There are 3 regrets I've had in job searching. What are yours?
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My 3rd internship at BlackRock, I was putting bologna on my plate with Ralph Schlosstein (Ex-COO of BlackRock, now CEO of Evercore) next to me. "Hungry are we?" Me: "Yeah what's a poor college kid to do?" I walk away not saying anything else to him.
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At Bloomberg B-Discovered Day, Dan Doctoroff the CEO gives a speech on taking risks and even tells us where his office is. I wanted to send a thank you or some sort of letter. I thought about emailing Mike Bloomberg after reading his book. "5 minutes of your time, it won't even cost you a dime." Never did. I prepared 4 weeks for BB. After a final round, rejected with a generic email.
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In 2008, Not asking my VP for a junior internship. Entire team gets laid off Feb 09. Called her to catch up and make sure things were okay, was told "if only you had asked [for an internship.]."
I believe in "80% of life is showing up" and "what's the worst that can happen if you ask?"
Make sure you don't ever have regrets. Go to that info session, call that rich uncle, follow up with that MD who liked you. Take the initiative and have CONFIDENCE.
I was a summer intern in 2004 at a bank in chicago and CEO talked to all the summers over lunch. As he finished up he said to email him if we had any questions.. That afternoon I emailed him and asked if he would like to have breakfast as I would like to learn more about how he spent the early years of his career. 3 weeks later he called me and asked if I was free for breakfast next day. Turns out in 6 years I was first person to email him. I ended up accepting the job and two years later resigned. He was first person I emailed and he said to stay in touch. We have overr the years and he is one of my best resources.