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.