This is a topic that seems arrogant to even write about, but two people have asked me to write a blog post about it, so I'm going to take a stab at it. We all have strengths and weaknesses, and one of my strengths is that I have had a fairly interesting life. This has opened a lot of doors for me, specifically doors that would have been closed to me based only on my abilities. I've also seen this same phenomenon in other interesting people. We tend to get more than we deserve.
And it also goes without saying that the ability to be interesting is, in itself, very lucky. It's a luxury to be able to dedicate time and effort to anything other than survival, so I'm thankful I've been given that privilege.
Caveats and justification out of the way, let's talk about being interesting. I'd say that the practice of being personally interesting is primarily the practice of having relevant and unknown things to share with others.
These things can take many forms, but I'd say that the biggest two are having relatable stories to share and having useful knowledge to share. The methods by which you share these things are important, but the most important thing is to have them.
I believe that there are two primary factors that have led me to be an interesting person. The first is that I am primarily interested in doing things that other people don't do. I am lucky that this was my default for some reason, but seeing the benefits it has had on my life has strengthened my preference further. I see one of my primary purposes in life as exploring things that few others explore and then sharing them with everyone from my friends to my readers.
So I have experience in all sorts of things, like gambling, pickup, cave exploring, real estate, tea, bungie jumping, fine art, several foreign cultures and languages, ballet, cruising, fashion, minimalism, and any other number of things. I'm not really an expert in most of these things, but if someone is interested in any of them, I probably have something to share. If you look at this set of interests, you may notice that they are all things which most people have no experience with. That gives me a large surface area of stories and knowledge to transfer.
I gained this experience through the simple practice of following my interests regardless of direct practical application, and by favoring things that are foreign to other people. This path isn't the best in every single way (a person who focused deeply only one one thing would certainly have some serious advantages over me in some ways), but one of its benefits is that it helps me be interesting.
In my twenties I basically just did whatever I wanted to do. This was nowhere near the optimal strategy for earning money, but it was pretty close for becoming interesting. I'm not suggesting that everyone drop everything for the sake of building up interesting experiences, but some of your life should be contributing to making you more interesting. Allow yourself to choose hobbies that don't "make sense". The weirder they are the more interesting they will be.
Physically doing interesting things is the most efficient route towards becoming interesting, but you can also just read interesting books. Don't read the same things that all of your peers are reading; read things that others aren't. If everything you do and read is the same as your peers, you will have very little to share with them.
You must also learn how to relate these things to others. Maybe counterintuitively, the correct method is with a gentle touch. Don't be afraid to share something interesting, but don't force the conversation. Try not to one-up people, because someone who feels like you are trying to outdo them will have adjectives for you besides "interesting". Enjoy other people's stories and conversations, and sparingly add your own stories and knowledge in a way that enhances the conversation.
It seems strange to focus on becoming interesting, but it's actually a very useful skill. People like being around you because they know that you're the only person from whom they'll hear the sorts of things you talk about. Just make sure to balance it with being a good listener. Don't be afraid to be in the spotlight, but don't require it all the time.
Photo is St. Matthias church in Budapest!
Wow. I don't know what I was expecting, but I got a ton of awesome feedback from you guys. Some people literally wrote a page or two.
So first of all... thanks a ton. I read every single reply (over one hundred total) and got a ton of good info.
I'll share some of the insights provided.
I just started reading Benjamin Franklin's Autobiography. This paragraph surprised me:
And lastly (I may as well confess it, since my denial of it will be believed by nobody), perhaps I shall a good deal gratify my own vanity [by writing this]. Indeed, I scarce ever heard or saw the introductory words, "Without vanity I may say," but some vain thing immediately followed. Most people dislike vanity in others, whatever share they have of it themselves; but I give it fair quarter wherever I meet with it, being persuaded that it is often productive of good to the possessor, and to others that are within his sphere of action; and therefore, in many cases, it would not be altogether absurd if a man were to thank God for his vanity among the other comforts of his life.
Fascinating! Thank God for vanity? Wow...
But you know, it makes some sense. It seems to me that modesty is good when it helps you achieve what you set out to achieve, and modesty is bad when it stops you from achieving what you set out to achieve. Whether modesty is effective or not depends on the situation. Some situations call for it. Some don't.
It seems to me that there's a certain kind of pragmatic humility that'd always be good to have. Knowing what you don't know, knowing that there's a lot of skills you don't have, understanding that even your best reasoned judgment of a situation might be overlooking some details...