Two Kinds of Failure
Robert Greene's distinction between two types of failure fundamentally reframes how we should think about risk and action. This insight from "Mastery" cuts through all the platitudes about "embracing failure" to reveal what actually matters.
The first comes from never trying out your ideas because you are afraid, or because you are waiting for the perfect time. This kind of failure you can never learn from, and such timidity will destroy you.
This first type of failure is insidious because it doesn't feel like failure at all. There's no dramatic moment of defeat, no obvious lesson learned. You just... don't try. The idea stays in your head, the project remains unstarted, the opportunity passes by.
It feels safer because there's no immediate pain. No rejection, no embarrassment, no visible setback. But Greene is right ... this timidity is ultimately more destructive than any bold failure could be.
The second kind comes from a bold and venturesome spirit. If you fail in this way, the hit that you take to your reputation is greatly outweighed by what you learn. Repeated failure will toughen your spirit and show you with absolute clarity how things must be done.
The second type of failure is what happens when you actually put your ideas into the world. You test them against reality, and reality pushes back. This kind of failure hurts in the moment, but it's productive pain. It teaches you something concrete about how the world works.
The reputation concern is real but overblown. Most people aren't paying as much attention to your failures as you think they are. And the people whose opinions actually matter ... potential collaborators, customers, mentors ... tend to respect the attempt more than they penalise the outcome.
Greene's warning about early success is particularly insightful:
In fact, it is a curse to have everything go right on your first attempt. You will fail to question the element of luck, making you think that you have the golden touch. When you do inevitably fail, it will confuse and demoralize you past the point of learning.
This explains why many naturally talented people plateau while less gifted individuals eventually surpass them. Early success can create a fragile confidence that crumbles when reality finally pushes back. People who fail early develop resilience and learn to separate their self-worth from their outcomes.
The most radical part of Greene's advice comes at the end:
In any case, to apprentice as an entrepreneur you must act on your ideas as early as possible, exposing them to the public, a part of you even hoping that you'll fail. You have everything to gain.
"Hoping that you'll fail" sounds counterintuitive, but it makes perfect sense. If you hope to fail, then failure becomes a successful outcome ... you're getting the feedback and education you were seeking. This mental shift transforms failure from something to avoid into something to actively pursue.
The key is understanding that failure is information. The first type of failure gives you no information. The second type gives you invaluable data about what works, what doesn't, and how to improve.
Every idea untested is a lesson unlearned. Every project unstarted is a skill undeveloped. The only way to apprentice as an entrepreneur ... or as anything else worth being ... is to expose your work to the world early and often.
You have everything to gain, because even the failures teach you everything you need to know.