insecurity 101

I was going to start this off with a really bold, all-encompassing statement like “the root of all problems is insecurity”, but then I thought about it for a minute, and realized that’s nonsense. Some of the worst problems I’ve ever dealt with professionally have come from people who were utterly and hopelessly secure about what they were doing, and in fact, those problems were in all likelihood largely a result of that confidence. Big surprise — most of these people were incompetent.

So anyways, like everything else, professional insecurity isn’t compatible with a snappy, Seth Godin-esque bumper sticker of a blog post. But it is a pretty big problem, and I’ll go so far as to say that most of the big problems I’ve had to deal with that involved talented, competent people resulted largely from insecurity about something or other. That being the case, it seems like something worth digging into a bit.

what do I mean by insecurity?

Not unlike Fight Club, the rules of workplace insecurity are short, and kind of meta. Most importantly, the first rule of workplace insecurity is that it’s almost impossible to exhibit workplace insecurity if you’re worried about your workplace insecurities. I know, what a relief.

What I mean by that is that everyone is insecure about something. That’s just life. Professional insecurity only becomes an issue when you lose track of it, and start thinking it’s something else, like a conspiracy to disrespect you, or a plague of implausibly exclusive incompetence that somehow affects everyone but you and a few people who allow you to complain to them. If you’re working on your insecurities — if you’re thinking about them, and being critical of yourself but pragmatic about how you can improve… well, it’s very unlikely those insecurities are causing anybody problems, even if they keep you up at night.

The truly dangerous insecurities are different, and they’re largely hidden. They often do sneaky things like project themselves onto others (so you can justify them), or create distractions that keep you from addressing them. Those are the ones I’m talking about here.

why are talented people insecure?

I’ve worked with a lot of talented people, and some of those people had insecurity problems that hurt their careers and/or their teams. Most of those people worked through those issues — in a few cases, I’d like to think I helped at least a little — and hopefully the rest will someday. With all of them, though, there were a couple of insecurity-causing scenarios that kept popping up.

(NOTE : There was almost always only one of these per person, although parts of one can overlap onto another.)

  • They took a disingenuous or unfair shortcut in their career, and deep down, they know they did.
  • Their life is based on achieving excellence relative to others, and as you get older and join higher performing groups, standing out from your peers gets harder.
  • Their personal identity isn’t really any different from their professional identity, so when they aren’t an awesome professional they feel like they aren’t an awesome person, and that scares the hell out of them.
  • They don’t want to do some portion of the work that’s necessary to truly excel (or they don’t think they have the ability to), but they aren’t comfortable admitting it.
  • They are objectively bad at something they think they (or people in their role) should be good at, and even if it doesn’t really matter, it makes them crazy.
  • Their job has required them to bullshit a lot (try raising capital, selling something that isn’t really done yet, or spending too much time arguing in favor of your subjective opinion, it’s hard), but they’re an inherently honest person and they feel, in some way, kind of guilty (whether they should or not).

I’m sure there are more than that, but even this list is a pretty broad swath of experiences that all contribute to the same kind of toxic behavior and thinking. In my experience, that behavior includes :

  • lack of empathy, and the feeling that empathy is often excuse making for others
  • a tendency to see weaknesses in a functional area as a result of someone else’s inherent, personal flaws
  • seeing the (often negative) outcomes you expect as inevitable, and any evidence to the contrary as someone’s attempt to deceive
  • frequent false positives that validate bad things about other people, or ideas, that the same person would normally detect as obvious confirmation bias
  • shutting down conversations or necessary arguments as “unproductive”, “pointless”, or “something we’ve already resolved”
  • exaggerated self importance (as if everyone cares as much about the person’s perceived weakness as they do)
  • projection of your perceived failings onto other people
  • the inability to concede portions of an argument and the tendency to conflate multiple, separate issues into a single, all-encompassing thesis people either “get” or “don’t get”

All of this sucks, and it’s frustrating whether you’re dealing with a friend, a boss, or someone you work with and are trying to build up. But… it’s not the end of the world, by a long shot.

the homer simpson boxing approach

For me, the only thing that’s ever allowed me to help someone deal with toxic insecurity is trust. Unfortunately, trust takes a long time to build — unless you’re a perfect match for someone socially, you aren’t going to build real trust overnight by going to a happy hour or on a weekend retreat. No, instead, you’ll work with them on something that triggers their darkest insecurity, and they’ll lash out at you in one of the many ways listed above.

At that point, I like to break out what I think of as the Homer Simpson approach, which is based on the awesome episode of the The Simpsons where Homer becomes an amateur boxer after his doctor determines he has an inexplicable condition that allows him to take repeated blows to the head without incident. Homer is a poor athlete and a terrible boxer, so his trainer (the always wonderful Moe the Bartender) convinces him to simply stand there while his opponents continually punch him in the face. Eventually, they’d become exhausted from all the punching, and Homer would then gently push them over.

It’s a great episode.

The point is, the reason many people act defensive towards someone else is because they are scared of how that person will react to something. Most of the time co-workers have aggressively approached me with complaints about a colleague, it’s a pre-emptive strike over an issue that multiple people (including the person complaining) are partially responsible for. Most of the time people react poorly to constructive feedback (sometimes by criticizing something unrelated I’ve worked on), they’re really just nervous that their work sucks, even if it doesn’t. But these aren’t firmly held beliefs, or even particularly well-thought out ones — they’re irrational, emotional fears, and they don’t last unless they get reinforced.

Hence, the Homer Simpson approach. When someone is exhibiting severe symptoms of insecurity in their interactions to me, I just… let them do it. I let them complain (although I gently remind them of oversimplifications or exaggerations in their complaints). I let them yell at me. I let them call me hypocritical, out of touch, blind, irrelevant, stupid, ignorant, and everything else in the book and simply focus on not doing anything to confirm or reinforce those assessments.

Eventually, unless someone is truly damaged (this does happen), they simply run out of defensiveness-fueled-rage, even if it takes multiple conversations. At that point, more often than not, you can get them to simply tell them what they’re really worried about. And once they do that, you can actually work on it.

postscript : the gandalf corollary

The Homer Simpson Boxing Approach is awesome, but it’s not a flawless answer — there are times where an insecure colleague will respond to your patience not with exhaustion and eventual trust, but by doubling down on the intensity of their attacks, or by incorrectly detecting weakness and turning those increasingly aggressive attacks on you.

When this happens, I’ll admit that I’ve been forced to apply the Gandalf from The Lord of the Rings Approach, demonstrated here by Gandalf himself.

This is one of my favorite scenes in any movie, period, mostly because it reminds me of the way my Dad used to deal with my notoriously explosive, self-righteous temper. He successfully applied the Homer Simpson Approach to my sister and I for years, constantly forcing us to exhaust our insecurities and defenses until we finally just gave up and leveled with him. But in certain moments, like Bilbo, we’d forget who we were talking to. Dad would talk to us as equals by choice — until we started thinking, maybe, just maybe, he was out to get us too! The subtle, clear change in voice he’d use when I was a kid to draw a line (“Now wait a minute…”, or “Hey!”) was never sharp, or defensive like us. It was just strong, almost like an audible reminder of the difference between making an argument based in fear and an argument based in wisdom. I’m pretty sure both me and my sister did that exact same cowering/running in for a hug thing that Bilbo does, except we were probably seven years old at the time, and Bilbo was like, a hundred and twenty or something. But still.

There are a million wrong ways to break out The Gandalf, so I’m incredibly careful with it. I’m sure lots of people (maybe me, sometimes) think they are doing it, but are really just acting on the same types of defensiveness and insecurity they think they’re disarming. But done properly, it’s often the defining moment in a professional relationship.

operational lessons from my mom

garbage apologies

In honor of Mother’s Day (that’s when I started to write this, so who knows when I’ll finish it or when you’ll read it), I’ve been thinking about some of the things she taught me, both expressly and by example. In my household, my Mom was most directly responsible for teaching me how to deal with my many screw-ups. (No knock on my Dad, here — he was first responder to a couple of doozies, like getting thrown out of Little League, but my Mom has him beat on raw volume.)

For some background, my Mom got stuck (or chose) to take on this particular aspect of child-rearing for a couple reasons. While both my parents worked full-time, my Mom’s hours resulted in more direct face-time with her kids. Plus, as a teacher, she had a better grasp than my Dad did of the problems that faced my generation, and a larger sample size to compare it to. For instance, it was very difficult to convince my Mom that I had a unique, acute attention deficit disorder when she dealt with 30 other rugrats all day who were sometimes even worse. My Mom’s career also made her particularly… err… “invested” in my behavior at school; if you really did have a bad teacher, circumstance, etc., there was no stronger ally to go into battle with than my Mom. But God help you if you weren’t honest about the situation, or were contributing to the problem yourself. I get chills just thinking about parent-teacher conferences to this day.

Anyways, the point is that my Mom was on the front-line of my countless mistakes, so her reaction, advice, and thoughts on them were probably more important to me than anyone’s, even if I vehemently disagreed with them at the time. And one thing she had absolutely no tolerance for were weak, forced apologies. “Sorry doesn’t do anything,” she’d say. “If you’re sorry, do something to make sure it doesn’t happen again.”

pivots as apologies

I could write a whole piece about the different flavors of cynicism, but for the sake of this particular argument, you just have to know that I’ve never thought of cynicism as a universally negative thing, probably because I was raised by a couple of New England yankees with limited tolerance for bullshit or self-serving rationalization, and we live in a world that seems increasingly full of those two things. I’ve read lots of historical takes about how Massachusetts and the Route 128 belt missed out on becoming Silicon Valley for a bunch of policy/regulatory/infrastructure reasons, but the Valley as we know it simply couldn’t exist in New England because it’s a creative engine of amazing economic potential powered by — let’s face it — a nuclear reactor of horseshit and nonsense. Even real companies out there like Facebook and Google are constantly hand-waving away limits to their business models with massive, ambitious, absurd attempts to enter new spaces and pretending they have any idea what they’re doing. That kind of thing just doesn’t fly in the original thirteen colonies… unless you’re related to someone. We have our own problems with that.

In venture companies, the closest thing to a common childhood apology is the pivot. This is where you stop doing something that isn’t working and try something different with the same pile of money you originally raised by saying, very confidently, that the first thing was totally going to work and make everyone rich. There are two basic ways to couch this kind of pretty obviously bad news.

  • Pivot as learning experience — “Hey investors, I know we were going to build the ultimate snack delivery company, but it turns out that the logistics of delivering snacks are a lot more complicated and expensive than we thought. BUT, in building out our amazing snack library, and serving our customer base, we’ve learned that we could create the same kind of value for our customers at a fraction of the cost by re-inventing the vending machine experience. So that’s what we’re going to do. We got rid of our delivery function and are building out a vending machine team.”
  • Pivot as a rationalization — “Hey investors, just want to let you know that we have COMPLETED OUR MISSION to disrupt the snacking experience, and are moving on to an even bigger challenge; the vending machine space. As the number one snack delivery provider, and best-capitalized vendor in the industry, we’re uniquely equipped to take the next step in achieving our vision of making the right snack available to everyone on the planet at the exact moment they need it.”

One of my biggest problems with VCs, in my limited experience interacting/dealing with/being affected by them is that in general they’re much harder on that first response than I think they should be, and much, much, MUCH more lenient on the second one. The result is that approach #2 is a lot more common than you think, even when it’s obviously ridiculous, and well-capitalized startups end-up being even more vulnerable to delusional thinking than large, established companies when it should really be the other way around.

the “make sure it doesn’t happen again” part

The costs of mistakes and incorrect operational decisions are pretty obvious — it’s the immediate thing you have to deal with when you screw up. But if you’re in any kind of growth phase (as a company or, say, a kid), the opportunity cost of hand-waving away mistakes as either GLORIOUS VICTORIES or random one-off outliers (“no one could have foreseen the breach of the levees”) is usually even greater than the cost of your screw-up.

I’m obviously not proposing ripping up every process the minute it doesn’t work — but just about everything can be iterated on, tweaked, or re-examined as situations, markets, and conditions develop. That’s simply how things get better, and how kids, entrepreneurs, and teams learn and improve, no matter how smart you are coming out of the gate. I think the best organizations operate like this whether they admit it or not, but the way this kind of thing is messaged (and encouraged by boards and management) matters, especially in growth environments.

So with all that said, I think I’ll put my Mom on the board if I ever end up running a company. Good luck trying to spin that disastrous Q3 product rollout to her as a validation of your strategy.

Everything ends badly, or else it wouldn’t end

Vice on an apparently incredibly well-known artist that I clearly have never heard of because I am overworked and a Dad these days:

There’s a stronger parallel to be drawn here, too. After the grunge explosion and the birth of so-called “alternative rock” brought on by Nirvana’s emergence in the early 90s, the rest of the decade’s mainstream rock airwaves were plagued by increasingly same-y sounding “post-grunge” acts that sanded down the depressive bile of their forebears until it sounded smooth, frictionless, and utterly corporate. Purely for analogous purposes, let’s say that M83 is Nirvana (wait, don’t go!), and the Chainsmokers are, for shits and giggles, Vertical Horizon—so far removed from the source material that the resemblance is barely there, but once you become aware of it, the soullessness it represents is impossible to shake.

Hey, I wrote about this phenomenon once, too, although I needed a clip from “Idiocracy” to make my point:

If Operation Ivy is Sears, or some other classic department store, then Blink-182 is CostCo, and the fat guy in this clip is your typical pop-punk band today. Yeah, in theory he’s emulating CostCo, but it’s been so long since that meant anything, he’s really just going through the motions, sort of hoping that by standing there and saying CostCo-related things that he’s successfully honoring his influences. “Welcome to CostCo” is basically “Defend Pop Punk“.

I actually feel better this also happens to genres of music I’m not interested in.

Incentives & Rules

One thing I’ve noticed over the last year or so is that I spend most of my time trying to get people to do things. I’ve been in marketing for a while now, and while I’d like my efforts to be focused on getting people to do things that make sense for them, at the end of the day I work for a business and the business is happy when our market does what I want them to do, and sad when they do not. So there’s that.

The other thing I’m increasingly involved in is management and organization or process building, where I’m trying to get people I work with, or manage (or maybe I work with someone who manages them) to do things. This sounds super manipulative, but it’s really not — I’m very upfront with everyone I work with about what I’m trying to get them to do, partially because I’m a terrible liar, and partially because every once in a while people will just do what you ask them to because you asked them to.

Most of the time, however, they don’t, because this is work, and what I’m asking people to do at work is usually annoying, counter-intuitive, or effort intensive for them — otherwise I wouldn’t have to ask for it. So here I am, with a thing I want people to do that isn’t interesting or valuable enough for them to do automatically, and two basic ways to solve it.

incentives

The first thing I can do is adjust people’s incentives. Messing with incentives is very in-fashion these days, possibly because it’s the information age and it’s easier to test things, or possibly because everyone I met in college had or wished they could have an economics degree, and all of those people are in their thirties now and writing books and getting into management. I suppose there could be a third reason, but I’m pretty sure it’s one of those two.

Traditionally, I’ve been very pro-problem solving via incentives, because like many (older) millennials, I am irritatingly conflict-averse and also slightly lazy, at least to the extent that I hate repetitive tasks with no obvious ending point. Unfortunately, my love of incentives has spent the last few years crashing into the brutal reality of actual implementation, and I’ve had trouble with a few things.

  • Money is a great way to create or adjust incentives, but people become irrational economic actors in a much larger number of scenarios than I ever imagined they would. Basically, people get really excited about the idea of controlling how much money they get out of doing something, until they end up having to actually do it, at which point they often choose to find a equilibrium between effort (or emotional satisfaction or whatever) and return that does not align with the outcome I’m trying to incentivize. I’m not saying this is unsolvable, just that it’s a lot harder to execute in practice than you might think.
  • Measuring behavior and outcomes accurately and with proper context is usually much, much harder than it first appears. Nothing is more frustrating than building out a logically air-tight incentive program, and then being told that you need to rebuild it without a key piece of information on which your program relies. Sometimes (many times), you can’t, or the resulting half-measure isn’t compelling enough to generate the behavior you want.

In short, I still love incentives and they are theoretically superior to any other way I’ve come up with to get people to do what I want, especially at any kind of scale. However, trying to solve everything with incentives in an actual business with resource limitations and plenty of other important things to do is often a great way to spend a lot of time in front of a white-board without, in the end, actually changing anything.

Of course, there’s another way…

compliance

Yes, that’s right — it’s the old “because I said so” school of management/parenting/Little League coaching, which was a staple of my younger days. In fact, I think one of the reasons young-ish professionals are so enamored with incentives-as-management is that they’re simply excited about the prospect of any incentive other than “not getting in trouble”. However, the simplicity of implementing compliance gets more and more appealing as you deal with the complexity of building and executing elaborate, often contradictory incentive schemes for different groups of people, and before long, it’s easy to find yourself fantasizing about simply crushing every obstacle in your way with the merciless hammer of autocracy.

To quote my favorite management consulting resource, Green Day’s 1994 album “Dookie” :

“Do you ever want to lead a long trail of destruction and mow down any bullshit that confronts you?”

If your answer is “yes, yes I do”, you’re going to love compliance, at least in theory. Unfortunately, the fact that implementing compliance is “simple” has zero connection to it being “workable”, or “effective”, and even in my limited deployment of this strategy, I’ve run into a couple problems.

  • Compliance isn’t actually all that different than incentivizing — you’re often just sort of threatening negative incentives, or maybe just inferring them if you prefer not communicating clearly. So in a lot of scenarios, compliance is just as complicated, because you have to build negative incentive schemes that are just as complicated, but much less exciting or motivating. For instance, if I just tell you to do something, what happens if you don’t? Is that clear? Is it established? Is it… anything? The idea of not being yelled at, or not disappointing someone, can be extremely compelling or not compelling at all based on lots of factors — it’s just that with most compliance plans we don’t think about any of it until later, so it seems simple enough.
  • Leaders, managers, and even governments all constantly overestimate their ability to enforce compliance. Keeping people from smoking pot by putting them in jail or harassing them (i.e., compliance) has never worked, and still doesn’t work, but there’s still a vast army of politicians, police administrators, and others who are so disgusted by the idea of soft, subtle positive incentives for good behavior (people who smoke a reasonable amount will perform better at work and generally be happier than people who are constantly stoned, etc.) that they’ll just keep banging the drum forever. When I worked at Efficiency Exchange, we spent a lot of time engineering the right set of positive incentives for manufacturers in developing economies to behave the way their customers wanted them to, and people were constantly baffled by the idea. They all just wanted to make requirements and throw them over the wall, assuming they had sufficient economic weight to enforce their will when they absolutely do not.

oh no, not a mix…

So no, neither of these are one-size-fits all solutions in the real world. I can’t imagine you’re surprised. I battle with this every day, and here’s what I’ve learned so far.

  • Start by removing positive, perverse incentives for actively undesirable behavior. There are probably more of these than you realize, especially if you have data problems. (hint: you totally do)
  • Save compliance for things where people have recently suffered from their own refusal to comply. Nobody wants to carefully fill out a report every Friday, but good people will do it if they remember terrible things happening due to a lack of good reporting. Same thing with project management behavior, etc.
  • Don’t resort to compliance just because you don’t feel like figuring out the incentives, or because you are annoyed by the fact that people who work for you aren’t just happy to have a job. It’s understandable, but I’ve never seen it work in the private sector.
  • Don’t create incentives you aren’t equipped to measure accurately — your flawless whiteboard theory is worth less than nothing if you can’t build an effective bureaucracy to execute it. And don’t be arrogant or dismissive about the way that stuff is calculated. If you can’t trace back a couple edge cases and audit the results yourself, you’re playing with fire.
  • Create a very simple, rock-solid incentive that is bigger than anything else, and more important than anything else, and then experiment on the margins with more granular, less important stuff. If your experiments are stupid, the bigger thing that works will prevent people from doing anything too damaging until you can fix the smaller stuff or kill it.

I certainly haven’t done all of this stuff yet, or done it well enough to get the outcomes I want, but I can at least say that this kind of thinking has helped me make a number of stupid things significantly less stupid. And I’ll take that any day.

GOP health-care bill: House Republican leaders abruptly pull their rewrite of the nation’s health-care law

GOP health-care bill: House Republican leaders abruptly pull their rewrite of the nation’s health-care law

Trump’s budget targets rural development programs that provide a quiet lifeline

Trump’s budget targets rural development programs that provide a quiet lifeline

White House tries to salvage GOP health-care proposal as criticism mounts

White House tries to salvage GOP health-care proposal as criticism mounts

health insurance in a mine

Here’s the Washington Post on Trump supporters facing the prospect of losing their medical coverage :

“As for the other problems in his life, he has put his hopes in Trump, who came to West Virginia saying he would bring back coal and put miners back to work. When Trump mentioned repealing Obamacare, Clyde wasn’t sure what that might mean for his Medicaid. But if he had a job that provided health insurance, he reasoned, he wouldn’t need Medicaid anyway, so he voted for Trump, along with 74 percent of McDowell County.”

Clyde here is 54 years old, and is currently an unemployed coal mine worker. Personally, I can’t imagine being in that demographic and thinking “a sustainable future scenario is one where I am back in that mine being a profitable asset for a coal company”, but my assumption is that a lot of people in this situation aren’t putting a lot of thought or research into market economics. 

That’s why I wonder if the nostalgia people have for Reagan’s America, or whatever fictional version they have in their head, is for the actual socio-economic climate at the time, or simply an era where they were thirty years younger. That would fix almost all of Clyde’s problems (health, impending financial needs of old age, lack of economic utility in his field of choice), but I don’t think there’s a policy for that. 

Georges St-Pierre Is Back Because The UFC Is Out Of Ideas

Georges St-Pierre Is Back Because The UFC Is Out Of Ideas