As Long As I’ve Got My Suit and Tie, I’m Going to Leave It Out On The Floor Tonight

I’ve never been very good at dressing up. My roots are in technical tinkering and the creative arts, with a healthy dose of New England punk rock (and think New Hampshire, not New York), so maintaining appearances was never interesting or natural to me. As a kid, I agonized over even basic, semi-formal requirements for things like school dances, performances, or graduations — never mind things like weddings.

This remained fine as I grew up, primarily because I went into tech instead of my other potential destination, journalism (or, God forbid, law). I interned as a clueless D.C. journalist in the fall of 2002 and enjoyed a lot of what I got to do, but still found myself jealous of the CSPAN cameramen who got to play with cooler equipment and dress like AV guys while I poked at the itchy collar on my shirt and my uncomfortable shoes. So when I started my career at a mid-stage Boston tech startup in 2004 and discovered that they cared a lot more about how fast I could format press releases and assuage customer concerns over the phone than whether I could tie a tie, I knew I had a path.

From then on, nothing brought me any closer to formalwear. Support, technical writing, product management, and eventually product marketing required me to be increasingly strategic, but not sartorially impressive, especially since I worked for bosses who understood my value and trusted my ideas and execution skills, but usually handled dealing with customers and company brass themselves.

As a result of all this, when I found myself running FiscalNote’s marketing team this fall, I suddenly found myself in the unexpected position of representing our company and our function at an executive level — even if somewhat by default. While in the past I had never felt any real internal pressure to figure out how to fit in with the suit and tie crowd, this seemed different. My company had given me a chance to step up into a role even I wouldn’t have thought myself capable of just a few years ago; why shouldn’t I at least try to meet those expectations on every possible front? Customer events, board meetings, etc. — these were important things I was being given an opportunity to attend, influence, and make as successful as possible.

Basically, while I still loved the idea of not wearing a suit (or anything other than Boston sports-franchise related t-shirt, to be honest), actively refusing to didn’t resonate with me the way it used to. That kind of line in the sand just didn’t feel like a part of my identity anymore, and I felt worse about the idea of letting my colleagues down (even just a little) than I did about wearing silly clothes.

Man, did that ever make me feel old.

this suit is black not

So I bought a suit. It wasn’t fancy, but it wasn’t cheap, either — the nice people at the nice store in the nice mall I usually don’t go to tailored it and told me it looked great and had me try on different jackets and stuff. My wife was very helpful, and didn’t laugh at me too much.

I went home, put on my suit, and went to work. Here’s what I learned about the dressed-up version of myself.

  • Clothes aren’t magic. Instead of feeling like a badass captain of industry, I felt self-conscious and stupid most of the day. Worst of all, I felt inauthentic, which I think is an even bigger hang-up for me than it is for most people.
  • I thought about my clothes a lot, which is not a great frame of mind to be in when you need to get work done. There are just a lot of things you can do wrong with formal clothes that people who wear them all the time naturally avoid, and I probably did them all several times.
  • Eating, drinking, sitting, leaning against things, bathroom breaks — pretty much everything is risky behavior when you’re walking around in what are basically pajamas made out of money, and that didn’t make me any more comfortable with my environment.
  • If you’re the kind of person who doesn’t wear formal clothing, and you’re suddenly thrust into an environment where everyone there is dressed up, there’s really no way to succeed when your goal is to fit in and not be a distraction. If you don’t dress up, you’ll make a scene. If you do, people will notice, and you’ll make a scene. (“Whoaaaa, look at this guy!!!”) Hopefully this gets better with time.
  • I’m pretty sure that my problem with most real-time interactions is my preference for honesty and candor. I’m certainly not rude, or inappropriate — I just have trouble naturally interacting with other folks with the right professional safeties on, so rather than say something stupid, I prefer not to say much at all. I don’t hate small talk so much as I’m actively bad at it. I’m not disinterested in you as a person, I’m disinterested in the stupid, safe topic we’re inexplicably discussing, but since many people are uncomfortable having honest conversations with people they’ve just met (myself included), that’s what we’re going to talk about.

In short, my trouble with suits doesn’t really have anything to do with work, or business — I’m actually pretty good at that stuff. The trouble I have is with many of our oldest, most irrational social traditions, and that’s been a problem that’s dogged me since I was a little kid. I literally just don’t understand ties, just like I literally don’t understand how to feign more interest in another person’s story than I actually have, or how to impress a girl in front of a keg in a frat house where I can barely hear what anyone is saying.

(That last one hasn’t been important in about 15 years, so at least I’m making progress.)

“That’s just how things work” has always been the exasperated response from my well-intentioned, more socially flexible friends and colleagues, and I’ve always grudgingly accepted it and never insisted or expected that anyone else think the way I do. The funny thing, though, is that when I am actually praised for my thinking, it’s almost always for clearly and accurately modeling a complex situation into something real and approachable. And yet many people are often surprised by the fact that this same person would struggle to integrate irrational, distracting bullshit into their natural behavior.

Suits and ties don’t make any more sense than skinny jeans, or those crazy things that make you have giant earlobes, or the safety pins on leather jackets kids at our shows used to wear. And while I understand that our society uses them to convey a complex series of social indicators (suits indicate business acumen and wisdom, or at least the possibility of wisdom, now hoodies sort of mean tech, etc., etc.), I’d be lying if I didn’t admit that I still think it’d be a lot more efficient if everyone was just honest with each other and evaluated what we all said and did on the merits.

The fact that I’m old and realistic enough at 35 to realize people aren’t going to do this doesn’t make it any less true, or any less the way my brain works. But I’d like to think being able to work around that is just another thing I’ve been able to improve about myself.

My Saw Man Argument (WOMP, WOMP)

One of the best parts of working at a relatively early stage — or at least growth stage — company is that there’s a general bias towards doing things quickly. This is great, because I’ve found that working with other people on just about anything tends to slow things down for a variety of reasons. More people means more opinions, more views to consolidate, and more fears about failure (both personal and organizational). In mature companies, this basically eliminates the ability to quickly try interesting things unless you set up some kind of specific environment to do so, which is why people like me tend to go crazy at mature companies, or just give up and read the internet too much. Fortunately for my career — and unfortunately for the message boards I used to spend time on in the mid-2000s — I haven’t worked at a mature company in about ten years. Instead, I’ve been working for businesses in the highly motivated “grow or die” stage, where standing still is the only thing you can really do wrong.

Of course, anyone can do lots of random things quickly — that doesn’t take skill, sound decision making, prioritization, or anything other than energy, really. And while doing that in an early stage environment gives you a lot of very satisfying dopamine hits, you also run the risk of generating — and living inside of — the illusion of progress. Yeah, you’re doing lots of stuff, but what’s really different than before? (Sorry, can’t take the time to answer that — have to do more stuff!!!) Marketing departments are often the worst at this kind of thing because they’re where a lot of companies turn for miracles, like unexpected press coverage, or some crazy stunt that suddenly changes undesirable business fundamentals. That dynamic is partially the fault of Marketing people who don’t like to be held accountable preferring to skip around from one crazy project to another, and partially the fault of everyone else for expecting white-elephant type events to overcome less exciting operational or strategic problems.

move fast and accomplish things

While I am abjectly terrible at construction and home improvement tasks, I do remember my Dad teaching me how to use a saw. When he first put a piece of wood into the vice in the basement and handed me his, I attacked the wood exactly as you’d expect a crazy seven-year old with borderline ADHD to. I wildly thrashed about, moving the saw as fast and as violently as possible in an attempt to cut it in half.

This is not a good way to cut wood. So my Dad taught me to slow down — just a little — and make decisive, high quality strokes with the saw. Keep it straight. Make sure the blade is really getting into the wood. Take five or six quality swings in a row to get a rhythm before you start trying to go any faster. Do that, and before long you’re positively flying through lumber at what seems like an unimaginable rate, you’re getting a better cut, and you’re not working nearly as hard.

At work, there’s a healthy cadence to the right kind of moving fast. It’s not chaos — I know the feeling of too many things going on at once, and that usually doesn’t work out very well. It’s also not a passive, stagnant feeling, where you’re waiting for a solution to unsolvable problems to fall out of the sky. Instead, the best environments have that perfect sawing rhythm, and when you’re really going, great progress seems almost inevitable. New process here, iteration here, letting something breathe over here, etc., etc., and so forth. Teams can feel when they are operating this way, and it feels good, as if even complex, existential challenges (while still difficult) are ultimately just waiting to hit the blade and be ground away.

effective speed is what really matters

Thinking this way requires a lot of things, but more than anything, it requires discipline. I’m not talking about the mastering-martial-arts kind of discipline, or even the learning-a-language kind. Just the kind you need to simultaneously realize what today’s limitations are while still understanding the extreme end of what’s possible, and then go out and achieve it. The idea that you can just get as psyched up as humanly possible, and then blast through your challenges like you’re running a Tough Mudder or something is, while in some ways laudable, usually mistaken. If you’re really trying to get somewhere quickly inside of a group, your effective speed — how fast you can actually get that group to make a lasting impact towards your goal — is a lot more important than how furiously you do various sub-activities, even if they seem like positives at an individual level.

You’re (probably) not going to solve the most important challenges with one great idea and ten bad ones all executed as quickly as possible, or a flurry of well-intentioned, disconnected exertion. You’re (probably) going to solve them by making well-executed, focused efforts, and yes… making those efforts a little quicker than everybody else. Because yeah, sometimes you just have to saw a little faster than the other guys.

Depth & Breadth

the most annoying people on LinkedIn

For me, LinkedIn has turned into a sort of career-focused version of WebMD. I almost never start poking around in there for an emotionally healthy reason — I’m either frustrated by something at work and looking to wallow in self-pity for a minute or two, or reading about whatever happened to that incompetent product manager I used to work with. And, as with WebMD, all I really get out of the experience are pangs of insecurity and a fair amount of eye-rolling horseshit.

Now, I have a decent amount of patience for the amount of terrible, uninteresting nonsense on LinkedIn. It’s an inherently self-serving environment, combining the narcissism of any social network with the naked greed and ambition that comes with private business and career advancement. My Dad, who has one foot in retirement after a long, interesting career, has the best LinkedIn profile ever (I’m pretty sure he only had it to look at people he was supposed to interview eventually). It has no accomplishments, no skills, lists one company he’s worked at, and has the same picture he’s used for everything that I’m pretty sure is from my junior year of high school. And it’s not like the twenty year old pictures some people have on LinkedIn, either. It’s not some idealized version of himself — it’s just the standard picture he’s used forever because my Dad places zero weight on your opinion of his appearance, or really anything else about him. Like, actually zero.

The polar opposite of my father — and the source of unquestionably the worst material on LinkedIn — is the insufferable “growth hacking” people, who are usually either digital marketing consultants (sorry, “CEOs” of their one person companies), or people who claim to have worked for like, eleven different startups in seven years. “NINE TIME STARTUP ENTREPRENEUR!!!” Uhh… congratulations?

You can spot these people by their long, self-congratulatory posts about how hard they worked, and how everything is possible through said hard work. (“AirBnB turned me down for a job out of school, but guess what? NOW I’M AWESOME!!!”) They are always white guys in their twenties, except for a couple of white guys in their forties, who are gods to the people in their twenties, and are advisors to no fewer than twenty-five different startups.


Obviously my resume is a little different, with fewer lasers and pyrotechnics. I’ve had real jobs producing some sort of fairly concrete business value since I got out of school thirteen years ago, in 2004. Other than one extremely difficult year in Cleveland, I’ve had steady, pretty intense employment at growth-focused companies the entire time, and I’ve learned at what I can only conclude is an above-average rate for a couple reasons :

  • the growth-focused thing; outside of Cleveland, I haven’t worked for a company on cruise control
  • the companies I’ve worked at have been pretty small, or early enough in their trajectory that you really need to pull your weight and often punch above it
  • most companies have had a strong technology component, and were in a new or rapidly changing industry
  • I’m a little bit of a generalist so I’ve gotten to have lots of different kinds of roles (support, product, marketing, leadership)

I’m very grateful for how all of this has played out, because I know for a fact that I work my hardest and do my best work in environments that really need me (this also explains my extremely inconsistent academic history). I’ve felt very strongly needed everywhere I’ve been since I moved to D.C. in 2008, and that’s not a feeling everybody gets to have.

But here’s the interesting thing; even though I’m really confident I’ve had an extremely productive, challenging, and enlightening first thirteen years of my career, I feel like I’m increasingly running into people who — on paper, at least — have done so much more. I’ll read a resume from a candidate with fifteen jobs, three major promotions, some kind of graduate degree, and one or more entrepreneurial experiences, and then realize they are three or four years younger than me. And the only thing I can think is… how did you do this? Are the annoying LinkedIn people right? Have I simply discovered a sub-class of superhuman professionals? Am I going to have to go back to working in the kitchen of that steakhouse from college again? (Just kidding, they’d never hire me back.)


This kind of thing used to freak me out a fair amount, until I started actually calling these people, interviewing (and sometimes hiring) them, and working alongside them. What I pretty quickly realized is that more often than not, these kinds of people take very little of substance from their experiences, maybe because they are so focused on title, perception, and the next step on their path. Once you experience this, the whole facade starts to crumble, and the realization is pretty jarring. If this is what this person wants to be doing more than anything right now, and they are just sort of so-so engaged, what does that say about their prior experiences?

This has been (and remains) my number one concern about going back to school for any kind of graduate business education. No, I don’t want to spend the money, and no, I don’t want to spend the time away from my kids, my wife, music, the gym, writing, and other things that have long track records of making me happier and smarter and better. But I really would consider sacrificing parts of those things if I wasn’t so worried that the whole experience is a great networking exercise bolted onto a bunch of faux-intellectual nonsense. Given that I have plenty to do, and great venues to do it in already, I’m worried that going to school is actually a less efficient way to learn than what I’m doing now.

I say that because, if you’re really in the gears of how a business grows and operates… holy smokes is there a lot to think about, design, execute, and learn from. That’s certainly true at FiscalNote, but it was true at Contactually, and EEx, and Bamboo as well, and even back when I was writing documentation and filing bugs, I always had access to the core questions and challenges of the business, and could feel the connection between them and my work.

I remember when our investors pushed most of the good people out at Bamboo (there was some personal stuff there). Almost overnight, it became obvious that we weren’t a “business” anymore; we were a bunch of people tasked with jockeying for the favor of our investor group as various people sought to extract cash out of what was left of the company. Some people saw that as an opportunity — “if I handle this right, I can be a vice-president!” — but I immediately knew I had to go even as it was made very clear to me that I was needed for this exercise. But what the hell is the point of working in business if you aren’t motivated by growing and improving a business? I had just turned thirty, so I left and spent the next couple of years frantically, maniacally building a functional company with my wife, which seemed a lot less crazy than whatever was going on Bamboo.

Five years later, I’m a little more sympathetic to the mortgage-havers and whatnot who didn’t have the luxury of my self-righteous professional/moral high ground. But many of those folks were further along in their lives and careers than I am even now, and had more to lose than I can fully comprehend yet. But the point remains that ladder-climbing and cache-gathering isn’t a cost-free exercise, whether you’re in school or at work, and that fact doesn’t always translate well to something like LinkedIn. Basically, resumes and the like are still great conversation starters and rudimentary framing devices, but at this point I now know there’s more depth beneath those titles and accomplishments than I may have fully realized in the past. Or in some cases, there isn’t, and that’s even crazier.

Tricky Business

One of my least favorite arguments — one that never seems to die — is that the government should be run “like a business”. Much like the “we should balance the budget the way I balance my checkbook” argument is emotionally resonant but logically absurd (do you pay you household debt service with your own unique reserve currency?), the idea of running the government like Facebook, or Catepillar, or a grocery store, is as stupid as it is inspiring.

Some of the big reasons are :

  • the government isn’t supposed to be profitable
  • lots of important societal problems aren’t profitable to address
  • the government exists to do collective things we can’t or won’t do on our own
  • governments can do things that businesses can’t, like put you in jail

… etc., etc., and so forth.

Now, to give people a little credit, I think most of us who get sucked into the appeal of a business-like approach to government understand that some or all of these limitations exist. They just want people who make decisions on behalf of the government to seek improvements to operational efficiency the way they feel people in business do, and there’s nothing wrong with that.

Well… except there is.

why are businesses efficient (when they are)?

While the driving force behind efficiency in the private sector everyone thinks of is competition, another one is self-interest. Salespeople hustle because they have commissions. CFOs cut costs because they have stock, or get bonuses for doing so. Even front-line employees worry about their productivity because they want a promotion (and the power and money that comes with it), or don’t want to get fired or demoted (at the cost of… yeah, power and money).

This is a super-powerful culture for doing things, but it’s also incredibly dangerous, and the worst-case scenarios for a badly-incentivized private organization are often significantly less terrifying than the worst-case scenarios for a badly-incentivized government since, as I mentioned earlier, the government has certain extra-scary abilities (imprisonment, border-closings, artillery barrages, etc.).

In other words, if you create perverse incentives for private industry, you get Wells-Fargo, or Enron, or AIG. That’s definitely bad. But if you create perverse incentives for the government, you get a collapsing Soviet Union, or modern-day Turkey or Venezuela. The problems aren’t containable by the glories of private organizations, because a functional government (of some sort) is a baseline requirement for those private organizations to even function.

And that’s exactly why I don’t want people thinking about the government like a business — the stakes are much, much, higher, and no one “owns” the government; you’re not a CEO when you run it, you’re a steward for society at large. Electoral incentives are already dangerous; whenever people inside the government start thinking about what they can do to nail their quarterly bonuses or whatever, we have a problem.

In fact, you know what part of the government reminds me of business? Civil asset forfeiture. The most aggressive departments are almost like employee-owned companies (I worked for a restaurant like that once), where the officers are both the employees and stockholders, and the customers are basically mayors or governors. When the employees “maximize revenue”, they get bonuses in the form of perks, benefits, and stuff — so of course, they go out and “maximize revenue” by using their abilities to get it. Except when the police are trying to maximize revenue, they have guns and the ability to ignore large parts of the law. Imagine if Comcast could shoot you, or put you in jail. Healthy business, right there.

So if you’re like me, and the idea of tethering economic self-interest to government scares you a little bit, the challenge of getting anything useful from a business-like approach to government becomes a lot trickier and nuanced. There’s still something there, but now you’re talking about much less about an ideological revolution, and much more about experiments on the margins. In that case, you’re basically trying to create little, contained boxes of private-sector style thinking inside the government. I think this is fine, but don’t expect that stuff to free you from the complexities (or frustrations) of getting a drug approved by the FDA or something.

defining “business”

I do think there’s something to be said for private sector experience being a point of reference inside the government, which is why I have no objection (and even somewhat of a preference for) leaders and subject matter experts in the government with a business background. I think there are a lot of areas where the government would work better if it was better at quickly spinning up a relatively lean organization tasked with some kind of measurable goal, and that kind of thing happens out here every day. People like me (better versions of me, but still) are pretty good at it, and if you made us ultimately answer to some senior bureaucrat but basically left us alone, we could do a lot of interesting things while minimizing a lot of typical risks and costs. Again, you can’t run like, the FAA this way, but give us the post office, or some kind of constituent services or something and I think that makes sense.

But you know what’s weird? Many of the people talking about running things “like a business” the loudest don’t have this kind of experience at all. People like Donald Trump, or Jared Kushner, who basically inherit a bunch of assets, and leverage them along with other inherited assets (networks, connections, name recognition) to acquire more, aren’t really operating at all. Ironically, a lot of the value Trump created for his business was by effectively screwing with the government (albeit at a local level) by bullying authorities into zoning exemptions that benefited him. On the other hand, his best-known cost efficiency came from simply not paying vendors for services provided to him, and using his existing assets as a block against those small vendors seeking legal recourse.

You can argue about whether that’s a morally acceptable way to do make money (I think it’s gross but your mileage may vary), but it’s hard to argue that on a level playing field, somebody like this is at all equipped to use creative, entrepreneurial thinking to find efficiencies in government. If anything, the only thing someone like Trump is good at is using existing, outside leverage to create an environment that allows him to profit from an otherwise unremarkable collection of assets. So it makes sense why he would benefit from being President — that’s some serious outside leverage, even for him — but it doesn’t really make any sense why we would benefit from it.

Trump’s argument, of course, is that because he’s proven to be so good at getting civic institutions to do his bidding, he’s the perfect person to run those institutions. That seems to have resonated with a surprisingly large chunk of the population (one that appears to be confused by either how business works or what Trump’s relationship to that really is), but seems to me to be the worst possible solution to the problem.

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.


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…


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