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
Roger Hobbs, Eric Beetner, Patti Abbott, Sam Wiebe, Albert Tucher, Christopher Irvin, Anton Sim, Garrett Crowe
James Silke, Frank Frazetta