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.

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.

Management & Me

A lot of crazy things happened to me in 2016, but the biggest two had to have been the birth of my first kid back in February, and a pretty dramatic change in my job where the number of people I was responsible for went from one to ten. That’s a 1000% increase!

Unsurprisingly, this changed a lot about what I needed to get done on a day to day basis, and forced me to deal with a lot of things I’ve never had to be especially good at. Still, since I started my management adventure back in June (after returning from paternity leave), I’m pretty happy with the results. Some of those results are simply the business performance of myself and the people who work for me, and some of them are how my group has dealt with various mistakes in judgment I made along the way.

Anyways, in the spirit of paying it forward, here are some very broad things I learned over the last six months or so that I think are worth noting. My situation is it’s own special little snowflake (aren’t they all?), so of course, you’re mileage may vary — but I think there are some universal truths buried in here as well.

1. get there the right way

Not everyone has this luxury, but for me it was extremely helpful to have already spent a lot of time working with the people on my team as regular old non-boss Nate, and to have done so as someone fairly senior. At some point in my career, I’ve done little aspects of everything our team does, so even before I got promoted, people tended to ask me for help and advice with things. That meant putting me in charge didn’t seem particularly risky for my colleagues — they could all be reasonably confident that I wasn’t likely to go on some massive power trip, and we all had established routines for working together and kicking around ideas. If anything, it was probably nice that my job required me to make time for this stuff, instead of it being a “favor”.

Given my personality, this is probably the only way I was ever going to be put in charge of a large team, so it’s not like I made some brilliant strategic move here. But I’ve worked with plenty of young ladder-climbers and seen promotions and management work out very differently for them. Pay your dues — not because “the man” says you should (screw that guy), but because it’s often really good for you and your relationship with your team.

2. communicate properly, and be yourself

I’ll admit it — I take an embarrassing amount of pride in being my own person, and not worrying about things that I don’t think are important. But that doesn’t mean, on the eve of running a multi-person team for the first time in my life, that I didn’t worry about stupid stuff like whether I needed to buy new clothes or stop cracking so many jokes at work.

In the end, I realized that was probably never going to work — as I mentioned, all of these people knew me, and authenticity was probably the best thing I had going for me (and the last thing I’d want to burn) as I tried to figure out how to manage properly. Of course, that doesn’t mean I don’t handle myself a little differently. There are things I need to keep from people sometimes, which sucks, and being the official arbiter of a disagreement between two people who work for you is a very different animal than being a friend who is able to give everyone candid advice. That took some getting used to, but I’m getting better at it.

Still, a large portion of my interactions with people are exactly the same. I didn’t suddenly become worthy of reverence just because I click the little button that approves people’s vacation requests, so there’s really no reason to talk to me differently, and frankly, I don’t think anyone does. I’m more than okay with that.

3. acknowledge reality

One of the ways I’ve been able to minimize the changes people have had to make in how they interact with me is to proactively make some changes in the way I interact with them. These are small things, and I learned a lot of them from my Dad, who went through similar organizational changes in his career. The basic principle is to acknowledge the fact that no matter how weird it seems, you really are someone’s boss, and they really do probably have the same fundamental “boss concerns” that everyone has when they interact with you. You probably do things that frustrate them, or things that they really want to make fun of you for but don’t feel totally comfortable talking about when you’re around.

Again, some of this is just my personality, but I definitely try to give the people on my team plenty of venues to blow off steam and probably make fun of me “behind my back” (which sounds way worse than it is). While we all make jokes at my expense to my face — it’s pretty easy — it’s a good idea to make yourself scarce now and then so people can take it to another level for a while. And hey, maybe people don’t do that, because I’m just so great. But I really shouldn’t be the arbiter of that, so I’m not.

It doesn’t hurt that my idea of a relaxing lunch is to sit alone and stare into the alley, either.

4. isolate problems and issues

Some problems are fixable. Some aren’t. But one thing that’s impossible — at least in the pretty dynamic business environments I tend to run in — is solving everything at once. There are just too many converging factors, too many data problems, and too many intertwined theories to figure everything out at once. In my case, my boss was responsible for creating an effective, scalable demand generation operation for our business, which is a pretty enormous, complicated goal. I saw my job as mostly trying to make sure we could provide her with clear, verifiable information about these efforts so she could make better decisions. It doesn’t sound that hard, but we were pretty in the dark when it came to a lot of information, and a lot of the information we did have was anecdotal or hard to pull regularly, so we had almost entirely apples to elephants comparisons that didn’t help us decide anything.

With nothing to lose, I basically set out to break down everything we needed to know, and honestly assess whether we really knew it or not, and if not (FYI, it was always “not”), what was missing that prevented us from knowing it. We simply chipped away at problem by problem, and since we have a bunch of smart, hard-working people on the team, my main job was to keep people from getting distracted by the larger problem, and focused on delivering concrete answers for the sub-problems. Once we nailed a couple of those, the larger answers became more and more obvious to everyone, and since we had the sub-problems permanently solved by process and logic improvements, we kept getting smarter and smarter. Anything that was too big to solve, we punted on, which was okay because we had a zillion problems to address.

What I wouldn’t recommend is simply demanding a vague form of excellence and performance in every task, and assuming that’s going to add up to a better functioning department or team. I mean, it might, but there’s no guarantee, and in my experience people (including me) hate being managed that way. Something is probably wrong at any given moment — so figure out what it is, focus on making it better, and let the rest of the stuff cruise until it becomes your biggest issue.

5. eat your disgusting dog food

Here’s something that I think is important for all managers, but particularly for new people coming out of functional positions — don’t ask people to do anything you’re not willing to do yourself, at least the first time. For me, the best example of this was reporting, which is really important in any kind of systematic demand generation, but is a huge pain in the ass when you don’t have mature, automated reporting. There’s a lot of manual collection, filling out spreadsheets, and discovering halfway through that your report structure is inherently broken or useless.

I knew it was crazy to ask a bunch of extremely competent but relatively inexperienced people to go through this nightmare themselves, hand me what I asked for, and then tell them why it wasn’t good enough and that it had to be done again. That’s literally the definition of an annoying boss, and the opposite of someone who is in the trenches with you trying to actively solve problems.

That’s why I built and filled out prototype versions of all our reports — each time I requested a change, I’d do it myself, so I knew exactly what was annoying about it, and what was reasonable to expect from the process. Frankly, the people who work for me are a lot better at this kind of thing than I am, so in my case I’d build a report, share it with our team, apologize profusely, and then our marketing managers would just fill it out and say “it’s not that bad” and maybe make a few suggestions we’d usually implement right away (and I would appreciate, having some experience doing the work myself).

This doesn’t mean you have to do this work forever, of course — one of the hard things for me has been acknowledging that, and letting people on our team take these things over (and improve them!) without me even necessarily looking at them every week. But working directly on the early versions of things is really helpful to make sure you aren’t just wasting people’s time and putting people through frustrating exercises you have zero empathy for.

6. acknowledge expertise

I got into this a little bit in the last section, but again, just because you’re responsible for people doesn’t mean you know more than they do, and just because you know more than they do doesn’t mean you’re better at everything than everyone who reports to you. Figure this out immediately, and start leaning on people to do things they’re good at.

I have no idea if I’ve done this sufficiently on my team, but I sure as hell realize the importance of it. I’d have had a complete nervous breakdown if it weren’t for the talent on my team, so you can be sure I’m always looking for the best way to take advantage of it, and foster its growth as much as possible.

7. set proper red lines

In even a mid-sized organization, one of the big things you provide as a manager is clarity on what people’s responsibilities are to work with and do things for other teams. This is certainly something I think our team was looking for when I was promoted — someone to very quickly draw some lines about what they needed to prioritize outside of their day to day work, and who could make those decisions.

In general, I think the goal here is to have some very basic red lines, and then a lot of flexibility for situations until they approach said lines. So for instance, when someone on another team wants a person who works for me to do a bunch of work for a client, my default response is to try to facilitate, and move things around on our end so that you’re not just asking your team do generate time out of thin air. But I’d also let the person know that this is one time thing, and not a permanent responsibility — if we need to do this for other clients, the person requesting this work needs to talk to me so we can systematically free up time going forward.

8. don’t panic

Again, related to the previous point, so much of the drama and daily conflict that goes on in the workplace is totally unnecessary. Maybe this is a startup thing, but everywhere I go, people are constantly distracted by various mini-turf wars or acts of perceived disrespect. The number one request I’ve heard in my adventures in startup land (this crosses several companies) is “role clarity”, which apparently refers to an unbreakable covenant that empowers certain employees to total control over various parts of the business.

This is obviously insane, because businesses aren’t about top-down, dictatorial control of channels and functions — they’re about problem solving, which often involves multiple channels and multiple stakeholders. If everyone has their channel under control, but problems don’t get solved, you won’t survive. That means instead of knowing exactly what they own, and who can and cannot parachute in with requests, people are forced to deal with the dreaded SITUATIONAL AMBIGUITY, and then they panic.

“What does this proposed solution say about my job? My performance? My skills? The way I’m viewed by my peers, and my bosses? My future at the company?”

Defusing this kind of panic requires a lot of explanations, a lot of empathy, and frankly, a lot of work. Sometimes the answer is just for people to grow up, but sometimes it’s really not — and either way, the last thing you want to do is add to the panic party.

For me, I’m always trying to keep the ship steered towards progress, towards solutions we know are better than the status quo, and towards general principles of good work and sounds strategy. If you do nothing else as a manager but reinforce this kind of thing among as many people as possible, in and outside of your team, you’re probably a net positive.

9. be useful!

I’ve referenced the importance of being someone who’s ready and willing to work alongside the people they’re responsible for, but really that’s just a subset of the belief that as somebody’s boss, the best thing you can do is whatever it takes to get them to do their best work. I think an unfortunate truth is that we gravitate towards things like “holding them accountable” because it requires the least amount of empathy and self-examination on our part — if we look hard enough, it’s actually pretty easy to see that a lot of people are in extraordinarily difficult positions, or can’t do their best work because of an obstacle they don’t have control over.

But you might. That might be because you have experience, or the ability to communicate clearly with another team, or relationships with people at work that can make solving a problem easier or less frustrating. Maybe you can approve a small expense, or dig up an example of old work you’ve done that can make things seem a little more manageable. Or maybe you just need to roll up your sleeves, divide that horrible Excel spreadsheet in half, and tag-team some particularly nasty, unavoidable administrative work.

Whatever it is, find that thing you can do to help, and do it, whether it feels like good “management” or not. More often than not, I’ve found that’s actually exactly what it is.

Why I Remember Accuracy & Precision

I don’t actually remember when we learned this, but for some reason one of the random school things I distinctly remember learning was the difference between accuracy and precision. Now, as it turns out, I don’t remember it 100% correctly (yes, I see the irony there given the subject), but I looked it up again and for the most part the difference stuck with me pretty well over the years.

Here are the basics — essentially, accuracy is the distance of a measurement from a reference sample (a.k.a., the objective truth), and precision is the variability of the measurements you take. So let’s say you throw three darts, and you’re within an inch of the target, but in three different places. Then, you throw three more, and hit the exact same spot three times in a row, six inches from the target. Your first “sample” of darts would be more accurate, and less precise, than the second sample.

That’s pretty much the gist of it. Now, the more philosophical takeaway from this kind of thing is that it’s possible to conflate hyper-specific knowledge of a situation with an accurate assessment of that same situation — and I think this is an increasingly dangerous problem in the information age.

Anecdotal Precision in Current Events

One of the obvious places I’ve noticed this issue is in the ridiculous, never-ending intellectual tire fire that we call the 2016 U.S. presidential election, and around politics in general lately. When I was growing up, and first started paying attention to political arguments, they mostly revolved around people’s different preferred best practices for problem solving, as opposed to especially damning quantitative facts. This wasn’t always great — for instance, certain candidates could get away with measurably irresponsible or dishonest policies because people felt like that person was inherently responsible and honest — but it also left a lot of room for discussion. When you’re having an ideological argument about the logic behind something like gun control, or free trade, there’s really no card that anyone can just pull out and say “you are empirically wrong”. You’re forced to argue about why you think certain things happen, and that can very instructive if you’re open to it.

Like anything else, accurate (there’s that word again) data is an incredibly helpful (and important) tool for grounding these discussions in reality, and the collection and understanding of data has exploded since my first election in 2000. Unfortunately, a lot of people have taken that the wrong way, and started looking for data that justified their largely unexamined, qualitative views — and of course, that’s easier to find than ever through perfectly legitimate online research, or lazier, vulnerable-to-confirmation-bias channels like Facebook.

What I find jarring is how comfortable people are falling back on data, but how bad they often are at validating any of it. I got the “there’s way more violent crime in the U.K. than in the U.S. because the police are unarmed” argument thrown at me the other day, and I was actually kind of frozen by it. “Really?” I thought. It seemed weird for a couple reasons that my brain immediately flagged :

  • It had never come up in any of the discussions I’ve had with gun rights advocates (and I live in VA, so those discussions are pretty common) before.
  • It didn’t make a ton of logical sense — were police being overpowered by armed criminals? Was the idea of being shot at some kind of deterrent for people who probably didn’t expect to be caught anyways?
  • If this was the case, why wouldn’t the U.K. react? Giving patrol cops guns (or taking them away) isn’t an insanely radical policy anyways, and you’d think it’d be something you’d experiment if you had an emperical policing problem.
  • It seemed weirdly specific, even though in some way that gave it an odd feeling of credibility.

But of course, this is me, so even though all these red flags went up, I was curious about what could have been a huge personal blind spot. So, as I often do, I started looking for information on the issue, and I immediately found two things that explained the conversation.

I can't believe people get their news this way.

  1. a low-resolution JPEG meme (pictured here) stating this same “fact” with a pithy rejoinder at the end about how gun control doesn’t work
  2. a long, boring Politifact examination of the argument which convincingly argued that the data indicated no such trend, but that the argument was effectively comparing apples and oranges and would require better information to conclusively make

So basically… this statement is bullshit, and once I thought about it a bit more, that actually seemed pretty obvious. And yet, I didn’t dismiss it the way I dismiss vague conspiracy theories. Why? I think it’s because of that last thing — the claim was so specific, and I feel like human beings (myself included) have a tendency to assume specific arguments are inherently more sound than broad ones.

And sure enough, when I think back over my interactions with different people, and I assess all the different sources of truth I’ve dealt with in the past — from outright liars to the well-intentioned but incompetent — this is really does feel like a pattern. It really does feel like I’m constantly (and increasingly) innundated with hyper-specific, objectively wrong arguments.

Data Illiteracy

I’ve read lots of things about the problem of financial literacy in a world where making good, often complex financial decisions is a bigger and bigger part of getting and/or staying out of poverty. I think data literacy is the professional corollary to this challenge. Sure, real data people are fine — actual data scientists, certified accountants, professional economists, etc., because they’ve always needed to be data-literate. But almost everyone else has seen data injected into their various professions and areas of expertise seemingly overnight, and while we understand many of the things all this data is supposed to represent, we’re often fundamentally unprepared to assess the data itself. Where did it come from? How are different labels and thresholds defined, and what happens to your data if you change them? What is a sufficient sample size for various measurements? What’s the difference between causation and correlation? Do you see things like daily tracking polls and Salesforce reports as objective facts, or is your initial response to ask about their methodology?

To those real data people I mentioned (i.e., not me), these are obvious, basic questions. To regular people in business functions, they may not seem important at all. I’m fortunate enough to have grown up as the son of an engineer who literally designed test & measurement equipment, so while I’m personally unqualified to do any kind of academically rigorous data analysis, concepts like accuracy and precision have an emotional weight to me that I don’t think a lot of people necessarily share. That, combined with just enough education to get by (thanks, Social Science Statistics 101!) has given me a decent toolset for challenging the kind of flawed data conclusions I encounter every day. Even when those conclusions are incredibly specific.

Tips for Non-Experts

Just like we don’t all need to become developers to benefit from a broad, conceptual understanding of how software works, we don’t all need to become data scientists to get better results from our increasingly data-infused careers. We just need data literacy, which to me is mostly the ability to understand what we know, and what we don’t. In my experience, that has a lot more to do with the ability to ask intelligent, often humbling questions and our own insecurities than anything else, which is probably why it’s such a challenge for so many of us. There are just too many people walking around, armed with “data”, who lack either the humility, experience, or skills to resist using it to clumsily justify incorrect assumptions.

For me, I’ve spent the last couple of years trying to figure out how I can get the most out of everything from business to product usage data, and I’ve had the most success doing the following :

  • Simplifying what I’m trying to track, and what I’m trying to conclude.
  • Using the extra time and effort I save from that to focus on consistency of collection and larger sample sizes.
  • Sharing what I find with people outside my functional area, and encouraging them to ask about my methods and logic.
  • Iterating on my methods based on holes those people find, including cutting my losses on things I’ve been tracking that aren’t useful.
  • Being generally skeptical of big trends you discover, and eager to poke holes in the logic behind them.

In other words, don’t start looking at data when you need to prove to someone else that you’re right about something really specific. Start looking when you can afford to prove yourself wrong about nearly anything — and use your findings to improve your process. Then, when you really do need to make a data-driven decision, you’ll hopefully have more relevant data, consistent collection methods, and some amount of fluency in thinking about it. That doesn’t necessarily mean you’ll make the right conclusion (remember, you still probably don’t really know what you’re doing), but it’s a lot less likely you’ll make the wrong one.

Hustling, Grinding, and Building

Here’s a tweet I saw the other day that made me — as the kids say — “LOL”.

Touche. This is a really, really annoying part of today’s cult-of-entrepreneurship. You can blame it on internet culture, or venture capitalists, or the way the media covers and informs the public about these things, but either way the end result is often a incredibly clumsy grouping of unrelated challenges into a single, stupid bucket. You don’t have to be an especially cynical person to roll your eyes at the idea of how “tech companies”, “startups”, “SaaS businesses”, or any number of vaguely defined groups of things are supposed to behave, because like any other vaguely defined group of things, correlation is easy to find and causation is extremely difficult to pin down.

What everyone from famous people like Elon Musk and Peter Thiel, to a million different poorly credentialed Forbes contributors, have managed to do is convince themselves and any number of hangers-on that the solution to every problem is intelligence, or their own self-identified hard work. If you buy that logic, their success is not only immediate validation of how intelligent and hard working they are (because problems can only be solved by intelligence and hard work, and they solved a problem), but validation that they can solve any problem they put their mind to (because, again, problems are solved by intelligence and hard work, and in this system, they have proven themselves to possess one, or more likely both, of these things).

In many ways, we have a tendency to do this with strategy as well as leadership, which is slightly less annoying but arguably more dangerous. I get this a lot when people want to tell me how to do marketing work, and get frustrated with its alleged complexity — here’s how company X did it, company X is successful and respected, why aren’t we doing what company X does?

If you are a frequent reader or someone who works with me, you can probably guess my extremely predictable response. What is company X selling? Who are they selling it to? What kind of resources do they have? How much risk are they willing to take on? Can we connect the success of this thing company X does with company X’s success? And finally, are there any major differences between these answers for company X, and for us? Because if there are, company X may not be what we want to emulate. Nobody really likes this answer, but for the most part I think it helps people to generally start to understand the complexity of the issue if they haven’t already.

Now, at a slightly more abstract level, I do think you can group business challenges (or any sort of productivity one, to be honest) into categories that can help you start to think about the best way to address them. These are more philosophies than they are tactics, but that’s ok — you have to start somewhere.


I define hustling as the frantic pursuit of any positive opportunity you can identify. Hustling is really important when you’re first starting out with an idea, because that’s when it’s the most unproven, and when it’s most likely that what you’re doing is worthless and requires you to radically change. It’s also important (although often times more depressing and less exciting) if you’re running out of money.

Some businesses are always about hustling, at least in theory — my guess is that commodity traders and venture capitalists are almost always in a hustling mode, running from thing to thing trying to maximize the chance that they’re in on the ground floor for the next great opportunity. People who are great at hustling are often thought of as “entrepreneurial”, even though building anything other than a ponzi scheme often requires that hustling eventually evolves into something else. But there is something really magical about professionals who can drop into hustle-mode when the time is right — those people are usually one (or more) steps ahead, and they can be a lot of fun to be around.


Grinding is the repetitive, iteratively improved act of day-to-day execution. If you start grinding before you’ve sufficiently hustled, your best case scenario is that you get really good at executing a less-than-optimal business. That’s not a necessarily a terrible thing, but it’s an obstacle to reaching your full potential, and the worst case scenario is that you get really good at doing something worthless. The later scenario is not uncommon, and that’s why “grinding” through your job sounds like a bad thing.

Still, grinding is important — essential, even — to building anything other than a hilarious frat-house startup, and contrary to what you might think, a ton of learning occurs during grinding. In fact, while you learn large, existential things while hustling, most of those things are useless in the long term, because you end up hustling on to something else. Things you figure out while grinding, on the other hand, get baked into your core business operations and help you indefinitely. Grinding is often thankless, but essential, and personally, I think most mid-stage startups fail or end up missing their opportunity not only because they failed to grind, but because they assumed grinding would be pretty straightforward and wouldn’t require a lot of focus.


Sometimes you hustle around and find the right opportunity, but there’s no way for you to successfully grind it into a real business. This is usually because you either don’t have an essential part of the necessary grinding process, or because it doesn’t exist yet. Either way, this means it’s time to build, whether that means creating a product, improving a technology, or changing the way your organization works and solves problems. Building is very rarely a direct revenue-generator, so it’s hard to get companies to agree to do it, and even harder to get them to agree to make it a priority over hustling and/or grinding (“you can build as long as we are hitting our numbers” is one I’ve heard a lot). The truth is that regardless of your cash or goal situation, the time may come when you simply can’t go any further until you build something, and that means you have to find the time and resources to do it, or else you die.

What these modes have in common, and what makes them different

If I were a betting man, my money would be on the average CEO responding to this breakdown by explaining that “the interesting thing about our business is that we really need to do all three”. This is, of course, a total leadership cliche and is not interesting at all.

Still, to some degree it’s often true, especially if your organization is big enough to have multiple major challenges. But that doesn’t let management at any level off the hook when it comes to setting the tone for the company as a whole, or for setting that tone on a team by team (or employee by employee) basis and not sending mixed messages about how each person should be approaching their job. Maybe inside sales is grinding as they improve their process for handling inbound leads, and business development is hustling as they go after new verticals or try to find someone to buy a new product. Maybe the back-end team is hustling as they try to figure out a cost-effective way to store all this data they weren’t expecting to be responsible for, while the QA team is building new tests. Maybe Bob is grinding through highly standardized marketing campaigns and looking to optimize results, while Barbara is trying to build an account-based marketing system and get it up and running.

The point is, these are really different workplace attitudes that have their time and place depending on what you’re trying to do. If you’re looking at a certain part of the business (or sometimes even the organization as a whole), and people in leadership have fundamental disagreements over whether you are hustling, grinding, or building, you have what I would consider a fairly important alignment problem.

One other thing that’s really interesting about these three very different mentalities is that none of them have a monopoly on any of the things we value at work, like creativity, or hard work, or discipline. These things are useful in all stages, but do have to be applied appropriately. One person’s idealized vision of hard work is really a form of hustling, and it’s possible they’ll see a highly efficient form of grinding or building as lacking in effort or urgency. Until fairly recently, I personally lacked sufficient appreciation for the subtle creativity that’s involved in effective grinding, or the discipline that comes with an exceptional hustling mentality.

More than anything, I find this type of classification useful to get a sense of why people think they’re doing what they’re doing. If you’re baffled by someone’s priorities, or feel like smart people are doing seemingly dumb, pointless things, it doesn’t take much more than a quick conversation to figure out what kind of mentality everyone is operating in, and where the source of the disconnect is.

Plus, you get to say “grinding” at work a lot, which is fun.

Why is it So Hard for Workplace Tech to Make a Difference?

The cyborg generation that never was

When I was in high school, the world was all abuzz about the fact that many people my age had “grown up with technology”, which really meant “grown up with personal computers and, for a while, dial-up internet”. The idea was that while our parents’ generation struggled to deal with trash can metaphors and concepts like double-clicking, to us bleeding-edge early millennials, digital technology would be second nature, and thus we’d all be really good at it. At the time, this made a lot of sense to me, and I eagerly awaited a world in which technological incompetence was effectively obsolete.

Well, more than fifteen years later, you know what I’ve noticed? Most people my age are actually pretty terrible with technology — even the kind we grew up with. Oh sure, we’re used to it. We use PC-like phones every day, constantly interact with different web applications at work, and voraciously consume things via various forms of the internet. But in a lot of ways, the technology really just caught up with us, by becoming simple, consumable, and socially ubiquitous enough that deep understanding simply isn’t required. Most people don’t understand why Netflix isn’t loading (or more importantly, why it’s not not loading), why their phone gets hot, or why some JPEGs look crappier than others. The products they use have just gotten better and better at making that knowledge unnecessary.

Is this how things get better?

I’ve thought about this a lot recently in the space I’ve worked in for a while now, which is information tools. In fact, for the last seven years or so, all I’ve really worked on is building, designing, and helping to sell tools designed to allow people to work with different kinds of relatively complex data. But in every place I do this, I run into the same problem — the vast majority of people (even paying customers) fail to use even fairly intuitive tools effectively to actually do anything. Many of them want to, and they often understand what the potential benefits would be if they were to figure it out. They simply get stuck as soon as they have to make a critical decision about how to use what we’ve handed them. And the fact is, most business productivity tools require you to make these kinds of choices, and most people are really bad at it.

Ezra Klein had a really interesting piece in Vox about a problem that I think is related to this — how technology has struggled to really change the way people work except on the margins, especially compared to how it’s changed the way people relax at home. If you’re waiting for a technology tool to make a paradigm-shifting difference in the way anyone other than highly technical specialists work, you’re going to be waiting for a while. That’s because (as has always been the case) most people simply aren’t that good at using most kinds of tools. For people who are, the right tool is amazing — but that number is often so small, you rarely see major social changes come from better tools alone.

(Notable exception : social tools, which don’t require high quality decision making to be used, or have a major impact in our lives. Actually, the fact that social tools are changing society even though most of us make poor decisions in how to use them is probably why we have such a mixed reaction to the post-social network world. But I digress.)

What about consumer behavior?

For the average person, I don’t think consumer interactions with technology are that much different from workplace interactions with it. The big difference is that:

  1. consumer technologies are designed to provide you with an end result — your favorite TV show, a constant, ample supply of laundry detergent, a ride to the airport, etc.
  2. professional technologies are designed to empower you to do something — share information, analyze data, make decisions, etc.

As I’ve indicated, my kind-of-cynical new theory is that radical improvements doesn’t come from empowered people; they come from technology eliminating the need for people to do something at all, so they can do other stuff instead.

So you don’t end up with better, smarter people. You just end up with the same people spending more of their time doing things they’re good at, or enjoy, and less time doing things they are terrible at.

For instance, hailing a cab is a pretty bad way to get a ride somewhere. If Uber was designed to enhance my ability to make cab-hailing decisions, it might be useful, but I don’t think it radically changes anything. Instead, it’s a big deal because anyone with the intelligence of a child can pull out a $50 piece of electronics, clumsily paw at a few pictures on a screen, and boom — they get a ride anywhere they want. That’s not improved, empowered cab-hailing; it’s the removal of cab-hailing from the list of things that people do.

Consumer internet technologies get this, and more importantly, consumers get it, because they are usually aware of their own laziness and incompetence, and are eager to mitigate it. Business technologies may or may not get this same principle, but businesses themselves — or at least the decision makers inside businesses — definitely don’t get it, probably because it goes against their self-interest. Consumers desperately want to remove as much effort and challenge from their life as possible; it’s in their interest, and it’s at no one’s expense for them to do so. Professionals want to do this too, but only to a degree, because most of them feel like if they were to completely eliminate one of their tasks, or a decision-making point, they’d be reducing their value to their organization. If I’m in charge of some critical accounting task at my company, and I find, test, purchase, and integrate a flawless accounting robot that does my task for me, I don’t get to stay on the payroll and go golfing. At many companies, I don’t even get promoted — I’m probably out of a job, especially if what I’m best at is doing the robot’s task.

Most professionals are not entrepreneurs (yet)

This artificial, self-interested inefficiency is a problem pretty much every organization larger than a couple of people has to deal with, and it’s such a normal, internalized part of professional culture that I don’t even think we really notice it anymore. We just say “big companies are different”, or “the enterprise has certain needs”, when 90% of what we really mean is that maximum efficiency runs counter to the best interests of the people who work at these companies, and anything you want those people to buy has to take that into consideration.

Of course, there’s one group of people whose interests are solely aligned with the efficiency of the company. Owners! When I showed my owner-operator friend how AdWords could handle many of the manual adjustments he was making automatically, he didn’t grumble, or get into a big argument about the value of human intelligence and intuition. You know what he said?

“This is great! I hate doing this, and now I don’t have to do it anymore!”

In most cases, you’re not going to hear that from middle managers, especially if they have vague, business-related titles, and even more especially if they have mortgages to pay. That’s a human problem that is going to continue to slow the pace of technological improvement in the workplace, especially since business technology vendors are smart enough to know it. That’s why so many of them tailor their offerings around it giving you lots of data, but not necessarily altering any of your work routines. Lots of dashboards, lots of analytics, lots of empowerment — and very little “we’ve simply removed this from the list of things you need to do”. No matter what inefficient, dumbass thing you want to do at work, there’s a piece of enterprise software that will help you do it with charts.

Now, there are also plenty of valid tactical reasons that get in the way of major technological change inside companies, too — security issues, regulatory hurdles, and the simple fact that it’s a lot riskier to screw with a revenue or customer-related business process than it is to screw with the way you watch Game of Thrones or order a pizza. But the human, psychological element really is enormous. Everywhere I go, I’m shocked by how hard it is for extremely intelligent people to feel comfortable with the idea of truly removing work from their daily routine.

(As an aside, in my experience it’s actually a bit easier to get the truly incompetent to buy into more aggressive technological change, because they’re less likely to make the connection between their irrelevance and their job security. They just think they have a job because they are awesome people. And that association with incompetence — the idea that you would only hand over your work to technology or process if you are stupid, or unacceptably, shamefully bad at doing it yourself — is yet another stigma technological improvement has to overcome in the workplace.)

Baby steps

There’s no easy answer to undoing untold years of professional insecurity inside our workplace culture. I wouldn’t even know where to begin inside of a large company, but in the startups I’ve worked at over the last couple of years, I’ve had some luck with leading by example and trying to demonstrate that you can be a great asset to a company and still be really bad at certain things. In fact, you can be bad at almost everything, but if you’re really good at finding cost-effective ways to eliminate the impact of those things on your company, you can actually be incredibly effective. (I probably won’t be putting that in my LinkedIn profile anytime soon.)

Of course, that’s not easy, or especially common. Instead, the situation I see most often is a very talented, knowledgeable professional who by their very two-handed, bipedal nature, cannot scale the same way an awesome system can. And while they often “get” the system, they remain hung up on things the system can’t do (usually edge cases and certain hyper-specific ways of reacting), while glossing over the much more damaging fact that compared to a system, they’re really freaking slow and mistake prone. That concern comes from a good place, but in a lot of operations work it’s ultimately limited. We’re not brewing artisanal coffee, here.

Anyways, I always try to be the opposite of that, and I express no shame at all. When channeled properly, a little laziness can be a powerful accelerant to productivity, because it keeps you from accepting the necessity of grunt work and pushes you to find better ways to get it done. But I’ve written about that before.

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.