There’s one thing about me that I’ve had to wrestle with for years: perfectionism. You know, that nagging little voice that says, “If this isn’t absolutely flawless, you might as well light it on fire and start over.” As a founder, this trait can feel like a double-edged sword. On one hand, it drives you to push boundaries and deliver exceptional work. On the other, it makes you feel like crap, even when you’re doing well. Because nothing ever feels good enough.

At the end of 2021, I felt like I spent years striving, hitting milestones, and still feeling this weird inner tension, like I was sprinting on a treadmill that wouldn’t stop. Then I stumbled upon Dan Sullivan’s The Gap and the Gain.

The concept? Simple but deeply profound. It reframes everything you thought you knew about striving for success. My problem wasn’t that I wasn’t delivering great results. It was that I was measuring myself against an impossible ideal, a moving target I’d never actually reach. The gap wasn’t in my results. It was in my perspective.

Add Gay Hendricks’ The Big Leap into the mix a few months later, and I started piecing together an entirely new way of thinking about achievement, happiness, and success. Let’s talk about what these two books can teach founders and entrepreneurs about conquering their inner perfectionist, stepping out of self-sabotaging habits, and finally feeling like they’re winning.

Let´s start with a powerful observation: Most high achievers live in the “Gap”. What does that mean? It’s the mental space where you compare where you are now to where you think you should be. That hypothetical, ideal future version of yourself who’s crushing every goal and never making mistakes. Spoiler alert: That version doesn’t exist.

Living in the Gap makes you feel like you’re constantly falling short, no matter how much progress you make. You could scale your business to seven figures, hire a dream team, and still wake up thinking, “Why didn’t I hit eight figures this year?”

The alternative? Living in the “Gain”. Instead of comparing yourself to some unreachable ideal, you compare where you are now to where you started. By focusing on progress rather than perfection, you start to see how far you’ve come instead of obsessing over how far you still want to go.

The Founder’s Gap

For entrepreneurs, the Gap is a familiar (and brutal) place. You land your first big client, and instead of celebrating, you’re immediately asking, “Why didn’t I get two?” You launch a successful product, but all you can think about is, “What about the next version?”

Living in the Gap doesn’t just rob you of joy. It kills momentum. When you’re stuck feeling like a failure, it’s hard to stay motivated, even if all the evidence says you’re crushing it.

Moving to the Gain

For me, shifting to the Gain isn’t just a mindset tweak. It’s a survival strategy. Instead of chasing some abstract future ideal, take stock of what you’ve actually accomplished. Look at the risks you’ve taken, the skills you’ve developed, and the hurdles you’ve overcome.

Here’s how I put it into practice: At the end of every week, I write down three things I’ve achieved. Not what I could’ve done better, but what I actually nailed. It’s a small habit, but it shifts the focus from “not enough” to “damn, look at all this progress.”

If The Gap and the Gain is about reframing how you measure progress, Gay Hendricks’ The Big Leap is about identifying the self-imposed limits holding you back. Hendricks introduces the concept of the “Upper Limit Problem”. The subconscious barriers that stop you from going all-in on your success.

The Upper Limit Problem

Ever notice how when things are going too well, you start sabotaging yourself? You finally land a huge deal, and instead of celebrating, you procrastinate on delivering the next pitch. You hit a personal milestone, and suddenly, your inner critic goes on overdrive. That’s your Upper Limit Problem in action.

Hendricks explains it like this: We all have a comfort zone for how much success, happiness, and fulfillment we think we deserve. When we start to exceed that zone, our brain freaks out and pulls us back down. Like a thermostat kicking in to keep things “comfortable.”

Entrepreneurs are especially prone to the Upper Limit Problem because the stakes are so high. You’re not just chasing success. You’re trying to prove something. To your investors, your team, your family, and yourself.

For me, this showed up as perfectionism. If I wasn’t over-delivering on every single project, I felt like a fraud. And when I did start hitting my stride, I’d find ways to undermine myself. Taking on too much, second-guessing decisions, or obsessing over details that didn’t matter.

The solution? Expand your comfort zone. Recognize when you’re self-sabotaging and push through it. The more you get comfortable with success, the less your brain will try to drag you back to where you started.

One of the most powerful ideas is the concept of your “Zone of Genius.” This is the space where your natural talents and passions overlap, where you’re not just working hard. You’re working effortlessly. For founders, this means delegating the stuff you’re mediocre at and doubling down on what you’re uniquely great at.

For me, this meant stepping back from micromanaging every detail of my business. Focusing on the areas where I bring the most value like strategy, vision, and problem-solving. It wasn’t easy to let go, but it freed me up to make bigger moves without getting bogged down in the noise.

Combining the Gap, the Gain, and the Leap

What happens when you combine Sullivan’s focus on celebrating progress with Hendricks’ push to break through your limits? You get a game-changing approach to both life and business.

1. Measure Progress, Not Perfection
   Start by living in the Gain. Every time you catch yourself comparing your current reality to some hypothetical ideal, stop. Instead, ask, “Where was I six months ago? What have I accomplished since then?”

For founders, this might mean revisiting your original business plan and realizing just how far you’ve come. It’s not about lowering your standards. It’s about recognizing the wins you’ve already achieved.

2. Smash the Upper Limit
   The next time you find yourself procrastinating or doubting your abilities after a big win, call it out for what it is: resistance. Then ask yourself, “What’s the worst that could happen if I kept going?” Nine times out of ten, the answer is “nothing catastrophic.”
3. Focus on Your Zone of Genius
   This might mean delegating tasks you hate, saying no to opportunities that don’t align with your vision, or setting boundaries around your time. The goal isn’t to do more. It’s to do what only you can do.

Why This Matters for Founders?

The entrepreneurial journey is full of highs, lows, and everything in between. It’s easy to get stuck in the Gap, obsessing over what’s next instead of appreciating how far you’ve come. It’s just as easy to hit an Upper Limit and convince yourself you’re not ready for the next big leap.

Don’t look at this as just another advice. See it as a blueprint for rethinking success. By focusing on progress instead of perfection, celebrating your wins, and leaning into your Zone of Genius, you can build a business (and a life) that doesn’t just look successful from the outside. But actually, feels fulfilling on the inside.

So, the next time you’re stressing over an unattainable ideal or second-guessing a well-earned win, take a step back. Measure the Gain. Take the Leap. And give yourself the credit you’ve actually earned.

Takeaways

1. Measure Progress, Not Perfection
   Stop comparing yourself to an impossible ideal and focus on how far you’ve already come.
2. Celebrate the Wins
   Living in the “Gain” means appreciating achievements, no matter how small, rather than dwelling on what’s left to do.
3. Break Through the Upper Limit
   Recognize and push past self-sabotaging habits that keep you from embracing success.
4. Focus on Your Zone of Genius
   Double down on what you’re uniquely good at and delegate everything else.
5. Success Is About Perspective
   Happiness and fulfillment come from how you frame your achievements, not just from achieving more.
6. Take Small, Consistent Leaps
   Growth happens when you expand your comfort zone incrementally, not all at once.
7. Progress Over Perfection
   Perfectionism is a trap; momentum and action lead to results.