Why it’s a mistake to be a startup superhero

Photo via Unsplash.

By Melissa Nightingale

You might not know it to look at me but I am a startup superhero.

If you saw me walking down the street downtown your eyes would probably bounce right off of me. I’m pretty Clark Kent these days — right down to my hip square glasses.

But deep in my closet, behind stacks of skinny jeans and branded hoodies, I’ve got a cape. On the back, in big yellow letters, it says STARTUP SUPERHERO. And then in tiny white letters underneath it says *look out*.

Well, I guess technically I’m a retired startup superhero.

It’s been ages since I suffered from startup superhero martyrdom but it’s a condition I’m deeply familiar with. I know the seductive siren song of problems only you can solve, 3am emails only you can respond to and definitely need a response right at that moment. I know all about the frenetic task swapping that is so easily confused for progress but is sadly just running in place.

This is the story of how I hung up my cape and discovered my true superpowers.

Let’s start at the beginning.

. . .

It’s 2000. I’m working at my first start up. I don’t have a good sense of where work stops and where my social life begins. My coworkers are my friends. Or, at least, I think they’re my friends. It’s hard to tell because it’s been so long since I’ve hung out with anyone else.

I’m in the office 6–7 days a week. I eat breakfast with my team. I eat lunch with my team. I often don’t leave the office until after midnight. But I don’t really mind because these are the concessions you make when you’re changing the world and planning to become a millionaire all at the same time. It’s a lot to juggle.

We have big aspirations. The internet is new. It doesn’t feel as new as it is. We’re early to an idea that won’t have legs for another five or six years at least. We talk about the democratization of media. We talk about citizen journalism. We talk about removing the gatekeepers. We talk about giving voices to the voiceless. We talk about media, streaming, and user generated content.

We have the urgency of our disruptive vision but lack important conditions of the strategy needed to fulfill it. We are right but we are way too early. Smart phones will unlock so much of the future we envision, but they are still a ways away.

Five years in the future, another company with a similar disruptive vision will come onto the scene. You may have heard of them.

A16 is happening in DC. This is right after the Battle of Seattle. And it’s about a decade before the G20 Summit in Toronto.

We have camera equipment. We have a website. We have branded tshirts. We have laminated press badges that we made. And we have moxie.

The day before the A16 protests, there’s a demonstration against the prison industrial complex. It’s April 15, 2000. Our startup office is within walking distance of the protest so we grab the camera gear and head up there to see what’s happening. We set up our cameras alongside CNN and the local affiliates. We get into fights with seasoned betamax veterans because they try to block our shots or move our tripods. We hold our ground. Our branded tshirts say “The Whole World is Watching” across the front. Our url is across the back. We wear them without irony.

Two of us break away from the main protest and go in search of a better shot. We want to be above the protest. We look around. It’s downtown DC. The only way to be above is to get access to one of the surrounding office buildings. Lucky for us, it’s a Saturday.

We approach the janitorial crew of a building right in the middle of the demonstration. We ask if we can film from a few floors up. We offer him a spare branded tshirt. He seems to think this is a pretty good deal and lets us in. The office is mostly empty and no one is there to tell the cleaning crew that letting strangers with cameras into your office building is a quick way to get fired in Washington.

From above, we can see everything. There is a photographer already set up. We position our tripod next to her.

We are filming when the police begin mass arrests below. We stop filming when plainclothes FBI agents enter the building and ask to see our ids. We show them our homemade laminated press badges. The photographer next to us shows them her Washington Post press credentials.

They demand to see ID.

The Washington Post photog refuses. We refuse.

They demand again. They say we will be arrested if we don’t comply.

The Washington Post photog complies. We comply.

They take our licenses and write down the details. They tell us to vacate the building but that we are free to go. We are careful not to get picked up by the police. We walk back to the office.

The Washington Post photographer is not so lucky.

Some of our startup employees get caught up in the mass arrests and are detained. Our camera gear is held by police while we’re waiting for the employees to be processed. It’s chaos. I feel the hum of adrenaline under my skin while I dial the number for DC central booking. I inquire about my missing coworkers, but, alas, there’s no record of anyone by that name. They haven’t been entered into the system yet. They haven’t been charged with any crime. They are still waiting. On buses. Handcuffed. For hours. It’s starting to get dark. I need to rescue them.

I go back to the office and keep calling central booking but to no avail. Later, as part of a class action lawsuit, we will learn that this was intentional, a tactic meant to distract and confuse protesters.

A couple of us stay at the office in case our coworkers are released. In case they call. In case there’s bail. In case we need to go get the cameras. In case they need us.

It’s late and I’m tired so I tip over a box of giant branded tshirts. They are all mens larges. It’s 2000. It will be many years before we get more than just mens L and XL shirts.

I pile the shirts under my head and stretch out my legs on the office floor. I am curled up in the morning, in a pile of white hanes shirts, when the sun glares through the windows of our Dupont Circle office.

. . .

There is so much nostalgia in this story. I’m smiling while writing it, remembering a time when I was that young, that idealistic, that green. Sometimes it feels like large parts of my life happened to someone else, me, but a different me somehow. Other times I feel like I’ve lived several lives consecutively, with just the one me but with a narrative that writes itself like rings on a tree trunk.

At the intro, I promised that this wasn’t just grandma @shappy telling tales around the campfire from the first dotcom boom. That this was a fable, a story with a lesson at the end.

These are lessons I have had to learn many times in my career before they finally stuck. And still, I work at them.

If you are secretly wearing tighty whities over leggings under your skinny jeans, this is for you.

Know where your work stops and your social life begins.

Tech is particularly good at creating the conditions that normalize this blurry line. Between booze in the office, drinks after work, offsites, outings, and all hands it can feel like a bunch of your social needs are well covered during working hours.

In the best version, your colleagues are all fun and awesome people you’d hang out with even if they weren’t paying you. They are the kind of people you’d go have a couple drinks with. They are the people you’d sit around playing board games with until 2am. It’s nice to like your coworkers. No one is saying you can’t have nice things. But…

If you can’t point to downtime that is separate and distinct from your uptime, you are at dire risk of burn out and there’s a really good chance you need to set better boundaries.

Go home.

The part of the story where I tip over a box of tshirts into a makeshift bed like I’m some sort of feral cat? Please.

That entire episode would have happened exactly the same way if I’d slept at home in my own bed, on my own sheets, with my own pillow. No one needed me to sleep on the office floor. Hell, no one even asked me to stay in the office overnight. I did that — just me, myself, and my big ol martyr complex.

At no point were DC police playing by the rules. The eventual charge they laid on the protesters was something ridiculous like “parading without a permit”. Me sleeping in the office did not hasten the release of my colleagues. Me sleeping in the office probably hastened the back issues that older me is grumpy about.

Have a plan for theoretical emergencies, execute the plan for actual ones.

The number of times the “in case” scenarios that showed up in my superhero rationale actually came to fruition? Zero. None of the “in case” scenarios actually happened.

Scenario drills are an important part of emergency response training but there’s a reason scenario creation/invention isn’t done as part of active emergency response. In an actual emergency, you need the plan to work when the context changes. For the above story, having a plan would look something like this.

Before sending staff out into a DC protest with expensive camera equipment and in the days of few cell phones, gather said staff in a conference room. Some person, presumably some adultish person who is in charge stands up and says: If we get separated, everyone meet back at the office. If you need help, here’s the one number to call. Write it on your arm in sharpee. Person who is on phone duty, you stay at the office. Answer the phone if someone calls. Go home once you have seen everyone who was out and all the cameras are safely back in the office.

Hang up your cape and lock the door on your way out.