Confidence : Organic vs. Constructed

One of the truisms I’ve run into in life is that “confidence is king”. This is one of my least favorite truisms, because I’m a naturally skeptical person who very intentionally applies that skepticism to his own ideas.

But that personal inconvenience doesn’t change the fact that everywhere I go, confident people are winning arguments, making decisions, and driving the institutions I care about — whether that’s off to fame and glory or an obvious, avoidable cliff. People worry about whether leadership is “confident” all the time, but so far in my professional experience, I’ve never worked for a management team that didn’t clearly exude confidence. Despite this, not every venture I’ve been a part of has been successful, which goes to show that at least some of those confident people I’ve worked with and for were… well, they were wrong, and probably wrong about one or more pretty important things.

The obvious question, then, is “does misplaced confidence hurt”. Twelve years into my professional life, I’m ready to say “yes, it does”, although that’s not true in every circumstance I’ve dealt with. Here are some things I’ve found require confidence whether it’s warranted or not :

  • raising venture capital
  • selling expensive things
  • getting hired somewhere cool
  • copywriting
  • certain kinds of leadership
  • shooting three pointers
  • singing in a punk band

I’ve had various degrees of trouble with all of these things, and for the most part, I’ve only succeeded at them when events on the ground changed, and I felt better that my confidence was warranted. It’s no coincidence that my career opportunities have gotten demonstrably cooler and more exciting as I’ve gotten older and more experienced — it’s only now, after going through my different experiences that I feel legitimately confident in the judgements and opinions that jobs like mine require. I needed a lot of reps and to face a lot of different, unexpected scenarios in a lot of different capacities to get to the point where I can tell someone I work with that their career track isn’t a dead end, or that a process change is worth the embarassment of acknowledging it and the headaches of implementing it. I needed to shoot a whole lot of three pointers at the park before I came to the honest-to-God conclusion that it made sense for me to shoot them in games whenever I got open, and that getting open for such a shot was the best way for me to help my team.

organic confidence

In other words, I built confidence in these things by spending that rarest of currencies — time. I literally put years into organically resolving these doubts by going through experiences, making mistakes, assessing why they happened, and filing away my conclusions. As someone who isn’t inherently confident about much of anything, having this kind of experience-driven confidence is incredibly powerful. While it accumulates slowly and painfully, there comes a tipping point with all of these things (or at least there did for me) that’s simultaneously exhilarating and freeing, when you realize that you really do know what you’re doing, and can just take control of various situations where that’s the case. When you present an idea to a group of smart people, and your first thought isn’t “oh crap, these smart people are going to find the holes in my idea and I have to defend them”, but is instead “this is great, these smart people are going to ask awesome questions and I’m probably going to be able to come up with good answers because I understand this topic as well as anyone”, there’s nothing quite like it.

Organic confidence is a pretty rare commodity, because it requires a combination of at least some aptitude, and a fair amount of experience — and experience takes time. It’s hard to be organically confident about more than a couple things, which is why the list above of the confidences I’ve built up is actually pretty complete. I’m not very confident in the kitchen, arguing on the spot, dancing, navigating, doing anything other than very rough math, or taking binding action in any number of other common scenarios. Not that I’m done trying to get better — I’ve improved my kitchen confidence since our daughter was born and I’ve taken over breakfast and basic dinner duties — but these things all take reps and there have only been so many hours and legitimately educational experiences in my life so far. That’s not a personal failing, it’s just the result of a bunch of reasonable choices.

constructed confidence

If you’re impatient, or even in a hurry for a valid reason, there’s a shortcut towards effectively exuding confidence. You can construct it, through a combination of guessing, imitating, and discipline. Sometimes constructed confidence is almost as good as the real thing. I’ve seen people gain confidence in public speaking that’s taken them from being very poor public speakers, to average or above average ones simply through coaching and discipline, even if they are still pretty bad on stage, and don’t really know what they’re talking about. Sure, they’re still bad, but they’re a lot better than they would be if they didn’t exude confidence. Before I developed organic confidence in my ability to drive, my Dad taught me to drive with more confidence than I naturally felt, and while it didn’t make me a good driver, it at least made me functional enough to gain some experience and become one organically over time. To return to basketball, you can be a better offensive teammate and make the defense work a little harder simply by looking like you know what you’re doing.

So confident! So wrong.

So confident! So wrong.

I think many of the people who achieve really amazing things in this world rely on a mix of constructed and organic confidence when they deal with other people, and that they’re successful because they find the ideal mix of the two. They only make critical, risky decisions when they’re organically confident that they know what they’re talking about, and they use constructed confidence when cirumstances paint them into a corner they’re forced to address before they’re really ready. We have a tendency to look at Steve Jobs as a genius, or a total sociopath, but I think he was just really good at balancing these two forms of confidence, to the point where it was often hard to tell which kind he was even relying on for any given argument or decision. Other people aren’t so hard to read — if Jeff Bezos walking onto a big stage and assuredly describing the world-changing nature of a ridiculous Amazon phone that buys things you point at isn’t a textbook case of constructed confidence, I don’t know what is.

constructed confidence is everywhere, and it’s become corrosive

I suppose a grosser analogy is to think of constructed confidence as the filler in the meat of organic confidence. Yes, you can stretch a limited resource in a useful way with judicious usage of filler, but the filler itself is pretty useless, and if you rely on it too much, you’re not really eating meat anymore. And that’s where we are with way, way too many people. If you know the usual axes I like to grind, you won’t be surprised that I think this has a lot to do with two things.

The first one is the pressure cooker we raise kids in today, and the pointless, surface level measurements we use to validate them. We probably should have seen this coming — the more your ranking relative to other people matters (college, internships, jobs, etc.), the more younger people are expected to gain competence (and by extension, exude confidence) in things with unrealistically low levels of experience. For all but a select few geniuses, it’s literally impossible to develop that kind of organic confidence so quickly and so completely, so it shouldn’t come as any surprise that college students and young professionals take the obvious, necessary shortcut of constructing it instead. Heck, we often coach them to do this. Then, since they’re already supposed to be experts at whatever they’ve sold themselves as, they’re under even MORE pressure to appear even MORE competent and MORE confident each and every day. That doesn’t leave a lot of time for learning anything, and it puts a lot of talented people in positions to fail very, very badly.

The second reason constructed confidence is so common is the almost child-like level of impatience we have with the progress of doing anything, including the fairly important act of making money through old-fashioned, non-financial-shenanigan value creation. At the simplest level, a business or a company makes money because it’s good at doing something — landscaping, building software, tutoring, manufacturing tiny metal objects, whatever. The fact that you have the great idea to manufacture tiny metal objects is nice (you probably had to read the market correctly and assess why it would be a good thing to do), but it doesn’t really matter if you suck at manufacturing tiny metal objects.

Unfortunately, doing almost anything well is complicated, and usually takes a combination of practice and mistake-making. That’s true if you’re a cop, or a cook, or a professor, or a chemical engineer, or just some mid-level business guy like me. If you don’t put the time in (and it’s a lot of time, and no, what you did in college probably doesn’t really count towards it because college is a giant laboratory monitored by professional evaluators), it takes an extraordinarily long, self-immolating process to get good at something, determine why you’re good at it, and eventually develop the organic confidence that comes from surviving the whole ordeal.

“Pressure makes diamonds.” Except, no, it doesn’t. Pressure and time make diamonds.

There’s plenty of pressure out there — but not a whole lot of time. So yes, “successful” people increasingly fake it, often because they’re encouraged to fake it, or directly coached to fake it. That leads to unforced errors, nervous breakdowns, and a never ending “confidence-war” among ambitious, insecure professionals that continually raises the stakes and values perception and alpha-dog posturing over skills and sound decision making.

yet another shortcut

Ultimately, the problem with constructed confidence is that it’s a quick fix for the wrong problem; a sugar rush of self-importance that anyone can generate but no one can sustain in a real-world environment without it eventually blowing up in their face, and the face of anyone relying on them. Maybe, if all you want to do is glorified consulting or public speaking, you might be able to float from one encounter to the next, confidently declaring things and moving on before your lack of battle-tested knowledge becomes apparent. But if you want to work with other people, or build something significant? The best outcome for using constructed confidence there is that you get through a situation you’re not prepared for and back to a core competency as quickly as possible — and then you figure out how to avoid that situation again in the future. It’s horrifying to me when a friend or colleague gets through some encounter they have no real qualifications for with nothing but bluster and bravado, and comes out the other side somehow more confident about their abilities, as if they’ve gone through some kind of crucible by successfully feigning expertise. Going to a bunch of meetups and hanging out with engineers doesn’t make you a developer. In my case, fumbling through Learn Python The Hard Way and never actually building anything other than a bunch of if-then-loop powered fart jokes than run in the console doesn’t do it either.

I am not confident in my carpentry/engineering skills. But that didn't stop me from building this pointless box and getting the tiniest bit less incompetent.

I am not confident in my carpentry/engineering skills. But that didn’t stop me from building this pointless box and getting the tiniest bit less incompetent.

But hey, it’s okay to be bad at some things, and it’s more than okay to recognize that and control your exposure to said things. You can even try them out in safe environments where outcomes don’t matter, like I do with programming. Go to open mic nights and bang on your guitar, or tell jokes, or present a pitch deck to other nerds. Get into an argument about finance with someone more qualified than you at a party, and see if anything you say actually holds up under scrutiny. If it doesn’t, ask questions and try to find out where you’re wrong. You might even get better at these things, and — over time — build up real confidence in your abilities that you can break out in real situations with real stakes.

But don’t use important situations to test out your “expert” poker face, even if you see other people doing it, and being rewarded for it. Sure, your peers may get promoted ahead of you for a while, or get media mentions, or become “thought leaders” in fields you know more about. Those people never do anything that really matters, though — because they don’t actually know how to do anything. And in the end, knowing how to do whatever it is you do really well is the most valuable, stable thing you can buy with that all-too-rare currency of your own time.