Think of a time in your life when you truly failed. You reached for something and fell short, or otherwise lived through a disaster that was at least partly of your own making.

What happened?

This is what Chris Guillebeau asked his readers this week in a blog post. I think it’s a great idea. If you have time today, this weekend, or next week, I encourage you to reflect on a time when you failed, missed the mark, or did something completely foolish. He’s asking for people to share their stories, so I decided to share mine with all of you. Even if you don’t submit your reflection to Chris, it’s a good exercise to do.

As many of you know, I'm a big fan of failure. I know that's an odd thing to say. And yes, I guess that makes me a bit of a pessimist, but that's only because I see the value in making mistakes (what Nassim Nicholas Taleb calls “antifragility”). Failure teaches us where our skills are, where they need to be, and what we need to work on. My failure rate is always higher than my success rate—and that's not a bad thing. If I hit grand slams all the time, I would miss out on a lot of learning opportunities. For me, failure is feedback. It is where learning begins. And because I'm always learning, I'm always failing.  

I didn't always have this mindset. My biggest failure (or, series of failures) happened when I was in school working towards my bachelor's degree. I was beginning my senior year and I had no idea how to make the next step from school to a career. I was told that going to school and getting a degree would unlock a stimulating career where I would earn a comfortable living. After 3 years at the university, I reaized that wasn’t entirely true. Despite having some good qualifications on my resume, I was rejected over and over … and over—from internships and entry-level positions.

To paint a picture, it was Michigan in 2011-2012 and the economy was still recovering. I was finishing a degree in Writing and Philosophy and hoping to work at any wage doing what I love: putting words on paper. I was applying for journalism jobs, writing copy at insurance companies, healthcare companies, government jobs, anything that popped up and had "writing" or "content creator" in the job description. Over 100 emails were ignored or rejected. I started thinking: If my writing degree is worthless, why finish? I dropped out during my senior year and in 2012 I packed a bag for Seattle, where I told myself, and anyone who would listen, I was going to be a writer. You know, a real writer. Dropping out of school was only the beginning of a long string of failures.

(This brings up the question: what is “failure” and what is “risk”? If failure is part of growth and development, it’s only truly a failure if one does not recover from it.)


How big of a failure was it?

It wasn't one failure, it was several. And I’m happy they came one after the other instead of all at once. I think it's better to fall off 10 five-foot rocks than one 50-foot tall boulder. I think that’s why people say: fail early and often because small failures build us up. If someone doesn’t have that resilience built up, they may not recover from the 50-foot fall.

When I dropped out of school and moved to Seattle, I “failed” because I was so close to graduating and I literally gave it the middle finger. (The digit in question was visible, poking out of the driver’s side window of my yellow VW Beetle, while the other hand was slamming down on the horn, trying to attract attention to myself in front of the admissions building. I shouldn’t have done that, but I was 22 and hadn’t encountered, or recovered from, any major failure. I had a 50-foot fall—failing to secure a career—and didn’t have any built-up resilience for it.) When I moved 2000-plus miles away from home, I left my community, my friends who were my emotional support, and everything else that felt like "home," all to go to a place where my favorite writers lived. I had student debt, little cash, little support from friends (because I was leaving them), and no job. In addition, when I moved to Seattle, I expected the people there to be as warm and friendly as those I grew up with in the Midwest. What I found was that the people were just like the weather: cold, damp, and kind of depressing. I learned that Seattleites like their privacy and were cautious of new folks who they assumed were taking all their jobs and raising their rent. Networking was tough. I had a hard time joining the established writing communities because they weren’t looking for new members. Who was I? And to be completely honest, I didn’t have much to offer.

Just like Spanish Captain Hernán Cortés, who ordered his men to burn their ships upon arriving in Mexico, I was forced to either die or fight, because retreating wasn't an option. I, too, had burned all my bridges that led back home. I found myself in a very expensive city (compared to Michigan) with no job, no friends, no money, no college degree, and no skills to find a job. It sucked. I immediately went into panic mode just to survive. I remember selling some silver coins my grandfather had given me to a pawn shop just to have enough money for bus fare. I lived on rice, carrots, and peanut butter because I couldn’t afford anything else. If this was a movie, it would be the part where everything has gone wrong and the best intentions in the opening act ended up paving a road to hell. 


Did you ever fully recover? If so, how?

I started locating the area homeless shelters, so I knew where to go if the worst came. Even though I was determined to succeed, I wanted to have a plan in place if it didn’t work out.

I was able to captivate the attention of a couple business owners who later became mentors. My opinions about the disconnect between school and the workplace resonated with them because they worked in creating training material for some of the biggest tech companies in the word. They also recognized that their generation is on the verge of retirement and hiring replacements proved to be incredibly difficult. They told me connecting with and hiring millennials was the hardest part of their job. Millennials, even the ones who graduated from top schools, have a hard time bridging the gap, and if they don’t find competent millennials to replace the key managers at their companies, the future of many companies looked bleak. I told one of them that I didn’t understand, because I had dozens of friends looking for a good job, but no one wanted to hire them.

Exactly, he said, we have a lot of young people applying for jobs, but few of them can do the work the position requires.

That became my mission: to help people my own age develop the skills they need to be successful in the new agile workplace. This included a lot of learning (and failing) in the process.

In the last six years, I have encountered a lot of failures and a lot of success. In the process, I was given the opportunity to work on exciting projects I had only dreamed about and I met people I used to read about. While working in Seattle, I finished my degree at the University of Washington. Even though it didn’t change my life or career, it was a note that added consonance to a dissonant chord in my life. In December of 2017, I published my first book and I’m in the process of outlining book #2. Currently, I am the Director of Apprenticeship at a company south of Minneapolis, MN, and I’m always the youngest person in the room when I meet with the Department of Labor and Industry and the Department of Education. It’s exciting and fun, but it’s the result of a lot of work in response to failure. I would have never gotten here if I didn’t burn my ships in 2012 and made massive mistakes. Because I couldn’t capital “F” fail, I was forced to see failure as feedback. For me, failure was never defeat, it showed me where my skills were lacking and where I needed to focus on to grow.


How much time has passed since the failure occurred?

About six years from the initial failure that set off my series of failures.


Looking back now, how do you *feel* about the failure experience?

As I said earlier: failure is not defeat, it is a necessary condition for success. If you look at anyone who is successful, their past is filled with failures they accepted and responded to positively.


Looking back now, what have you *learned* about the failure experience?

I don’t share my experiences to say, “If I can do it, so can you.” I’m not a fan of that kind of bragging, because it doesn’t really help anyone. It doesn’t provide any actionable steps that can be replicated. What I can say is since I have experienced a lot of failure, I have learned tools and strategies I can share with others who are struggling to find the motivation to respond positively to failure. The key to making failure work in your benefit is directly linked to your resilience. Soft skills like emotional intelligence and emotional resilience are the most important factors in achieving your goals.


Is there anything else you’d like to share?

Everything we do is a risk. But without risk, there is no reward. And if it’s a reasonable risk, the action itself is rewarding, even if it doesn’t play out exactly as you planned.



Andrew J. Wilt is the author of Age of Agility, a book that addresses the skill gap between school and work. He can be reached at and on Twitter @andrewjwilt
how to deal with failure