If You Want to Be Successful, You Need to Fail as Many Times as Possible

Here are 5 reasons why.

I have an intimate relationship with failure. I’ve failed at almost everything I’ve tried in the past decade. I dropped out of university in my final year of Engineering school because my mental health was suboptimal. And that led me down a series of unfortunate events.

Regardless, I got a software engineering job to support myself. That didn’t work out either. Every day, like clockwork, I got headaches at around midday. It was impossible to remain productive throughout the day. So, I quit and decided to venture into writing.

I had a simple plan: write and get paid on Medium (Easy!). Wrong! I needed a Taxpayer Identification Number (TIN) to get paid by Medium. To get a TIN in Uganda, you need to either have a job or have a registered company. I had neither!

So, I changed tactics. I decided to do other online jobs until I had enough money to support my writing dreams. I tried everything: Proofreading, online tutoring, affiliate marketing, content mills, transcription, online surveys, and so on.

There was always a catch, though: the most lucrative jobs required me to have a University degree (I did not have that). Others didn’t hire from my country, and the rest just had an unfavorable payment system: PayPal (There is no direct way to withdraw funds from PayPal in Uganda).

No matter, I soared on.

I would find a perfect transcription job, prepare for three days, go through the two-hour application process, get rejected in the end, and repeat this process the following day.

Eventually, I got tired. I realized that if I was going to fail repeatedly, it might as well be while doing something I am passionate about. So, I embarked on writing on Medium once more. Here are five lessons I learned in the process.

1. Failing so many times forces you to focus on one thing

“The successful warrior is the average man, with laser-like focus.” — Bruce Lee.

Repetitive failure forces you to focus on one thing. It’s the wildfire that sets all your bridges aflame — forcing you to embark on the journey before you without turning back. There is nowhere to return. You have tried everything, and it didn’t work out. Either you charge ahead, or you drown in your pain.

When I chose to apply to a million online jobs, I had one underlying assumption; I assumed that making money from an online survey, a transcription job, or a data entry job would be easier than plunging into writing unprepared. Boy, was I wrong!

Repetitive failure taught me that everything is equally as hard as everything else. The hardship might not show up in the same way, but it will still feel the same: excruciatingly painful.

It was basic math, to be honest; If I was going to go through excruciating pain, it might as well be while doing something I love. So I focused on writing.

2. There is no better motivator than the need to avoid suffering

You remember the pain of failure so vividly; your mind can no longer trick you into indulging in otherwise self-sabotaging behavior.

Human beings learn by repetition; Experience is the best teacher. We are explorative, experiential beings. Someone can tell you about all the pitfalls of getting burnt, but it’s not the same as the vivid memory you would remain with if you got burnt.

Here is the thing, if you don’t experience failure first hand, if push comes to shove, you will always wonder if you would’ve succeeded. You would continuously be split in your decision not to explore the option in question.

When I told my big brother that I was applying to online jobs, he was very skeptical. He said that in Uganda, it’s hard to succeed online. I didn’t listen. “I am going to put everything in this until I succeed,” I thought. I failed so horribly instead.

My brother had wished to spare me the agony of a dead-end process he had gone through himself. But I was too motivated to take it from a third party. I needed to experience the pain of failure first-hand: otherwise, I would not have moved on from my endeavor.

Part of me would have been consumed with infinite “what ifs” What if I had applied to Rev.com? Maybe I should try out a content mill again. I do not have to wonder. Been there, done that. It didn’t work out. I remember the pain of failure so vividly; my mind can no longer trick me into indulging in otherwise self-sabotaging behavior.

3. At some point, giving up becomes pointless.

There’s nowhere else to go but up. Either you go up, or you go up.

Sometimes when you fail at something, you tell yourself: “Maybe this is not meant for me.” And you move on to the next thing guilt-free. And maybe you succeed in your next endeavor. And if you don’t, you move onto the next opportunity and so on. But when you fail so many times over continuously, you eventually hit rock-bottom. And you realize there is no point in giving up. There is simply nothing else onto which to move.

When I regrouped and put all my energy into writing on Medium, I had to go through the dizzying journey of processing a TIN again. The TIN office kept tossing me around in circles that, at some point, I became depressed. “I am just going to let this Medium thing go. I will try something else,” I thought.

I spent about one and a half months enveloped by this darkness. I did not write anything. I did not apply to any other online job (I couldn’t go through that process again). And then one day, I asked myself: “What else? What else are you going to try out with your almost non-existent savings?”

There was nothing else. I had tried and failed at everything else. So, I clawed my way out of that pit, held my head high, went through the TIN application process for the second time.

I still got rejected.

It was still excruciatingly painful, but at that point, there was nothing else for me to do. Either I got my TIN or drowned in more pain.

That’s the beauty of hitting rock bottom. It shows you that there’s nowhere else to go but up. So, the following day, I got up, powered through the pain, and tried a different route. After about a month, the TIN office approved my application.

4. You become comfortable with the discomfort of failure

Fear turns into a mere feeling of discomfort in your stomach. All you have to do is wait it out.

You start to notice your limitations: those that keep you in the grips of failure for longer than necessary. You begin to see a pattern within yourself. And you begin to extend that experience to other areas in your life.

I got rejected so many times that I slowly became more aware of my internal reaction to rejection.

First, there is an uncomfortable knot of fire in my stomach that eventually pulsates throughout the rest of my body. Then, I sink into a feeling of worthlessness. At that point, the self-loathing thoughts set in, and finally, this existential urge to escape the wrath of those thoughts takes over me. Before I know it, I am curled up in bed, deep into binge-watching the second season of Brooklyn nine.

Sometimes, the fear of experiencing this discomfort keeps me from trying out new things (submitting to Medium publications, for example). But after feeling it over and over, I got used to my inner reaction to failure. It no longer stretches out for days like it used to. I am used to experiencing the discomfort of rejection, that most times, I can sit with the pain — the fear — long enough without it escalating into chronic procrastination and depression.

When you fail so many times, at some point, fear becomes a mere feeling of discomfort in the stomach.

5. You become honest about your competency

Sometimes, we don’t know what we don’t know about ourselves.

You quickly become aware of what skills are lacking in your arsenal. This realization saves everyone a lot of time.

I knew I had a problem with cramming, but I was unaware of how bad it was until I kept on failing exam after exam.

“You did not pass the entry exam. Please re-read our transcription guidelines and try again.”

I received an email containing a message such as that more times than I care to remember. One thing stayed with me, though. I could not cram five pages of anything if my life depended on it (Unless I had a whole year to prepare, of course). I thought I knew how to, but it turns out I was wrong. In the future, If I have to work on a project that required me to cram, I know to take a short course on cramming beforehand.

Final thoughts

I will leave you with this quote from Eckhart Tolle:

“Some changes look negative on the surface, but you will soon realize that space is being created in your life for something new to emerge.”

Last month, I earned my first pennies on Medium. Nothing fancy, but just enough to know that my labors are starting to pay off. To me, this is a success. I would not have come to a place where I can sit and focus on writing one story to completion if I had not failed as many times as I did. I wouldn’t even have a story to tell in the first place.

I have learned that we have to fail as many times as we need to. Not less and not more than necessary. And It’s not just because the world is a complicated unfair place but also because failure prepares us for success. Think of it this way: If you’re failing over and over again, you’re not yet ready for your wish. Failure is simply the fire molding you into the perfect vessel to receive your desire.