Watch your ego

The perils of the ego, and a framework to moderate it.

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I’ve always been a competitive person.

Competitive with myself—yes, but also with others. In high school and university, I was heavily involved with competitive sports (basketball, volleyball, track & field). I’ve also always been obsessed with martial arts, and favored hobbies with a highly competitive element, like chess.

With competition, comes explicit success and failure. You win or you lose. You can spin failure into a learning experience (and a win in that regard), but in reality, you lost. And when you lose, it hurts your ego.

If you’re like me, you’ll naturally go through cycles of highs—success and wins, and lows—failure and frustration.

Often times, it’s your ego that causes that frustration.

It activates your defense mechanism—excuses, victim mentality, justifications—to rationalize failure. Your ego will do anything to create a narrative to shelter itself from defeat.

This is the largest inhibitor to growth in a competitive environment.

“[E]go is the enemy of what you want and of what you have: Of mastering a craft. Of real creative insight. Of working well with others. Of building loyalty and support. Of longevity. Of repeating and retaining your success. It repulses advantages and opportunities. It’s a magnet for enemies and errors. It is Scylla and Charybdis.”

— Ryan Holiday


Regulate your ego

Through my experience of dealing with competition, success, and failure, I’ve learned to implement a system to regulate my ego, and to maintain balance between humility and confidence.


Here’s a framework to keep your ego in check:

To challenge your ego, you need to surround yourself with a wide range of people.

People who are superior to you in a task or activity or area. You need folks who are more skilled and experienced in the domains that you’re interested in. They’ll help you grow by actively teaching you and guiding you, and providing the wisdom to get to the next level. These are your teachers, instructors, coaches, advisors, mentors, and counselors.

People who are equal to you in a task or activity area. These folks will challenge you by encouraging you and inspiring you to put in effort. Effort is the most important factor in growth and development, and often times peer support (and competition) is the catalyst of motivation. These are your peers.

People who are less skilled than you in a task or activity area. You can coach, guide, and advise these folks, and as a result, learn more by reflection and teaching. This will also help promote humility as you’ll focus on helping others succeed, rather than watching your own success. These are your students, mentees, and apprentices.


Keep an open mind, as these people aren’t always who you’d expect them to be.

Some personal anecdotes:

  • I’ve learned the most about specific domains (venture capital, startups, eCommerce) from folks 4-5 years younger than me, who are fresh out of undergrad

  • I’ve advised people with more than 10 years of work experience than me, on how to interview, pivot industries, and be a competitive candidate in the tech space

  • Some of the inspiration behind improving my principles, optimizing my decision-making, and calibrating my lifestyle has come from people in a wildly different industry and life stage


Every person you meet is an expert in an area who can teach you something.

Try this: Next time you meet someone new, try to figure out what their area of expertise is. This will encourage genuine curiosity, invoking questions, and good conversation.

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