How much money do you want to make? Here’s what you have to do to get there

I didn’t want a raise. What I walked away with was far more valuable — and I spent the next 2 years learning everything I could about sales.

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I told my boss I wanted to make more money.


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I had been working at an advertising agency in downtown Chicago for about two years. During those two years, I had gone from an entry-level copywriter responsible for writing social media copy for small, local brands, to writing billboard copy for national brands. I was the best writer at the agency, and I got to work on some of the agency’s biggest projects.

The problem: I was barely making more than a barista.

“What do I have to do to make more?” I asked.

My boss and the company chairman sat opposite me in the back office. The chairman was very rarely in town and an investor to multiple companies — a very successful businessman.

For all my hard work, I felt I deserved a raise

Very calmly, as if remembering being in the same position 25 years prior, he asked, “How much do you want to make?”

I wasn’t prepared to answer that question. I thought “more” would suffice.

When my silence spoke for me, he continued and said, “Here’s a simple way of thinking about it: however much you want to make in life, all you have to do is figure out who is willing to pay that amount, and for what skill — and then go acquire that skill.”

The moment he said that my entire perspective on raises shifted.

Instead of thinking I had to become a better writer, I started to think about what skill would be worth more to the agency itself.

And they weren’t willing to pay a writer more.

But they were willing to pay a salesperson more

I didn’t walk out of the room that day with a raise. What I walked away with was far more valuable — and I spent the next 2 years learning everything I could about sales.

In typical Cole fashion, I watched The Wolf of Wall Street 127 times in my studio apartment.

I found a friend who had a bootleg copy of Jordan Belfort’s Straight Line Persuasion video course.

And then I started emailing people, tapping my network, and trying to sell our agency’s services to anyone I could find — from family friend’s, to random people I met at the gym.

It took me almost 9 months to make my first sale.

3 months later, I made my second.

Until eventually, I was leading pitch meetings and was eventually responsible for bringing in one of the biggest development projects of the year.

My commission check was equal to 2 months of my salary as a writer

“There are two types of employees,” said the Chairman on the phone, right after I received that big commission. I appreciated him for wanting to teach me, more than he wanted to simply have me chasing carrots.

“There are people who work with the tools, and people who sell or manage the people who work on the tools.”

“A writer works with the tools,” I said, vocalizing what this 2-year lesson had taught me.

Software developers work with the tools.

Account managers work with the tools.

Salespeople, however, work on the tools. They are one of the few roles that can have a direct impact on how much revenue goes into the company — not how well the revenue that comes in the door gets executed.

Both skills are necessary for a profitable, successful business.

But one is “worth” more.

This article first appeared on The Ascent


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