When does Confidence Become Pride?

Over the years, I’ve generally tried to become less proud of a person, though I’ve always found pride to be kind of a slippery personality trait to pin down.

Even if you’re aggressively meta and willfully self-aware, it’s still hard to clearly check all of your character blind spots. And when you self-examine through a prideful lens, it’s easy to interpret flaws merely as personality quirks.

Growing up, I think I struggled with the traditional elements of pride. I overestimated my abilities, I didn’t like taking the blame for things, and I dealt with failure ungracefully. I’m pretty sure I single-handedly ruined the roster of my first church softball team because I ranked my own skill level way too highly on my league application.

Over time, the level of competition around me – the filters and environments I’ve willingly chosen to pursue – has become more and more intense. I think a result of that intensity has made the feelings of pride come and go much more wildly.

Over the past decade, there have been moments where I felt like I was exactly where I was supposed to be, but there have been even more moments where I felt like a filthy imposter.

I think the unstable nature of pride is normal, but its shapeshifting tendency makes me wonder what it takes to have a sustainable and healthy self-image. To be confident and bold enough to go after what we really want without misjudging our abilities.

How do we strike that balance – to believe in ourselves without being excessively proud?

The Positive Benefits of Pride

I think that a lot of traditional areas in life (business, the operating room, public debates) incentivize being slightly prouder rather than slightly humbler.

Personally, I definitely perform better when I feel confident in my own abilities. I know that some ‘statisticians’ say that clutch does not exist, but I definitely feel super un-clutch when I’m unconfident in something. Even if the source of my pride is slightly misplaced, I have found my performance to be better when I feel comfortable and my ego isn’t threatened. I’ve found this to be particularly true if it’s a performance art, say like a piano recital or an Excel speed formatting competition.

Here are the main things that I would identify as the positive traits of pride:

  • Pride tends to be a reflection or manifestation of one’s self-identity and we are strongly motivated to protect our identity. In this way, I think having pride in certain accomplishments or features can motivate us to extremely work hard to achieve related goals and further our identity.
    • If you went to the Scripps National Spelling Bee as a kid, you’re probably unusually defensive when people try to correct your grammar. You might feel more compelled to write most of the content in a group project or read more books than your peers.
  • Pride insulates us from self-doubt and helps us more easily move out of our comfort zone.
    • I find that more often than not, it’s confidence that leads us to take on new initiatives and expose ourselves to potentially wonderful risks. I think this is helpful because I find that I grow most quickly outside of my comfort zone. The counterpoint here would be that excessive pride can make us scared of looking like a beginner.
  • Pride and self-assuredness is typically better at inspiring team morale.
    • From a leadership perspective, I think that confidence is important to instill a sense of certainty in a group. I’ve found that if the leader is cynical or unsure about the team’s situation, then the rest of the group doesn’t stand much of a chance of being motivated. Too much ambiguity is bad from the vantage of a subordinate.

The Dark Side of Pride

I think many proud people tend to be or become overconfident and insufferable because of how most feedback loops in life work. If you are proud and you continue winning, it’s most likely that you will continue to become prouder. Winners are tempted to attribute their success to their own merit, even when it comes to arenas that are not particularly skill-oriented.

There’s a classic finance paper that tries to disentangle the drivers of skill and luck in investing. The paper arranges different activities on a skill-luck spectrum.

The paper says how we are often tempted to exaggerate our own skill levels when we feel like we are in control.

This illusion says that when we perceive ourselves to be in control of a situation, we deem our probabilities of success to be higher than what chance dictates. Saying it differently, when we are in control we think our ratio of skill to luck is higher than it really is. Remarkably, this illusion even holds for activities that are all chance.

Untangling Skill and Luck by Legg Mason Capital Management (now ClearBridge)

I view the characteristics of evil pride as such:

  • Pride makes us overly protective of our egos and sensitive to criticism.
    • I think pride can make feelings of failure much more painful and amplify our responses to hardship. This kind of pride is what leads us to have chips on our shoulders and interpret legitimate feedback as destructive or malicious.
  • Pride makes us ignore our own flaws and failures.
    • I think pride mixed with laziness can lead us to willfully ignore our own flaws. We can become tempted to identify certain characteristics as entertaining or just part of who we are, instead of troubling (e.g. that we drink so much on the weekends, that we sleep so little, or that we work so much).
  • Pride leads us to treat others differently or negatively as a result of disparity in perceived ability.
    • Externally, excessive pride often leads us to be insufferable and kind of a dick. I think confidence crosses the line and becomes pride when it starts to impact how we treat others. Condescension and exclusion are common byproducts of pride.

An Optimal Balance of Confidence

I generally think that confidence is based on legitimate historical accomplishments, while pride is based on anything else. If you dunked a basketball last week, you can feel confident that you can dunk one again this week. That wouldn’t be pride to me. But say, if you never exercise or work out, it’s probably excessively proud to think you can dunk a basketball based on sheer will. When the assertion is based on no evidence, I’d say it’s pride.

But what should we do when we encounter completely foreign situations which happens all the time?

When we have no relevant experiences or goalposts to anchor off of, should we just try to believe in ourselves because we’ve overcome adversity in the past and because we know doing so will probably lead to better performance?

In his autobiography, Bob Iger wrote about threading transparency, humility, and an eagerness to learn in order to perform well in new situations.

The first rule is not to fake anything. You have to be humble, and you can’t pretend to be someone you’re not or to know something you don’t. You’re also in a position of leadership, though, so you can’t let humility prevent you from leading. It’s a fine line, and something I preach today. You have to ask the questions you need to ask, admit without apology what you don’t understand, and do the work to learn what you need to learn as quickly as you can. There’s nothing less confidence-inspiring than a person faking a knowledge they don’t possess. True authority and true leadership come from knowing who you are and not pretending to be anything else.

The Ride of a Lifetime by Bob Iger

I would say that more recently, over the past few years, I’ve definitely struggled with the opposite of pride – a lack of self-confidence.

Part of the charm of starting small ventures is seeing them grow from nothing, but the early stages, when they’re still just mostly nothing, is pretty dispiriting.

I mean, do I really have any legitimate reason to believe that I will succeed outside of finance, aside from some nebulously placed trust in myself?

On the other hand, is it proud to think that I will succeed?

At the end of the day, I think it still is probably more productive to err on the side of being slightly too proud. Even if pride may come with a mild personality grievance and may occasionally steer you into embarrassing situations, life is difficult enough that it’s too costly to constantly be doubting yourself.

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