My friend Josh recently suggested that the ninth year of a decade is more stressful than the entry into the next. You’ll spend your twenty-ninth year dreading thirty, thirty-ninth year dreading forty and so on.

Now I’m forty-nine I’m not dreading fifty but it’s on my mind. Thirty and forty were cool years, like I had made it to something. I just find it odd that I’m going to be fifty. I’m on blood pressure medication and my feet hurt after I play soccer on the hard turf but is that old? I mean the thirty-year olds’ knees and ankles hurt after playing too. You know, the guys in their mid to late thirties, those whippersnappers.

It’s more that a fifty-year-old should be more accomplished. A fifty-year-old should be married with children have a steady career. If you don’t have those things then what the hell were you doing for fifty years? I had a career in web development for twenty-five years but now I’m unemployed. I teach and perform improv. I hit open mikes. I watch and play soccer.

I’m on the verge of being confounded and professionally stymied by AI. Having an emerging technology make you obsolete seems like a legitimate cause for entry into the ranks of old, like when my dad insisted on turning off his PC after every use so he wouldn’t get a virus or my mother with anything more technologically advanced than a lighter.

And yet, I don’t feel old.

I know people in their fifties. I know people in their sixties. I see them at storytelling shows. They’re still living. I think that’s the disconnect between what I thought fifty would be and what it will end up being: I think there are great decades ahead.

The reason I’m writing this isn’t because fifty is on the horizon. It’s because ten years ago I wrote Some Thoughts on Thirty-Nine and I wanted to continue the pattern.

The featured image of that post is a surprisingly grainy photo of me in the subway with hair and the corduroy jacket from Uniqlo that I wore out. Ten year later, my head is shaved, the lines in my forehead are deeper and it appears that selfie camera lenses and subway lighting have improved significantly.

At thirty-nine, I mentioned how I was sick of talking about how old I am. My friends – among whom I am reliably the most cynical and whiny – still do it often but I don’t join in. I like being bald because I save money on haircuts and never have to worry about how my hair looks in pictures anymore. There’s gray in my beard, but I don’t really care. My marathon days are behind me, but I’ve taken a hundred-mile bike ride twice in past two years and I hope to do it again this year.

It’s interesting to reflect on a decade ago, though. Donald Trump was still a joke. I was oblivious to being four years away from a pandemic. The relationship I mentioned ended badly and I obsessed over it for far too long. I quit drinking. I adopted a dog. I said goodbye to her and then I adopted another dog.

I continue to judge myself harshly but no one has it together. People I know with all the proper life milestones have shared their struggles with me privately. There’s no magic bullet. Every day is a gift. Better men have been through worse. You know, all that shit.

But I like this phase of aging. Choices have been made; expectations have been lowered. I’m a fan.

This spring, I bought a snowboard on sale and I’m looking forward to using it next season. My dog Elby’s gotcha day is coming up. The chihuahuas I’m fostering are slowly getting used to me. The improv team I coach keeps getting better. At the end of this summer, I’ll be two years sober.

Things could be worse.