A hand holding a cup full of clouds
A cup of clouds, courtesy the amazing Diya banerjee

This is a collection of learnings over the last couple of years — multiple journeys, unforeseen roles, messed-up responsibilities, and more things that I have learned along the way.
This is not just a reflection, or a memoir, or an anecdote, nor is it intended to tell you what to do. These are conversations that have happened in my head, some gleaned from conversations with others, and others distilled from here, there, and everywhere. This is a documentation of insights and situations where I have stubbed my toes. It’s not clean, it’s messy, and it is not intended as life advice or something you should do too.

The last couple of years have been a roller coaster, there have been highs, both the real and metaphorical. I have transitioned from a wide-eyed, unsure sophomore, to hopefully a more self-assured senior. Admittedly, this sense of self-assuredness did not come without its fair share of misplaced self-aggrandization, hubris, and messed-up ideals. It has been far from a perfect road. There have been more wrongs and rights, and I hope that if you are reading this, it would help you in some way. How? Don’t ask me, this is just a silly 22-year old and his rambles.

First things first — understand that you would screw things up. And that you would screw them up big. And there would be scenarios where you have to deal with this thing called ego before you even turn to the root cause behind the purported situation. When you are thrust into a leadership role, there would be moments of hubris, there would be moments when you would do the exact opposite of what you had planned all along. you might inadvertently pull someone down, instead of boosting them up, and you might end up rationalizing your decision based on this weirdly flawed concept that you need to experience the pain to gain something, or that hustle is all you should care about, or that you need to have an opinion about everything.
Why am I saying these? I have been here, done that. Preached absolutely stupid things, have talked way more than I have listened, have proceeded to give extremely irrelevant unsolicited opinions.

If you are reading this and want a piece of unsolicited advice — don’t.

Care about the people more than the processes. Care about the little things more than the grand gestures. You would have to overcome hubris and the ethos of LinkedIn that would subconsciously creep in and prevent you from doing the very things you had set out to do. Understand your behavioral flaws and take adequate steps to fix them. It is okay. The change does not happen overnight, and people know that. If you are trying too hard to change — stop. That’s not you. There is a fine line between being someone else and fixing your flaws. Find that line.

You do not need to optimize every connection, every relationship, every bit of time. You do not need to be productive like crazy. If you want to be — sure. Go ahead by all means. But is far more helpful to be empathic, to take a break, and recharge every once in a while. Read good books that Twitter does not rave about, spend time with your loved ones because life is transient. So is time. Spend it so that you do not regret ten years down the line.

Understanding who you are talking with and figuring out when to talk, or just listen, or offer value, takes time, patience, and practice. Chasing clout would always make you talk more and listen less. And whatever more you would talk, belong to the same recycling bin of contents from a handful of people. It is difficult to acknowledge your own flaws, own up, and change problematic traits. But it is not impossible.

Leading a team is a whole new challenge. You think you are prepared, then you fumble, then you fumble some more until you put together a team that either makes or breaks the org. The org can be as simple as a college club, or a start-up. To be honest, you cannot really prepare for something like this. You would make mistakes on the job. If you are leading a team for the first time and claim that it would be smooth sailing, you might as well continue working alone. Build a team that has the same commitment and wants to grow with the org. For a small/early stage org, bringing in someone super important who would claim to be the one who can fix everything might prove counter-productive. Try things out, by all means. but understand boundaries and thresholds, and how much time and resource you should focus on something/someone before pulling the plug.
If you are a leader trying to improve how you communicate, practice delivering a crucial piece of information clearly and if possible, with no ambiguity. Timing is a factor of transparency. Do it too early and might prove disastrous in some cases. Do it too later and you open the possibility of a third party to intervene and deliver — transparency suffers.

Every thing to promise, commit to, has a half-life (reference to the lifetime of subatomic particles, not the game). Act on your words before they get stale. And while this might seem difficult, and humongous, start with acting quickly on the smaller things before you think of the bigger pieces. If you feel something would be delayed, communicate. Let your stakeholders know about the delay and a revised timeline, and most importantly, do it before you cross that half-life, when your message no longer holds value. This applies everywhere — your home, with your friends, and not just in your capacity as a leader.

Leading an open and collaborative community with the littlest of frictions is often a tough and thankless job. You might antagonize a lot of people. You might not be able to help someone out in a way you would have wanted. You would push away people close to you because you have “work”. You would struggle to prioritize.

At times, take a step back and eat the humble pie, and ask for help. As a leader, your job is not to have the answer to every question. Set up a continuous feedback cycle with the same urgency you set up a continuous integration pipeline, listen to folks, tweak and fix your ideas, measures, and initiatives. You do not get to be an arse and cite Steve Jobs or Elon Musk as an excuse to get away with it. Just because they did it, does not make it right. Also remember, that a lot of folks applauding what you do does not make it right either. What you do might be getting a keen audience but if it’s not morally or ethically right, hit the brakes if you can. Go back to the drawing board, and start all over. Avoid doing something solely due to majoritarianism.

Zoom out. Learn to observe things from a distance. You would get better clarity of what works, what does not — behaviors and initiatives that work and scale and the ones that don’t. You do not need to do something simply because someone else is doing it. To be an effective leader, the longer view and clarity are a whole lot useful than trying to go down the micro-managing rabbit hole. It is easy to fall down that hole.

The process is not the answer to every problem. It is a fairly easy and obvious choice to throw at tricky and/or complex situations and is more often than not, a wrong answer. You need to dig down to find the gaps, understand the reasons, and figure out a specific solution rather than putting in place a blanket behavioral change exercise.

Trust, the value of initiatives, excitement, and fun are all important elements to every single interpersonal relationship. The erosion of faith is often irreversible, or at best, extremely difficult to reverse. If you promise something or commit to something, follow through. Ensure your team camaraderie is fun, and folks are excited to jump onto the next thing, and next, and next. Erosion of these value systems often leads to resentment, demotivation, and in a team — churn. When folks put their faith in you and your words, respect that, do not take it for granted and give it back. Trust your team, and ensure that you have the mental models in place so that your team can get things done even when you are not around.
Give up on the notion that you are the best in business. You are not. There are always folks you can learn from.
Accept that you are replaceable. And while it is a tough pill to swallow, this would allow you to dissociate your entire identity from a team, and value individuals in the team for their worth. If you think you are replaceable, identify and train folks who you would want to replace you. If you can put mental models in place that the team can face complex challenges without you around, you have already succeeded to a certain extent. Leverage this momentum, and carry it forward.

There are tons of materials out there that talk about the success stories and the hustle that went on behind creating some of the most inspiring companies/communities. And while they talk about measures you need to take to make those consistent jumps up the ladder, few mention pitfalls, and something you, as a human, or leader should be mindful of. And this account is not just applicable to communities or start-ups. They are equally valid for most (if not all) interpersonal relationships. I am no expert, I am not here to share my two cents with you. What you read, is not advice, but accounts and notes I have accumulated over these years. If I could go back in time and say these to my 19-year old self, I would. But in the absence of a time machine, the best thing would be to preserve a document.
It might help you, it might not. Either way, if you are reading this — thank you.

The artwork on top is from Diya Banerjee, and she is amazing.
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here.
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CS @ Heritage Institute of Technology. Product Designer, Winuall // Auth0 Ambassador. Learning ML. Loves music and photography. Star Wars Nerd.