Ego is the Enemy

When you blindly chase success, it’s easy to let the ego get the upper hand, and if you do, things tend to end badly - as Ryan Holiday explains in his book Ego is the enemy.

In his book, Ryan identifies three phases people go through in their professional journey: (1) Aspire, (2) Success, and (3) Failure. And, for each of these phases tells a story (good or bad) about real life people dealing with real life situations - highlighting how ego effected how they navigated those situations (good or bad).

Here are things that resonated with me, for each of the three phases:

Aspiration phase

The importance of being an eternal student. It’s impossible to become better if you naively pretend that you know everything. It can be hard being vulnerable about these things. When you do, however, you unlock rapid growth. As you get more senior in your field it can sometimes be hard to show vulnerability and admit what you don’t know - after all you’re the person that’s supposed to know stuff now! I’ve personally struggled with this after becoming a team lead, but by actively trying to be vulnerable about the things I don’t know I’ve been able to learn a ton from the people on my team (regardless of their seniority).
Get out of your own head. It takes courage to live and take in the presence. It’s easier to get stuck in your own head, imagining how fantastic the future will be. Living with the tangible and real can be uncomfortable, but that’s where the real learning happens. I often fall into the trap of “conditional happiness”, where I think everything is going to be just perfect once I get to that next level. But, I’ve slowly learned that the key to real satisfaction is to learn to love the journey, not the destination.

Success phase

The importance of building systems to be able to scale with bigger responsibilities and problem surfaces. It’s easy to brute force things and “just” work more hours than anyone else when you’re in the small leagues, but that won’t scale forever. There’s a roof. We can’t tie our success with just putting endless energy into something without end. That’s not a good definition of success. Moving from a mid-level IC role to a team lead role was a good challenge in this area for me. As an IC, it was easy to have full control over all the variables related to my work. After stepping into management, I quickly had to get used to being involved in a lot of things that I don’t have direct control over, and success becomes more about the systems you build (prioritization, communication, delegation, and team alignment). The Problem Upgrade Chart concept was a huge lightbulb idea for me around this.
Be clear with your goals. Endless ambition is easy, but it leads to undisciplined pursuit of more with no end in sight. To borrow from Aristotle: “what’s difficult is to apply the right amount of pressure, at the right time, in the right way, for the right period of time, in the right car, going in the right direction”. In other words, it’s more important deciding what to do, rather than just doing a lot of things without a clear end goal in mind. It’s so easy to fall into the business trap in the day-to-day work as a team lead, but staying focused on the top goal and what you’re trying to achieve in the long term, that’s the hard part.

Failure phase

Failure is part of any great journey. What matters is understanding and accepting the situation, and then move past it. Especially relate to this one from a Growth team perspective, since in a Growth team the goal is to learn. And to learn effectively you need to test a lot of things, where most of them will not pan out.
Alive time or dead time. Are things happening to us (dead) or do actively take on the challenges and bullshit that life throws at us (alive). It’s easy to play the victim or cast blame, but it takes real courage to take real ownership, even for things outside of our control. It’s easy as an engineer to have things happen to you: “that bug was caused by changes made by the other team”, “the requirements weren’t made clear enough by my PM”, and so on. But, the real A+ engineers are the ones that take full ownership over the business outcomes from end-to-end, regardless of what other people are doing, as explained by Geoff Charles from Ramp.