How to 10x Your Career


Welcome to In the Trenches. It’s great to have thousands of you here. My goal with this newsletter is to be all signal and no noise. To that end, make sure you let me know each week how you liked the content.


I am a firm believer that most people can achieve an order of magnitude more than they believe. Why? Because over the last 15 years, I have seen so many normal people achieve incredible outcomes. It is true that many of these outcomes have had a flavor of luck in them. But luck was only the accelerant - it determined how large the outcome was; it did not determine whether there was an outcome or not.

Upon analyzing these outcomes, I found there was a consistent theme that permeated across all of them: Non-linearity. None of these careers make sense “on paper.” Sure, many of these Founders / Investors went to great schools or worked at great companies, but at some point (often early in their journey), they did something non-obvious. They took a step that wasn’t “on the path.”

This is the gating factor for most people: most people in life want one-of-a-kind outcomes. The problem is, in the quest to get there, most people follow the same path as everyone else.

Let’s explore this through the lens of an analogy.

Imagine you are in college and it’s Friday night. It has been a long week and the party of the year is happening at the local bar. You get to the bar and you run into a huge issue. There is a massive line outside. You do what most people do. You stand in line in the freezing cold for an hour. You are tense and start to worry. You frantically call a friend of yours who managed to get in and ask:

Is there room inside? Can you talk to the Bouncer for me? Is my (questionable at best) ID going to get me in? You leave your destiny up to the fate of the universe.

This is what most people do with their careers. They take the front door; they follow the same path as everyone else. And what happens? Well they get the same results as most people. It’s hard to stand out. My advice to those that are seeking to 10x their career: forget the front door, enter the side door.

Back to the bar analogy - the side door is in some alley in the back. You have to find it and even when you do, you have to jimmy the lock. Then you probably have to run through the kitchen and fit in for a short period of time only to have to convince another Bouncer you are in the right place. But what happens as a result if you make it all the way through? You find yourself in the VIP section.

The side door isn’t as easy as the front door. However, when you take the side door, you are 1 of 1. Not 1 of 1000. And therein lies the opportunity. You play the same game as everyone else, but with a different set of rules.

Now here is the thing about side doors - they aren’t just “sitting there.” You have to think creatively and out of the box. You have to take risks. It requires immense courage and mental toughness. This is where most people quit. The people that take the side door have a strong desire to figure things out and a willpower to persist through rejection. In return, their journeys are met with outsized outcomes.

The side door relies on 3 things that I firmly believe in:

The best opportunities in life are often self created Changing the rules in the game pushes the odds in your favor Creative, out of the box thinkers matched with relentless tenacity will always be valued Remember: If you want an n-of-1 result, don’t take the 1-of-n road.

Until next week,

Romeen


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In The Trenches

Bootstrapped my business to $60M, brought in PE and currently in the next leg of the journey. Angel investor in 75+ companies. In this weekly newsletter I break down lessons learned, practical frameworks, tools & tactics to level up in business and life.

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