The Worst Advice I Ever Got

My first job out of college was working in a sales role at an insurance company. They liked to think they were doing holistic wealth management, but all that meant was once all your insurance needs are filled, they could also sell you a financial plan and sprinkle in some mutual funds.

It’s easy to look back now and see what was going on, but as a 23-year old who spent his life not taking anything seriously, I felt very lucky just to be there. Everybody came to work in a suit and most of the big producers, of which there were many, were at their desks by 7, ready to conquer the world. The group that I started with sat in a bull pen and arrived with their adrenaline on full blast, ready to spend the next ten hours dialing and filling up their calendars.

There was one kid in particular that was very talented on the phone. He was confident and appeared as if he actually knew what he was talking about. So I asked him how he’s getting so  many people to agree to meet with him. He smiled and said, “fake it till you make it.” I had never heard that before.

I don’t remember having a visceral reaction to it, but when I think about it now, it makes my skin crawl. Fake it till you make it. There might be some professions where this makes sense, but finance isn’t one of them. The biggest problem with that line, not ethically but actually, is that faking it might get you the meeting, but it didn’t help you in the meeting.

It was late 2008 and I was making at least a hundred cold calls a day. On a good day, five people would hear me out, and I would get one or two to submit to a meeting. In person, it was pretty clear that I was faking it, so only a few people were willing to meet with me a second time.

One of these times was with a woman who was probably 10 to 15 years away from retirement and was ready to get serious. She brought me her financial life in a folder; Brokerage account statements, employee benefits and bank account information. But the problem was none of these things meant anything to me. I was faking it.

As I examined the contents in her folder, I could feel her squinting back at me. There was a few awkward pauses and a lot of me tripping over myself. I didn’t know the right questions to ask and when she had questions, I didn’t have the right answers. Few things are more transparent than somebody who’s faking it and all it took was five minutes for her to realize just how full of shit I was.

This was a watershed moment for me. I never wanted to be caught faking it again.

I understand that young people in sales roles have to fake it to a certain extent. They have to appear confident, to act like they’ve been there before, even if they haven’t. But there’s something about kids and faking it and financial products that just doesn’t mix.

If you’re faking it, just stop. You’d be surprised how receptive people are to honesty. There’s something incredibly refreshing about speaking to somebody who doesn’t pretend to have all the answers to everything.