Do Cool Sh*t (6 page)

How to Go for It When You Think You Can’t

In order to succeed, your desire for success should be greater than your fear of failure.

—B
ILL
C
OSBY

I
waited with bated breath for the coach of the New York Magic to call out the starting lineup.

This was the biggest moment of my career as a soccer player. It was bigger than when I was four years old and scored my very first goal ever, or when I made it to the national championships as a teenager. Here I was, up against a hundred of the top college athletes, and I had already dug so deep to make it there. I knew that if I made it on the starting lineup of this team, then it would all have been worth it.

First, let me rewind a few months.

September 11 and the days that followed were the motivation I needed to realize that life can be so short and that I needed to start living the life I wanted to live now. The first thing I did was make a list of the big life goals I had for myself. It looked something like this:

• Play soccer professionally.
  
• Make movies.
  
• Start a business.
  

Short. Simple. To the point. Each of the items on this list was a dream I’d had for a while. At the time, I was still working at my investment banking job, but I decided that it was time to set about accomplishing the first goal on my list.

Soccer was first up for one reason. It’s an incredibly physically demanding sport, and I knew I’d have a better shot at playing professionally while I was younger and more physically fit. As much as we’d like to, we can’t ignore biology!

In college, I’d won Rookie of the Week when I scored two goals and had two assists in my first game ever as a Division I college player. (Radha wants you all to know that she assisted both of my goals.) I had started every game and was named All-League twice. But regardless of my strong college stats, the competition at this next level was way more hard-core.

I did some digging, looking into the New York women’s soccer leagues. The New York Power was the main professional soccer club, but unless you played for a winning college program (Cornell’s record was never fantastic, though we were a Division I school), it was hard to even get a tryout with them.

There was another route I could take. It was the Women’s United Soccer Association (WUSA). This was the equivalent to the minor leagues, from which the pro teams look to pick their players. This was called the semiprofessional league, where players were given equipment, travel fare, food, trainers, physical therapists, everything a player needed—except a salary. I decided that it would be totally worth it for me to get a part-time job (maybe in the film business—goal number two!), and play soccer semiprofessionally until I could move up the ranks and score a tryout with the Power. I would get paid peanuts, but it would be enough to live on and, most important, I’d get to do what I loved every day. I even dreamed of a Nike sponsorship. You have to dream big! OK, OK, that was Step 5; I was getting ahead of myself.

Step 1 was to make a team.

I didn’t know exactly how it would all go down, until I found out that the New York Magic were holding tryouts in Brooklyn. Step 1 was a go.

Unlike with the Power, any female player could try out, and the process would take two months, during which time the coaches would eliminate players at every practice and make their selection of eighteen players at the end, right before the season began. There would be scrimmages, real games, timed runs, and every ounce of our strength, stamina, and willpower would be tested.

The tryouts were held on Tuesday and Thursday nights from six to nine. Uh-oh. My first major hurdle: How on earth was I going to leave my banking job early enough to make it to tryouts twice a week? This meant that I would have to leave my office in Midtown at 5:00 p.m. at the absolute latest to barely get to tryouts on time—forget all about stretching, warming up, and mentally preparing myself. I was going to be up against the toughest competition of my life and definitely needed time to switch from “banker head” to “soccer superstar head.”

Investment banking analysts work an average of ninety to one hundred hours per week, which amounted to about five dollars an hour when I did the math (best not to do the math—too depressing). It was meant to be one of the most prestigious jobs you could get right out of college, but long hours in the office were the norm and the bank owned your life. It was basically a sweatshop for naive college graduates.

I checked Google Maps and it said that it would take one and a half hours via subway or about fifty minutes via car (without traffic) from Midtown. I didn’t have a car. I was screwed.

But then it hit me.

The car service guys downstairs! They were my buddies. One of the perks of working for an investment bank was having free car service late at night so you can be driven home and not have 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 work in the past several weeks and that they took notice. This will help so much when you make your request.

Step 1: Approach the kindest person in your company who is in a senior position, who you either directly report to or is a peer of someone you directly report to.

Wait for them to stop what they are doing and fully give you their attention. Don’t continue speaking until they are completely focused on you since this may be your one shot to get them to say yes.

Step 2: Be specific with your question.

“This opportunity requires me leaving the office for x hours x times per week.” You must be as specific as you can without compromising the opportunity. Say the number of days and the hours involved. The more specific you are, the more likely they can wrap their minds around it and agree to it.

Step 3: Establish that you have their back.

“I know my job is of utmost priority, so I will make sure that everything I need to do will be completed on time and I will work late and on weekends if need be in order to honor my commitment to this project.”

Step 4: Ask for their blessing.

“I am asking for your blessing to help me fulfill a dream of mine.” Place the person in your shoes, helping them share in the excitement you have for this particular plan. This would make it very hard for any boss to say no.

You have to follow through and do your work. If you don’t follow through after the first couple of weeks, they will take this opportunity away from you. It’s entirely up to you to go above and beyond at your job and make them happier and subsequently not care that you are leaving for a few hours here and there every week.

There is now a big trend in many businesses toward more flexible work hours. It may not work in banking (although it did for me!), but in many offices, flexible hours can be established. There is also a trend toward allowing more employees to work from home (it saves the company money if they’re in a cramped office space). Whatever the dream is, finding out about your company’s flexible work hours policy would be helpful in the “ask.”

Also, be prepared to answer some hard questions.

In the event that your passion project may cause you to leave your day job, your employer may want to know if you are planning to leave. In this case, at first say, “This is a thing I
have
to try or I will forever regret it, and it has been a long-term goal of mine. I am, however, committed to this job too, so I plan to see it through at the same time.” Don’t worry them until you really have to give them notice.

After you spend a few weeks on your passion project and if you really want to move forward with it and leave your day job, walk into your boss’s office and say: “Thank you so much for letting me discover what I’m truly passionate about.
You
helped
me
, and I want to help
you
find and train the new employee who will replace me.” This way, you are really honoring your boss and they may be grateful that you are ending this relationship respectfully and seamlessly. Give them at least three weeks to find and train a replacement. Do a great job training your replacement, as it’s important to maintain good relationships with former employers. You never know when you may need them again. Create a training manual for the person who is replacing you if one doesn’t exist. Go above and beyond. It’s good karma and will bless your next endeavor.

Bill asked me that
I keep my tryout plan on the down low, understandably, so I had to figure out how to escape the other investment banking analysts twice a week for two months. I started by putting some papers in a FedEx box and pretending like I was going to the mail room, and then I would walk outside, turn the corner, and jump in the car that was waiting for me with my soccer bag in the backseat. I had to change into my soccer gear, stretch, and mentally prepare in the car. I asked Ahmed to put a James Bond soundtrack in the CD player so that I could get pumped up on the way. I have to admit, I kind of felt like 007.

When I got to the fields on the first day, there were one hundred girls there, all suited up, with rolled-up ankle tape as headbands (hard-core soccer-chick style) and ready to go. I hadn’t touched a ball in a couple of weeks and was worried I’d have trouble finding my confidence. I reminded myself that I was playing soccer by age three and scoring eleven goals in one game at age eleven and attending national championships by age fourteen. I belonged here. I grabbed a ball and started dribbling down the field, warming up. I was small compared to the other girls but knew my strengths and where I could beat the others. Still, I knew I had to figure out a way to stand out from the rest of the girls. I had to do something different.