“You earned 500 EXP!” Playing a real-life RPG in San Francisco

Tl;dr: I just returned from a 5-week trip working out west in the SF startup ecosystem, and I’ve never felt more productive in my life. But at what cost?

My initiation to West Coast Life

“…but will it scale?”
“…until the next round of funding.”
“…HR violation…”
…no longer the fastest growing sector in the economy.”

Take out your earbuds on any street in San Francisco and these are the types of conversation snippets that you’ll inevitably overhear.

I’ve been working in tech for awhile, but being based in NYC, I hadn’t previously experienced this phenomenon of “all tech, all the time.” Yes, I made enough trips to San Francisco to know to never, ever refer to it as “San Fran,” but I’d never spent more than a week at a time in the Bay Area.

I knew that needed to change.

Given that my role at Union Square Ventures is to get to know the people across our portfolio network and identify opportunities for people to collaborate in building better businesses, it helps to have a bit more face time and exposure. After my first year at USV, I knew that I needed to spend a bit more time with our SF Bay Area companies (home to one-third of our portfolio, which clocks in at 7,000 total employees worldwide), but I hadn’t quite figured out the proper strategy.

So when my husband told me he’d be working from San Francisco for five weeks in early 2017, I knew this would be the perfect moment for my full-on “West Coast Immersion.” In the middle of February, we packed up our NYC apartment, took the cat on a plane, and headed West.

Shortly after my arrival, I realized that while New York may be the epicenter for many things, it’s not the only epicenter for any one thing. Suffice it to say, walking around the streets in NYC, you never really get the sense that the streetside chatter is just like having the volume turned up on your own internal running monologue of work tasks.

By contrast, being in San Francisco felt like being in an old-school RPG where every single person you meet on the street is someone that can help you on your journey.

If you’ve ever played Chrono Trigger or Pokemon as a kid, you’ll start to get a sense for why this can be so appealing. Everybody you interact with prompts a conversation that is directly relevant to your end goal. You may receive a helpful game play tip, an item that you’ll need for the task at hand, or a reference to a contact that you may want to meet later on.

Here’s a peek of how this plays out in old-school Pokemon when you’re just starting out in your quest in your hometown, Pallet Town:

Playing my real-world RPG

Obviously, the the real world is very different from a video game like Pokemon. For one, in Pokemon, you only interact with NPCs (non-player characters), but in real life, everyone is also playing their own version of this game (more like a MMORPG). That said, I felt like my time in San Francisco was the most highly concentrated experience of acquiring additive relevant information to help me on my own “journey” of navigating this tech ecosystem.

Here are some examples of this phenomenon during my SF stay:

If you’re a productivity freak like I am, it can be pretty addicting to realize that essentially, the more time you are awake and engaging with the world around you, the further you are advancing yourself on your mission.

Since I only had 5 weeks out West, I realized from the start that time for me was pretty limited. So I hit the ground running. By the end, I had hosted about 10 events, gave 5 presentations, taken a 3-day general management bootcamp, met dozens of people, and literally crammed my days all the way down to whatever pit stops I needed to make in my 30-minute in-transit periods between meetings.

Looking back, I already know that this period may go down in history as my personal best in terms of output and productivity (serious Leveling Up).

In case you’re wondering, to keep up this pace, my weekday schedule ended up looking a lot like this:

Daily Schedule — SF Life

5:30 a.m. Alarm goes off. Sneak out of bed quietly to avoid waking up my husband before the crack of dawn.
6 a.m. Scour the city to find a coffee shop that opens at 6 a.m.
7 a.m. Get to the office, hash out emails and meetings with East Coast counterparts
10 a.m. Leave for first coffee meeting of the day or leave to host all-day event
12 p.m. Lunch meeting
2–5 p.m. More meet-and-greets or prep / follow-ups for next event
6 p.m. Happy hour or dinner event
9 p.m. Maybe get something to eat
10 p.m. Meet up with my husband (maybe)
11:30 p.m. Sleep(ish)

Basically, it was 12–14 hour days for 5 weeks straight. And I’d never felt more alive.

The dark side of productivity

By about week three, I started to notice that this lifestyle didn’t come without consequences.

You may notice, for instance, that my daily schedule overlooks a few basic components — like making time for myself, seeing friends and family, or going to the gym. Here are some other ways I started noticing behavioral changes in myself:

  • Eating: I began de-prioritizing meals unless it happened to be built into my event / meeting load. This wasn’t helped by the fact that most of the restaurants in the immediate vicinity to our apartment closed between 9–10 p.m. and as a New Yorker, I had gotten used to eating on the later side.
  • Sleeping: My sleep schedule became less of a “wind down and reset” and morphed into an annoying (albeit essential) interruption to my constant flow of work. After a couple of nights in a row where I spent more of the twilight hours planning out my next presentations rather than sleeping, I re-upped on Melatonin.
  • Caffeinating: My coffee consumption increased 3x. I was having a morning coffee at 6 a.m., a “first coffee meeting coffee” around 10 a.m. and then a third primal caffeine kick around 3 p.m. when my energy level started to dip.

Still, I felt as energized as ever. Kind of like the feeling you get when you make it all the way through battling Pokemon in the Power Plant and finally get to catch the mythical Zapdos at the end of the maze.

So I kept playing.

My husband started telling me that I was acting like I was 0% relaxed, all the time. To be difficult, I asked him to compare to my average “relaxation state” in NYC and also to my most relaxed state on vacation. His responses:

In an attempt to provide some sort of counterbalance to this observation, I took up photography on the weekends.

This newfound hobby ended up triggering one of my favorite parts about West Coast Life: Getting out of town. Unlike NYC, where I tended to just stick around in the city during the weekend, out West, I found myself spending more “outdoors” time hiking or walking along beaches to enjoy nature at its best. Just look at this shot from the top of a hike we took in LA:

So I started stacking my weekends with as much of this “free-form, nature-infused” time as possible. And it was one of of these “get out and breathe” moments about a month into this adventure that a troubling thought struck me:

“Was my RPG hard-core gamer approach to my work life clouding my judgement with what was really important?”

I thought back to a few decisions I’d made recently:

  • Agreeing to speak on a panel on women in technology
  • Saying yes to a coffee meeting with another VC
  • Sitting in on an impromptu presentation at a startup during lunch

It had been so easy to say yes to all of things things. There was immediacy in each request, an overall instinctive “positive” gut check reaction, and a very easy to rationalize value add for each component. Speaking on a panel is helpful for people in the room and helpful practice for me. A coffee meeting is an opportunity to learn more about somebody else’s work and build a new relationship. A presentation is free learning on a topic that may be less familiar.

But how much was I relying on those basic criteria alone to make decisions? How had I been making decisions about how to occupy my time? How much time was I giving myself to think and to process? Was there something different about the way I was absorbing, processing information, and making decisions in SF vs. NYC? Was I getting caught up in some “group think” that was compelling me to overschedule myself in this way?

Maybe. But anyone who knows me also knows that I’m a habitual “over-scheduler,” regardless of my context. This has literally been a theme of my life since the fourth grade when I wanted to be in both band and chorus. I remember my mom saying, “Well that first year of music class was fun, but now you have to choose. What’s it going to be? Band or chorus?” My answer, naturally: “Both!” Thus began the overarching parental worry of my life: “You’re doing too much.”

Here’s proof of this conviction from a flute performance in the 5th grade. (You’re welcome.)

Okay, so maybe it wasn’t necessarily the quantity of activities that I was saying “yes” to in SF that felt different from my life in NYC. But what else felt different about my decision-making process in SF? How to explain that RPG feeling I experienced on the streets?

Where you keep your ketchup

When reading about diversity and inclusivity practices, one anecdote that stands out to me the most is the idea about where people keep their ketchup.

This Reply All episode explains it best, but here’s the gist: Some people tend to keep their ketchup in the refrigerator; others keep it in the cabinet. And while doesn’t really matter whether or not you prefer to keep America’s favorite condiment at room temperature, things get interesting when you see what happens once people run out of ketchup.

If you’re a “fridge ketchup keeper,” you’ll likely look for immediate substitutes in the fridge. Instead of ketchup, for instance, you may opt for mustard, mayonnaise, or relish. But if you keep your ketchup in a cabinet, your array of alternative options in immediate view are much different. Instead, your go-to substitute might be something like malt vinegar — or maybe you stumble upon a jar of peanut butter and decide to make yourself an entirely different sandwich.

The point being: If you believe that considering a wide range of options at the onset of a problem helps you make better decisions (and ultimately choose a better solution), you have to switch up your vantage point. That may mean walking across the kitchen and opening up a bunch more cabinets and drawers. It could mean going out to the garage to see what’s in your second fridge. Shifting perspectives is everything.

That’s why, when thinking about this in the context of team-building, to maximize that idea generation and initial brainstorming phase, an ideal team should include a mix of cabinet and fridge ketchup-keepers. And maybe also include people who don’t like ketchup at all.

Then it hit me: It wasn’t the quantity of activities that made things feel so different. But by stacking my days with all things tech, all the time, I was never allowing myself the opportunity to look somewhere else that may be less obvious to find an answer to a question or expose myself to an altogether new perspective.

I was confining myself to the cabinet.

Return to the East

I’ve been back in NYC now for just over a week now.

But I keep thinking about this question in the context of the decisions I make in a typical day in NYC. So I jotted down a few decisions I made on my first full day back in the city:

  • Taking a high-intensity workout class with my husband at the gym
  • Agreeing to attend a friend’s final recital performance at Julliard
  • Leaving work early to catch up with my brother on his work in energy systems

Just like in SF, each of these decisions were extremely easy to make. They fell into my lap, really. I just had to say yes. But the difference is — even in just one day, I had expanded my vantage point to access different perspectives or industries.

Whereas life in San Francisco feels like pulling all of your ingredients from the same cabinet, NYC makes it just as easy to continually access many other parts of your kitchen.

Don’t get me wrong — there’s a cost to this as well. For one, my “tech brain” isn’t operating 24/7 anymore. I’m not always feeling like I’m on the precipice of the next big break. There’s nowhere near the amount of insane, focused energy on the streets about the industry that I work in. I’m not executing nearly as quickly or urgently as I had been.

But I do like knowing that I have a little more space in my brain to let my mind wander and ruminate over a bit more surface area. Maybe that mental space will give me the room I need to stumble upon a better way to solve a problem.

Until then, it’s back to the NYC street chatter.

And what’s the first thing I overheard from a passerby on our first night back on the Upper West Side?

“…she’ll stab you in your sleep.”

Well…nothing’s perfect. But it’s good to be home…even if everybody is playing a different RPG.

VP @ BolsterTalent, alum of @USV, @StackOverflow and @NorthwesternU, board member at @CompSci_High and @NUalumni, co-founder of #BeyondCodingNYC