526. The High Achiever’s Paradox

 

Jay Papasan:
We’d like to believe that everything gets easier with success. We have more money, we have more resources. Maybe we even have a team to help and everything just gets easier. And sometimes that’s true. But strangely, there’s also kind of a high achiever’s paradox. Some challenges actually become harder with success. It’s like they compound. 

So, think of it as maybe it was a chronic problem, a chronic mistake that maybe you’re making, that if unaddressed gets bigger and bigger over time. It’s like that dripping faucet that slowly becomes a trickle, and that trickle can then become a flood, and suddenly, you’ve got a major renovation on your hands. That’s how, like, chronic problems and chronic mistakes can compound if we don’t nip them in the bud and we don’t have a good approach for them. 

So, today, I’m gonna share some observations we’ve made. We took lots of our coaching transcripts, lots of our discovery calls with executive and coaching clients, and we were looking for patterns. We uploaded them all, put them into AI, and we discovered at least three things that jumped out at us that are part of a larger trend. And I wanna share what those trends are today. So, whether you’re a veteran or a beginner, you might just recognize one of the three, if not, all of the three, as challenges you’re currently facing. And all I can tell you is in our experience, if you can nip these in the bud, it actually gets easier than if you wait until you’re “successful.” So let’s dive in.

I’m Jay Papasan and this is The ONE Thing, your weekly guide to the simple steps that lead to extraordinary results.

So, here’s how the paradox works. So, you have more opportunities, which actually means you have more distractions. You have a bigger business, which means you have to make more decisions. You have a bigger team, which can mean that you have to manage more people. The stakes become higher, so you have more to lose, and a large operation actually brings more complexity.

So, there’s something about the scale of success. That our natural talents show up for, and we’ve been good and we’ve been good, and then suddenly we’re not good anymore. Or maybe we weren’t good in the beginning and the bigger the business gets, it feels like the problem that we are facing just becomes more and more insurmountable.

Now, when we were writing The ONE Thing, one of the chapters we cut that I don’t ever mention very often, it was one of the thieves between you and success. And if you remember the three thieves, we kind of go through those in detail, well, there was another one and it was called maintenance. And it was this idea that as you become wealthy and successful and prosperous, you start to accumulate stuff, right? Maybe you have not just your primary business, but that grows into like a little mini empire. You have subsidiaries. You might have a house, and then you have a second house. You have a car, and then maybe you have a weekend car. Success ends up adding more stuff to your life. 

And here’s the problem with stuff, and this includes people, they require routine maintenance and repairs. Things break. Now, that summer house that you bought in Colorado, which is awesome when it’s really hot in Austin, Texas, but now you’re getting a call saying that that leaky faucet turned into a flood and your basement needs to be redone, or maybe the air conditioner’s out or the heating is out, whatever that is, it tends to compound. Instead of one roof, you’ve got two. Instead of two cars to get maintenance on and oil changes, you’ve got three. Things start to compound, which means it’s more and more likely, every single day, that a low percentage thing can happen. 

If you have a hundred employees, any 1% chance that an employee will do something could happen every single day. That’s how it works. Your world gets bigger, and even things that feel like edge cases start to happen more frequently, and the challenges kind of just show up again and again. 

So, that’s the big idea of the high achievers paradox. It’s the pie is getting bigger. You are hopefully celebrating that you’re becoming more successful. But the unexpected thing is that big success comes with big challenges. 

So, there were three that kind of jumped out when we kind of analyzed all of these conversations. And the very first one was the challenge, not with blocking our time, time blocking, making appointments with ourselves to do our most important work, what we saw is when people hadn’t mastered the art of protecting their time, the more successful they became, the harder it was for them to honor their time blocks. Sound familiar?

So, I’ve seen this again and again and again in my discovery calls and in my coaching calls. People are doing the hard work of identifying their priorities. They’re even getting them on their calendar. But because their world is so big, it becomes harder and harder to protect that time. They have more people knocking on the door. They have more emergencies that require them to step out of their time blocks. And people sometimes resort to absolutely extreme measures. 

I was talking to one gentleman who literally had left the country. He had left his country – not county, country – to go to a friend’s condo so that he could actually do his work undisturbed. Now, that takes a certain level of success to even think about that as a strategy, but they’re literally looking for an escape hatch, so they can get a little focused time. So, honoring your time blocks, it’s not just about discipline. You’ve gotta maybe have better systems for protecting that time when more people, and more projects, and more complexity, demand more of your attention. 

So, that was pattern number one. And it shows up an awful lot. And one of the big deals here is something happens early in the day, and you blew an hour with an unexpected emergency. 

The other kind of compounding thing that we see is people have this all-or-nothing idea. It’s like, “I’m gonna have a perfect day,” or “I’m just gonna let the whole day go into triage.” And so, they get interrupted early. And then, they just say, “What the heck?” And it just rolls downhill, and they fall into this cycle of kind of busyness because they didn’t protect that first time block that got kind of undone. And then, that rolled downhill, and a blown hour becomes a blown day. 

So, number two, delegation.

Maybe the second most frequent, at times it’s the most painful, you got really good at what you do. That got you to your level of success. A lot of times, the very skills that allow us to start a business, to get a big promotion are the things that can actually hold us back, because we’re really good at doing these things, but the demands of our work have changed.

I’ve gone from a salesperson to a CEO. I can’t just be the star sales guy. I now have to step into this brand new role and do new things that (1), I’m not very good at, and I have to also delegate the old stuff. So, there’s this weird moment of transition where some people get lost in their identity. I was so great and now, everything feels new and hard, and they also don’t know who to trust. And the longer we wait to practice this skill, the better we become at the things that we’re doing, and the bigger the gap we see between how we do it and how the new person might do it. 

And we get frustrated. We’re like, “Gosh, it’s gonna take you 10 times as long to do it as I will. I’m just gonna do it for you,” which sounds a lot like my strategy with laundry with my mom when I was a teenager. If I messed it up just enough to get her irritated, she would jump in and fold the clothes. I don’t think that our people are doing that to us, but it’s that frustration level, that “Just let me do it.” We self-sabotage. 

And instead of learning the fine art, and it is kind of an art, of allowing other people to fail forward until they become as good as us and often better, like those skills that we do, they don’t all contribute to our success. Some of them, yes, but we got really good at a bunch of stuff because we had to. Maybe some of the things that we got good at, we don’t even love, but we’re good at it. And there’s someone who will wake up every day and do that one-fifth of your old job at a higher level than you ever did because that is their focus. That’s their calling. 

But that trap is we don’t learn to start saying, “This is yours and this is mine.” Start sharing the load, delegating the work early on. We look up and we become trapped in this competency trap. Talked about this with Brandon Turner when he was on the podcast. He literally had to sell his tools because he kept wanting to step in and do his own renovation work when he should be solving much bigger problems worth thousands of times more than the little problems he was trying to solve – fixing a toilet he saved $300, might have cost him $300,000 because he was doing little work with his high competence instead of stepping into this uncomfortable area he was unfamiliar with, that had much higher value. 

Number three is kind of a kissing cousin. It goes along with this delegation. It’s got to do with our need to be doing and how much we’ve excelled by being doers. It’s the conflict between our need to be more strategic versus tactical. And this is where our hands-on approach is going to undo us because we’ve been doing it for so long to get ahead, knocking out the work, going on the appointments, closing those sales, doing whatever it is that is your core work. Now, as you level up to this next stage, leadership demands more thinking time, more strategic vision. 

And guess what? We don’t do that as well when we are in fast motion, when we’re doing lots of stuff. It doesn’t happen in the background. We need space. And the challenge, and we’ve seen it again and again, is that people who’ve made busyness of their drug, rest will feel like stress. So, not being in motion actually creates anxiety for people. They look up and they’re like, “Man, people are gonna think I’m just blowing off my day. I’m just sitting here and I’m staring at the paper trying to come up with strategic vision.” They get  frustrated, they quit too early, and they end up self-sabotaging.

So, thinking time is what I would call it. Their need to become more strategic as they become more successful, they have to look up and see a bigger and bigger playing field. But if you’re always tactical, if you’re always in the doer’s mindset, you will self-sabotage again and again. 

So, all three of those, when you look at them from a broad, not honoring our time blocks, not being able to delegate the work and get out of our own way, and then this failure to do the vision work, the strategic work, take the thinking time, those get harder and harder the more successful you become. That’s the trend that I’ve seen.

I also think saying no can become harder, but it also, in some cases, be easier. But those are the big three where I just looked again and again, conversation after conversation, “I’m not setting good boundaries,” “I’m doing too much of the work that other people should be doing,” and then finally, like “I know how to do the work, but I don’t know where I’m going. I don’t have a strategic plan.” Those are three big themes, and guess what? They all add up to the same message. We have to level up our approach. 

Here’s the thing, when I hear those, what we know, what we know and our coaches know is that that individual has been relying on their natural talents that got them this far and they haven’t yet adopted a system or a model to take him to the next level. It’s what we call going from E to P. And after this short break, we will dive into exactly what that means and how you two can do it. Let’s take a quick break. I’ll see you on the other side.

All right, welcome back. Let’s break down what we mean by E to P. First off, let’s just say what the E and the P stand for. E stands for entrepreneurial and P stands for purposeful. And entrepreneurial is just a placeholder for what a lot of business people do. And whether you are an entrepreneur or not, it might apply to you. What it means is we’re doing it the way we know how to do it, our natural way, how we showed up at work, like how good are you at sales, that’s where you are today, and you’re applying your natural talents and what you’ve learned so far to do it. 

And a lot of entrepreneurs are entrepreneurs, not because they’re great at everything, because they’re kind of willing to do it all. If there’s a million jobs in the business in the beginning and there’s just you, you do ’em all. And you do them all with a level of ownership because at the end of the day, there’s no one else. So, he is like, “Well, I’ve gotta do it. I’m gonna grab this mop and I’m gonna be the cleaner for today,” or “I’m gonna pick up the phone and I’m gonna be the salesperson today.” You do all the roles because you’re the owner. And so, entrepreneurs will do them all to their current level of ability, and they’ll do them with a great sense of ownership. The problem is, for most of those things, we have kind of a low ceiling of achievement. 

So, moving from E to P is kind of a journey. And if you could imagine kind of there’s this wall above you, it’s a ceiling, and it’s that ceiling of achievement that you will hit based on your current level of abilities, you will wrap your head against it as you kind of go, “Whoa, wait, I can’t do this anymore.” Like, “Why is it that I keep skipping my time blocks? Why is it that I just can’t give the job to my assistant and let them actually have it instead of micromanaging them and taking it back?” I keep going through assistant after assistant, I hear this again and again. I’m on my fourth EA, and it’s because they’re self-sabotaging along the way.

And so, all of these things, that idea that you’re bumping your head against the ceiling, but you can’t quite break through. And what’s really challenging about that is it leads to this cycle where we start to lose faith in ourselves. We’ve failed at this thing so many times in a row, we start to believe that maybe it’s not possible for us. Maybe worse that everybody thinks that we’re successful, but we’re actually not as successful as people believe. Maybe we’re kind of a fraud, the imposter syndrome. And that can lead to this kind of disappointment and resignation. 

And what some people do is they just kind of quit and move on. Like I’ve tried it and I’ve tried it, and it’s just not for me. The area I hear the most is like people will say, “Well, I tried the time block, but you know what? It just doesn’t work for me. I’m gonna work from a to-do list.” And they don’t get any better, but they also are now just doing what everybody else does. So, there’s no judgment for themselves. But the one that’s most painful for me to hear is like, I’ve tried to hire people, I’ve tried to use 1099s or W2s, however you want to call it, an employee or a contractor. I’ve tried it, I’ve failed. It’s not for me. 

And the challenge with that one, that’s the hardest one of all, is that for anyone to actually be a business owner, to grow a business, you have to go from “I do it,” to “We do it” to “They do it.” And when it’s I and we doing it, I’m doing it, we’re doing it together, you are still earning your income like a job. The moment it goes to, “They do it,” now, you have business income. That is income that can happen when you’re not doing those things, and that’s an incredible thing. That’s why so many people grow and they grow into their business over time. They may hit that ceiling, but the breakthrough when they’re allowed to do that, allows them to grow at an exponential rate.

So, all of these things show up as us hitting that ceiling of achievement. How do we break through? Most entrepreneurs put on their football helmet, they back up, and they feel like they can just ram their way through it. They’re just gonna be like, “Well, I’m gonna work harder and I’m gonna work longer, and that’s how I’m going to break through.” Well, you don’t often break through that way or if you do, there’s another ceiling right above it. What usually happens is you break down. 

This idea that more time and more effort is the solution may have gotten you long ways, but there is a point where that seedling of achievement will be very hard and you need another model or a system to break through.

And here’s what I mean. If you’ve ever gone to, like, a top golf or any of those places where you have to swing a golf club, there is the natural way to hold a golf club and there is the right way. And if you’ve ever had a golf lesson, you will know that the right way to hold a golf club is so unintuitive, so unnatural. It is unbelievable. What do you mean I have to have my pinky over my index finger? It just feels completely awkward. But if you hold a club that way, you can actually consistently hit that little white ball more or less straight. If you hold it like a baseball, man, I’m sorry you’ve watched Happy Go More, it’s not gonna work for you. It’s not gonna work consistently, that’s for sure. There’s not a single professional golfer that’s gonna hold their golf club that way because the model, the best practice is something else. 

So, a lot of times, we hit the ceiling and all we need is a new approach. There is a better approach. And we have to look for examples of people who are on the other side. If I wanna learn how to protect my calendar, I don’t wanna start surveying entry level employees. I wanna look at C-level executives and founders, people who have hundreds of demands for their time every single day. How do they protect it? Who do they have around them? What are their systems? So, those models exist. And when we adopt them for ourselves, we then get to break through. The ceilings that we’re hitting are as big as the models that we’re using and the systems we’re using for our work and our life. Just a truth. 

Going from E to P just means you’re just admitting it. “Okay. I’ve gone as far as I can go. I need to adopt a model. I’m going to be purposeful. I’m gonna look for a solution. I’m gonna research it. I’m gonna look on Google. I’m gonna ask AI. I’m gonna read a book, and I’m going to adopt a model, a different approach that will allow me to break through.”

I personally experienced this in a huge way in 2019. We were in a big transition. We had just gone from one CEO to another in my role here at Keller Williams. And I, at that time had two small departments, maybe seven or eight employees. I went on a medical leave, I had a big back surgery, so I was out. And when I came back, I found out I had five departments and my number of employees had increased sevenfold. I had all these direct reports, multiple departments, multiple budgets, and every system that I built for my life broke all at once. 

I had a system from doing my one-on-ones and tracking. That broke.I had a system for managing my week. That broke. I now had so many direct reports. Even just meeting with them biweekly for 30 minutes would take up sometimes a third of my week just by itself. I’d gone from being someone who did a lot – I was a writer, I was actually doing a lot of the work and managing a little bit – to someone who had to manage a lot and had very little time left to do. 

And that conflict undid me for the entire summer. And I remember my coach just asking me the question, “Well, it sounds like the models that have gotten you here no longer work, but start looking for some new models.” And I remember I went to Trello. I started using project management software. I started looking for bigger examples of people leading bigger teams to take how I thought about work, but put it into a new system that actually scaled higher.

That was my journey. And I will tell you, hitting my head against that ceiling was very painful. I had to work long hours. I was trying to solve it with time and just focus. I’m gonna grit my teeth and make it go away. It took my coach to help me get the breakthrough and help me find really just three new models that allowed me to get to the other side.

So, we have to go from E to P. If you’re experiencing some sort of chronic failure, I just keep failing to do these things, like those three examples I gave you, some of them are gonna get harder the longer you put ’em off. So, it’s always in our interest to just ask the question, if I keep having the same repeated limitation or failure, I am missing a model and, occasionally, a relationship, and that’s usually gonna be a coach. ‘Cause what do coaches do? They guide us to models. They guide us to solutions. So, that’s like the shortcut in my book. But I’m missing a model. I’m missing a system. That’s what I need to make my next breakthrough.

The good news is if you adopt the biggest models that you can imagine would be useful to you today, you can ride them a very long way before you’ll hit the next ceiling. The challenge for a lot of people is that they can fall along this trap, and then they hit that ceiling and they just decide it’s okay. They get complacent. Like even if they don’t quit, they just say, “Well, I guess I’m a hundred thousand dollars salesperson. I’ll never be a millionaire.” They just decide that this chronic failure is actually a sentence. Nope, it’s a symptom. It is not a sentence, it is not sentencing you to stay at that level forever. It’s just a symptom that you’re missing a model or a system, and it is your job to go from E to P, to move from natural, probably to unnatural in order to take the next big leap in your business. 

I’ll give you one more nuance. If you’re listening to this and you’re in startup mode, a lot of people right outta the gate, they’re starting a new business, are gonna hit a lot of these. We tend to hit a lot early on and we adopt quick models for solving them. I don’t have a database. I’m gonna use post-it notes. I’m gonna use the spreadsheet. And we adopt something that solves the problem now, but will probably short circuit us later. 

The next stage is scaling. And when your business takes off, that is when these problems that you neglected during the startup phase, or you put a bandaid on it, get big really fast. Yeah, when you only had a hundred customers, those post-it notes kind of worked, that spreadsheet kind of worked. When you go from a hundred to a thousand, now, it doesn’t work at all. You actually need a CRM. You need a bigger model for managing those relationships. 

So, we look up, we go from startup to scaling. Eventually, we will break. Doesn’t matter how big your systems are, eventually, the operations will break down and that’s when businesses pause and they stabilize, so that they can go and scale again. And just realize, if you’re in one of those places where you’ve hit that plateau, think of it not as failure but I’m stabilizing. This is my opportunity. The world has signaled to me that I’ve hit the ceiling. I need to stabilize. I need to find my model, so I can go back to scaling and head the other direction.

So, I wanna add on one little kind of bonus caveat. You’re gonna go from E to P. And because I know you’re a high achiever, you’re listening to this podcast, you might be a founder, you might be a leader, you might be someone who’s aspiring to be one or both, but you’re trying to be your best or you wouldn’t be listening to this podcast. In my experience, when I’ve been working with you or our team’s been working with you, you have this kind of go for broke. We think big and you’re gonna go big too. What I want to caution you on, especially if this is a chronic problem, you need to solve, not just the problem, you also need to solve the confidence problem.

If you’ve been failing at this a long time, there’s probably a little voice in your head that’s saying you’re not good enough or you can’t do it. And I’m sorry if that’s the voice you’ve been hearing ’cause it sucks. I’ve been there too. What you need to do is pick the smallest domino. The first domino, where can you begin such that it almost feels ridiculous with your success mindset, but the purpose here is not to lower the bar. You’ve got a high bar for success, I get it. But we’re gonna lower it in the beginning because what we want to do is build a momentum and confidence. 

So, whatever it was that you need to solve and you got that model, you can pick a big model, but you’re gonna start small. You’re gonna build trust. You’re gonna start collecting and stacking those wins, so that you can start and return to that place where you believe, “You know what? I can solve this. I can do hard things. I can pivot. I can learn new things, and I can grow into them.” And you will be surprised at how quickly you’ll be able to ramp up if you just build a string of wins in the beginning.

So instead of saying, “Oh man, that strategic time block. I need this strategic thinking. I’m gonna block all day Friday.” And I’d literally know people that have no-work Fridays. That is their thinking time. They’re doing their creative time. And I’m a little bit, in all of them, I’m like, “Wow, I can usually get an hour or two a week. I don’t get a whole workday. God bless you for doing that.” But we hear about that big model and we go for broke. 

Have that vision if that’s what you want. I want to have one thinking day a week, great, but start small. Start with how about just 30 minutes on Friday morning with a journal, maybe an hour on Saturday with a notebook out, and you’re just asking and reflecting, how did it go? What can I do better? What is working that I need more of? What is missing that I need to put into my schedule? Just ask a few reflection questions and you can level up.

Delegating. Maybe you don’t need to take your entire “not to-do list,” all the stuff that you shouldn’t be doing and go find someone tomorrow. Maybe you just need to take one big task. What’s the thing that’s eating your lunch the most frequently? Take a small bite, and assign it to someone else on the team, or hire a VA or hire someone virtually and say, “I just need to outsource this one task.” And start practicing the skill of delegation and feeling the success of it, and then scale from there.

So, in any of these, we can take a big solution, a big model for success. If I’m an executive, if I’m a founder, I know that I eventually want an EA or a chief of staff. I don’t need to start with the chief of staff. But I need to learn the art of delegating to someone who earns my trust and then gets more and more of my 80%, so I can focus on the 20% that matters for me. That’s how it works. 

So, the pro tip here is once you realize that you’ve been hitting the ceiling, you’ve decided to adopt a big model, start small. Don’t go for broke right outta the gate ’cause you might stumble, and then you’re right back into that lack of confidence. “Man, I’m just no good at this. I wasn’t meant for this.” Don’t want to hear that. Start small, build confidence, build on your successes, stack them up, so that you can then scale and go big.

All right, we’re bringing it to the end. So, I’ll go back to the three areas that we see all the time. We have people who don’t honor their time blocks. We have people who fail to delegate, and we have doers that aren’t making any space to dream. They don’t have any thinking time. On each of those, figure out which one of those is the number one way you self sabotage. And I want you to just go small. Right? What’s the one thing that you could do to start protecting that important time? Do I need to break it down into smaller bites? How can I start delegating maybe one task at a time? How can I get thinking time, maybe in smaller blocks, to scale it down? That’s your assignment.

And in fact, that is the challenge for this week’s episode. We’ve got these chronic problems that we’re experiencing. The longer we put off solving them, I promise you, the harder it gets. So, you might as well pick the biggest one for you and start today. So, your homework assignment is to identify what is that chronic challenge that you’ve been facing, that you’ve been putting off, or you’ve been trying to just grit your way through it. Identify it, and then go on a journey. Ask what system or model am I missing? You might be so surprised if you just start asking around how many people might say, “Well, you don’t use this app. Have you tried this?” You will get a lot of suggestions for how to solve that problem. And then, the next step for you will to be implemented in that small way.

I hope that you’ll take one baby step towards going from E to P between now and next week. And if you practice that day after day, just one tiny step, I promise you, you will look up and the dominoes will get bigger and they will continue to fall, and you will be surprised by how fast you will grow. That’s how going from E to P works. We level up with a model or system, and then we find out that we can go so much farther than before. 

But that’s it for this week. Going from E to P is how we break out of the high achievers paradox, where these big problems get harder and harder to solve. We have to just go from E to P as soon as we can feel that it’s a chronic problem that we need to address, we need to find that system or model and implement it in a small way. It’s a big lesson in life. And if you are on a journey of achievement and you’re reaching for extraordinary, you will hit it again and again.

Frankly, if you’re looking for your possibilities, what’s possible for you, you will hit ceilings of achievement throughout your life. And a really cool skill is learning how to navigate them. You learn the skill of modeling up, of going from E to P. Anyway, that’s what I wish for you. It’s one of the biggest gifts in The ONE Thing, and it is right there for the taking, if you will just commit to going to E to P.

Next week we’re bringing my friend, Todd Sattersten. And I say this not lightly. I’ve known Todd for probably over a decade now. He became the publisher for The ONE Thing when Ray Barr retired. We’ve become friends, we are colleagues, and he has just released his first book in a very long time. He read, I believe, 2000 to 3000 books, so that he could identify the 100 best books for work and life. 

Todd is a renowned expert on business and self-help books. He’s been a publisher. He’s been a CEO in this field. And he has been a publisher, my publisher for a long time. He studies it. He went out and wanted to know, for all of the big problems that we face in life and work, what are the very, very best books that we can read? You’re probably here because you’re a learner. Most high achievers are. This episode will reveal his selection process. How did he narrow it down? How do we choose when we have a problem in our life and we need to go get educated to find a solution? Join us next week, Todd Sattersten, for the Hundred Best Books for Work and Life. 

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