1: When you’re given a chance, knock it out of the park

NickBastone
Some things I learned at Square
3 min readAug 3, 2015

Right before I left Square, we hired a new grad to our team. I felt really bad that we’d never have the chance to work together, so I wrote some stuff down. Square was my first job out of college as well, and so I wanted to pass along some of the major things I learned. The hope was that these lessons would help her avoid the same mistakes I made and allow her to find even greater success along the way. Hopefully they’ll be helpful to you as well.

Sometimes it’s hard, especially early in our careers, to recognize an opportunity when it’s right in front of us. It’s like we expect someone to shake us and tell us to our faces, “This is a once-in-a-lifetime opportunity. Don’t screw it up!” Unfortunately, opportunities aren’t always so obvious.

When we are savvy enough to spot an opportunity, we often want to know ahead of time that the payout in the end will be worth the effort up front. But opportunities in the “working world” often don’t work this way. They will usually require us to take a leap of faith — putting in the hard work before knowing what the payoff (if any) will look like in the end.

My first job at Square was a contractor gig down in San Diego — a friend and I had thirty days to sign up as many merchants as possible. We saw this as a huge opportunity! Even though it wasn’t a full time job and even though the pay was pretty minimal, it was a foot in the door. We worked thirty days straight and went to every farmer’s market, swap meet, and food truck event in the San Diego Area.

After the thirty days were up, we were shocked to hear that the overall program had failed. Of the twenty cities where Square was running the experiment, only two proved to be worth the investment. The problem wasn’t the product — we were introducing mobile payments to people for the first time and completely transforming their businesses. The problem was the people hired. Where San Diego and Houston (the other successful city) had hundreds of sign ups after thirty days, other cities would have ten or five or in some cases, none. It was pure lack of motivation. People didn’t see the huge opportunity right in front of them and/or they weren’t willing to put in the hard work before being guaranteed a full time job. In the end, all three reps from San Diego and Houston received full time jobs at Square. We were given a small chance and we knocked it out of the park.

I tried to carry this mentality with me when I moved to San Francisco and started working in the office. Anytime anyone sent me a ping, I saw it as an opportunity to add value and prove myself to that person. You won’t recognize any payoff after helping one or two people. But after six months or a year of consistently knocking these small questions out of the park, you will start to see the snowball effect taking place. You’ll develop a reputation throughout the company for being reliable and someone who’s eager and capable to take more responsibility. More and more opportunities will come your way.

Neil Gaiman said (in his now famous commencement speech) that you only need to do two of these three things to be successful — be quick with your turnaround time, be great at what you do, and be a pleasure to work with. I think it’s important that we strive to do all three. Even with the seemingly menial pings you receive, you should always strive to provide thorough answers in a timely and friendly manner. The payoff won’t be obvious in the beginning, but the trust and respect you’ll build along the way will be worth your efforts.

Again, opportunities are often subtle and there’s no guaranteed payout. But if you start to recognize them and start to consistently knock these opportunities out of the park, I guarantee you will be rewarded in the end.

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