Failing Greatly: How to Fail Upward, and Look Great Doing It

I was meeting with a student over coffee last summer when he proposed an interesting question: “If you could go back and tell your 18-year-old self something, what would you tell him?” “Great question,” I responded with no immediate response. Generously giving me a few minutes of silence to think about it, I came up with three things I would tell my 18-year-old self, nearly 20 years later: 1) Surround yourself with a group of great guys, meet with them regularly for support, and never stop this habit. 2) When dating, do NOT radically change your routine, but be steadfast in incorporating your new found love in your routine, and find time to saturate yourself in her routine. 3) Fail often and fail greatly! Surprisingly, with over a year separating my encounter with that student, I’m still satisfied with my answer. Of the three life lessons, the third has convicted me the most, and it is the one I would like to explain in greater detail.

Leaning Into Failure

To be honest, the first two answers came relatively quickly. The last one did not come until the end of our meeting together—almost as an afterthought. Looking back over my life, I see that it was my fear of failure that prevented me from building strong and committed male friendships, and it was my fear of failure that swept me off my feet in dating to the point where I would forego every previous passion and responsibility in the name of romance. The reason why I was so accommodating, easily to get a long with, and altogether malleable was because I did not want to lose the things I had. What I was telling myself was, “You do not deserve the things you currently have. Don’t screw this up by inserting yourself into the picture.” Of course I was going to avoid any chance of failure, because that would mean I inserted myself in the picture. How seductive this line of reasoning was. The end result? A conflation of two words: me and failure.

If only I could grab my 18-year-old self by the shoulders, shake him, and say, “Lean into failure! Realize that failure is the raw material of a life well lived. Anything else is a sham, a lie, and a pathway to regret. The quickest way to lose your life, is not to risk losing at life. Be courageous, be steadfast, and do NOT be afraid to be yourself.”

Thomas Edison Quote

Rehabilitating Failure

  • For failure to become attractive (or at least worthy of risking), it must be rehabilitated. Currently, our culture perceives failure as a manifestation of our true potential: failure means we have no potential, and that we are a fake. I believe this perception comes from a recent type of entertainment I would like to call “social voyeurism.” This is where we watch the successes and failures of people from afar, finding entertainment in someone else's drama. In essence, this is what reality TV is about. The problem is that we are perceiving an overly simplistic picture of the individuals on screen, and this provokes us to make insensible conclusions. We wrap these shallow perceptions with tag lines like, "What a loser," or “Once a failure, always a failure,” or “He/she was made for success.” Moments later, we begin comparing ourselves to the shallow images on screen, and thus the prison sentence begins. Such a sentencing enshrines a static and impermeable image of ourselves, ensuring our real possibilities are safely protected behind bars. We end up creating a self-fulfilling prophecy by molding ourselves into a much more limited human being than what we could have been.

  • Failure is the raw material of success. Without failure, we are blinded to the path of self-fulfillment. The more we can lean into failure, the more we will learn, the more we learn, the better equipped we are to make better decisions, and the better decisions we make, the closer we come to self-fulfillment. To be clear, failure is not the goal. Rather, our goal is to succeed with the understanding that failure is a critical component to success. Here are three ways we can better lean into failure, making our setbacks the linchpin to success.

Prepare to Fail (and Succeed)

  • What would it look like for your plans to achieve unprecedented overnight success? What would it look like for your plans to become a complete failure? There is no reason to be caught off guard by successes or failures. Make plans for both ahead of time. It isn’t unheard of for unexpected successes to become failures due to a lack of planning.
  • Reduce your opportunity costs as much as possible. In other words, start small. By starting small, you provide the opportunity for quicker course corrections. Learn from the many businesses who spent years working on the next big product, spending hundreds of millions of dollars only to hear crickets on release day. By then, it is simply too late. Start small, test the waters, and allow for quick iterations of feedback along the way (i.e.. friends, family, co-workers, test markets, etc.).
  • Create a tripwire to prevent unrecoverable loss. The last thing you want is for your failure to follow you for years-on-end. Rather than blindingly pushing ahead, set predetermined check points along the way. For instance, instead of going tens of thousands of dollars into student loan debt, you may decide not to entertain anymore than twenty five hundred dollars of debt per year. You decide that the financial remainder will be paid through scholarships, grants, and working a part time job. If the loan amount reaches twenty five hundred before the academic year ends, you immediately stop to evaluate the options available (i.e. look for a higher paying job, more grants, or scholarships, taking a semester off to build up a little nest egg, or evaluate the opportunity cost of taking on more debt).

Fail Greatly

  • With a plan in place, lean into the risk of failure. Rest with confidence that the plan you have in place will keep you from undo harm. Remember, when and if failure occurs, you have just brought yourself one giant step closer to success.

Fail Upward

  • Those who fail upward are the ones who continuously see setbacks as opportunities for growth. They lean into the learning experiences from failure.
  • Do not take failure personally, and remember that those who you admire most have failed there way to admiration status.
  • Unearth the veins of gold hidden in failure by growing from it. With serious analysis in place, determine whether it is time to pivot or persevere. If the majority of information points to moving forward, then persevere. Michael Jordan is a hallmark example of perseverance. Not making varsity as a sophomore in high school, rather than quitting altogether, Jordan persevered to become the greatest NBA player in history. On the other hand, the creators of the widely popular communication tool Slack is an example of pivoting. Initially trying to achieve financial stardom through the creation of a video game called Glitch, they created their own internal communication tool to help them collaborate better. The video game was a complete failure, but what they ended up unintentionally creating was a new one billion dollar business through their communication tool, Slack. Talk about a successful pivot!

Rinse and Repeat

Don’t stop now. Keep going and don’t quit. Realize the gift of failure, plan accordingly, lean into setbacks, and when and if you fail, fail upward! See you on the cover of Forbes.