The Failure File

Once we learn how to handle failure, we can use it to our advantage.

Photo by Anete Lusina on Pexels

Author’s Note: This is part two of a two-part series on failure. You can read part one here.

One morning in early January 2018, my phone alarm buzzed at 8 am. Bleary-eyed, I got out of bed to begin my workday routine. Ten minutes later, as I stood in front of the coffee machine ready to scoop grounds into the top, it hit me: I had no job to get ready for. I was unemployed. There were no meetings on my calendar. No tasks I needed to complete. Nothing. My schedule was a blank slate. 

I climbed back into bed. As I closed my eyes, I tried to clear my mind and drift back off to sleep. Instead, I ruminated on the big-picture question I had been avoiding the last few days: 

Now what? 

I had quit my job a month before and still didn’t have an answer. The uncertain feeling that now permeated my life was both terrifying and liberating. At first, the devastation of my professional failure had cast a pall over the Christmas holiday. It took several weeks to process the emotions. I was thrown into a horrible funk, but once the dust settled, shortly after the New Year, I realized that I had made the right decision. My sleep had improved, and I no longer felt like I was going to have a heart attack every day. That alone made it worth it.

But at some point, I would have to face the future. I had bills to pay. I had to get my career, and my life, back on track. As I fluffed my pillow under my head, I wrestled with the direction of my life for a little longer before deciding to get up.

Twenty minutes later, I was sitting at my desk, unsure how to start my day. I didn’t know what to do, only that I had to do something. I was a creature of habit and regimentation and knew that the longer I went without structure, the worse off I’d feel. 

In the back of my mind, I could hear a voice scolding me for not having a better plan. I had quit my job on a whim without a blueprint to deal with the aftermath and now I was paying the price. I was yearning for direction. 

After reading up on the previous night’s Uconn men’s basketball game, I began to Google famous people who had dealt with failure. I needed inspiration any way I could get it. If I could see that someone successful had dealt with a crushing setback in their life, it might help me better come to terms with my own.

I hit the jackpot. I found example after example of people from all walks of life - both famous and ordinary - who had encountered various failures and setbacks and who used these low moments as fuel for something greater. 

This provided a small glimmer of hope. Maybe my failure wasn’t so unique after all. This knowledge - that once I properly processed my failure, there was a way I could use it for good - encouraged me to pick up the pieces of my life and begin anew. The future was scary, but no longer soul-crushing. If others could do it, so could I.

In the weeks and months that followed, through trial and error, I was able to transform my circumstances. My low moment became a catalyst for a better life. Five months later, I started a job that was a much better fit for my skill set and career aspirations, one that I am still in today.  

But even though I was able to get my career back on track, I knew that I needed to document this process. I needed to log which techniques worked in handling failure and which didn’t. Which strategies yielded benefits, and which ones left me spinning my wheels. 

By the end of the process, I had a series of notes in Evernote - what I would later call my “Failure File¹” - that I could reference for inspiration and guidance any time I experienced a setback. 

Evernote is what I use to record my notes. OneNote or another equivalent program works well too. Photo courtesy of Evernote.

The road to success is littered with past failures

In my previous newsletter, we explored how to frame failure and put it in its proper context so that it becomes less fearful. Although unpleasant, failure is something we all experience, and it is important to know how to deal with it when it strikes.

If the first step is to develop a healthier relationship with failure, the next step is to use failure to our advantage. That is the goal of today’s newsletter - to share with you some of the strategies and techniques that have helped me over the years, the same strategies that are in my “Failure File”. 

This is not an exhaustive list of strategies by any measure. Some of the techniques might resonate; some may not. That is okay. It is an individualized process, but it is good to know at least what options are available. 

A quick note of clarification: learning from failure doesn’t automatically mean that success is right around the corner. In fact, the learning process frequently leads to more failure (such as when you are running an experiment and testing different hypotheses). The learning process also might simply tell us what NOT to do next time. 

We can’t eliminate the pain of failure, but if we are prepared to deal with the pain head-on so it loses some of its potency, that is half the battle.

The following strategies can help to accomplish this goal:

1. Commit to staying the course

The simplest - yet often the most difficult - step when encountering failure is to commit to staying the course. It is not easy to say yes to opening yourself up to more failure. But if you really want something, or want to move beyond a crushing setback, you have to be prepared to face your fears. It won’t be easy, and it requires a level of vulnerability you may not be comfortable with at the moment. But the only way past failure is through it.

There is a quote by Lance Armstrong (who I know has a complicated legacy) that I think about often:

“Pain is temporary. It may last a minute, or an hour, or a day, or a year, but eventually it will subside and something else will take its place. If I quit, however, it lasts forever.”

I don’t mean to go full-blown motivational speaker here, but his quote is instructive. In our darkest moments, when we’ve encountered a painful failure (or repeated failures), the urge is to quit. If we pick up our ball and go home, or delay facing our failure yet another day, it might make us feel better in the short term. But long-term, the lingering pain is often much worse than the failure itself. We can’t run away from it forever.

So before you do anything else, you must ask yourself: is this failure going to define you? If the answer is no, great. You are ready to move on. If the answer is yes, then unfortunately none of these remaining steps are going to matter. 

I have to answer this question all the time after a failure, when I am tempted to let my frustrations snowball out of control. I have to recommit to staying the course.

The closest I came to letting my failure define me was after I quit my job. I had to remind myself over and over that I had done hard things before and that I would eventually get through this tough time. It took several weeks before this affirmation sunk in. I also had to ask myself if I was going to be okay experiencing additional failure on my upcoming job hunt. I had to be 100% sure that if I burned out again in my next job, I would vow to continue, even if it required a lifestyle adjustment. 

Only when I was confident that I would stay the course, no matter what, did I feel comfortable moving on.

“The phoenix must burn to emerge.” - Janet Fitch

2. Reach out to your network

Failure is a humbling experience; so is asking for help. When we fail, the urge is to hide it away out of sight and not tell anyone what happened. If someone asks, we either lie about it or deflect. But sometimes, telling others about our failure is one of the most productive steps we can take. Not only can our family and friends offer emotional support, but they may also provide advice, offer assistance, and in certain instances, introduce us to others in their network who can lead us to where we want to go.

For me, asking for help was just as difficult as resolving to move on from my failure. How would I tell people that I chose a job that was a poor fit and had to quit in order to maintain my sanity? It embarrassed me just thinking about it. 

Eventually, I summoned up the proper courage and reached out to contacts in my network in the hope of landing some consulting work. I had bills to pay after all.

I let my contacts know about my situation, which required being honest about being out of a job. Fortunately, they had freelance work available that they could send my way. Other contacts I reached out to connected me to people in their network who were able to provide advice and guidance on what types of healthcare roles I might be interested in. These conversations helped to hone my interviewing skills and clarify what I wanted to do next. I realized that I wanted to work in the neuromuscular disease space, preferably in a research role.

The timing could not have worked out better. One of the contacts I reached out to let me know about a Muscular Dystrophy Association (MDA) conference taking place in Washington, D.C. that March. Would I want to attend and write a blog post about my experience? I jumped at the opportunity. In addition to attending, which was exciting in itself, I would have the chance to network with professionals in the muscular dystrophy field. 

A month later, because of contacts I made at the conference, I had a job. I was hired by MDA to conduct research on the biotech and pharma industries and identify companies MDA could partner with. Five years later, I am still at the organization and enjoying it. 

Had I not let people know about my situation, even despite my initial hesitation, I would not have the job I have now. I came to realize that people want to help in any way they can. You just have to let them know.

Don’t let failure embarrass you. Put others to work on your behalf to search for solutions, make introductions, and keep you in mind when they hear about an opportunity that might be a good fit. 

“There is only one thing that makes a dream impossible to achieve: the fear of failure.” - Paulo Coelho

3. Find failure role models

Role models are a recurring theme on this website. This is because there are so many people in the world who have been through what we’ve been through, even if their circumstances are slightly different from our own. Using these examples is instructive in avoiding unnecessary pain and heartache.

As I mentioned earlier in this newsletter, there is no shortage of stories on the internet of people who have failed. Each story can teach us what to do and what not to do. By reading about someone’s journey, we can pull back the curtain on how they got to where they are today. In almost every instance, failure was a constant companion. Their achievements did not come from an unbroken string of successes. 

My two loves are sports and writing, so I tend to gravitate towards examples from these realms. There is a lot of failure in sports - lost games and competitions. There is even more in writing - rejected manuscripts, writing submissions, book proposals, etc. 

Here are a few different examples in my “Failure File” that I like to reference in low moments:

• Michae Jordan: The best basketball player who ever lived missed out on making the varsity basketball team in high school twice before making the team his junior year.

• Stephen King: Before he became a household writer in the horror genre, King was a struggling writer flooded with rejection letters from publishers unwilling to publish one of his stories. His first big break was the novel Carrie, but he disliked an early draft so much that he threw it in the trash can. It was only after his wife, Tabitha, retrieved the draft and read it that she encouraged him to keep going. 

• The Virginia Cavaliers: Perhaps the most extreme example of failure inspiring future success is the 2018-19 Virginia Cavaliers men’s basketball team. In 2018, they were the #1 ranked team in the country, only to lose in the first round of the NCAA Tournament to the 16th-seeded University of Maryland Baltimore County (UMBC). A 16-seed had never beaten a 1-seed, let alone by 20 points. Many thought it could never happen. Despite the public humiliation, Virginia recovered to win the national championship the very next year. 

• Oprah Winfrey: Before her eponymous TV show became a worldwide phenomenon, Oprah failed in a primetime news anchor role in Baltimore. She was moved off the anchor desk into a writing and reporting role, which led to several years of TV purgatory before finding her true calling as a TV show host.

• Actors who almost gave up on their dream: There are many examples of actors and actresses who didn’t find success early on in their careers, who struggled to find hope in the midst of one failed audition after another. There is John Krasinski. Jon Hamm. Halle Berry. Then there are all the major winners at this year’s Oscars. Short Round from Indiana Jones and the Temple of Doom (Ke Huy Quan) didn’t have an acting credit for 19 years and almost gave up on his dream. Now he has an Academy Award!

Whenever I fail, I always have that brief moment when I feel like I am alone in the universe. When I recall others who have encountered failure, especially those who are successful today, it makes me feel like what I am going through is perfectly normal.

This is one of the first books that made me realize that failure is an essential part of success. Image courtesy of Amazon.

One book I found particularly helpful on the subject of failure is Getting There, by Gillian Zoe Segal. In the book, Segal profiles several celebrities and successful businesspeople who share what they’ve learned on their career journeys. As she compiled these interviews, Segal was struck by how many of them cited failure as their key to success, and how the reader can look to these examples for inspiration:

“After completing this book and hearing so many people I admire describe their own trajectories in an honest, human, and identifiable way, I feel confident saying that no one sails through life without encountering some rough waters. No matter who you are, how far you’ve come on your own personal journey, or what you have achieved in your career, you can always benefit from a great role model."²

4. Self-Reflection: The After Action Report (AAR)

Eventually, we will reach a point when we are ready to analyze the failure we experienced. In this post-mortem, nothing is off the table. We must scrutinize each detail and deconstruct what happened.

One helpful way to perform this analysis is the After Action Report (AAR).

In his memoir, Can’t Hurt Me, David Goggins describes his process for learning from failure. Goggins, a former Navy SEAL now well-known as a motivational speaker, ultramarathon runner, and for other feats of endurance, became a master at creating AARs in his career. Navy SEALs conduct AARs to review missions and go over every detail - what worked, what didn’t, and where to improve next time. 

According to Goggins:

“In the military, after every real-world mission or field exercise, we fill out After Action Reports (AARs), which serve as live autopsies. We do them no matter the outcome, and if you’re analyzing a failure like I was, the AAR is absolutely crucial. Because when you’re headed into uncharted territory there are no books to study, no YouTube instructional videos to watch. All I had to read were my mistakes, and I considered all variables.” ³

It is a process Goggins swears by and uses in all areas of his life. When he attempted to break the world record for most pull-ups in a 24-hour period, he relied on AARs after every failed attempt to figure out what worked and what didn’t, so that he could get closer the next time. He eventually broke the record. (It’s 4,030 if you were wondering.)

Goggins recommends the following when conducting an AAR:

• First list out what worked. Even when we fail, there is usually something we did right.

• Think through your mindset before and after the failure. Analyze your preparation and execution.

• Then review what didn’t work. Go through the failure in detail, calling out anything you can fix next time.

• Review the AAR periodically and keep it handy for the next attempt.

Goggins contends that we can’t eliminate every unknown. Some aspects are out of our control. But as the AAR shows, there is much we can control and improve upon if we are honest with ourselves. 

This AAR process was extremely helpful for me in the weeks after I quit my job. I realized that I made the right decision to take the role on a consulting basis, but erred in my decision-making when I applied for the full-time role. I didn’t take into account the misalignment with my career aspirations or the amount of work involved vs. my energy level. 

It would not be a mistake I would make again.

5. Recalibrate

Perhaps in your review process -  whether or not you use the After Action Report - you realize that what you once considered to be your criteria for success has now changed. Maybe a goal you were striving towards no longer feels important anymore. If you have been trying and trying for a certain job and it isn’t working out, maybe you need to take a step back and take a class that will make you more qualified, or find another type of role that could utilize your skills. That doesn’t necessarily mean you have failed. If your heart isn’t into something, there is no point trying to convince yourself otherwise just because you thought that was the only way to succeed.

Another form of recalibration is moving the goalposts. Don’t let perfect be the enemy of good, they often say. If you feel that you failed because you tried to be perfect, could you still succeed if you make a mistake or two? Perfectionists often get bogged down because they feel like they can’t afford to make a single mistake, otherwise they are a failure. Yet, a few mistakes may still be okay in order to achieve an objective. 

As a writer, I try to write the perfect article, the perfect newsletter, the perfect email. I read what I write over and over and over again. But I eventually come to the realization that I can’t be perfect, and strive instead for “good enough.” That is a freeing moment.

“I have not failed. I've just found 10,000 ways that won't work.”

- Thomas Edison

6. Iterate and Experiment

If after reviewing your failure in detail, you might want to consider trying things differently than before. For example, if your experiment failed, perhaps you can test a different hypothesis. If you lost a game, maybe you need to train differently to improve endurance or alter your pre-game diet. If you are applying to jobs without getting an interview, maybe you should consider reaching out to a recruiter or asking a contact to set you up for an informational interview at a company of interest. 

Each failure is an opportunity to do things differently next time. To iterate and try new methods until you find one that works is the essence of self-improvement. 

If you would like to accelerate this learning process, there are ways to do that. For example, in business, there is the idea of failing quickly. Companies test different hypotheses in rapid succession, sometimes simultaneously, so they can more quickly determine what features customers are truly interested in. If a product idea fails, at least they didn’t dedicate too many resources or hours to come to this realization.

We can do this in our own lives. The quicker we can receive feedback on whether something works or doesn’t work, the quicker we can iterate and adjust. It doesn’t mean we have to mail it in every attempt, but rather, we can resolve to learn as much information as possible until we achieve the breakthrough we are looking for. I am a very deliberate person, so this doesn’t come naturally to me, but it is helpful in certain situations. In my job hunt, I tried several approaches simultaneously until I found the connection who suggested I attend the MDA conference. It is helpful to have many different lines in the water.

Six months after starting at MDA, I got to meet Derek Jeter. Not bad!

After you’ve succeeded

Today we’ve reviewed several different ways to turn around failure. With a few different techniques in hand, and your “Failure File” up and running, you can fight back against this unpleasant experience. Next time failure occurs, you can be ready.

Someday, you will be able to look back on your failure and see it as a turning point. That’s what happened after I quit my job. It ended up being the start of a newer, better chapter in my life.

When you move past your failure and are in a better place - if you are comfortable - make sure you tell people about it. The more we can normalize our failures and share our stories, the more failure loses its power over us. 

“That which we persist on doing becomes easier, not that the nature of the task has changed, but our ability to do has increased.” - Ralph Waldo Emerson

1. By later I mean just now.

2. Getting There, P. 14

3. Can’t Hurt Me, P. 313