failure, authenticity, decisions

Life has a way of repeating itself until you finally learn the lessons it’s trying to teach you, both personally and professionally. This edition of the newsletter focuses on those types of lessons - nothing new or groundbreaking, just some common sense with a pinch of a wake-up call.

failure

“Let me fall if I must fall. The one I am becoming will catch me.”

~Baal Shem Tov

There’s something oddly spiritual and empowering about failure. It breaks down your beliefs and principles, leaving you to gather the pieces and reimagine the picture you want to create - all while feeling like the world is laughing at you. At least, that’s how it feels the first few times you face a major setback. But once you move past the self-pity, the real fun begins - the rebuilding process. The true intrigue starts when you realize that many of the things you once believed were true were actually just illusions. In that way, failure becomes incredibly liberating.

I find it amusing that the fear of failure often comes down to one question: "What will people think?" But here’s the thing - whether you succeed or fail, someone, somewhere is going to judge you. In fact, even if you don’t fail, just putting yourself out there is enough for someone to pass judgment. Those who judge are usually not the ones who have built anything meaningful themselves. True achievers never ridicule others for making an effort. In fact, I’ve yet to meet a successful and accomplished person who mocks someone else for trying. The reality is, the opinions of those who haven't taken risks don’t really count. In the end, no one truly knows if they're on the "right path"—we're all just figuring it out as we go.

We easily forget that as we consume social media as if it is a place where people are genuine and authentic. Instead, we should perceive it as a place where people perform. Although there’s a new tendency for people to share their mistakes and be more open (thanks, Gen Z, we needed that), it’s still highly glamorized. We could easily get into the endless carousel of thinking that everyone else is doing better than us. And honestly, does it really matter? Of course, there will be people doing better than us, and that is great - this is proof that all we want is possible.

In that sense, the internet has indeed brought us closer, but not to our true selves. Instead, we're busy connecting our polished online personas, while our real, imperfect selves stay tucked away. It gave us the opportunity to become whoever we want but it ripped us from our genuineness. We stopped doing things for the sake of self-expression, inspiration, and beauty and started doing it for likes, comments, and approval. But is there anything more authentic than failure? Isn’t it in those dark moments, when we realize we don’t have it all figured out and have to rebuild and rediscover ourselves, that life truly becomes meaningful?

This is the tragedy of our time: we possess the freedom to be and evolve into whoever we want, yet we often flee from that very truth in order to conform to the public.

See how we’re trading authenticity for approval? Not demure, not mindful at all.

authenticity

This section was inspired by Ren Gill. As one comment on his YouTube video put it:

“This man is what happens when you time travel and combine Eminem, Beethoven, and Shakespeare into a single human being”.

Authenticity is rooted in vulnerability. Vulnerability involves embracing all facets of ourselves - the good and the bad, the beautiful and the flawed, the strong and the weak. It seems that the people who are the most authentic are the ones who have taken a long walk in the darkest and steepest corners within themselves. Once you confront and accept these aspects, there’s little that can truly intimidate you. However, reaching these depths requires either a natural inclination towards self-exploration - an uncommon trait since our brains generally prefer to maintain the status quo - or a difficult experience that forces you to confront these darker parts of your soul. Sometimes, it takes a touch of darkness to bring in the light.

Authenticity requires courage. At some point, we all experience rejection - it’s just part of life. Many people believe it’s wiser to express qualities or beliefs that aren’t truly theirs, thinking it’ll minimize the risk or ease the pain of being rejected. Couldn’t be further from the truth. Rejection stings even more when you’ve been pretending because you eventually realize that all along, you could’ve just been yourself. When you’re authentic and true to your beliefs, rejection loses its power. You become more open to evolving those beliefs, knowing it brings you closer to who you truly are. The real pain comes when you recognize how much time you’ve wasted being anything less than yourself.

That being said, entrepreneurship is one of the most challenging yet rewarding paths you can take because it forces you to confront who you really are. That’s what I love about it - you can’t fake it, at least not in the long run. A partner from YC shared something surprising (to me) in one of their YouTube videos:

Most startups that apply have ideas that fall completely outside the founders' areas of expertise.

And guess what the most common idea is? Yep - a social media platform for connecting with friends. Why? Because it sounds cool, and someone else has already done it, so maybe adding a slight twist could make it more interesting and appealing to the 3.5 billion DAU across other platforms. When I heard that, it kept bugging me - why do so many smart people choose the same path instead of pursuing truly innovative ideas in fields they deeply understand?

I kept reaching the same conclusion: while many people are actively searching for a business idea, finding a truly valuable startup concept - or rather a significant problem worth solving - requires profound self-reflection. You must confront both your strengths and, equally important, your shortcomings. Self-reflection matters in many aspects of life, but when you're risking your savings, effort, time, and relationships, the stakes are too high to avoid it. Yet it seems that so many smart people do.

Why? Do we circle back to the fear of failure or should we evaluate our

decisions

You can truly say a lot about someone’s character when they’re faced with a tough decision.

Recently, I had a conversation with a friend about her first experience with firing someone. Let's call her Suzanna. Suzanna works at a rapidly growing scale-up, where the team expansion has been as quick as the company's growth. She lacks hiring experience yet she was rushed into the process with tight KPIs. She decided to first consider individuals within the company who she knew were looking to leave or change positions, and whom she had previously worked with, to see if they might join her team. Unsurprisingly, this was a smart move, and the people whom she managed to recruit from within the company, turned out to be a great fit.

The process of hiring outside the company was less smooth. While the procedure was structured and well-documented, one crucial element was not taken into account, and in all honesty, it couldn’t be - the human factor. Many candidates can make a strong first impression, but things often shift as communication progresses. There are insignificantly small signs that may indicate someone won't be a great fit. Some call it intuition, but it's really about those subtle, hard-to-define details you pick up on without fully realizing it - details that create a gut feeling guiding you toward the decision. However, if you don’t have hard-coded data for such an important decision, it’s difficult to rely on your intuition and rationalize it. With enough experience, you start to clearly articulate why you believe a candidate might not fit the culture or why you might not get along. But before reaching that point, it's often just a gut feeling.

My friend had this exact experience - she had a sense that the candidate she was hiring might not be the best fit, even though their resume looked impressive and they performed well on assignments. However, during the time spent working together on various tasks, something felt off. She couldn't pinpoint the issue clearly enough to justify her concerns to the HR team, so she proceeded with the hire. Ultimately, she ended up firing the person three weeks later, fully understanding why she shouldn’t hire this person in the first place. The reasons were so obvious and easy to articulate after the firing that she said “I should’ve known”.

Was the hiring decision right or wrong?

And what about the firing?

What does make a decision good or bad?

First and foremost, not avoiding it.

I’ve been reading the book How To Decide by Annie Duke where she explores all these questions and provides practical tools to help you make better decisions.

She opens the book by highlighting the significant difference between a good decision and a good outcome, a distinction we often blur. This confusion can prevent us from accurately assessing the quality of our decisions and identifying areas for improvement. She introduces a valuable exercise and defines the concept of "resulting" to help clarify this point:

The tendency to look at whether a result was good or bad to figure out whether a decision was good or bad

In other words, if you’ve had a bad outcome, it doesn’t mean that you're decision was bad per se. While decision quality and outcome quality are related, they don't always align perfectly, especially in one-off decisions where the connection between them can take time to reveal itself. Every decision you make opens some paths and closes others, affecting the possible outcomes and their likelihood, but it doesn't guarantee any specific result. Developing the discipline to separate decision quality from outcomes is crucial for identifying which decisions are worth repeating. To do this effectively, it's important to take the time before making a decision to thoroughly analyze all available information, consider the human factors (emotions, biases, etc.), and anticipate potential outcomes. The greater challenge, however, lies in evaluating the decision itself, regardless of the result, after the outcome has occurred, even if that outcome takes years to unfold. This reflection process can start with smaller decisions. The focus should be on the quality of the decision, not just the outcome. The goal of a good decision is to increase the likelihood of favorable results within a range of possibilities. As Anne Duke says:

Two things determine how your life will turn out: luck and the quality of your decisions.

One thing is certain - your life’s quality will suffer if you avoid making tough decisions and standing by them, whether it's about hiring, firing, getting married, or breaking up. The more you focus on pleasing others rather than understanding who you truly are and what you stand for, the worse those decisions will be. Luck rarely favors those who play it safe. This is what sets people apart.

See you next time,

A