There are 3 regrets I've had in job searching. What are yours?
1. 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.
2. 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.
3. 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.