The paradox of success and why even smart, self-aware entrepreneurs don’t escape it

Lynn Rivest
2 min readApr 29, 2022

I have a fear of success.

A big part of success for me is having a profitable business that helps many people and that fuels the lifestyle I want. Because I haven’t saved enough money for the future, success means making more money than I ever have before. And I’ve seen what it takes to make that kind of money.

I don’t want to find myself in the same situation I see many successful entrepreneurs end up in.

In his book, Essentialism, Greg McKeown talks about the paradox of success with four predictable phases.

Here’s how the paradox of success breaks down for successful business owners:

Phase 1: By getting clear on your purpose (aka defining your niche to enable you to have the most impact), you become successful. You have a profitable business.

Phase 2: Once you’ve got this traction and have a successful business, you’ll get attention and more people will want to work with you. You’ll have more options and opportunities.

Phase 3: With more options and opportunities, you will take more on. Many of them will seem exciting and interesting and you’ll end up getting spread too thin. Your efforts become diffused.

Phase 4: A number of areas of your work and life will be diminished because you’ve got too much going on. And that keeps you from focusing on the things that matter most. The things where you can make the highest impact.

“The effect of our success has been to undermine the very clarity that led to our success in the first place.” ~Greg McKeown

You find yourself scrambling to keep up and doubting how sustainable this success really is.

I’ve seen this first hand in my work with entrepreneurs.

Their relationships and mental and physical health suffer. The momentum of their success got away from them and they feel like all their efforts were for nothing but more money in the bank. They end up feeling a whole mix of shitty emotions and it just sucks.

These successful people are smart, self-aware business owners. And yet, they couldn’t escape the paradox of success.

There is a different way to do this.

Knowing what happens as you get more success, you can plan for it. At its core, this is what building a minimalist (or essentialist) business does. It keeps you focused on the essentials so you can succeed without compromising your values in the process.

It’s not easy but by embracing simplicity and specificity, and checking in consistently, it is absolutely possible.



Lynn Rivest

I talk about building a minimalist biz + aging boldly as a midlife entrepreneur.