How Epic Failure Leads to Massive Success

coaching entrepreneurship expert advice goal setting goals online business woman entrepreneur Aug 25, 2021

We can’t talk about entrepreneurship without bringing up that four letter word FAIL!

If you’re reading this, and you’re an entrepreneur, then I’m going to assume that you know that failure is a good thing. 

I’ll assume you know putting yourself out there as a business owner, making mistakes, and learning from them is how we grow as individuals and as entrepreneurs… and it’s also how we grow our businesses. 

So I’m not going to share WHY failure is necessary because you already know that. I’m going to talk about failing on purpose.


Stick with me as I dive into the Failure File.

I learned about the failure file from Ramit Sethi who is the author of I Will Teach You To Be Rich and the book Your Move: The Underdog's Guide to Building Your Business.

Here’s the deal (and any successful entrepreneur will tell you this), if you want to be more successful then you need to double, triple, or quadruple the amount of failures that you experience.

You want to be successful - you need to fail more.

The failure file is failing on purpose. Let’s say you commit to making three failures a week. These are failures where you are seriously stepping outside of your comfort zone so if it doesn’t go as planned... you feel it.

Then you document all your fails in a failure file.

Create an excel spreadsheet or a Google Doc, and record all your failures. This will allow you to constantly fail and try new things. 

When you are focused on making a ton of mistakes the fear dissolves. When your focus is failing on purpose it takes some of the anxiety out of the process. 
It slightly lessens that daunting feeling because there’s really nothing at stake… other than the speed of your success.

As you start documenting your failures, you'll experience a bit of a charge! You'll see the list getting larger and larger, and in a strange way it will trick the brain into motivating you to do more.

Look, as entrepreneurs we are going against the human condition, we are constantly walking directly towards pain - and as humans we’re wired to move away from pain and towards pleasure.

Entrepreneurs are different - in order to build successful businesses, we must constantly walk towards pain.

So when you plan these fails and document them, and recognize, "Hmmmm, I didn’t die…", you'll start reprogramming your brain.

Now... will you still have to deal with all your doubt demons telling you you're crazy and to stop putting yourself through this? Yes, of course!

Many of you will also have to deal with your friends and family telling you to stop because they might see what you’re doing as masochistic!

What they’re not seeing is by you CHOOSING to put yourself in a position where you will most likely fail… you are speeding up your journey to achieving the outcomes you are working towards.

And here’s a little secret I’m sure you’ve already figured out… As you do this, guess what’s going to happen? Some of these goals you set for yourself you’re going to achieve!! But they wouldn’t have happened unless you set them up as one of your fail goals.

So, what could some of your fail goals be? 

Let’s say your fail goal is to sign up 15 new clients over the next 7 days.

For those of you who are thinking, "15 new clients over the next 7 days?! That’s never going to happen". GREAT! Go for it anyways, work towards making it happen, and at the end of the week add it to the failure file.

There’s something so satisfying about adding your fails to the failure file list. You feel like you've achieved something, because you have! You committed to a goal, worked at it, and then added it to a list that shows growth and determination.


And bonus win if you ended up adding 1 or 2 new clients because of your efforts. Do you see how this works???

Set up your Failure File, and then set goals for yourself that really put you outside your comfort zone.

Share your epic fails with me and we’ll celebrate together!

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