Posted on December 11th, 2015

My friend Colby is a cud-chewing trust fund baby. Every month – rain or shine – money drops into his checking account. This 6-figure chunk of change is untaxed and contingent on absolutely nothing. It’s not fair. 

Colby says the trust was set up by his dad, who either felt guilty about having ignored his son or didn’t have any confidence in Colby's ability to get a job and make his own way. These days Colby’s life is a black comedy featuring dirty martinis and a platinum (or black) Amex card. It’s all a bit precious and more than I can afford. 

I’m jealous, of course. My silver spoon turned out to be plastic, so I have to work for a living. Colby says I make my money the old-fashioned way. To which I say, you mean because I earn it? Clearly, my slightly Calvinist work ethic is different from Colby’s. His ambitions are like his watercolor paintings: pretty to look at but soft and gauzy without much definition or focus. Most days, he eats organic eggs benedict for breakfast and takes a yoga class in the afternoon. He can afford to be fervently self-absorbed. But because he lives in a bubble protected from the challenges of everyday life, he’s boring. There, I said it. Boring. He’s not lazy or even bratty; he’s just too comfortable for his own good. 

A few days ago our somewhat frayed relationship came apart. He called me and wanted to meet for a smart cocktail after his Bikram yoga class. I knew he was stressed-out because his voice was unusually feisty and demanding. It had been one of the worst days of his life, he said. Everything had gone wrong, and he was feeling fed-up with everything. “Yeah, Colby, I know how you’re feeling,” I lied. “My day has been been one-missed-deadline-after-another. I’m down for a drink.” Then, feeling I should be more supportive, I asked Colby to explain why he was having a melt-down. Maybe I should have kept my mouth shut; Colby-land wasn’t a place I wanted to visit just then.

While waiting for our gin and tonics, Colby ran his hands through his receding hairline and sighed. Long pause. For a moment, I thought he was going to cry. Instead, he told me how he’d spent the entire day trekking from one Home Depot or Loew’s Home Improvement Center to another, searching for “perfect towel bars,” as if they were some kind of Golden Fleece or Holy Grail. He’d driven almost 300 miles in this quest. Looking skeptical, I explained that towel bars are something you buy on eBay. But when you have nothing but time, I guess you learn how to waste it.

Because Colby can have anything money can buy (well, almost anything), he enjoys the illusion of self-sufficiency. But here’s the rub: he also has one foot in the sink-hole of regret because nothing is ever good enough - simply because everything could be better.   

In some ways Colby and I aren’t really so different as I pretend we are. Sure, he’s got cash to blow, and I don’t. But in my heart-of-hearts I know that we both use objects -maybe towel bars, maybe other people - to bolster our self-esteem. In that way we’re very much alike, and I fear what that says about each of us.