The High Achiever’s Paradox (4 Min Read)| Vol. 172

October 10, 2025

“We cannot solve our problems with the same thinking we used when we created them.” – Albert Einstein

The High Achiever’s Paradox 

We’d like to believe that everything gets easier with success. More money, more resources, maybe a team to help, and everything just clicks into place. Sometimes that’s true. But there’s a strange paradox – some challenges actually become harder with success. They compound.

Think of it as a chronic problem or chronic mistake that, if unaddressed, gets bigger and bigger over time. It’s like that dripping faucet that slowly becomes a trickle, then a flood, and suddenly you’ve got a major renovation on your hands.

Here’s how the paradox works:

• More opportunities = more distractions
• Bigger business = more decisions
• Bigger team = more people to manage
• Higher stakes = more to lose
• Larger operation = more complexity

Your natural talents may serve you early on, but your challenges will grow with your success whether you do or not. You’re great until you’re just good. You’re good until suddenly you’re not.

Success adds complexity to your life. Your primary business grows and spins off new divisions or subsidiaries. One house becomes two. One car becomes three. All that stuff requires attention. Your world gets bigger, and even edge cases start to happen more frequently. If you have 100 employees and a 1% chance that an employee will have a crisis requiring your help, it’s likely you’ll be interrupted by at least one knock on your office door every day.

Big success comes with big challenges.

Three Challenges That Compound

I recently analyzed coaching transcripts and discovery calls with regular and executive clients. We uploaded them into AI and discovered at least three patterns that jumped out as part of a larger trend. Whether you’re a veteran or a beginner, you might recognize one—if not all three—as challenges you’re currently facing.

1) Not Honoring Time Blocks

People become high achievers by time-blocking their most important work and getting it done. But when they haven’t mastered the art of protecting their time, the more successful they become, the harder it becomes to honor those time blocks.

The world gets bigger. More people knock on the door. More emergencies demand attention. I talked to one gentleman who literally left his country—not his county, his country—to go to a friend’s condo so he could work undisturbed. That takes a certain level of success to even consider as a strategy.

Honoring your time blocks isn’t just about discipline. You need better systems for protecting that time when more people, more projects, and more complexity demand your attention.

Something happens early in the day that blows an hour with an unexpected emergency. You get knocked off track early. A blown hour becomes a blown day, as you fall into a cycle of busyness. 

Activity masquerades as productivity. 

2) The Delegation Dilemma

What got you here won’t get you there.  Often, the very skills that allow us to launch a business or get a big promotion become the things that hold us back.

The demands of your work will change as you grow. Maybe you’ve gone from salesperson to CEO. You can’t just be the star salesperson anymore. You have to step into this brand new role and do new things that you’re not very good at. And you also have to delegate the old stuff.

There’s this weird moment of transition where some people get lost in their identity. I was so confident, and now everything feels new and hard.

The longer we wait to practice delegation, the better we become at the things we’re doing. And the bigger the gap between your skills and the abilities of anyone doing your old work. Cue the mounting frustration and impatience.

Instead of learning how to let others fail forward until they become as good as us—and often better– we self-sabotage and take over. 

Competency becomes a trap.

3) Doing vs. Thinking

We’ve excelled by being doers. Now, as you level up, leadership demands more thinking time. And guess what? Strategic thinking doesn’t happen in the background. It doesn’t happen when we’re in full go mode. It needs stillness.

Here’s the challenge: If your identity is built on doing, downtime equals distress. Your addiction to doing fills every pause with withdrawal symptoms. Your knee starts bouncing under the desk. Your eye twitches. Thinking time feels like wasted time. 

Without planning and perspective, our business becomes freighted with the weight of compounded neglect. Process gets traded for speed. Hustle and grit substitute for models and systems. Problems compound.

Burnout awaits. 

The solution to all three is a shift from our natural approach to a proven model. It’s what we call moving from E to P – from an entrepreneurial to a purposeful approach. For a deeper dive into these three challenges and some solutions, check out this week’s podcast.

One question to ponder in your thinking time: Where do I need to level up my approach to break through?

Make an Impact!
Jay Papasan
Co-author of The ONE Thing, The Millionaire Real Estate Agent & author of The Rookie Real Estate Agent