What 20 Years of Failure Taught Me

I want to talk about an important subject here: The major failures I've had in my career -- but also how they've led to major wins! One of the ones I talk about in this video was hitting a cap on what I could charge as a freelancer and how rethinking how I price myself led to tripling my freelance rate overnight. Anyway, I'll get to that.

A while ago, I was asked to speak at an event in Paris, alongside Dan Roarty, Ash Thorp, Neil Blevins, Ryan Church and about a dozen other amazing speakers.

​I originally wanted to talk about branding, but then I pitched this to them: "What if I actually talk about all the failures I've had over my career?" Because to me this is much more valuable than anything else.

I think a lot of us just assume that there are certain people who "made it" that had instant success and continuous success throughout their career. If you have followed me for a while (Then: THANK YOU!), you probably know how I see failure. I see it as part of the process. And I welcome failure, because:

  • ​It helps me determine what worked and what didn't;
  • ​Helps me learn and better myself;
  • But ultimately, it helps me reach that success point!

​In the beginning of my career, I failed a lot. I got rejected a lot. I almost gave up on my career and went back to school because everyone told me I wouldn't make it, and everyone told me to get "a real job".

And as much as you want to say fuck it -- and know that one day you'll prove them all wrong! -- after the 10th, 100th, rejection, it's very easy to start to question yourself. It's easy to start to replay all those voices telling you you're going to fail, and that it's all just a waste of time.

"I look at failure in every win that I have, 
and I look for lessons in every failure
that I have. 
The one thing I don't beat myself up about -- 
is failure."

I shared this talk because I wanted to tell you how I managed to fail so much -- and so often! -- in between all the wins. And that I don't see failure as a negative thing, unless you continue to make the same mistakes. I look at failure in every win that I have, and I look for lessons in every failure that I have. The one thing I don't beat myself up about is failure.

Don't get me wrong: There have been times when I've failed in a big way. I got fired, I got kicked out of the home I was staying in, I had no money to my name to get me out of the situation. There have been situations like this in my life that have really impacted me -- but that also fueled me to say, "NEVER AGAIN!" Because those failures have drastically impacted my life, they've taught me to do whatever it takes to prevent those things from happening again. They taught me to work harder, taught me to check in with my employers, the people I live with, to prevent unforeseen circumstances from ever reaching that boiling point.

But there have also been those situations where things aren't all that bad. They're just not where I want them to be. I discuss this in the video as well. For example, I wanted to raise my rates, but I hit a cap. I couldn't charge any higher, I was "too expensive". Still, I felt like I was undercharging. And so I plateaued. I hit the same price point for many years. That is until I rethought how I should price myself -- and I was able to triple my freelance rates overnight.

I want to share all of these insights that I've reflected on over the past 20 years. I hope they're able to help you not to have to experience them yourself -- and to piggy-back on the big "Aha's!" I've had across my career.

I'd love to hear your thoughts on this video, and perhaps some key insights that might relate to your own career. Shoot me an email: [email protected].