Why You Should Put Yourself Out There

 In Inspiration, Productivity

The apartment building Laura and I live in is three floors with three units. We’re on the second. And last night I saw that the downstairs neighbors were moving out. These weren’t the first people to go; that apartment has seemed to have a revolving door over the six years we’ve been there, with five different sets of occupants. What I realized last night was that despite not knowing the current tenants very well, I really liked them. Then I felt a bit of regret because I didn’t try harder to get to know them—something that I’ve avoided with most people for a lot of my life.

I’ve always been pretty shy, and it wasn’t until recently, when I decided I wasn’t happy with how I’ve been living, that I started putting myself out there more. The results have been fantastic and I’m often stuck wondering how much different my life would be if I’d been this way all along. I’ve probably missed out on a lot of really great things—and a lot of really great neighbors.

While the apartment below ours is always being rented out by new people, the one above us had been pretty consistent up until last year. There was an older gentleman living up there—it’s significantly smaller than the other two units, so I don’t know if there’s room for more than one person or not—with whom I’d been uneasy since the day we moved in. I don’t know why this was. He’d never done anything to me. He seemed a little like a loner and was definitely eccentric, so maybe I let that put me off and cause me to do the worst thing you could ever do to someone: pre-judge them. I didn’t know anything about this man, and yet I tried to steer clear of him because of things I’d imagined. I think one day he heard me on the phone with my mother as he was making his way up the stairs to his apartment. I was looking for someone to check in on our cat, Pinky, while we were out of town and she suggested him. I explained that I get a weird vibe from him and didn’t want to do that.

A few days later I saw this man standing by his car in the parking lot and he said to me, “You know, I’m just a normal guy.” My heart sank because I knew immediately that he’d heard my description of him. I also knew in that moment that my own insecurities caused me to assign traits to him that just weren’t real. I think a lot of us do this all the time and it’s very limiting. I know that now because from that day on I spoke to this man whenever I saw him and he would tell me the most amazing stories! He was a musician who played concert piano in Manhattan, used to be in a band with former Eagle and fellow Montclairon, Joe Walsh, and how he used to meet with famed editor Thomas Congdon for coffee all the time (this led him to tell me some details about how Peter Benchley’s Jaws came to get its name that might not be widely known). But even with all of our interactions, I still feel like I didn’t give this man enough of my energy, and when he died last year I felt a lot of regret.

Would the downstairs neighbors have stories as interesting as this man did? I don’t know. But it would’ve been nice to find out. And that’s what I’m committed to doing with future neighbors and just people in general. It took a lot for me to overcome shyness and self doubt to the point where I even felt like I could talk to people. But since I have it’s enriched my life greatly by allowing me to hear great stories, share my own, and just connect with people. It’s even helped me with my work: I’m not afraid to speak up in a meeting anymore; I’m less hesitant to talk to a stranger on the street if I want to take their photograph, and I have a lot more overall self-confidence.

So how did I achieve this?

As part of this year of change for me I began watching interviews with and reading the books of Brené Brown. Daring Greatly was especially helpful to me because it reminded me that it’s OK to be vulnerable and courageous, that it doesn’t matter what most people think if you’re putting yourself out there because they might not be “in the arena” with you, and therefore their opinions hold very little weight.

I recommend reading that book (available here), and to get you started with Brené, here’s a great interview she did with Chase Jarvis:

Another thing I did was apply some techniques for talking to people that I learned from Ramit Sethi. One of the biggest things that held me back from talking to people was that I’d have nothing interesting to say. And I worried that if I did, I’d be wrong and challenged on it. I realize now that these scenarios are completely unnecessary to even consider when you approach a conversation with a plan. My general plan, which is now nearly automatic so I don’t have to think about it, came from these blog posts on Ramit’s website:


These titles might seem a bit hokey. But I’m telling you, if you’re a shy person, applying the things discussed in the posts will make a world of difference.

Ultimately, the takeaway is to not overthink it, ask good questions (But not too many), and be genuinely interested in the person you’re talking to. Offering up relatable, interesting information about yourself is helpful too.

The point to all of this is that I’ve missed out on a lot of interesting opportunities and experiences throughout my life because I lacked courage and self-confidence. But I worked to changed that (it’s definitely in progress though; I’ve come a long way, but still have a lot to learn and apply) and my life is a lot better because of it. So if you’re like I was—shy and unsure of myself—read Brené Brown and check out these simple and effective tips from Ramit Sethi, and I’m certain you’ll be on the path to changing things for the better. You’ll meet people, hear what they have to say, and offer them things of value. Life is a lot more interesting that way.

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