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. 

Hunting for Numbers

A haunting description from David Simon of analytics and “accountability” gone bad in the Baltimore police department :

“How do you reward cops? Two ways: promotion and cash. That’s what rewards a cop. If you want to pay overtime pay for having police fill the jails with loitering arrests or simple drug possession or failure to yield, if you want to spend your municipal treasure rewarding that, well the cop who’s going to court 7 or 8 days a month — and court is always overtime pay — you’re going to damn near double your salary every month. On the other hand, the guy who actually goes to his post and investigates who’s burglarizing the homes, at the end of the month maybe he’s made one arrest. It may be the right arrest and one that makes his post safer, but he’s going to court one day and he’s out in two hours. So you fail to reward the cop who actually does police work. But worse, it’s time to make new sergeants or lieutenants, and so you look at the computer and say: Who’s doing the most work? And they say, man, this guy had 80 arrests last month, and this other guy’s only got one. Who do you think gets made sergeant? And then who trains the next generation of cops in how not to do police work? I’ve just described for you the culture of the Baltimore police department…”

Sure, the worst case scenario is probably right here, with this kind of thing happening to law enforcement. But that doesn’t mean this shouldn’t be instructive to everyone else. Measurable goals are great, if and only if you really want the logical extreme of that goal. Think long and hard  about that the next time you talk about how you want your team, department, or company to be more “results oriented”.