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. 

What’s Wrong With the NFL

Reading about Mike Tomlin’s headset conspiracies and Ben Roethlisberger’s “unwritten rules” has highlighted what’s really sucking the life out of the NFL for me these last few years — growing anti-intellectualism.

I know that sounds like a pretty obvious potential problem with a league known for massive, systemic brain injuries, but bear with me here. Because what’s really bothering me isn’t people being stupid. It’s how angry the league and many of the people in it get when someone is smart.

I grew up playing a lot of backyard football, and one of the real joys of actually playing — presuming you aren’t a very good athlete, like most people — came from what are literally called trick plays. Trick plays are great, and football as a sport is a wonderful canvas for drawing them up, as there are eleven guys on offense who all matter at all times. You can do tons and tons of crazy things to open up a game that, at it’s most basic and unoriginal, is basically a bunch of guys smashing into each other for a few seconds. But of course, the secret to making a good trick play isn’t doing the craziest thing possible; it’s doing something just crazy enough to confuse the other team, while still being something you can execute properly. And you know who’s really good at coming up with things like that?

Bill Belichick. And everyone in the NFL hates him for it. I’m not talking about deflating footballs or messing with headsets, two “scandals” that (a) no one has any decent proof had anything to do with him, and (b) have nothing to do with the actual game of football. I’m talking about the on-the-field shenanigans that drive football robots like John Harbaugh and Mike Tomlin insane, because it requires them to think about things other than DISCPLINE and SERIOUS LOOKING BASEBALL CAPS. Listen to Ben Roesthlesberger the other day :

“In my years of playing, a defensive guy can’t bark stuff or move in the middle of a cadence. I was arguing the fact that he shifted in the middle of a cadence and I thought that there was a rule against it. Maybe there’s not – maybe it’s a written rule – I don’t really know. So, that’s what I was upset about. They do that. We saw it on film that the Patriots do that. They shift and slide and do stuff on the goal line knowing that it’s an itchy trigger-finger type of down.”

Ben, what are you even arguing here? You’re admitting that (a) you don’t even think it’s actually illegal, and (b) you’ve seen them do it on film. What do you think would make this fair — do they need to give you a hand signal they’re about to try to trick you? And the defensive guy can’t do this, but when you go up there on 4th and 2 and yell “hut hut HUTTTTT” in an attempt to draw an offsides penalty, that’s somehow football in good faith?

This reminds me of Harbaugh freaking out last year when he got bamboozled by some trick formations Belichick came up with. His argument was similar — okay, maybe it’s not illegal, but it was strange and weird to me, and it felt illegal, so people shouldn’t get to do it. You’re the coach. You don’t have to run or jump or tackle anybody — you just have to know the rules (the real rules, not the ones in your football coach’s heart), and prepare your guys for whatever they’re going to mean on gameday.

Even just a few years ago, the common refrain to guys getting caught with their pants down in a game like this was more along the lines of “haha, you’re a terrible coach, Jack Del Rio”. But today, the collective reaction seems to be a collective hissy fit of self-righetousness because the nerds outsmarted the jocks. Even worse, all of this is getting combined into a collective “cheating” argument, as if turning off the other team’s headset, or a coach tripping someone as they run down the field is the same thing as inventing a weird formation nobody has ever used before that’s “technically legal” (or as I call it, “legal”). But in modern NFL culture, it’s all lumped together as counter-cultural hippie voodoo that needs to be stopped by the incompetent, top-down authority of the worst commissioner in sports. Quick, someone call Ted Wells.

Football, as a game, is like a giant, real-time chess match, only with a lot more variables and potential insanity. It should be something that brilliant tacticians like Belichick are constantly pushing, and turned into a beautiful mix of raw athleticism and situational mind games. But today’s NFL culture doesn’t give it’s own sport enough credit — they want a live-action Tecmo Bowl, where if Tomlin or Harbaugh guesses the right one, they’ll never be surprised by the outcome.

Unfortunately, I don’t see a new enlightenment coming during the reign of Roger Goodell, whose incompetent leadership, circular logic, and reflexive superiority complex are antithetical to anything other than grandstanding and self-importance. Maybe we can have a book-burning at halftime of the Super Bowl — that’ll show those nerds.

This Is Why We Can’t Have Nice Things


I saw this piece in the Washington Post today about the trouble Indiana is having recruiting teachers. What’s the problem? According to the Post :

“Pretty much the same thing as in Arizona, Kansas and other states where teachers are fleeing: a combination of under-resourced schools, the loss of job protections, unfair teacher evaluation methods, an increase in the amount of mandated standardized testing and the loss of professional autonomy.”

People with their finger on the pulse of these things can debate the specifics, but my mom was an public elementary teacher for over thirty years, and one of my best friends has been a public high school teacher since 2004 (when my mom retired, coincidentally), so if nothing else I have a pretty good sense of what it feels like to be a teacher. And the long and short of it is that as a society, we had something — public school teachers — that we decided we could yank around and tweak for our benefit, amusement, or popularity. When they complained, we yelled at them and passed laws and told them to shut up, until — WHOOPS! — people stopped wanting to be teachers.

the internet

You know what else was cool? The internet for marketing people during the last ten years. Compared to print media, we could learn way more about different audiences — what they liked, didn’t like, etc., — and even serve them advertisements that fit with what they cared about. Think about how amazing that is!

Like teachers, though, we decided to push the envelope just because we could. We started “optimizing” every square inch of screen real estate to drive certain actions. We cavalierly added multiple tracking systems to everything we made, even if we didn’t really understand how they worked (“just add this code to your page header!”) or how they affected essential things like loading time, responsiveness, or power usage. Finally, we completely outsourced advertising to awful ad networks based on whoever provided the greatest return, again ignoring what those ads looked like, what additional tracking garbage came with them, or how awful they were to experience.

And guess what? People have had it, and now you’re not going to be able to track anything, or even display ads. Enjoy the dark ages, marketing people!

we suck at moderation

I don’t know what causes people, organizations, and entire industries to think this way, but it’s a myopic, arrogant, short-sighted, and often costly way to do things. It doesn’t take some kind of futuristic behavioral model to determine that people with bandwidth-limited cell phone plans are going to eventually reject slow, heavy web pages full of tracking garbage, or that a company like Apple might take steps to fix the problem. Nor does it take a psychology degree to realize that if you turn the work experience of teaching into a financial and organizational nightmare you’d never want to be a part of, you’re likely to run out of teachers (especially good ones).

Remember when the Affordable Care Act was being cobbled together, back in 2010? David Frum (who I disagree with on many things, but seems like a rational, intelligent fellow in general) had an extremely prophetic piece after the law passed, where he cited the obstruction versus negotiation approach of the Republican party as an enormous missed opportunity for conservatives to help define the future of health care policy.

“Barack Obama badly wanted Republican votes for his plan. Could we have leveraged his desire to align the plan more closely with conservative views? To finance it without redistributive taxes on productive enterprise – without weighing so heavily on small business – without expanding Medicaid? Too late now. They are all the law.”

In policy, or business, this is what happens when you press as hard as you can, all the time, in your preferred direction and simply wait for the rest of the world to react. More often than not, you get a giant, sub-optimal mess you could have avoided by employing a ounce of empathy and narrative logic. Not everything is the American Revolution, or the Civil Rights movement — enormous, ideological tipping points where the consequences are less important than the principle. In most cases, the consequences are what really matter, which means you should probably think about them more than you usually do.

All Good Things

Guess what? Last Friday was my last day at Contactually. That’s because a few weeks ago, I took a new job several blocks down the street at FiscalNote, where I’ll be heading up Product Marketing.

Wait… why go?

That’s a good question, especially since the last year and half at Contactually has been, on the whole, an awesome experience. I got to play a big role in helping an emerging company basically triple its revenue, and I got to do it by doing lots of things I’m good at. I had a blast working with a bunch of people I care about, admire greatly, and am lucky to have met. On top of all that, the company is in terrific financial shape, the product is *vastly* improved, and we even moved to a better office! 

I guess the simplest explanation for why I decided to leave is that despite all of this, (or maybe because of it) I’m clearly burned out from the realities of my day-to-day routine. I hear a lot of people say “startups aren’t for everyone”, but I think the reality is that at certain stages, startups aren’t really for anyone. After doing this a couple of times, I’m starting to think that if you really do what it takes to get the most out of a startup experience — get emotionally invested, spend your free time uncontrollably thinking about work, constantly try to protect the mental health of your equally insane, idealistic coworkers — it’s impossible for anyone who’s not a sociopath to avoid burning out at some point unless you have extremely well-considered operational systems in place to prevent it. And while we have a lot of great things at Contactually, that’s something that’s not in place yet.

What happened?

One of the most obviously appealing parts of a startup job at a small-ish company (I was employee #18 at Contactually) is the opportunity to do lots of different things, and have control over a variety of important things that matter to you. But as you grow, the ever-desired “control” often turns into the less-sexy “responsibility”, which itself often turns into “stress” and even “guilt”. “Why doesn’t the navigation load properly on Firefox?” “Are these images retina?” “Did you see this before we emailed it out?” “Why don’t we have a video for this?” ‘What metrics are you using to justify this decision?” “Why isn’t this in the wiki?” “Couldn’t we just hire a freelancer for this?” “Why does this form work this way?” “Why don’t you just do it this other way?”

When I started, these kinds of perfectly valid questions never stressed me out, because I either knew the answer, or I didn’t. But as the months went by, and more and more legacy decisions came from me, the more I started stressing out about why I didn’t necessarily have a good answer. Why don’t we have a video for that? Should we just have hired a freelancer? 

I was a little surprised by how stressed out I got, actually. I’m 33 years old, and I’ve worked at plenty of crazy companies. I haven’t had a boring, safe job in almost a decade. But it wasn’t the amount of responsibility I took on at Contactually, or how crazy it was, that was the problem — it was how quietly I tried to take it on and manage it. I suggested we consider getting a full time development resource in Marketing, when the reality (whether I fully realized it or not) was that if we didn’t get one soon, I was going to go insane having literal nightmares about WordPress and probably quit. I over-insulated our contractors from the demands of my coworkers, and my coworkers from the limitations of our contractors (and reality, sometimes). I constantly tried to underpromise and overdeliver — something I still think is generally a good approach — but the result was that I spent a lot of time explaining to people why things were difficult, or sometimes impossible, which gets exhausting after a while. There’s a difference between feeling appreciated, and feeling understood. I always felt appreciated at Contactually, but over time, I felt less and less understood. 

How DO you know it Might Be Time to go?

No matter what kind of environment I’m trying to assess, I usually find that there’s more to learn from the decisions I made inside it than there is from the environment itself. I’m fortunate enough to have avoided being rejected from a school I really wanted to go to, or fired from a job, or thrown out of a band, so most of the difficult situations I get myself in are entirely my own doing. That’s certainly true of the difficult parts of my time at Contactually; the stress, the communication challenges, and the occassional inability to focus or properly iterate on things that mattered to me. And to be honest, if I worked at some enormous corporation, I could probably address a lot of these things and stay with the company — I’d just have to throw my hands up at some things, maybe apply for a different type of role in the organization, and reset. 

But Contactually, and exciting young companies like it, aren’t like that. You get so emotionally invested in the success of the business, and the success of the people you work with that you literally can’t let go of these problems, especially if they actually matter (and our stage, they often do). I thought about this on one of my very long train rides home from the office one night, realizing exactly how many things I had stupidly over-invested myself in, and how impossible it was going to be for me to ever do them the way I really wanted to.

Of course, I didn’t decide to leave based solely on that — I’m from New England, for God’s sake. You know, where no one gets divorced, and we insist on giving directions based on landmarks that haven’t existed in twenty years. Call it stubborness, loyalty, or fatalism — the end result is that we don’t bend easily, no matter how much pain we’re in, or how wrong we are. Just ask the British.  So I got home, went to band practice to blow off some steam, and applied for exactly one job before I climbed into bed and passed out. 

The FiscalNote Era Begins

That job was at FiscalNote, and while I don’t start until next week, the reasons I ultimately joined are pretty straightforward. 

  1. FiscalNote has resources I’ve never had access to before. At Bamboo, EEx, and Contactually, I did everything with proverbial duct tape. While I’m sure I’ll always be doing that to some degree (it’s part of my value, after all), I’ve never been able to work somewhere in full go-go-go mode. I expect Contactually to get there soon, but not before I would have likely become a cynical, burnt-out shell of a person.
  2. The marketing team is run by a fellow product marketer, something else I’ve never had a chance to experience. Remember that bit about feeling misunderstood? 
  3. The product (and the underlying value proposition of the company) better align with my outside interests. In a previous life, I was a political science major — what FiscalNote is doing interests me more than sales and network building (or SharePoint, or Chinese manufacturing, or any other space I’ve been in) ever has. 

If I’m being honest, there’s also the non-trivial factor of benefits and operations, something Contactually hasn’t been able to focus on yet due to the realities of building a healthy business that can attract the major investment necessary to pay for these things. But as I said, I’m 33 years old with a mortgage in the suburbs — I increasingly don’t have the time or the brain cycles to figure out the inner workings of, say, my commuter benefits. At FiscalNote, I can put all of my effort into doing awesome stuff. 

So there you have it. It’s probably the most bittersweet moment of my career, and hands down the most difficult professional decision I’ve ever had to make. But with that being said, I’m really, really excited about FiscalNote; the more I think about the opportunity, the more fortunate I realize I am to have it, and the more eager I am to roll out a better, smarter, more sustainable version of myself. Here’s to the conclusion of one great adventure, and the beginning of another.