The Power of Failure

A Short story

Matt DeMichele
7 min readMar 14, 2021

It’s funny how the things that teach us the most are not usually the experiences we expect to be learning moments. I learned that lesson earlier this week.

This year, I decided to make some radical changes to my life. To bring about that change, I decided to act on a few new sets of habits and a new daily routine. Part of my new routine is waking up at 4:15am every day of the work week. This is no small feat for me. I am neither a natural early riser nor someone who can get by on very little sleep. In the past, I had found the need to set eight or more alarms for myself on days I had to be at work early. Often, I still found a way to sleep through the alarms anyway.

Regardless, on Wednesday, I carried out the new habit and woke up at 4:15am. Being that it was finals week for me and the start of a new job, I woke with a little jolt of extra motivation. After a few minutes of brief struggle, I somehow managed to drag my half-asleep body out of bed, slumped through my bathroom regime, and plopped myself wearily on the chair at my desk. There, I began to carry out habit number two, which was to write down my daily goals and journal. Perhaps still in a mental fog of sorts, I don’t remember the process of writing. All I remember from the morning was that the words felt intentional, and my mind felt engaged in the task. Here, in its entirety is what I wrote:

“Executing on a vision is the area that I struggle the most in. I know that I’m capable of doing a great job at the things I set my mind to, but seeing progression is often difficult. Executing on goals involves a lot more discomfort than I previously imagined. It’s not comfortable to wake up at 4:15am to go run when you have the goal of running a marathon. It’s not comfortable to try things you’ve never done before in the attempt to carry out goals you’ve never executed on before. Execution nearly always mean pushing yourself past what is comfortable. That inevitably leads to failure.

I have been trained to avoid failures. It was instilled in me as a kid to never fail at things. In sports- especially team sports- if you failed, you got put on the bench, so I never failed there. In school, if you failed, you got a bad grade, so I never failed there. I became paralyzed by the fear of failure.

I have to seek out incredible failures. I need to fail harder than anyone else. When I fail, I will be given the incredible opportunity to learn things that only those who have failed get to learn. What an opportunity!”

With those words, I closed my journal, carried out the rest of my morning routine, and began my day. From there, I remember getting to the office early around 7:30am. I dutifully undertook the tasks of the day, and before I knew it, it was 5:00pm, and it was time to go back home.

On my way home, I took care of a number of errands: grocery shopping, a brief workout at the gym, and a few other easy tasks. As I parked my car back at home about a few hours later, I got a text asking if I could pick a few friends up from the airport. I didn’t have anything planning in my mental schedule, so I happily said yes. I couldn’t think of a good reason not to, and after all, I always take care of my friends.

Well, after a run to the airport and a few more hours had gone by, I finally sat myself back down at my desk around 9:00pm. I had set the goal for myself of finishing my two final projects by the end of the week, so I opened my computer and began to work.

To my shock and horror, however, I suddenly discovered that I had miscalculated the deadline of one of my final projects. The project I thought was due in three days was due that night.

Worse yet, the night was almost over, and to add insult to injury, I had forgotten another assignment that was already three days past due. I had a little under an hour to finish both the final project and to turn in the overdue assignment. Being that I was hopelessly far from finishing either assignment, I worked furiously but inevitably turned both in in half finished and wildly discourageable condition.

I was furious. Scowling and acerbic, I sulked around the bedroom, clenching my fists and biting my lips. I sulked to bed and lay there for what felt like an hour.

It seemed like I was on the brink of a meltdown. I had been waking up at 4:15am and going to bed around 11:30pm every day that week. I was working harder than ever before, trying earnestly to balance full-time work, entrepreneurial aspirations, and university classes. Was this finally the moment it all came crashing down?

I felt as though a mountain of stress had been building atop my shoulders and was now ready to come crashing down. What a terrible end to an otherwise productive and meaningful week. It seemed like the entirety of the week was a failure.

That is, until I remembered what I’d written early that morning. My night had indeed ended in sudden and annoying failure. But wasn’t that exactly the thing I said I wanted to experience? I had just failed. In fact, I had failed utterly and miserably. Wasn’t that the very opportunity I was looking for?

That realization washed over me. True, I’d failed on what felt like a massive scale for me. I failed to plan for a deadline and, as a consequence, failed a final project that made up the majority of my grade for the class. I had most likely failed the class. Being an adult student who has spent the last six years trying to struggle my way towards completion of an undergraduate degree, this wasn’t small failure.

Yet, beneath the waves of crushing anger and disappointment at myself, there had to be something to learn, right? If I had failed spectacularly, weren’t there underlying reasons?

As I lay in silence on my bed, I pondered that sentiment over and over again. The longer I considered it, the more I realized it was true. There were really underlying reasons I missed the deadline.

Although I’ve always considered myself to be a smart and responsible student, I hadn’t written down the deadline for the project anywhere. I checked the deadline in my syllabus several times, but I hadn’t taken the steps to write that deadline in a planner or calendar. I also didn’t set an alarm to remind me of the impending date.

Those were really the reasons I gave my time away to help friends out because, in the moment when I thought through my schedule, I didn’t have something to tell me what I actually needed to accomplish with the rest of the night.

Beyond that, I only needed to get groceries that day because I hadn’t gone to get them on my day off. Clearly, I hadn’t been taking care of my physical needs or keeping my living necessities in order. I was feeling that mountain of stress because I was trying to do too many things at once that week rather than prioritize tasks by deadline and importance.

After bringing these things to light, I slowly realized that the missed deadline was a jolting illustration of the many other underlying habits and patterns that needed to be fixed in my life. I had a broken system, and that broken system had caused the failure. Indeed, there were so many broken parts of the system, perhaps it was the pain of seeing just how much needed to be addressed that was keeping me from making the necessary changes. Overwhelmed by the task of fixing these things, but relieved I had come to some kind of catharsis, I finally fell into an exhausted sleep.

When I woke up the next morning — again at 4:15am — I clearly saw what had occurred the day before. Painful though it was, my failure to plan for a project deadline had been an invaluable exposure of the broken or non-existent systems in my life. If I hadn’t missed this deadline, perhaps I wouldn’t have seen this flaw until I encountered a much bigger project, with much more consequential deadlines. The failure, which initially threatened to ruin my week, was really an incredible opportunity to develop better systems of planning and organization. Armed with this knowledge, I paused before finishing my morning routine to write down four simple organizational improvements I wanted to make with my life.

  1. Write down every deadline in a calendar. Actually read the calendar and set alarms for every deadline.
  2. If a task doesn’t have a deadline, give it one and prioritize it according to its deadline. If I don’t have time to do that task now, push it back to a later deadline so that I can focus on the more important immediate tasks.
  3. Plan out the necessary, regular tasks in my life. For instance, plan when to get groceries, when to clean and organize the house, and when to eat meals. If I don’t plan these tasks, I won’t know how much time is left over for the more important projects.
  4. Be more intentional with my time. Although friendships and relationships are always the most important thing, I shouldn’t be afraid to check my schedule before agreeing to give my time away. Handle priorities first.

Armed with these simple rules of thumb, I felt a surge of confidence in my ability to meet deadlines and plan for important projects. These were necessary changes that may never have revealed themselves to me without a colossal failure of some sort. Rather than angrily curse the school for my poor grades, I was able to use the experience to become a better student and better person in the future. As I discovered, failure, far from being the bastion of destruction we imagine it to be, is in reality a stern catalyst for change which will change our lives if we allow it to. And somehow, this change in perspective makes all the difference.

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