I was sitting there at lunch, sweating, staring at the stranger across from me. I had no idea what to say, no interesting topics to bring up. The lone thought racing through my mind, other than wishing this would end, was the disappointment I felt in my inability to make simple conversation for even 10 minutes.

That was the first day of my social workout.

Two years ago, I made a conscious effort to work on improving my social skills. Around the time I started Roommatefit (while still in college), I realized my mediocre interpersonal skills weren’t going to help me succeed. I needed to get a lot of help from others smarter than me, and talking to people via email and Twitter wasn’t going to cut it.

Beginning my junior year, I made it a habit to grab coffee with at least 1 new person each week. The summer I was in San Francisco, I got coffee or lunch with a new person 3x per week, and went to a startup event once a week with the goal to initiate at least 5 conversations. At the beginning it was horrible. I would jump from awkward conversation to awkward conversation, have one good one, and follow it with a painfully strained exchange of sentences that some would characterize as talking. But I practiced, and I improved.

I know since I consciously started working on this I’ve been a lot happier. Today, for example. I went to a lunch with a friend, an acquaintance and a few other people I didn’t know. Two years ago, such a situation would have made me nervous – I would have been unsure of myself, forced conversation and had a horrible time. Now, it’s not a big deal. I had a great time, met some cool people and am grabbing coffee with one of them later this week.

Being a pretty awkward guy has also helped me relate to others who may not have spent as much time practicing their social skills. I understand how others are feeling when meeting someone for the first time, and it’s easier for me to lead conversations to a place where both parties are comfortable. Even a slight improvement in my social skills meant a big leap in my ability to connect with people, which has led to new and better relationships.

Now, although my social fears are (mostly) gone, I’m still working on them. Telling better stories, using more pauses, and adding verbal inflection (I’m a pretty monotone speaker), are all things I need to work on. I’ve learned that your social skills are like a muscle – you can let them wither, or you can work on making them stronger. Improving them followed the same pattern as lifting: you suck, you suck, you see some improvements, you suck more.You don’t have to be that quiet guy forever. After working on this for 2 years I have met more than 300 new people, many who have become friends.

The point of this isn’t that I’m some amazing socialite. I’m not. The point is that I’m better socially than I was, and happier for it. Working on my social skills have had a larger impact on my life than anything else I’ve tried to improve.

Thanks to Nate Speller and Dan Shipper for reading drafts of this. And to all my lunch and coffee partners for their patience over the past two years.

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