 20 or 30 years ago. We have deducted $500 additionally from your account for the mortgage dispensation fee. Signed, TD Bank.”

That’s a real kick in the teeth, right? That’s not a great way to close up the deal. But this is how they did it for years. So they actually have a division inside the organization that’s now working on human touch, and they did this audit that I’m talking about and said, “Maybe we could put a little polish on this thing.”

And so, what they did — now the way it works, you pay off your mortgage, you get a telephone call from the branch manager who invites you and your partner, if relevant, to the office for a special meeting. You go to the meeting in their office, they’ve got a cake, and the whole staff gets together and gives you some applause for paying off your mortgage. And then, at the conclusion of that meeting, they give you a $500 prepaid gift card as a congratulations.

So instead of taking $500, they give you $500. Now, does that cost them a lot — a $1,000 difference per completed mortgage? Yeah, but in the banking business, the one thing you don’t want is customer churn, and one thing you don’t want is negative customer sentiment. And so they’ve discovered that the $1,000 investment is absolutely worth it from a lifetime customer value perspective.

And that’s the mindset shift that leaders have to get into. People think that doing bespoke human touch things is expensive. Number one, it doesn’t have to be. It’s probably not free, but you have to look at it as an investment in lifetime value, not an expense.

Susan Drumm: Yes. And overall, what could also be present for the person is, there’s going to be future loans or maybe other things. Right now, they’re freed up with whatever the cost of their mortgage was.

Jay Baer: Great point.

Susan Drumm: You could even take that further and say, you know, you could put that towards some type of savings. What if you kept it similar, but now you put it towards — let us show you the product.

Jay Baer: Yeah, let’s roll this into our new investment product.

Susan Drumm: Right?

Jay Baer: Yep.

Susan Drumm: And here’s how this could benefit you. You won’t feel a change to your lifestyle, because you’ve always been putting this out, but here’s how it could benefit you long term.

Jay Baer: Absolutely.

Susan Drumm: I really love that. Well, you know, we talk a lot about shifting patterns, breaking patterns. This is just one example where a company is stuck in a pattern over years and years and years — didn’t even really examine it, because it was like the water they swim in. I mean, think about how long they’ve been doing that. Finally, they did. Finally, they started to see it, and there was sort of a mindset shift around, “Huh, let’s put ourselves in the experience of what the customer is actually—

Jay Baer: Yep.

Susan Drumm: —going through,” right? Let’s talk about you, because with every guest that I bring on the show, I want to talk about their own patterns that they’ve had to shift. And so you’ve more recently gone through a pretty big shift, as we talked about, I think—

Jay Baer: Yeah.

Susan Drumm: —two and a half weeks ago. We can talk about that, or we can start earlier if there’s a pattern that you had to shift earlier in your career as well.

Jay Baer: Let me touch on briefly what you’re saying about businesses. As somebody who’s spent decades as a customer experience strategist, it’s so common that businesses think about all of their operations and their customer interactions from a very process-driven perspective, and they think, “What’s the most efficient way for us to do this as a company?”

And even when you’re looking at adopting new technology like AI — let’s look at chatbots. Chatbots can be pretty cool, and they’re getting better all the time, clearly. But it’s very rare that a company says, “Hey, let’s implement a new AI chatbot because it’s better for the customer.” They’re implementing it because it’s better for them, right?

So for me, that’s the pattern shift. It’s to say, “Let’s look at all the ways we interact with the customer — whether the pet passes away, what do we do next; somebody completes their mortgage, what do we do next; we get a big customer, what do we do next.” Instead of thinking, “How can we make this most advantageous for us,” what if we realize that we wouldn’t be here at all if it wasn’t for the customer? And say, “How can we turn this to the customer’s advantage?” If the customer wins, you’re going to win eventually.

So one of the little techniques that I used to teach is to think about each of those interactions on a 100-point scale — almost like a pendulum — and say, “All right, let’s take this mortgage dispensation issue. On a 100-point scale, how much does that benefit the company versus the customer, the way it’s architected?” Well, in the past, it’s probably 98 company to customer, right? The only thing the customer gets is, “yes, we’re not still charging them for the mortgage” — that’s the only win for them, right?

But now it’s probably 90% customer, 10% company, right? And so if you actually think about all those intersections with that sort of scale in mind, and map that, it actually helps you not only see the pattern, but also break the pattern.

Susan Drumm: Yeah, yeah, for sure, for sure. So mapping specific experiences that your customer — their journey with you — and what are ways you can get more connected to and empathize with what their experience is, and then leverage that.

Jay Baer: It’s one of the great challenges that companies have as they grow. They get further — especially executives — they get further from the customer. It’s a natural outgrowth of company scale. You forget what it’s like to be a customer of your own business. And you always end up treating customers like a number. We don’t want to, we know we shouldn’t, we know better, but we always do, right? We start looking at a spreadsheet and we forget that behind each of those integers is a real person.

There’s a company I used to work with called Pella Windows and Doors — they make custom windows and doors, they’re great at it, they’re definitely the best in the industry from a net promoter score standpoint, etc. They work really hard at customer experience, really hard, and they’ve got excellent reviews. But it’s a pretty complicated business — it’s not perfect.

And the way they start every executive meeting — every meeting, they’re in the headquarters, right, big walnut conference table, super comfy chairs, you’ve got the whiteboard, the video conferencing system, the whole thing, it’s right there, big window — every meeting they start it the same way, Susan: they start the meeting by reading a one-star customer review, every meeting. Because, despite their success, despite their growth, and despite the fact that they’re the best in the industry, they never want to forget that every single day they disappoint a customer. And I love that approach to business and customer experience.

And so, from my perspective, I got to the point that I never wanted to disappoint my friends, my family, my loved ones. And where I first broke this pattern is during COVID, right? I used to travel 48 weeks a year and had for decades. And during COVID, obviously, I had to stop that. So I went from running a consulting company — doing global consulting, the kind of work we’re talking about here — and being a full-time keynote speaker and author, to only doing one of those.

And I realized once I stopped traveling that I was actually a lot less happy than I thought I was, and I was more happy not traveling. So I subsequently sold my consulting company — I said, “I’m not going to do this anymore.” So I sold the consulting company and was just a speaker, and that made me happier, less busy, less stressed out, less unavailable.

But then I started making tequila content, and then, as entrepreneurs do, turned that into a full-time job. So then I ended up with two full-time jobs again. I went from two full-time jobs, sold one, somehow manifested a second full-time job. And so now I had to get out of—

Susan Drumm: How close? How close between a gap where you only had one company?

Jay Baer: Six months.

Susan Drumm: Okay.

Jay Baer: Six months. Yeah.

Susan Drumm: Yeah.

Jay Baer: Which, looking back on it, was a pretty great six months — I didn’t realize it at the time. You can’t see the label of the jar you’re in, goes the saying, and I’m definitely living proof of that. What’s hilarious is I remember very clearly when I sold the company, my wife said, “Now listen, you’re a seven-time entrepreneur — don’t go starting another company now just because you have time on your hands.” And she was exactly right.

But I’ve realized that I’m not happy when I’m not busy, right? I have to be busy, like so many executives. But I’m also not very happy when I’m too busy. And so the pattern I’ve tried to identify, and now break, is to try and keep it in the sweet spot — normal busy, which is superhuman busy for a normal person, but for the people who listen to your show, is normal busy, right? For my friends, they’re like, “Your normal busy is insane.” I’m like, “I get it, but different scale.” But when it gets too crazy, I get less happy and I’m disheartened to be around.

Susan Drumm: So noticing that balance between what’s the right level of busy, and I’m not going to fill it just because I have the gap. As even what we talked about before with AI and freeing time — for leaders, being really intentional: what are you going to free, what are you going to put in place of that time? Maybe it’s the human touch of the customer, for sure, on the business side. But I see a lot of people, you know, relationships with the people around them — more investment, more investment in their health and—

Jay Baer: Exactly. Yeah, those two for sure. But I think also — and this is having already gone through this unsuccessfully once — I think if your solution is to fill it with something else, you don’t actually have a solution. It’s like when people quit drinking — and please don’t do that, because I don’t want to kill a newsletter — but when people quit drinking and then they start smoking three packs of cigarettes a day, right? It’s not really a net gain.

I think the only way you can truly find happiness when you are intentionally being less busy is really adopting the principle of enoughness — not with regards to assets, but with regards to how you spend your time. It’s okay to give yourself permission to just screw around. It’s okay to read a book for pleasure. It’s okay to take a walk without a destination. It’s okay to try a new podcast, like The Enlightened Executive. All those things are okay.

But I think as executives, we find ourselves — and I’m certainly guilty of this pattern for decades — we find ourselves in this position where, especially when we look at our peers who are also busy and successful, if we’re not sort of subscribing to this hustle mindset, that somehow we are shirking our duty to our company, shirking our duty to ourselves, to our own family. And that’s a mindset that eventually is going to grind you down.

Susan Drumm: I call it the busy badge, you know?

Jay Baer: Yeah.

Susan Drumm: You ask anybody, you know, “How are you?” “Busy, so busy,” right? I’m not busy all the time — am I just like, “Oh, I’m actually doing great, I have a nice, balanced life, I’m doing this”? Like, how many times do you hear that versus “I’m just so busy”?

Jay Baer: Never. Never. And it’s funny, because my daughter lives in Paris — she’s lived in France for four years, getting an MBA there now. And it’s a uniquely American phenomenon. Their relationship to work there, even amongst executives, is so different than the relationship to work in the United States. It’s crazy.

I could never be an executive in Paris, because people are just like, “Yeah, we’re taking August off.” I’m like, “Wait, what do you mean?” “Well, we all take August off.” I’m like, “Who’s all of us?” “The whole company.” “Well, who answers email?” “We don’t — we answer it in September.” This is like how it works, right? And it’s like my mind is literally exploding right now. But everybody’s cool with it, right?

And so it’s okay, like it’s going to be fine. There’s no such thing as a tequila emergency, really. And I’m not saying I’ve got this licked at all, by any stretch of the imagination, but at least I see the pattern. Whether I can do something about it successfully — bring me back in six months and we’ll see how I’m doing.

Susan Drumm: Yes. And so why did you decide to go full-time into the tequila side?

Jay Baer: Like a lot of people who are part of this community, I love the making-stuff part of it — I love the starting from scratch, the entrepreneurial side of it. This is my seventh or eighth company. I like that part, right? Once you’re there, it’s still fun, but it’s not as fun as trying to figure it out from scratch.

And in this, we actually built something that’s never existed before, period — it is a category of one. A fully scaled tequila newsletter didn’t exist until we made it. And there’s lots of different divisions and departments that we’re building out. So I really like that part.

And it’s fun to have a business now that doesn’t require me to get on an airplane to get paid, other than to go to Mexico, where I have a house half the year anyway. I think there’s definitely some lifestyle advantages, and also some intellectual advantages, to being back in entrepreneur mode.

Susan Drumm: Okay, great. Well, if someone’s listening and they’re sensing that something in the way they’re leading or working isn’t working for them, what would you suggest they do tomorrow to help shift their own pattern?

Jay Baer: Let me tell you a story about when I started my first company. I’m from a family of entrepreneurs — I’m a sixth-generation entrepreneur, my son’s a seventh-generation entrepreneur. So when I was a kid, it wasn’t really a question of whether I would be an entrepreneur — it wasn’t even a conversation I remember having, it was just sort of assumed, it was in the air, right?

But I didn’t do it. For a lot of reasons, I got fortunate and had some really good, fairly well-paying jobs right out of college. And so I’d always thought about starting my own thing, but I never did. I was like, “Things are going pretty well, I’ve got a wife” — at that point I had a baby — “I don’t want to just walk the plank, because what if it doesn’t work out?”

So I was 30 years old, so I hadn’t started anything. And my best friend since second grade had married my wife’s sister — so if you’re following along, my best friend became my brother-in-law.

Susan Drumm: Wow.

Jay Baer: Which I really recommend — if you can piece that together, that is excellent social engineering, it makes Thanksgiving way more fun. And so we spent all our time together — we lived in Phoenix as well. And he called me one day and said, “I just got back from the doctor and it turns out I have brain cancer.” He was 30, I was 30, we were all 30. And I walked in the next day and I quit my job. I haven’t worked for anybody since.

And what happened between that phone call and the next morning is I sat down with a piece of paper and I wrote down all the things that scared me about breaking that pattern. And once I wrote them down, I realized they weren’t that big of a deal at all. Like, “oh, maybe it won’t work out — I could go get a good-paying job doing a lot of other things, I’m good at what I do, I know a lot of people.”

If you’re concerned about a pattern and how to break it, for me, the best way to do it is to write it down, because when you write it down, it robs it of all its power. What keeps us in place, what keeps us stuck, is sort of the amorphous black cloud. And when we give form and definition to the things that scare us, it makes it a lot less scary. So just grab a piece of paper and a pen and make some notes about what you think is really holding you back. And I think you’ll realize that some of those things aren’t that big of a deal at all.

Susan Drumm: And are they true? I think that’s always the question—

Jay Baer: Yeah, well, there’s a lot of negative self-talk as well, yeah.

Susan Drumm: —that that would happen?

Jay Baer: Yeah, yeah. And obviously, you’ve got to — you know, you’re clearly at least more than average risk tolerant if you’re an executive listening to this show anyway, right? So you’ll figure it out.

Susan Drumm: Thank you so much for being on the show. Where can people find out more about you, your work, and your Tequila Report?

Jay Baer: Oh, thanks so much. If you go to Amazon and search Jay Baer, you’ll see all the books — there are seven of them, I’d love your support there. And Tequila Report is tequilareport.com. It’s totally free — we send it two newsletters a week, Tuesdays and Thursdays: tequila reviews, stories about the families who make it, buying guides, all that kind of stuff. Totally free.

Susan Drumm: Awesome, thank you. And if you like this episode, you’re not going to want to miss my interview with Jake Thompson, where we unpack why the most dangerous moment for any team isn’t failure — it’s success. 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 and the bell to get notified when we release new content. I’ll see you on the next episode of The Enlightened Executive.