The High-Achieving Entrepreneur’s Biggest Challenge

Lynn Rivest
2 min readMar 12, 2022

In school, I was a high achiever. I played by the rules. I knew how to do well on tests and assignments to get a high score in the game.

Like most games, the game of school provides consistent feedback and rewards through grades, gold stars, praise, certificates, ribbons etc.

The dirty truth about being a high achiever

There are a ton of articles out there about the traits and behaviors of high achievers. None of them mention the need for external validation.

But there’s no doubt that getting points and ‘winning’ is part of what drives us.

After school, when you enter the traditional work world, the game continues. You can collect points through promotions, raises, and accolades.

But after years of working and climbing the corporate ladder, trying to break through the glass ceiling, you see and feel the limitations of this game.

You no longer want to play by someone else’s rules.

Your top player status doesn’t transfer to your business

You want to do your own thing, to play a different game where you are the intentional creator of your work and life.

And if you’re like me, you soon realize that the lack of structure and predefined systems isn’t so easy to overcome.

No one is waiting for you to show up. No one is giving you a deadline. No one is giving you a job description and helping you to set goals.

As a past top player, you now see that your high achievements were often predicated on these systems.

You get to define your own rules for success

So now that you know this, you can step up your entrepreneur game. Embrace the creation of your own structure and systems. They will define what you need to do to succeed and achieve in this new world.

You’re now playing a whole new game. Your own.

This post was created with Typeshare

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Lynn Rivest

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