Joe Webber
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Now That Failing Is Cool – 3 Lessons From Failing College

12 years ago I received an email that would change the rest of my life. I failed out of college. Pack it up kid, you’re done here. Time to go home and flip burgers. Enjoy the rest of your mediocre life in debt living paycheck to paycheck.

Fast forward to 2020. A year where, statistically, I should be out of work and scrambling to get by. I walked away with an income of $90,000. It hasn’t been easy (check out the graph below). So If you’re looking for a get-rich-quick scheme I’d turn around now.  

Find one goal and make it your top priority

How many of you set New Year resolutions? How many of those did you see through to the end? One? Two? None? That’s the problem with goals. For the majority, there’s not a strong enough why behind them. 

How many of you have lost a job? Been behind on rent? Lived paycheck to paycheck? Did you have a goal then? My guess is you did and you smashed the hell out of it. 

At the end of 2017, I lost my job. Forced to live at home. My girlfriend dumped me. On top of all that, I was trying to find a job in Chicago and being rejected left and right. One day, at the end of my rope, I had two choices. Either give up on the dream of living in a city that I’ve been pursuing for more than a year. Or push through one last time. I chose to push through. A few weeks later I accepted a job and signed a lease in Chicago. Oh, and I won the girl back. We’re getting married this May! 

Find a strong enough why behind the what and you’ll move mountains to get there.

Don’t wait for things to go your way

The saying “A watched pot never boils” is bull shit. Sure, a watched pot sitting on the countertop is never going to boil, but if you put a flame underneath, that sucker’s eventually going to boil.

I started my sales career in 2015. I was bright-eyed and bushy-tailed but lacked any confidence or backbone. For the first 6 months, I apprenticed under your typical sales guy. Type A, super cocky, and if you did something wrong, he let you know (Andy, if you’re reading this, I love ya bud, but you were a pain in the ass). With all that being said, his phone rang off the hook and his inbox was flooded.

I’ll never forget the day I moved off his desk. Silence. No phone calls. No emails. Nothing. I quickly learned the sale isn’t coming to you.

If you want it bad enough, go get it. Don’t wait for it to show up on your doorstep. “Action begets action”.

It’s okay to fail*

Over the years I’ve failed college. Been fired. Made redundant. Started 3 companies all of which crashed and burned. Lived at home twice (thanks mom). And was dumped. At the end of the day, I’m stronger because of the experiences I’ve been through. 

Think of your failures as trials and errors. As Nassim Taleb says in Antifragile, “If every trial provides you with information about what does not work, you start zooming in on a solution–so every attempt becomes more valuable, more like an expense than an error.”

*This section comes with an asterisk. The key to being antifragile is limiting the downside of your failures. For example, imagine I were to skydive from the Sears Tower (Willis Tower if you must…). Sure, there is a small chance that I was a Red Bull skydiver in a previous life, but one mistake, and I’ll see ya in the afterlife. On the flip side, I can start a company for less than $30 and if it goes belly up, I’m only out a round of drinks at the bar. However, if it works…

Go fail! But fail small, learn from your mistakes, rinse, and repeat.

Want more?

I share all of my trials and errors on Twitter. You can follow me there as I continue to document my journey.

Published February 17, 2021

About the author

Hi, I’m Joe Webber. I write a daily blog to remind myself of where I want to go and the steps needed to get there.

In 2017, after failing out of college and 10 years of aimlessly floating along, I woke up and realized there was more to life than just going through the motions.

Since then, I’ve been on a relentless pursuit to ditch average and live a life worth talking about.

I write about my wins and losses so others can avoid my mistakes. I hope you’ll follow along:

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