Author Robert Cringely writes in his book Accidental Empires that there are three types of people required at different points in the life cycle of an organization or project: commandos, infantry, and police. 

Commandos are the first troops to see battle, whether invading countries or markets. 

A startup’s advantage is speed, and that’s what commandos live for. Commandos work hard, fast, cheap, and often with a low level of professionalism. But this is often acceptable, “because professionalism is expensive.”

As Cringely puts it: “Their job is to do lots of damage with surprise and teamwork, establishing a beachhead before the enemy is even aware that they exist.”

In a company, commandos are best suited to roles that defy convention and established practices, such as rapid prototyping. Ideally, this prototype is for a product “that is so creative, so exactly correct for its purpose that by its very existence it leads to the destruction of other products.”

As the commandos do their work, the infantry is gathering offshore.

These second-wave troops “take the prototype, test it, refine it, make it manufacturable, write the manuals, market it, and ideally produce a profit.”

Because the infantry troops are so numerous and their duties are so varied, they need processes and rules for getting things done – “all the stuff that commandos hate.”

Once the commandos and infantry have finished their work and head off to conquer new territories, the third wave of troops arrives: the police. 

The police hate change: “They want to fuel growth not by planning more invasions and landing on more beaches but by adding people and building economies and empires of scale.”

AT&T, IBM, and other established companies are third-wave enterprises. For example, engineers in these companies work on just part of a product. They view their work as a job rather than an adventure.

Problems arise when there’s a mismatch between the type of person and the work that needs to get done. 

For example, if you put a commando person in a police role (e.g., compliance officer, project manager), they’ll probably rebel and create havoc. 

Similarly, if you put a police person in a commando role (e.g., building prototypes, creative deliverables), they’ll likely freeze up and stall.

Entrepreneur and AngelList CEO Naval Ravikant says in an interview that to achieve outsized success, your goal should be to become the best in the world at what you do. 

For Ravikant, it’s not enough to pick something arbitrary. For example, you can’t say “I want to be the fastest runner in the world” and then you have to beat Usain Bolt. That’s too hard.

Instead, he recommends that you keep changing your objective until it matches your specific interests, knowledge, location, position, and skills. Your objective and skills should converge to make you number one. 

As Ravikant notes, this is the path that people like Oprah and Joe Rogan have followed: “Oprah gets paid for being Oprah. Joe Rogan gets paid for being Joe Rogan. They’re being authentic to themselves.”

Ideally, you want to be able to say: This is something I can be amazing at while still being myself.

Author and researcher Josh Kaufman writes in his book The Personal MBA that there’s a big difference between liking the idea of performing some role and actually doing it.

It’s easy to like the idea of being a manager. But it’s harder to like the demands from executives, surprises from your direct reports, and the need to defend your turf in a political environment. 

It’s easy to like the idea of being self-employed. But it’s harder to like the fact that all of your income comes from your own effort, and that if you make a mistake, you’re the one who will face the consequences. 

It’s easy to like the idea of being an author. But it’s harder to like the solitude, self-doubt, and the long hours that consistent writing requires. 

It’s easy to like the idea of being a celebrity. But it’s harder to like the loss of privacy, scrutiny, and the constant fear that people will lose interest in you.

Kaufman writes that mystique is a powerful force: “a little mystery that makes most things appear to be a lot more attractive than they actually are.”

Here’s what Kaufman recommends you ask them: “I really respect what you’re doing, but I imagine it has high points and low points. Could you share them with me? Knowing what you know now, is it worth the effort?“

This conversation can only take a few minutes, but what you learn could be priceless. 

As Kaufman notes, no job, position, or project is flawless. Every course of action has trade-offs.  

“Learning what they are in advance gives you a major advantage: you can examine an option without idealizing it, then choose if it’s really what you want to do before you start.”

“Know yourself thoroughly – your innate tastes and inclinations, the fields that naturally attract you. Work every day on improving those skills that mesh with your unique spirit and purpose. Add to the needed diversity of culture by creating something that reflects your uniqueness. Embrace what makes you different. Not following this course is the real reason you feel depressed at times. Moments of depression are a call to listen again to your inner authority.”

- Author and researcher Robert Greene in his book The Laws of Human Nature