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.

Parents with Great Jobs

“This is my daughter.”

I keep saying that as often as I can because it doesn’t seem possible. But since Sunday morning, it’s been undeniably true — this little freaking person lives in my house and loves me and my wife more than anyone in the entire world.

There’s a playbook for having a kid when you’re someone like me; a.k.a., a college educated white guy professional in his early-mid thirties. Not everyone follows it, but a lot of people do — having a child changes the way you see everything, puts your high powered career into perspective, and makes you add “Dad” to your Twitter profile. If you have a daughter, you ocassionally blog about Gamergate and say “I have a daughter” and people tell you how brave you are.

Maybe, like a lot of things, that playbook is just public-facing nonsense and nobody’s being honest. Or maybe people really do act so predictably in response to something that most people go through at similar points in their life. I have no idea, and honestly, I’m not particularly interested in finding out. What I do know is that so far, being a parent has been small, incredible moments surrounded by a mix of boredom, guilt, and a strong motivation to care about things you’ve never been able to before. Again… it’s been two days. I’m going to let it breathe for a while.

Parenting and My Job

My situation is unique for a lot of reasons, but the most interesting one is that my employer has a wildly progressive parental leave policy that allows me to stay at home with my new baby for an extended period of time. This is simultaneously a very small amount of time in the life of a growing person, and an enormous amount of time in the life of a busy, rapidly growing company (which is what we are). That puts me in the weird position of feeling like I am both entitled to every minute of singing and rocking and napping with my little girl, and impossibly negligent when it comes to doing something I am really, truly passionate about — building a great company and revolutionizing an industry.

If you know me, and my endearing, often cynical brand of gallows humor, you’re probably waiting for the punchline here. But there isn’t one. I really feel this way about what I’m doing, and as a result, for the first time in my life I think I really understand the challenge some people face in making family their top priority. That reality hit me in the face when I came down the stairs on Saturday morning to work on some dumb slides for work (okay, they aren’t dumb, they’re actually really cool, and I’m saying that without a trace of irony). I only had about a week until my wife’s due date, but my colleagues and I had a pretty good plan for wrapping up a few things and getting both my team and the teams we work closely with on a great path for the next few months.

“Hey!” my wife said, as I scrounged around the living room looking for my laptop. “Wanna have a baby today?”

Wait, what?

So of course, everything blew up in high-speed slow motion. I worked on my dumb slides (again, not really dumb) in between contractions, typing the same sentence over and over again before realizing I wasn’t getting anywhere, and watching The Goonies until labor starting getting serious. We had our kid at home (which was an amazing process, I could write a whole post about our midwife team), so we pretty quickly transitioned from “casual Saturday” to “AHHHHHHH!!!!” before I really knew what hit me. And while I have a million very typical “new Dad” thoughts on the whole thing, the weirdest thing is probably how much I thought about work. Not about some form I had to fill out or anything, but about my actual purpose there, and how real the cost of my departure was going to be to the things I was trying to do, and to at least some degree, the things that people I work with are trying to do.

The fact that this cost exists is not a bad thing. Who wants a job where their departure doesn’t matter? What does that say about what you do all day? But if you care about what you do and the people you do it with, that doesn’t make acknowledging the cost any easier, and the fact that you love your new little kid (someone you barely know, but immediately know really well, which is very weird) doesn’t make that cost go away. It just makes you think “this enormous cost is worth it”, which is the kind of thing I associate with buying a new roof, or maxing out the RAM in my laptop, not using my amazing parental benefits.

an honest acknowledgement of a real cost

When I first found out about the benefits at FiscalNote, my first thought was “how can they do this?” After really diving in there for the last six months, and taking just three days of those benefits, I now totally understand it. Having a family has an enormous personal and professional cost, for an enormous personal gain, and a very nebulous professional one. It’s not some magic, everyone-wins scenario where my company benefits from me being gone for months at a critical time in its growth. It’s just the acknowledgment of the truth — a lot of people you’re going to want to have at your company are going to want to have families, and having them take a measly couple of days off for the birth of a child like they’re taking a vacation to the Jersey Shore instead of bringing a brand new human into the world doesn’t reduce the cost of the endeavor. It just hides it, or offloads it onto your employees marriages, creativity, mental health, or some other finite personal resource that, once depleted, has a high risk of destroying them as a professional and a team member. Sure, you can expect Mom and Dad to be back at their desks and passionately arguing for their choice of action at the next product development meeting, but you can’t expect the emotional and intellectual cost of doing so to evaporate simply because you’ve determined that you don’t want to pay it. Employees are people. People want families. Families take a lot out of people. The math is pretty straightforward.

So yes, I desperately want to be here for my daughter, and I absolutely, 100% want to go into the office tomorrow. What can I say? It’s on me to reconcile those things. It’s on my company to give me the opportunity to do so, and in my case (unlike with most jobs) that’s exactly what they’ve done. I’ll never forget that I had this opportunity, not because I think it’s a gift or a bribe that shouldn’t exist, but because it takes a lot of faith in your people and your business to acknowledge real costs of life and allow your team to pay them.

I’m paying them now, and trust me, it’s expensive. Expensive, and hilarious, and enlightening, and wonderful.  

(… and by the way, there’s something extra validating about a company that supports things like this also enabling its newest Dad to get off to a great start with his daughter. Warrants mentioning.)

The Proper Work Metaphor

junior varsity disclaimer

Since I’m about to extol the benefits of sports (or at least some of the thinking behind them), I should probably clear up a few things. While I’ve always loved sports, I am not an especially good athlete, and never have been. I was an abjectly terrible baseball player who quit Little League once it started becoming clear that how well you played baseball had very little to do with how much you loved baseball (so about 11 or 12). From there I floated around, playing pickup basketball and football with normal kids, until at 16, I managed to carve out a spot at the end of the bench on my high school basketball team.

That’s it. By any measure, I’ve always been better at school than sports (which isn’t saying much, but still), so it’s not like I’m some jaded meathead pining for the days when I could solve my problems by shoving someone into a locker. I was much closer to being the one getting shoved.

But the fact is that I’ve learned a whole lot from sports, particularly as an adult without any of the social or identity pressures that come from playing on a team as a kid. And as I get older, the number of problems I’m able to solve by thinking like an athlete seems to grow, while the number of problems I’m able to solve by thinking like a student — even a good one — keeps shrinking.

Here I am, solving problems with my awesome band of basketball misfits. 

what’s wrong with the student mentality

I’m of a certain generation of people who grew up in an interesting time. I’ll spare you the navel-gazing “old millennial” think-piece, but the long and short of it is that a lot of the “alarming trends” that affect people coming out of college these days started to gestate back when I was that age. For instance, when I was in high school, things weren’t nearly as competitive and Hunger-Games-y as they appear to be now. I was a pretty lazy high school student who generally stayed out of trouble and got by largely by drawing my teachers attention to things I was already good at, and simply gritting my way through terrible grades in things like Physics and Calculus (I was inexplicably in the smart-kid versions of both of those). I wasn’t cutting class or smoking cigarettes in the parking lot or anything, but I basically did everything at the last minute and tried to avoid doing work whenever possible. I also assumed I’d get into a decent college — if I couldn’t afford whatever would let me in, I had good enough grades and test scores to go to the University of Rhode Island for basically nothing, which seemed like a really good idea to 17-year old me.

Anyways, this is all besides the point, other than that while I was skating through high school reading ahead in American History while literally losing my Chemistry book, something else was happening. People were panicking about their own futures. Not just kids who desperately needed scholarship money, or who needed to stay close to home to help a sick relative or something. Regular old upper-middle-class kids, freaking out about whether we had enough AP classes, or how many valedictorians we’d allow if fifteen different students ended up with perfect GPAs. By my junior year or so, I was actually encountering situations where individual students — mainstream, popular ones — were more motivated by their own academic performance than they were the social well-being of the group. They wanted the class to be hard, and they wanted people to know it was hard. They cared about (and worried about) our high school’s academic reputation, which seemed absolutely ludicrous to me; I was much more animated about, say, whether we’d get to go outside for Physics lab. Obviously, this kind of thing rolled right on into college and got significantly darker, as I watched people cheat on exams, commit blatant acts of plagiarism, and increasingly look out for number one as they prepared for whatever prestigious environment was next on their life agenda.

Looking back, I guess that behavior makes sense, given the way this works. None of these social institutions were permanent — that simply didn’t occur to me as an immature goofball of a kid who grew up in a small town and went to school with the same people for my entire childhood. I valued the “community” I was familiar with, (could we get the teacher to skip this book if we stalled them long enough?) while my more mature classmates knew our social ties would be meaningless at the next level, and thus were prepared to cast them aside for their own benefit if necessary.

My understanding is that this kind of thing is no longer the exception, and is more of the rule. College is more competitive, internships are currency, and entry-level candidates are expected to have resumes you can critically evaluate, which seems absurd to me. But hey, I don’t make the rules, and if that’s the way it is, it’s hard to blame kids for hoarding their professional chips. Sometimes that takes the form of the morally dubious things I witnessed in college, but more often it’s simply a mindset that develops that doesn’t prioritize group success at the expense of things that end up on your personal list of achievements.

So keeping that in mind, follow the professional development track from infancy to entry-level employee.

  1. compete to get into preschool
  2. compete to get into gifted programs/travel teams/camps
  3. compete to build a college resume
  4. compete to build an undergraduate resume
  5. compete for internships
  6. maybe keep doing this for graduate school if you like debt
  7. compete to get hired

All these steps have two things in common — one, they’re all about you; specifically preparing you for something more important. Two, they’re all disposable environments that only exist to determine your next environment. That’s fine (if a little cynical) for places that exist to serve your needs, like school, or your expensive university. But it’s less fine if the place you’re using to build yourself up is simultaneously trying to use you to build itself up, which is — hello! — what actual for-profit institutions do.

And so you run into the problem with the academic model. It’s entirely about the individual, and presumes that the environment is disposable.

why the team sports mentality is better

Now, don’t get me wrong. Helicopter parenting and insane soccer coaches and all that have done their best to turn sports into the same worthless college-prep exercise that school is for many kids. But in general, teams are a much more difficult environment to be truly selfish in, and often map to the challenges of everyday professional business a lot better than school does. While some professions (pure research, and certain transactional activities like sales or trading) map perfectly to individual performance, most do not. In many cases, smart, inexperienced workers are asked to go from a world in which their own performance and skill determines success, to a world in which their only hope is to improve the performance of someone else by any means necessary. While this is baffling and weird to a lot of great students, it’s painfully obvious to anyone who’s ever needed someone to grab a rebound, or hold off the approaching defensive end for another two seconds while the tight end goes down the seam.

In other words, one of the most important lessons in life is that you can’t do everything yourself, and that truly great accomplishments in life can often only be done by enlisting and facilitating the help of someone who is better at something than you are. If you’re an artist, or a dictator, or genius, it’s possible to live a very large portion of your life without figuring this out. If you’re a point guard, you probably learned this before you hit puberty.

constructive failure

There’s another great lesson from team sports that I’ve found extremely useful at work, and that’s the concept of constructive failure. I’ve been on a lot of terrible teams, and part of a lot of broken plays where someone essential either forgets to do their job, or is incapable of doing it. What then? When you’re working alone, the most efficient solution is simply to stop executing incorrectly, and if all you ever do is work alone, pretty soon that’s going to become your preferred method of problem solving. That’s why Type-A managers who aren’t creative problem solvers often see poor performance on their team and think “this person is a poor performer”, or “how can I change this person”, instead of thinking about ways to restructure the environment or the system to make that person a part of something that works. That’s not to say certain people don’t need to change, or can’t be unacceptably bad at something critically important. It’s just that many individual-oriented managers tend to default to that assessment, which doesn’t leave you with a ton of options. 

When you’re on a team with a broken component, it’s amazing how creative you can get when it comes to solving problems. My beloved Boston Celtics dominated basketball and won a title in 2008 with two guys who couldn’t shoot by giving them creative roles that maximized what they were good at, and actively facilitated shots for the other three. The guys who couldn’t shoot didn’t see themselves as ineffective basketball players — they saw themselves as essential parts of a larger process that required them to excel at their specialties in the context of a team offense. The longer I play on adult rec teams, the more my thinking has shifted from “what am I good at” to “what can I do to make this team better”, not out of some virtuous elder wisdom, but because winning is fun and causing winning by being smart and observant and building up other people is even more fun. When we didn’t have any guards, I started bringing the ball up. When we didn’t have any size, I started throwing my weight around in the paint. Even professional sports reinforce this kind of subsuming of ego with great examples every day. Watch Stephen Curry hit shots from the locker room tunnel, and still make the right pass out of a double team every single time. Watch the San Antonio Spurs do literally anything.

It’s easy to watch this and think “oh, all these guys are high performers”, but they’re all wildly different players who are all actually terrible at variety of important basketball-things. But the system they’ve built stresses what they’re good at, minimizes what they’re bad at, and as a result generates incredible, impossible looking results. It’s wonderful, and the Spurs continue to re-invent themselves every year as necessary. The idea that their coach, Gregg Popovich, may be the greatest coach of all time is not crazy. 

this is learned behavior, and you have to get good at it

Unselfishness is a lot more complicated than simply not being a jerk, or caring more about the outcome of something larger than yourself. It’s understanding, and coming to terms with the power of putting aside your own abilities, and sometimes your own judgment, and making the leveraging of that power as natural as breathing or waving to a co-worker in the parking lot. It’s about seeking out skill and potential you realize you may be able to unlock, and seizing that opportunity with the same or greater excitement than you would the opportunity to excel yourself. It’s not necessarily about “deferring” — it’s about getting excited to make a block that frees the runner, or more aptly, to make the pass that leads to the pass that leads to a better shot. When you love doing that, and go to sleep smiling after your games because of it, you know you’re in a good place as a teammate.

Very few people operate this way right out of the gate. I sure as hell didn’t, and I’m not even particularly good at anything — I’m just yet another irrational lunatic who gets nervous sitting on a plane because I’m not actually controlling the plane. But you can start learning how to think this way at any point just by trying. If you’re lucky enough to work in an environment with a lot of talent waiting to be channeled (like I have been at many spots in my career), it’s almost impossible to not notice the results. 

Let’s Talk About $$$

I’ve been meaning to write about how people in my kind of work get paid for a while, but it’s a tricky thing to talk about in any kind of publicly consumable form. That’s because people — even myself, regrettably — can get incredibly sensitive about how they and their co-workers are compensated. So let’s get a few things out of the way, for the sake of everyone’s emotional health.

1) I really like my current job, and I think I get paid a fair amount, based on my admittedly limited knowledge of the job market. I also like the way my company has handled talking to me about my pay, benefits, and everything else. So this isn’t any kind of reaction to my daily events — I’ve been meaning to write about this for literally years, but it’s a thorny topic and I’ve always wanted to get it right.

2) The only job I ever actually left over money was my first — in 2005, I got a job offer as a technical writer, which was a huge improvement from the peanuts I was making out of school as an support/email monkey. When I told them I had another offer, my department head at the time took me out for a sandwich and asked me if it was an offer they could match. I told him what it was, and he said “good luck, it was nice working with you.” Other than that, I’ve been fortunate enough to be able to pick my jobs based largely on opportunity over money (partially because my wife also works, and we haven’t had any mouths to feed).

Anyways, now that we’ve got that out in the open, let’s get started.

Three approaches to $$$

It's actually kind of amazing anyone was willing to pay 22-year old me $12.20 an hour in 2004, to be honest. It’s actually kind of amazing anyone was willing to pay 22-year old me $12.20 an hour in 2004, to be honest.

In my experience, there are three kinds of emotional/logical impacts salaries and money can have on people. Here they are, in order of complexity and general weirdness.

$$$ as a need

I don’t know if you’re aware of this, but you do need some amount of money to survive. Technically, you can probably survive without any money at all, but it’s very complicated — in general, there’s a certain income level most people need to be at in order to live normal, healthy lives, especially if they want to avoid constantly borrowing against their future. I haven’t had to make decisions based on this perception of money very often, but I’ve definitely been there.

When we lived in Cleveland, I had friends who thought I had a lot of money just because I didn’t take out payday loans or buy things on installment plans (instead, I bought almost nothing). But to me, barely being able to pay your rent without borrowing money from someone else qualifies as an appropriate time to start thinking about income as a need. When that happened to us, we left Cleveland for greener pastures (an option not everyone has) soon after.

$$$ as a resource

Most “regular” people (ahem) who are doing pretty well in the 21st century economy — i.e., usually college educated or at least highly skilled, in some kind of growth industry — don’t have to make money decisions based solely on survival. Instead, money is more of a tool or a resource that allows them to do things they want to do. Buy a house, have a family, take a trip, get a dog, watch movies on a big TV, play the piano, whatever. Everyone knows at least one person who’s taken a job they hate in order to get enough resources to do something outside of work they love, but in my experience most people regret it unless it’s extremely temporary.

I got the biggest raise I’ve ever gotten in my life in 2011, when I got another offer and considered leaving Bamboo. I didn’t need the money in order to pay my rent or anything, but it did allow my wife to work on her fledgling business without us reverting to Cleveland-style “don’t spend any money” mode, which was a huge improvement to the quality of our daily life.

$$$ as a scoreboard (eww…)

Now, where things get really weird and complicated is when people start thinking about money as something other than compensation — an indicator of how much people value (or should value) their opinion or judgment, how much authority they have to direct other people’s work, or how much responsibility they should bear for any problems the organization is having. This is why salary disclosure is such a minefield (it’s not necessarily bad, just complicated) for all but the most radically-transparent organizations — and why handling compensation on a strictly employee-by-employee basis can result in so many problems down the road.

I’ve never turned down more money from an employer (unless I was leaving altogether, which I guess counts), but I’ve also been very judicious in how tightly I tried to turn the screws in the few instances where I had a lot of leverage and was trying to get a raise for whatever reason. Part of this is just the way I’m wired, and some of it has to do with the fact that my work is often very deliverable based, so I usually have a really good sense of whether people value what I’m doing. When I’m outperforming my salary, I can usually tell. That’s probably not true for people wedged into some kind of byzantine, managerial structure where you’re not sure exactly what anyone does. I have plenty of friends in the latter situation, and a lot of them make more money than I do — but they’re also more frequently worried about whether they’re properly credited for success, or if they’re missing out on a potential opportunity for a raise. Since their value is hard to measure or even witness directly, it’s often determined by the dreaded “optics”, or how valuable they look. The sad truth of the allegedly efficient private sector is that many people make a lot of money simply because they’ve made a lot of money before, which creates an unhealthy incentive to “get there” as quickly as possible, by whatever means necessary. This usually doesn’t end well, and even with well-intentioned people frequently leads to insecure people with vague authority running around trying to be tangentially involved in lots of things so they look and feel productive.

Side note — one of the fun parts about being any kind of technical person is that you can often break this informal structure (the kind of thing various people I’ve worked with have referred to as “the game” or something similarly creepy and rich-person-sounding), and it drives people who depend on it absolutely crazy. I think that’s why so many executives and investor people are obsessed with figuring out a way to control how much software developers get paid — you can lecture those guys all you want about the value of different business units, or quote some book about organizational structure to them that dictates why they should do what you say, but at the end of the day, the person who knows how to build stuff have all the cards. Do you want this database to work or not? If you’re so smart, and I’m so dumb, why don’t you do it? Professional suits can pull this with work like pointless reports, boring PowerPoint decks, or other things everyone/no one is actually good at. But they can’t fake technical skills, and that doesn’t change no matter how much anyone gets paid.

My approach

I don’t think anybody — at least anybody I know — is completely above any of these motivations; we’re just all on different parts of the spectrum for each. Once I got settled in D.C. in my mid-20s and got a little momentum going, I went several years without thinking about my salary as meeting some kind of survival-themed need until we started doing the math about having a kid. Just like that, it was 2006 again, and I was biting my nails thinking about whether I could afford to go to Subway when I already went last week. I didn’t leave Contactually for a bigger salary, but the simple fact is that the (admittedly complex) insurance math that resulted had a non-trivial impact on my decision to join FiscalNote.

As for the “salary as a signaling device” thing… well, left to my own devices, I’ve never been especially curious about how much people get paid. What I need is pretty much exclusively between me, my boss, my wife, the mortgage processing guy, and maybe the guy behind the counter at Guitar Center when things are going well. But the fact is, a real-world office environment never really leaves someone like me to my own devices. The company has bad quarters, or someone underperforms, or somebody gets a big raise and then starts walking around like they’re Lumburgh from Office Space, and people start asking questions. Eventually, some number starts floating around — whether it’s accurate or not — and it’s hard for people with hopes, dreams, or actual financial responsibilities to keep from wondering if they’re being stupid for leaving money on the table. That’s the feeling you really want to make sure your employees don’t get.

I’m not sure exactly how you prevent it, but a lot of the best practices I hear out there are good places to start. Don’t hire people for the smallest amount you can get them at — pay a market rate as soon as possible. Try give people consistent small raises, instead of putting out fires by dumping big promotions on people who you’re suddenly worried about losing. Be careful just throwing around big titles to make less experienced employees happy in the short-term (especially when you can’t pay them enough), or you can end up with a company full of people who think they’re in charge of each other. Create real, time & achievement-based paths to advancement for people (think quantitatively and qualitatively), and make sticking to them an actual, operational priority. Remember that employment is a two-way street, and that employees who are also responsible, adult citizens are obligated to look out for themselves in ways that won’t always align with what your company needs right now — and don’t take it personally.

There’s also a generational component to compensation and promotion that I’m not sure even a lot of people my age (early/mid 30s) are able to fully comprehend. Remember, outside of government, careers are often constant works-in-progress. The days of digging a nice little cave in Accounts Payable and living in a big house in the suburbs are over — now, if you’re not moving, you’re dead. And while people pay lip service to this realization (often while clinging to one of these old school careers and complaining about young people), today’s 20-somethings are living it. Most of the professionally skilled ones are highly educated, and more-importantly, come from a world where some kind of performance — and acknowledgement of that performance — is the currency of their lives. In general, the young white-collar professionals I’ve worked with see their first job as a direct extension of their super-competitive college experience, where things are broken up into semester-length goals, and most importantly, there’s a clear path to advancement where not advancing is failure. That’s how school works, remember? I never really thought about things this way — I enjoyed high school, but never thought it was very good way to evaluate people, and I outright despised everything about the culture at my faux-elite private university. For me, joining the working world was exciting because I got to escape constant, often-arbitrary quantitative evaluation (getting a numeric grade for a written paper always made me crazy) and return to the more nuanced world of everyday professionalism. That’s not how a lot of kids are wired now, but it shouldn’t surprise anybody — we wired them that way so they’d get into these schools and these achievement/reward cultures in the first place.

Don’t blame people for being rational

Like a lot of things, I think the most useful quality in dealing with compensation is real, honest-to-God empathy — it’s the only way to figure out which of these various perspectives on money is currently driving a given employee, and respond to them with something that makes sense. If someone is freaked out that their career is stagnating, it’s important to be able to tell the difference between someone who’s dealing with a necessary ego correction, and someone who is legitimately scared they aren’t going to be able to survive the increasingly real pressures of the 21st century without making a career change. It’s easy to tell a 25 year old that “everything is going to be fine” when you’re the one who has the most control over that possibility. Do you know how much your employees pay for rent? Do you know what their student loan situation is like? If their parents are counting on them for support? You don’t necessarily need NUMBERS for these things (that seems a little too prying for my taste, and is probably an HR violation of some kind, anyways), but if you don’t know the relative impact of them on someone’s life, it’s easy to misinterpret why someone wants to get paid.

Besides, remember the last time you got a raise that changed the way you felt about your career? I sure do. Don’t forget how important that feeling is to people to who haven’t experienced it in a while. Or ever.

It Sucks to Grow Up (but Everybody Does)

Truly entrepreneurial people are usually pretty action-oriented. Sometimes I meet rich people who describe themselves as entrepreneurs, and it’s immediately apparent that they’re pretty averse to doing any actual work. I know this because (except for the being rich part) I’m kind of like that. I’ve actually had to build up an alternative work personality that’s extremely production oriented to combat my own navel-gazing strategic dithering, so I totally understand where these people came from.

(Side note — about five or six years ago, my productivity-oriented work personality then doubled back on me and started taking over my hobbies and personal life, which was unexpected to say the least. I think this is how a lot of parents become uncool.)

But basically, if you somehow manage to scrape together a functional business from nothing (and no, not some bullshit consulting vanity project) with a product or service, and paying customers who yell at you when you do something stupid, odds are you’ve had to do a lot of things. If you’re in any kind of innovative or competitive space, you’ve probably had to do a lot of these things very quickly — more quickly than you would have liked, with results that, while impressive in a vacuum, could have and probably should have been better with a little more time.

All of this is okay. Chances are, you simply did the math, looked at your options, and made a bunch of very ordinary, very necessary sacrifices to survive a competitive market.

You are a 2 year old german shepherd

Here’s the problem — once this approach to putting something together from scratch is successful (as it has been at some key point in the life of most new ventures), it often hardens into a religion about how to solve business and product problems, especially if you’re like, twenty five years old and this is (a) your first rodeo, and (b) something you are personally and emotionally invested in.

In this scenario, you’re probably a little like the german shepherd puppy my friend and his wife got a couple years ago. The dog was adorable, and my friend used to chase her around the table in their little apartment, in a big, dumb, cute circle until she collapsed on the floor for belly rubs.

Over the next two years, she got too big for the apartment. But every time I went over there, she’d try to play the run-around-the-table game, even though she was so big she could barely squeeze through the side by the wall, and her giant tail would constantly whack into the lamp and almost knock it over. She didn’t care. The game had proven it’s awesomeness at a critical juncture in her life, and no amount of lamp breaking and wall banging was going to change that.

The point is, if your company is growing as fast as my buddy’s dog, the most effective way to generate the results/progress you want is going to change. And — this is the important part — it’s not just the actual activities that will change. It’s the very process of figuring out what those activities are, and the very process of executing them.

This isn’t because “it’s grown-up time” or some business-cultural nonsense like that, either; just think about the dog again for a minute. It wasn’t “time for her to act her age”. It was time to get a bigger apartment, and probably time to stop trying to get exercise by running in circles around a table that’s barely bigger than you are. These weren’t problems of age or appearance; they were problems of size, nature, and the logistics of getting the results you want.

When a company grows, you are going to start doing more things by committee, which is annoying, frustrating, and inefficient. It’s also completely necessary in the vast majority of cases, because most lucrative opportunities to build something are really complicated — if they weren’t, any lazy idiot who likes money could just go do it by themselves. Ventures like Instagram throw off the calculus for everyone (“let’s make something worth $2 billion that has 12 employees!”), because they rely on a bunch of dependencies other businesses either don’t want or can’t have. Do you have the patience, resources, and cojones to build a product with no revenue until someone swoops you up? Does that someone even exist? If not, you can’t be Instagram. And if you’re not Instagram, you’re going to have to build value the old fashioned way — by doing difficult things that require a lot of hard work from a bunch of people who disagree on lots of things, which by comparison feels like herding cats.

Complaining that this is frustrating, or that it was “better” before, when you could “just do things”, is like an eighth grader complaining about how he wishes school could be like kindergarten again, when he got to play with blocks and go home at lunch. Well, guess what? Kindergarten is only there so you can build more advanced things on top of it — as a member of society, you — like your interesting, unprofitable, mid-stage startup — have basically no value while you’re in kindergarten. You have to go through the whole process, learn from it, and adapt before you’re of any use to anybody. It seems obvious with people, but maybe we wouldn’t feel this way if we gave five year olds valuations based on their future earnings, and labeled some of them “unicorns”.

Bottom line — if you don’t have the stomach to suppress your need for immediate executive gratification in everything from marketing campaigns to product development, you probably don’t have the stomach to build a big, valuable company. At some point, your desire for action devolves into a childish need to feel productive and important. At a strategic or leadership level, that’s not an engine for your business — it’s an anchor.

“But Growing Up Is For LOSERS!!!”

I can already feel the dismissive scorn from mid-stage startup founders towards this argument. After all, what do I know? I’m just some freaking guy who hasn’t started anything. The only startup I was really on the ground for failed, in no small part due to my hesitance to inflate the importance and readiness of unfinished products, or do things before they (or we) were ready to do them with any level of competence. I’ve worked for other really cool early and mid-stage companies, but I’ve neither brought them to life from nothing, or dragged them across the finish line to permanence or acquisition.

But that doesn’t mean I’m wrong here. To return to my last metaphor, I remember being in eighth grade. I thought I was smarter than my teachers, and it’s entirely possible that I was right by at least some measure (after all, lots of eighth graders are probably smarter than I am today). I already knew how to do lots of things they didn’t learn until they got into college, and a number of other things they would literally never understand (“wait, what’s the difference between disk space and RAM again?”). But you know what they knew, that I was completely clueless about? How to get out of eighth grade.

NOBODY knows how to get out of eighth grade better than eighth grade teachers, no matter how smart or accomplished (or not) they are. And until my little arrogant self, with my 5th grade achievement tests and 6th grade writing awards, came to realize that, I was going to struggle. Some kids never do, and it keeps a lot of them from ever capitalizing on all that self-important promise.

Objectively, I didn’t learn that much when I was in eighth grade. The most important thing I did learn was that life was more complicated now, with a ton of factors and repercussions that I’d never considered before but could no longer ignore. That, and that I had to adapt to all of them if I wanted to do anything worthwhile in life. I have a feeling that my teachers would all be very happy if they knew that got through to me, regardless of how poorly I retained the literary symbolism of The Lord of The Flies.

Activity VS. Productivity

So think of me as your business’ eighth grade teacher for a minute. I know — you don’t want to be like me, I keep telling you to think about boring things that don’t seem important, you’re convinced I’m actually kind of dumb, and I wear stupid shirts and make dated references. That’s all fine, so long as you learn one thing from me that I actually know, and then go on your merry way, connecting Snapchat to Waze and somehow raising $200 million to monetize the transaction data.

Here’s my one thing. Activity is not productivity.

To make progress in anything, from building a band to hitting a layup to just getting your Sunday afternoon together, you need strong, decisive moves. You can’t make strong moves if you’re making a thousand different ones, and you can’t make decisive ones if you’re distracted by a shiny object halfway through it. “Holy crap, I have a great idea!” is still a valuable thought — it’s just not the beginning of a real, productive, executable action plan anymore, so you have to stop thinking and acting like it is. Again, if you don’t want to live in a world like that, it’s okay — but you probably can’t build a valuable company unless you’re willing to.

If you are, here’s what to do. Think. Stop. Breathe. Ponder who would execute your idea, and talk to them to better understand what it would really entail. Compare it to what you’re already doing. Contemplate switching costs. Figure out if you really like your idea, or just something about your idea that your company could do through an existing activity. Be open to the possibility that your idea is terrible, infinitely more complex than you realize, or motivated by an irrelevant conversation you had with some other CEO, or some investor who was just babbling and never considers any of this. Do not respond to obstacles presented with “we need to think bigger” (everyone is probably thinking big, they just may have a better grasp of what big ideas require than you do), or “all I’m saying is…” when that’s not all you’re saying. When you want to move fast and break things, ask yourself — whose things are you breaking? Who is going to clean them up, and what important things are they going to have to stop doing in order to do it?

You don’t have to turn into Oracle (in fact, please don’t, one is enough). You don’t have to have subcommittees and use terrible enterprise intranets and resent your customers and become everything we all hate about large, financially successful companies. You just have to challenge yourself to honestly assess what’s going on around you every day, and be ready to accept the fact that if you’re doing your job well, it’s often going to be different than it used to be. And this is a good thing, provided you steer into it and not reflexively away from it and into a ditch.

If you can do that, I swear to God, you really can run a company, and focus on non-self-inflicted challenges, like technology, business development, building great products and good stuff like that. I wouldn’t love working for such crazy companies as much as I do if I didn’t really believe it. 

Why OKRs Kind of Suck

The last two companies I’ve worked for have used OKRs, a system for company, team, and employee goal setting popularized (and possibly invented, for all I know) by Google. Personally, I’ve been very frustrated by OKRs, and if anything, they’ve made me less productive. I don’t think I was alone, and that’s one of several reasons Contactually scrapped them last spring.

It’s not a bad system, but like a lot of a business theories coming out of the startup world these days, it suffers from a desire to constantly evaluate everything quantitatively that isn’t matched by an ability to effectively measure things that way. In fact, OKRs are kind of the embodiment of this philosiphy, where for some reason startups still attempting to do basic things like define what their product is for and how it works decide that they’re going to operate like Google, a billion dollar public company with one of the most (if not the most) advanced data infrastructures in the world.

The motivation behind being data-driven is fantastic, because it’s a motivation to not be driven by bullshit or blind ideology. This is a truly wonderful characteristic of the stereotypical venture-backed startup, and probably the main reason why I enjoy being a part of them so much. These companies want to do things that make a difference, not just things that make them feel like important companies, and that’s a big part of why startups have successfully shaken up or even dismantled long-established markets.

But that’s the emotional drive behind OKRs; the practical application is another matter altogether, and one that I think a lot of organizations have really struggled with. Recently, I’ve heard marketing people start referring to being “data-informed”, instead of “data-driven”, which I think attempts to fix the wrong part of the term. What you really want is to be reality-driven, where data is often an idealistic proxy for reality. If I’ve learned anything from the last ten years of work, it’s that getting reliable data and making sense of it is actually very difficult, and very expensive in both time and dollars. It’s easy to say “let the data decide”, until two people are waving contradictory Salesforce reports at each other that they both spent hours on — hours that could have been spent doing unquestionably useful things like talking to customers or fixing obvious problems in your product.

Basically, despite all of our wishful thinking, even rudimentary data science is still really hard for most businesses. But we’ve allowed the still-young analytics industry to convince us that it doesn’t have to be, as long as we buy the right tools. Well, by now I’ve used many of the best analytics tools, and while lots of them are really cool, none of them make the full business data experience — gathering, analyzing, interpreting, and auditing — easy, or even predictable, for a company without significant dedicated resources. Not one.

Back to OKRs

That brings us back to the OKR, an acronym that stands for “objectives and key results”. The “objective” part is fine — OKRs are designed to nest goals so that everything everyone is trying to do ultimately bubbles up to a company goal. If you do OKRs right, they ensure that everyone’s individualized little tasks are all generally pointing in the same direction, which is important if you want to make any significant progress as an organization. Strategically, it’s a really, really good way to operate, even if it’s essentially just a framework for continually using common sense and proper priorities in the workplace.

The problem is the second part — “key results”. See, with OKRs, your objectives aren’t really objectives unless they cause measureable change, which can be a problem for several reasons. If you’re trying to measure something qualitative, for instance, the reflexive OKR-style approach is to bolt some kind of metric to it. Unfortunately, this has a tendency to cause people to radically oversimplify extremely complex, qualitative parts of their business with iron-clad sounding, but actually very dubious logic.

“If our messaging is bad, and we improve it, our conversion rate should go up. Ergo, if our conversion rate doesn’t go up, the messaging isn’t any better, or messaging doesn’t matter. We will let the data decide.”

But wait — why are we assuming that effective communication is directly related to people doing what we want transactionally, like clicking a button? Where’s the statistically significant data that demonstrates how people interact with our messaging, evaluate our product, and eventually make purchasing decisions? In other words, where’s the data that validates our approach to data?

The fact is, for growth-based companies doing anything remotely new, that data is often completely non-existent. So ironically, many companies using OKRs end up building up highly quantified evaluation methods that are powered almost entirely by subjective, qualitative assessments of data. You’re not eliminating subjective decision making — you’re just obsfucating it behind a layer of numbers that make everything feel less random.

Worse than nothing

People who desperately want to be data-driven (for good reasons) often respond to these observations with the argument that some data is better than no data at all. I’ve always vehemently disagreed with this, probably based on the fact that I’ve justified a lot of really dumb things in both my personal and professional life with an incomplete, or logically flawed subset of technically accurate data. A simple example — I make pretty good judgments about personal spending. I’m inherently conservative about cash flow and what I “need” versus what I want, and that’s served me well through a series of wildly different personal finance scenarios, from having literally no money and no job, to buying a house and starting a family.

But you know what I do when I want to justify a bad financial decision of mine, or push back against something my wife wants to spend money on? I go online, and I start pulling data. How much cash we have. What we’ve spent recently. What we can cut back on. Anticipated future costs. Because we’ve never successfully built a strong enough financial model to respond to various purchase ideas with a simple, 100% metric-based “good idea/bad idea”, instead it’s up to me to equip myself with whatever amount of data I find useful, and make a decision from there. And unsurprisingly, whatever I thought before I had any data turns out to always be the conclusion “the numbers” indicate as well. What an amazing coincidence! To cite one of my favorite quotes, “If we have data, let’s look at data. If all we have are opinions, let’s go with mine.”

And that’s the Achilles heel of the OKR system, as well — tying qualitative objectives to quantitative key results outside of anything other than the most transactional jobs and tasks requires huge logical leaps of faith, and radical oversimplifications that in the end, rarely help you build a stronger business. “Building a product people love” becomes “increasing logins per month”, which probably makes sense in a thousand ways, and makes no sense at all in a thousand other ways. “Increasing brand awareness” becomes “unique blog visitors per week”, because hey, we need a key result, and that seems like something we can measure that would be good. But when the end of the quarter comes, you’re no longer thinking about brand awareness. You’re thinking about unique blog visitors, and in that way, OKRs are often responsible for shackling your team’s very powerful, entrepreneurial brains and turning them into stressed-out, metrics-hunting robots.

Accept that you can’t know why everything happens, all the time.

The bottom line is that everyone is at work for a reason, which means they already have a goal. And what’s ultimately important is that they get as close to reaching that goal as possible, and don’t do things that make reaching that goal more difficult. Marketing teams are probably going to be responsible for generating leads. Product teams are usually supposed to build products that work well and provide value. Sales teams have to close. None of this is rocket science — the real numbers that matter to those teams are obvious, and should be religiously tracked (although it helps to have the patience and perspective to not fool yourself into thinking you can immediately, effectively respond to daily, weekly, or even monthly tracking).

But micro-tracking at more granular layers is often little more than a vanity exercise, and the kind of pointless, administrative navel gazing that startups should be avoiding, not installing. What’s more important is for team leads to look at that one number that really does matter — be it sales, close rate, inbound leads, or whatever — and use their powerful little human brains to assess if the things their team is doing are aligned towards that goal. “Why am I doing this?” is a great question to ask yourself at work every day, and at home, too. When I talk to frustrated co-workers (especially younger ones), and I ask them why they’re doing something they think is a distraction or a waste of time, the answer is still too frequently “because (senior person X) wants this by the end of the week”, or even worse, “because it’s one of my OKRs”. To me, for all of it’s theoretical, well-intentioned benefits, that’s the sign of a system that’s not working. 

Well, That Escalated Quickly

Once upon a time, in Washington…

One night, in the fall of 2002, three twenty year old kids from Rhode Island were, once again, driving to band practice somewhere out in the less-tourist-friendly inner suburbs of Maryland. They were early in their junior years of college, and two of them — the annoying bass player and the goofy drummer— were visiting from far away schools. The world’s worst rhythm section had convinced each other that a semester somewhere else would be a great way to meet girls, which probably says a lot about how well that had been going for them back in Richmond and Chicago, respectively. Fairly often, the out-of-towners would badger the neurotic guitarist — who was a full-time student at George Washington University — for introductions.

That night, he finally had something, although it wasn’t exactly what his friends had been looking for. But as it turns out, he did live down the hall from a very available lunatic from Florida, who quoted famous motivational speakers, sold knives door to door, and had once used the opportunity to meet Tino Martinez. As they barreled down Wisconsin Avenue, he (the neurotic guitarist, not Tino Martinez) told the annoying bass player that he just had to meet her, if for no other reason than to confirm her ridiculous existence.

A week or two later, the loud, friendly, and fairly obnoxious-sounding band had a show on the GW campus. The neurotic guitarist convinced everyone he knew — including the lunatic from Florida — to attend, mostly out of guilt. After the show, she unplugged her ears and struck up an animated discussion with the sweaty, exhausted, annoying bass player, which peaked with him forcefully demanding to hear her translate “my dog is on fire” into Chinese.

Three years later — exactly ten years ago today — they got married in Okemos, Michigan in a park.

Then they had a lot of fun, forever. The end. 

We Should Care About Why We Get Paid

The amoral dumpster fire that is online advertising

I very briefly touched on this a few weeks ago, but to state the obvious once again — online advertising is a mess. The landscape is a rapidly changing free-for-all with multiple business interests (wireless providers, hardware makers, publishers, social media platforms) all trying to shake money out of consumers. For instance, wireless carriers want to charge you for data as if you had any idea how much data you need, and publishers want to load up 100kb web pages with 15 megabytes of animated ads and javascript trackers as if data usage didn’t matter.

There are a couple arguments out there, and I have reactions to all of them as someone who’s been in online marketing for a while, someone who reads a lot of things on a phone, and someone who writes a fair amount.

Argument #1 : If you don’t like a site’s ads, don’t visit the site.

This is the “it’s like software piracy” argument, and frankly, I don’t find it compelling at all. What you get from people who visit your site is totally opaque to them — they don’t get to decide if you’re worth what they have to give up because they have no idea what they are giving up, or because they have to give it up first before ever actually seeing anything. Do you use non-tracking, unobtrusive ads from The Deck? Do you follow people around forever, monetizing their visits to other sites that have nothing to do with you? Either way, in most cases the user has no idea, and they definitely have no idea when they’ve never been to the site before. This is not a fair market exchange. I suspect publishers are a little blind to this argument because they’re understandably myopic about their site, but in reality, cruising around the internet like a normal person involves constantly visiting places you’ve never been before. You can say that shouldn’t be the case — that readers should have long term relationships with their publishers, like they did with print magazines — but then you’re kind of making an argument for a smaller universe of content, which is better served by either native apps, or subscriptions. If you’re a big proponent of media being consumed via the “open web”, I think you have to consider how that open web is most likely going to be accessed by the general public.

Speaking of subscriptions… paywalls are fair market exchanges. You describe what you have to offer in advance, in whatever form you find appropriate. If people are interested, they can pay for access at the price you’ve specified. End of story. Consumers can get pissy about paywalls if they want, but the truth is that they just don’t think access to said content is worth the money, and that’s fine.

Some organizations use paywalls. However, most do not, because they do not want you to decide if visiting the site is worth the cost you pay, because it’s not a cost most people are willing to pay. So, like anyone else who wants to sell something for more than the market is willing to pay, they’d prefer to obfuscate the cost through advertising and undisclosed tracking. That way, not only do customers think the content is free (when it’s not), but you can actually change the price people pay (more tracking, more ads, etc.) without telling them (and hopefully without most of them ever even figuring it out), which gives you control over what you’re charging.

I don’t have Slate Plus, for instance, but I’m also not running around trying to steal Slate Plus content. I understand what’s there, and occassionally it sounds pretty compelling, but I forgo hearing/reading it because I don’t want to pay for it. This is a normal, fair market interaction. I have zero resentment for Slate putting Plus content behind a paywall. I don’t think they are “misleading” people or anything like that — and best of all, they are taking control (and responsibility) for their revenue model. At some point, they may offer content that is valuable enough to me (maybe because it improves, or maybe because I have more money) that I’ll pay to access it.

Argument #2 : It’s only okay to block tracking and “bad” advertisments.

This is an oversimplified version of John Gruber’s argument; basically that “ad-blocking” has really become “garbage blocking”, and that there are plenty of ads that aren’t garbage.

I am pretty receptive to this, although I don’t think the industry will ever coalesce around this thinking. It allows for a floating definition of “bad” that I will probably agree with when Jason Kottke defines it, and wildly disagree with when a Conde Nast executive is trying to hit a growth number. I guess someone with a really good grasp of how this stuff works (not conceptually, but literally how different networks and marketing platforms are implemented) could build the “right” kind of blocker, but I certainly don’t blame regular people for saying “the hell with it” and just blocking external calls for data. Things have simply gotten that bad.

Argument #3 : This is really about moving people away from the open web and into closed platforms (Facebook, Apple News, etc.)

You know what? This is totally plausible. You can follow the money pretty easily, and see why the company that’s forcing this confrontation — Apple — stands to benefit (even marginally) from a world where online advertising as we know it dies. If people on the open web can’t monetize through whatever crazy, convoluted technical shenanigans they want, everyone will have to go through controlled channels, and the owners of those channels will obviously benefit.

This is Nilay Patel’s argument, and it’d be a lot more convincing as the primary thrust behind all of this if he wasn’t completely unable to defend his publication’s (The Verge) advertising & tracking policies, which are abhorrent. His responses to criticism so far have been so flippant, and so obviously dimissive of clear evidence, that I can only assume he’s either personally hurt by this debate, or is emotionally unprepared to deal with a world in which he’s in any way morally culpable for how his business makes money. Given how brilliant of a writer and thinker he is at his best, it’s difficult for me to believe he really and truly sees this as nothing more than a platform power play from Apple, a company that already makes more money than God from selling devices that made mobile open-web browsing a reality for the mainstream.

Publishers — and journalists — aren’t ready for this kind of responsibility.

Journalism is a funny thing. It’s pretty much always had to function inside capitalism, but for large periods of time, economic conditions insulated it from how capitalism actually works. For a long time, newspapers had geographic near-monopolies, and safe, reliable revenue streams from things like classified ads. Even print magazines had protection from competition due to the simple fact that making a magazine was inherently expensive.

All of that has been blown up, and while journalists and pundits have practically reveled in analyzing the disruption of music, television, and other forms of mass media, the idea of it happening to them seems to simply be too much to process. To me, Patel’s knee-jerk “this is an attempt to kill the open web!” response reflects a general uncomfortableness with thinking about revenue at all; that it’s inherently the responsibility of someone else. That’s what we’re talking about here — the complete outsourcing of advertising (and whatever that entails) to a third party. The Verge brings eyeballs, someone else does whatever they want to make money off those eyeballs, and gives some of that money to the people who write on The Verge. If you have a problem with that, you apparently have a problem with the open web.

Bullshit. I have a problem with publishers refusing to take any responsibility for how they make money in the name of editorial independance. It’s a false dichotomy, just like it’s a false dichotomy for the engineers at my companies to have to choose between working in development, or weighing in on who we sell to and how we do it. They do both, leaning on the business team to make front-line decisions, but demanding transparency and visibility into what we do and pushing back when they think something doesn’t align with their values. It’s their company too, and they deserve to know (a) how we can afford to pay them, and (b) whatever moral quandaries arise from doing it. Those conversations are often fascinating, as idealistic bubbles run into business realities, and messy, but morally acceptable resolutions are hammered out.

everything_is_fine_dont_worry.js (250kb)

But in Patel’s view, there’s no solution here to determined, other than that mobile browsers should take on the responsibility of more seamlessly handling the megabytes of trash publishers inject into pages. The market value of The Verge isn’t to be determined by the people who might want to read it; people who stumble onto the site are expected to allow themselves to be monetized in whatever manner The Verge finds most optimal, or else they’ve committed a moral violation. That lets writers and pundits to simply shrug away the reading experience (“not my job!”), or better yet, to complain about it without taking any responsibility.

I’ve always considered the possibility of getting into digital media — I even applied at Vox a few years ago (The Verge’s publisher), as they’re in DC and seem like an interesting company. But I’ve never been interested in creating content for money in an protective cocoon that insulates me from where that money comes from. That’s what this site is for.