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Dissecting Failure

Louie Bacaj
Louie Bacaj
7 min read
Dissecting Failure

Nobody likes to fail, and some of us hate it so much that we hide our failure. Blaming it on bad luck, bad timing, and even others is all part of the human condition. Failure is something we can build on top of, and failures are like scars; and Nicholas Taleb says that "scars signal skin in the game."

In the book Thinking in Bets, Annie Duke talks about how we are prone to building a Matrix-like world for ourselves, but unlike the movie, it's not machines constructing that world; it's our minds. She says that our brains have evolved to make our world a comfortable place for our egos. We believe our beliefs are almost always correct; to ourselves, favorable outcomes are due to our skills, while unfavorable ones are from bad luck. We always compare ourselves favorably to everyone else. She explains that taking the red pill, owning our failures, and figuring out how to make hard objective decisions might be uncomfortable at the moment but leads to far more success and a better life in the modern world.

The easy road of blaming losses, failures, or mess-ups on luck and crediting success to skill means our decision-making is guaranteed never to improve. As we learned from Annie Duke, complaining about bad luck in failure is a human condition, but it fails us every time and makes those failures much worse. When we do that, we miss opportunities to see where we could have done better in our decision-making.

Nipsey Hussle said, "nothing beats a failure but a try."


We can fail, not lose everything, and still get something to build on.


Some of us also fear failure so much we may never try. Failures can lead to our ruin. Nicholas Taleb, the author and modern philosopher talks in-depth about risks that can ruin us and how to detect and avoid them. For example, one such risk may be playing Russian Roulette, where failure could be catastrophic for us. While those risks at failure are not the subject of this piece, even more, mild failures impact us in interesting ways and bring about pain.

I once went on 15 technical interviews with different companies and only managed to land two of them, all in a short period and in a row. Each one involved a grueling all-day session of drilling on a whiteboard. All of this was at an earlier point in my career, and I was incredibly stressed financially and looking to land a job that paid me a little more. The rejections led to reinforcing imposter syndrome like I didn't belong in this field, like my bachelor's and masters' degrees in it were worthless, like I had accomplished nothing so far, and it hurt like crazy.

I remember one of those interviews, in particular, it started at 11 AM, and I was still going at 8:30 PM. I went into the bathroom every hour to splash water on my face. They drilled me on a whiteboard, and in pairs, they brought over sample code I had to find bugs in. They asked me to go through a bunch of inefficient queries and fix those. They asked me to write a bunch of things from scratch; they asked me to go down and meet some of the other developers who were having a beer at 6:30 PM, then back up to meet with the management. All-day technical interviews on a whiteboard are not fun, and then the icing on the cake is being told, "Sorry, but we are going to pass"; that hurts even more.

Why would any sane person keep going on interviews after that?

I have experienced failure many times on my side projects that I have worked on my nights and weekends. The first one was shortly after school and was meant to become a way to manage real-estate inventory for agents trying to sell or buy homes, my friend, who is an agent, said they managed that inventory with spreadsheets. We called it Realintory and got to building it. No one cared to use it; it was more of a pain to use than excel is. Then we did another one in real estate where you could put offers on unlisted homes, and we would automatically send snail mail to homeowners asking them to get on and see the offer. No one wanted to put offers on homes sight unseen, except some investors that were lowballing homeowners. Then there was the crypto platform, Dealbit, earn ethereum or bitcoin into a wallet while you shop online, we got 800 active users, and we were losing 2-3x more money than we were paying out because of the crazy transaction fees in crypto. Then there was the AI reader App that we got onto both the iOS and Android app store, Articulu. This one would scrape any article you wanted from the internet, minus the ads, and use some nice AI models on the backend to convert articles to audio so you could listen to them on the go, like a podcast. It cost us more to run the AI and ML pipelines in the cloud than we were making with our 15 paid users and 1500 nonpaying ones.

The last two, the crypto affiliate site and the audio reader app, arguably were not terrible failures, and with some iteration, we might have been able to make them work. Still, we did not feel they would ever be big enough, and I want to do something big.

After realizing that the project would not work anymore and I wanted to kill it off, I always remember the excruciating feeling of defeat sinking in. It can be debilitating.

When dissecting these failures, some things come to mind; first off, none of these failures killed me, and I doubt any amount of interview failure will kill any of us. Similarly, none of my side projects failing and not taking off led to ruin. Every single side project failure, my brother and I got closer and closer to product-market fit, closer to something that could be big.

Why should we risk even more failures?

A reason for risking failure is learning and growing. Scott Adams says that where you are headed is far more important than where you are and that you will feel happiest when moving in the right direction. Things can't move in the right direction without the risk of failure.

Another major reason to risk failure is to make yourself more susceptible to luck. In his book "How to Fail at Almost Everything and Still Succeed" Scott Adams says that luck and timing are a funny thing, and it is never a complete accident when luck finds us. We have to be in a position where luck is most likely to happen. He gives the example of a hunter going hunting, and when he gets to the forest, he looks for the right spot, the best and most successful hunters, intelligently selecting a location in the woods, not any random site. The hunter still needs the luck of having a deer walk by, but he manages his situation to increase his odds. The point is that you must put yourself in a position for luck to find you, and to do that, you need to risk failure.

"In an age of permissionless leverage, judgment, not work, determines success and failure." -Naval


I believe we build good judgment via failure; at the very least, we intuitively begin to understand why something does not work. It is one thing for someone to tell us; it is a whole other thing to try and fail. If we properly attribute our failures


How do we overcome failure?


In his NY Times best-selling book, Can't Hurt Me, David Goggins talks about callusing your mind to the pain of failure. Calluses are small areas in your body where the skin has become raised and hard; this could be from repeated friction or rubbing. It could happen from labor-intensive work, at the gym, from running, among many other ways. David Goggins says that we could also callus our mind to pain and failure the same way the body does for physical activity.

David goes on to say that the process of callusing the mind to pain can make you look like a lunatic and like you have gone crazy. You have to do the things that you might fail at, those are the things that scare you, and that can make you act a certain way because you've been putting up with pain. Someone may look at you and think any number of things about you during that process; you have to get comfortable with that too.


"My biggest fear in life, a bigger fear than death, is not being what I'm supposed to be. My biggest fear coming out of this life is I get to heaven, and you know God knows everything and I believe he has a chart, God pulls out his chart and says 'you never made it to what you were supposed to be.'" -David Goggins

I keep getting asked why you would keep working on side projects, wasting your nights and weekends if they all keep failing?

Something helping me get past comfort and the fear of failure is remembering all the crazy struggles from my past. The hopelessness I may have felt at one point or another in life. I like going back to that paralyzing fear and remembering that I am still here, that even that was overcome.

If failure is like scars for your mind that signal to the world that you tried something and invested skin in the game, then callusing is what happens when you grow used to it. The best way to overcome failure is through more action, more chances to fail, more tries, getting used to all of it, and remembering that you will survive.

In Conclusion

If we all make sure to do everything we can for luck to find us, stay optimistic if we try out many ventures. Put in the energy. Prepare by learning as much as possible. Most importantly, and this takes perseverance, stay in the game long enough for luck to find us, imagine where we would be.


Despite all those failures at those interviews I mentioned earlier, I eventually landed something high paying. Each time we start a new side project, my brother and I do better and get faster, and we get reused from our previous work. Nothing goes to waste. Learning about all those other industries has all translated into growth and promotions in my professional career. I wouldn't have ever been exposed to all those things from just my professional work.

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