What a Sales Job Taught Me about Anxiety and Extroversion

“Hi! This is Jonathan calling. Can I talk to you about a service that can save you time?”


So went the 73rd cold call of my day, as indicated by my on-screen call log. I was 22 years old, 2 weeks out of college, and slogging through another day at my first full-time job.

As a sales rep at a software start-up, my job was to call dozens, sometimes hundreds, of software engineers every day, to entice them to buy a product whose benefits that I, a non-engineer, could barely get my head around.

Why did I take this job? Why did I subject myself to being cursed at, hung up on, left for dead on hold? Why did I endure forced small talk about the weather in Wisconsin (or wherever), about technology I didn’t understand, about Big 12 Football? “Why,” I thought, “am I wasting my time?”

Part of it was practical. Just out of college, I needed something to pay my rent, which was a hefty $400/month.  But there was another motive: I wanted to transform myself from an introvert to an extrovert.

Like many people who are on the quiet side, I had always felt jealous of the extroverts. It just  seemed like they were having more fun, starting conversations, making small talk, dominating conversations. I felt trapped in my shell, and I figured that this job would be the thing to force me out.

At first, I was all nerves. Lead generation is largely about taking rejection, and whether polite or rude, rejection is no fun. I hated doing cold calls, with their 5% conversion rate. And I dreaded sales presentations, with me trying to sound tech savvy, trying to force conversations, trying to interpret the silence on the other end. Were they even paying attention? Did I sound clueless? Was I hearing actual crickets?

But the nerves didn’t last forever. Because there was a basic psychological principle at work: Exposure.

Pick something you’re scared of doing. Now, do it. Do it again. And again. Is it still scary? No. This is life experience and science talking: Exposure overrides anxiety. Anxiety goes away. It is a basic truth of behavioral psychology.

As expected, the reliable miracle of practice overriding fear, happened for me. When I pushed through the nervousness, I experienced that high, that you get from finally doing something scary. The phone calls became easy. I stopped worrying about people saying no. If they weren’t buying what I was selling, so what?

And, I become more facile at small talk, more at ease on the phone. It became easier to carry on conversations that previously felt awkward or forced. I found it easier to build a rapport with people. In many ways, my experiment was working.

Now, it didn’t work entirely. It didn’t change me into the Most Outgoing Man in the World, as I had initially hoped. I never grew to love the small talk. But something else happened. Once I knew I could be outgoing, I usually didn’t feel the need to. And the things I had read before, about the upside of introversion, about the value of being reserved and thoughtful, I started to sincerely believe them. I stopped thinking of myself as someone held back by anxiety and insecurity, and rather than becoming the exact opposite of that, I simply started to focus on other things. Meeting people became less of an opportunity to overcome my limitations, and more of an opportunity to learn about them.

This was hugely valuable, of course. Did it propel me into a sales career? Not at all. I actually found that, once I got over the rejection thing, it wasn’t for me. Just another early career learning experience. But since I was clear on my original motivation, it wasn’t hard to leave.

Still, I don’t look back on the job as a waste of time. I got over something that was difficult for me, and I developed a deep faith in our ability to overcome emotional and habitual limitations through practice, which is something I draw upon every day in my present work. So, all in all, I’d say it was worth it. Sometimes you set out to learn something, and you end up learning something completely different.