2: Always err on the professional side

I always told new hires that Square was a trap. I’m not trying to scare you — just trying to give you fair warning because no one told me when I started.

Square (like I’m sure is true for most startups out there) is full of young people. They are everywhere and there’s no way to tell who is who. Most are wearing T-shirts (or the proverbial Zuckerberg hoodie) and no one has an office. Yet behind this laid back, egalitarian front is hierarchy. It seems so obvious that hierarchy would exist, but when you walk in and see the smiling faces and open floor spaces, you forget. But don’t forget. It’s not a negative thing — you just have to know it so you can navigate it.

When you’re new and young and trying to figure it all out, always, always, always err on the professional side. Dress like a professional, even if you see people walking around in old T-shirts and no shoes. Those people have likely earned the right to dress like a slob! You haven’t. You just started. And be careful what you say! Even if co-workers are talking about their weekends and all the (work inappropriate) things they did, don’t lose sight of your professionalism. You’re just starting off and don’t want want to draw attention to yourself for the wrong reasons. This applies to any time you’re around co-workers, including breakfast or lunch or any work related event. In fact, the less formal the setting, the more important it is to keep your professionalism. I learned this the hard way.

It was literally my first day in the office and back then, everyone stayed for dinner. We ordered pizza that night and when it came, we all huddled around to scarf down our slices. I was loving it — I hadn’t felt that sense of comradery since college (which I missed dearly). I was also just so excited to be in San Francisco and in Square’s office. It was literally a dream come true.

I was coming off my thirty day stint running around San Diego and had a ton of stories tell. I had these guys laughing pretty hard talking about some of the crazy situations we got ourselves into down there — like working shifts on food trucks just to prove Square wasn’t a scam and sneaking into the LA County Fair to sign up more merchants. I had them going pretty good. And the more laughs I got, the more casual my tone and thicker my SoCal accent became. Lots of “dudes” and “bros” were being thrown around.

I thought I had killed it. A couple guys got up and left the table and when they did so, my boss gave me this glaring look that I’ll never forget. “Do you know who that was??” He said it like someone really important had just left the table. But I was confused — there was no one sitting with us that could have been more than a few years out of college. “That was the Head of Growth!” But what he really said was, “Dude, what the hell were you thinking?” I was nervous at first, but then quickly decided I didn’t care. I was just being myself and if he didn’t like me for who I was, that’s his problem.

It turned out to be my problem. Every job I wanted for the next year and a half was on the Growth team. And every time my name came up for consideration the response was, “Too young. Not enough polish.” I screwed up. And I don’t hold any grudges because being in his position, I would have thought the same. First impressions are so crucial and if you make a bad one, it’s so difficult to dig yourself out.

I’m not saying to not be yourself. Authenticity can be one of the most effective qualities in the workplace. But be authentic in a professional manner. Let others be the super casual ones and always hold yourself to a higher standard. You will be better off for it in the end.