to pay for a taxi or take the subway at 3:00 a.m. I had already befriended all of the car service guys because they were real salt-of-the-earth people, unlike some of the stuffier banker types. I snuck them food from time to time and always spent a few minutes shooting the breeze with them. We shared some laughs together and really connected as friends.
The same day I found out about the tryouts, I set the wheels in motion.
It was this opportunity that taught me how to just ask for something that is meaningful and important to me. It was this experience that taught me the power of empathy.
I approached my favorite driver, Ahmed, and told him all about my dream to play soccer professionally. He was from the Middle East, where soccer is hugely popular, so he got it. I then told him about my plan and how he could help. You’ll find that most people will do what they can to help others fulfill their dreams; it’s a powerful feeling. He loved the idea of my being able to try out for a semiprofessional team and agreed to drive me.
I then went to my other boys, the security guards Jamaal and Steve. I told them about my plan and asked them if they’d be willing to store my soccer bag behind their desk and bring it outside and give it to Ahmed at 4:30 p.m. The security guards were not allowed to store anything behind the desks, but they could tell how much this all meant to me and agreed.
All I needed to do now was to find an ally in my group at the bank who understood why this dream was so important. I knew just the guy—the managing director, Bill, whom I became close with after 9/11 (he and his family had actually put me up in their house for a week or so after the attacks since it became too hard to commute across the Brooklyn Bridge). He was the one who I knew would empathize with me and had the power to actually give me the permission to do this. He had played soccer in college—it was actually what we first connected about when I got to the bank—and this gave me the courage to just ask him for what I wanted.
I made sure to have a plan when I walked into his office. I needed to establish why this opportunity was meaningful to me and make sure to convey that I also understood my responsibilities at the bank.
“Hi, Bill, how are you?” I said.
“Good,” he replied, still looking at his computer screen. “What’s up?”
“Listen, I wanted to talk with you about something that really means a lot to me.” He stopped reading his e-mail and focused on me.
“I have a once-in-a-lifetime opportunity to try out for the New York Magic, the WUSA soccer team. I know I can make this team if I put my mind to it, and I know you of all people can understand why this is such a special opportunity for me. I also understand that I have responsibilities here at the bank. The tryouts are twice a week from six to nine p.m. for the next two months, and I will come back to the office after the tryouts to finish whatever work I have left. I have enough energy to do both, and I am committed to making both work. I am asking for your permission, and if I make the team, I’d love for you and your daughter to come to a game! I can teach her a few tricks too!”
He really couldn’t say no. I knew I had some serious work cut out for me, but I’d proved that I could be trusted to come back to the bank on those nights to finish the work that I missed. He knew I wouldn’t let him down. A good boss will understand the importance of going after your dreams, even if it may mean no longer working with them. Bill understood.
Do Cool Shit Takeaway
How to Ask for What You Want
If you need to escape your day job for a couple of hours per week to follow your passion project, approach the person you think would most likely say yes and be an ally for you. Find out beforehand what their hobbies are. Use that knowledge to connect with them about what you have in common. Also, prior to approaching them, make sure you have particularly excelled at
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