Dan Waldschmidt

by Dan Waldschmidt

September 4, 2018


You’ve heard that motivational question before: “What would you do if you knew you couldn’t lose?”

The intent is to get you to think bigger. To realize that your perceptions of reality and deep-seated beliefs control the size of your dreams. 

If you think something is impossible, you act like that. You might attempt to achieve the impossible, but you won’t have enough courage, enthusiasm or tenacity to keep on fighting after you’ve failed a few times. 

The question is a good one. You should ask yourself if your dreams could be bigger. If your goals and beliefs are grand enough. 

But maybe, at the heart of the matter is a more powerful question. A question that gets to the heart of your daily reality. 

What will you do knowing that you are going to fail? 

You know it. I know it. Everyone knows it. You’re going to fail more than you don’t fail. The times that you win are the minority. 


No matter how good you are at what you do. No matter how much knowledge you’ve gathered over the years. No matter how many connections, advocates, or luck you have in your corner. 

Small failures are all around you. They are inescapable. A part of your daily existence. Your hourly existence. Your minute-by-minute existence. 

And while it could be a depressing reality, it doesn’t need to be. And it shouldn’t be. 

The idea of winning wouldn’t exist without the reality of failure. Failure should cultivate your thirst for achieving big dreams. 

Every time you try something new, you are choosing to win. 

You could give up and not try anything. That would stop most of your failure. At least the public kind. 

You can go through the motions and pretend like you’re trying. That too would stop a lot of your failure. 

But there is something magical and deeply inspiring about giving something a “go” even when you know it could backfire magnificently. That you could lose money and time and reputation. 

It’s also the simplest path to success. 


Knowing that you’re likely to fail and still heading into the battle with the belief that no matter what happens you’re going to get back up and try again. Time after time after time — until you get to where you want to be.

What will you do?

About the author

Dan Waldschmidt

Dan Waldschmidt doesn’t just talk about leveling up. He’s obsessed with it. He's set records as an ultra-runner and been the personal strategist for the leading business leaders of our time. He wrote a book, called EDGY Conversations that accidentally became a worldwide bestseller and continues to share his insights from the stage as a keynote speaker and on the blogs and podcasts you will find here. Most days, you'll find Dan heads-down, working on breakthrough strategies for his clients at EDGY Inc, a highly-focused, invite-only, business strategy execution company based out of Silicon Valley.