A Portrait of the Artist As an Old(er) Man

I got checked out by a woman when I went out a couple weekends ago.

Hang on, it’s not what you think.

It was around 9:30 on Saturday evening. I wouldn’t say that the streets were packed, but it seemed like a busy evening. There were groups of people milling about outside the restaurants and more making their ways through the streets, plus a few who seemed to just be standing and listening to the music echoing from the concert at the stadium nearby. I had stopped at an intersection to wait for the light to change when she walked by.

She looked to be in her early 20s. She had done her hair and was wearing a dark jacket and jeans. I had been watching the oncoming traffic when I heard her heels clacking against the sidewalk. I looked up just in time to see her smile and quickly return her attention to watching herself in her phone as she ran her fingers through her hair.

Actually, it was really more of a smirk than a smile.

The differences between us couldn’t have been clearer. She was talking to someone on the phone as she walked; I was standing alone. She was going “out;” I was going to Target. She was young, I was old (…er). She had clearly put effort into her appearance; I was wearing this:

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I’m fairly certain I’ve had these exact clothes since I was in college.

She wasn’t checking me out because she thought I was attractive; she was laughing at me.

Before I go any further, let me be very clear: I was not insulted. I remember being 20-something and feeling like the world was at my fingertips. That’s how 20-somethings are supposed to feel. They are supposed to think that the world is full of possibilities and that they are at the center of it all. They are supposed to think, at least to a certain degree, that they know everything; at least, certainly more than anyone who is old (…er!) or who doesn’t fit into their social circle.

There I was, standing on a street corner, two days shy of my 34th birthday, with two finally sleeping children and an exhausted wife at home. I looked less like an gainfully employed adult supporting a family than I did like a college student taking out the garbage in the hallway of his dorm.

I found myself asking two questions. The first, obviously, had to do with what other people were thinking as I walked by. My feelings were clear: I was under-dressed to even be making a quick run to CVS, let alone moving among people who were out for a night on the town. I felt conspicuous, as though every person who saw me was immediately thinking of some sort of judgment about me. “Look at that guy,” I could practically hear them saying to their friends. “He’s got the drawstrings hanging out of the front of his shorts, he’s wearing flip-flops in 50-degree weather and he’s probably had that sweatshirt since he was actually in college. That must have been like twenty years ago.”1 My usual impulse to play the contrarian role seemed to have less will behind it on that particular evening.

The second was, “Why should I care what they’re thinking?” By most typical measures of success in life,2 I have it made. As I mentioned, I had two beautiful sleeping children and an unbelievable wife – who was not yet sleeping – at home. I have multiple jobs, including a private therapy practice, a post-graduate education and a savings account. What do I have to feel uncomfortable about? Am I really that insecure or was I just temporarily yearning for the times when I was young(…er)?

I decided that what I was feeling was normal. I imagine that, to a certain extent, everyone longs for a time when they had fewer responsibilities and had the luxury of putting their effort into spending time with their friends or going to parties instead of making late night runs to the drug store. On a more basic level, I imagine that many adults at least think about the difference between first going out at 9:30 at night and having been wearing one’s pajamas for twenty minutes by the time 9:30 comes. It wasn’t about the girl or my clothes or the fact that my glasses and the stubble on my face from not having shaved combined to spell “exhaustion” across my forehead. It was about being reminded of where I am in my life and being happy with what I have.

I’m thankful for the fact that I’m employed, even if it feels like the work never ends. I appreciate the fact that I’m able to support my family financially so that my wife can stay home with our children. I’m lucky to have access to resources and the awareness that I’m significantly privileged so that Trudy and I can impart the same awareness to our kids as they get older. There are some challenges in my life, to be sure, but they’re not nearly as severe as those than many other people face on a daily basis. I wouldn’t change a thing.


1. I finished my bachelor’s degree in 2005. It was twelve years ago.

2. Including The Game of Life, where the very object of the game is to get married, raise a family, make a whole bunch of money and retire. This game may end up being the subject of a future blog post.

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