It seems we often relish “wins against the odds” more than we do simply achieving expectations. That’s fine as far as it goes. However, it’s easy for this to become a defense mechanism, a crutch — at best — or a self-defeating mindset at worst.
We don’t want things to be harder than they need to be, do we? Surely we don’t want the odds to always be stacked against us.
So then why do we seem to get so much validation from draping ourselves in the guise of an underdog?
Many, many times I have heard (indeed, many times I have said), “look what we accomplished against incredible odds!” How often have we bragged about our own team — or wondered in awe about another team — punching above its weight?
But really…how much do we think this is simply a framing mechanism applied after a success? And given the heroic feelings it engenders, how much should we worry that we actually manifest this condition into existence in the first place?
Size Matters
The phrase “punching above your weight” derives from the world of boxing, where competitors are grouped by “weight class” (literally, how much they physically weigh). Punching above your weight in boxing means fighting against folks who are actually larger than you are.
This notion of weight classes is at least a couple hundred years old and relatively sensical. It’s dangerous and unfun to watch a beefy goliath beat the crap out of some pipsqueak. Weight is a broad brush, and size is only one component of ability in the ring, but it’s pretty straightforward to measure and enforce.
A boxer can choose to fight an opponent in a higher weight class, but it rarely ends well; and even when it does, the rewards barely cover the risks or, you know, actual pain. A boxer who punches above their weight is less heroic than…foolish.
Of course, the phrase has long been generalized to refer to any endeavor where one successfully competes beyond expectations based on, well, pretty much anything: size, experience, expertise, financial backing, intelligence, age, whathaveyou.
I think my general distrust of sports metaphors is well established,1 but they are nonetheless hard to get away from! So here we are.
And as we can quickly see, the dangers of the metaphor leading us astray are manifold. But here’s a good one: for a boxer to win a fight, the other boxer has to lose. It’s quite literally zero-sum. So when we generalize this notion we have to create some kind of imaginary opponent in the ring.
Remember, a boxer isn’t going into the ring to fight against a sack of potatoes that’s about their same weight — they’re fighting another boxer, who also wants to win. So who’s our other boxer?
Was finance really trying to “knock you out” when they redirected resources from your project to that other one? And did you triumph against them by getting your project shipped anyway, on the backs of your under-resourced team?
Or — follow me here — did finance make a bloodless decision based on business intelligence? And did your team’s triumph against that adversity actually make them look smarter? (They got the project shipped with fewer resources!)
See, it's almost never true, not really. It’s just a way of narrativizing our own insecurities. Sometimes we do it proactively, sometimes retroactively. Doesn’t really matter — it’s fiction either way.
Here’s an exercise I have personally found valuable. Close your eyes and think back to that time a big project went exactly the way you expected: when you had all the resources you needed right when you needed them, when the team came together like two-plus-two-making-five all day long, when the market conditions were better when you shipped than when you started. I’ll wait.
Remember that time? Of course not. That’s not how things work!
Put a group of people together and set them about a complex task and stuff is bound to go wrong (or at least differently than expected). People are complicated! The world is ever-changing! Expected resources fail to materialize, new markets don’t pan out, the board gets indicted, things happen!
To create anything is to fight against the odds. That’s the baseline. When we succeed, that’s always the backdrop against which we succeed. That’s the weight class.
Defense mechanisms are good. They defend us. Sometimes.
I once argued with a coworker who tried to turn this perpetual underdog notion into some kind of affirmative credo or something. We had a rather animated discussion about it and I said something like, “wait, are you saying it’s more valuable to you to win the race in the clapped out VW than it would be to win the race in the brand new Ferrari?” The response was, “yes, because that shows I’m playing on my own terms.”
We left the conversation off as I could see there was little agreement to be had. The late addition of a “racing” metaphor to my “boxing” essay notwithstanding, I thought this demonstrated a really dangerous mindset.
To me, if it shows anything, it shows literally the exact opposite of playing on your “own terms.” If you were playing on your own terms, those terms would presumably advantage you, right? You’d say, “all I’ve got is my crappy Beetle so I’m not competing for lap-times, I’m competing for fuel economy. And I beat a Ferrari every time. I win. QED. My terms!” But that’s not actually how the world works.
Sure, you might stuff the Ferrari into the wall and lose anyway. Possible!
But the danger is that if you value that kind of win over any other, you’re going to make sure to bring a beater bug to the track every time, just to keep proving you can overcome those odds. You’re going to keep getting in the ring with some oaf twice your size.
It’s perilously easy to develop a taste for this kind of thing. And as soon as that happens, you’ll build it into everything, even from the start. You’ll set yourself up to probably fail, so you can get that rush when you don’t.
Especially for people in creative professions it’s one of the most common (and, honestly, effective) defense mechanisms. If you go into the project thinking it’s a virtually insurmountable task, you protect yourself against the reality that, yeah, you might not actually surmount it. And the odds probably are against you, anyway! Why make them worse?
Making them worse could manifest in any number of ways: you commit to those overly aggressive timelines, you roll the dice on that unproven tech, you underestimate the bureaucracy of the approval process. Man, this victory will be sweet. That big guy will never know what hit him.
If you start to feel the only true win is the come-from-behind win, you’re going to start ensuring — even maybe unconsciously — that that’s the kind of race you’re running. If you start to feel that beating the guy in the next weight class up is more heroic, that’s the card you’re going to put together. Who doesn’t want to be a hero?
Okay, so what’s the harm? A little defense mechanism deployed in what really is a vulnerable situation seems reasonable enough, doesn’t it? Sweetening the celebration a little with an exaggerated sense of accomplishment feels good, what’s wrong with that?
Case-by-case there’s nothing wrong with it, and we all do it. But when it becomes a pattern, it’s definitely cause for concern. And if we do it as leaders, it’s a really unfair position to put our teams in. It’s going to be hard enough to succeed as it is; adding difficulty is perilous. Punch your own damn weight.
Never mind that one of my most-read essays is called “Manager Judo”…still, it’s a general distrust.