How to Ask For Help

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After I left the insurance industry, I struggled to find a job. My resume was lousy, I had no experience, and I had no idea what I wanted to do. It also didn’t help that the financial world was still reeling from the Great Financial Crisis.

I had two meetings with people from the financial world during that time, and I was reminded of one of them this week. I’ll get to this in a second.

I love that our inbox is full of personal emails from people in the industry who are trying to find their way. This business isn’t easy, and so I’m all for seeking guidance from those who are where you want to be. Given my struggles, I’m thrilled to be in a position to help people who might need some course correction.

I hate emailing general advice, so I’ve been giving my number and getting on the phone with these people for the past couple of months.

I can’t help if I don’t know who I’m talking to. I need to hear their voice, find out where they are, and get a feel for their personality before I can say anything worthwhile. Generic advice to strangers might do more harm than good.

I was on a call this week, and the kid started the conversation by asking me how I got into the investment industry. I was a bit taken aback because I took the call to help him, not to be interviewed. I gave a quick answer, and then he said, “Okay, my next question is, how did you meet Josh, and what are your day-to-day responsibilities?”

“Hold on,” I said. “Not to be rude, but I took this call to help you, not to be interviewed. Tell me about yourself. How can I help?”

It turns out that his boss is taking advantage of him—a common story I’ve heard many times before. The kid is not properly compensated for all the work that he’s doing. He didn’t know what to do or how to go about asking for a raise. I told him what I would want to hear if I were his boss, and it turned out to be a worthwhile call for the kid after a stumble out of the gates.

I’m sharing this story not to embarrass him but to help you learn how to ask for help.

I was in this kid’s shoes way back when. As I said earlier in this post, it reminded me of a meeting I had that went nowhere. I can’t remember who I met with or what he did exactly, but he had spent his entire career on Wall Street.

I vividly remember at one point during our conversation, he asked if I wanted to be on the buy side or sell side. I didn’t know what that meant, so I said, “Whatever side will have me.” That was the wrong answer.

I get that young people by definition don’t know a lot, but when you’re talking to someone who is in a position to help, you need to be as specific as possible. “I just love the market” doesn’t mean anything.

Asking for help is hard. Especially when you don’t know what you’re asking for help with. But if somebody is taking time out of their day to help you out, help them help you. Don’t talk in generalities. Be specific. Be confident but humble. Persistent but not annoying.

If you’re in the financial industry and need some guidance, I’m happy to talk.