Alex Schiff / Uncategorized

Hacking Your Introversion (Alex Schiff)

Flickr Creative Commons // DJMCG

Last month, I took a Myers-Briggs personality test for my management and organizations class. I received an ENFJ score — extroverted, intuitive, feeling and judging. But in every category besides extroversion, it was a “weak” result in that if I answered a few questions differently it could have gone the other way. The only thing that Myers-Briggs could definitively tell me was that I’m an extrovert.

If you met me 5 years ago, this would have been a laughable characterization. I may have had extroverted tendencies growing up, but it was always cased in a thick and unbreakable introverted shell. I would think about going up to people for one reason or another and then get anxiety and stop myself. “No, she’ll think I’m weird” or “well, he looks busy” were common mental roadblocks. Occasionally I tried, but it always just came off as lacking confidence.

So I hacked my introversion.

When I worked at Benzinga, my boss Jason would regularly hand me the phone and say, “I just dialed <name>, the head of <major financial media site we want to partner with>. Go pitch him on why he should want our content.” I stumbled, mumbled and outright panicked my way through these phone calls for months. When someone actually picked up, I would get so nervous I would shake. It was a classic (and painful) example of throwing the baby in the pool to teach it how to swim.

Over time, I got comfortable talking to these people. I watched how others in the office handled themselves on the phone, at conferences, etc. and incorporated what I could. I noticed little things, like that there was always at least two minutes of small talk before getting down to any real substance. I learned how to get people to talk about themselves and listen for key words about their families and personal lives. Most importantly, I figured out how to get into a “flow” when pitching that didn’t make me sound like a shy 19-year-old. I observed, tested and iterated.

Enter entrepreneurship, where I have done an absurd amount of presenting, phone calls, meetings and more that demand people skills. Fetchnotes would not be where it is today if my co-founder and I hadn’t spent days of going up to strangers in coffee shops to get feedback on our ideas and designs. There’s no room for introversion when you need to make people comfortable enough that they can tell you exactly what you’re doing wrong or why your idea sucks. This also extends to the web too, where I do an equally absurd amount of cold emailing to try to forge connections with people that can help us.

This was entirely forced interaction at first. I had to plan, What will my opening line be? Who looks most willing to chat and be helpful? What’s my overall game plan for this conversation with a stranger? Moreover, I had to shed my inhibitions and repeat, there’s no reason not to. It was a very calculated extroversion.

Last fall, I noticed that I didn’t feel like I was forcing myself to do these things quite as much. After about a year of consciously making myself think, “there’s no reason not to,” my brain had ceased to think there was a reason not to. It was second nature to go up to someone and ask them what they think about an idea, present to a room full of people, etc. The introverted “well…maybe I shouldn’t” shell has thinned, and I’ve been a much more natural extrovert ever since.

The funny thing is, as soon as this flip switched and I became naturally outgoing, I started getting really lucky. I won things like trips to the Sugar Bowl and free t-shirts. Incredible business opportunities presented themselves at my feet. I made a ton of new friends. And frankly, I’ve just had a lot more fun.

You can hack your introversion. All it takes is a nudge (or maybe a shove) and a concerted effort to be the person you want to be.


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