Last weekend we attended the 40th birthday celebration of my college roommate, a woman I’m incredibly thankful to have had in my life during some very formative times. It was a pretty good sized event (maybe seventy people or so) which was a significant contrast to the intimate dinner with friends I’d chosen to celebrate my own milestone birthday. The next morning we had breakfast with some friends who had been at the same party, and the conversation quickly led to their ages (39 this year) and what they each hoped to do for their own milestone celebration.

Sarah quickly informed us that Lucas is a birthday grinch. He explained that while he doesn’t hate birthdays per se he does see passing years as the, “foreclosure of possibilities.” He went on to tell us that while he isn’t a Simpson’s guy, there’s an episode  in which Homer suddenly realizes that he could be a milkman that loosely illustrates where he’s going with this. Lucas then rattled off a handful of varied careers and hobbies that, given many many more years, he’d love to try his hand at.

He mentioned that his 40th will fall on a Saturday, and Sarah joked that it’s a good thing funeral parlors aren’t often busy on Saturdays because they could hold his party there. Kristin and I suggested a sort of salon of despair; we pictured lots of black berets and performance art.

Jokes aside, it was a really thought provoking conversation. I have no such fears (yet) about aging or being 40. But it did remind me of a piece that I love and often send to people when they’re considering life’s choices and the fact that we can’t choose it all. The advice in this column, and the consideration of the ghost ship that didn’t carry us, is profound and beautiful.

A day or two ago while looking up something for work I stumbled across an article about Jenny Lewis’s new album. As I read it, there was one passage in particular that almost made me laugh out loud because it was just so good.

As Rilo Kiley’s front woman, she sang with an assertive candor, revealing her deepest vulnerabilities around sex and heartbreak and familial relationships through soaring, irresistible power-pop choruses. Her personal style, comprised of vintage baby-doll dresses and an array of rompers, landed on the enviable side of mid-aughts twee. She reclaimed elements of a male-dominated rock scene and made them accessible for openhearted young women. Lewis released her first solo album, the country-tinged Rabbit Fur Coat, in 2006, giving her credibility with millennial indie fans as a stand-alone artist.

Her influence from that era is best summed up by the actress Kristen Stewart, a paragon of blasé self-presentation, who told James Corden that Lewis was the one celebrity she was most nervous to meet. “I couldn’t breathe,” Stewart said of her now-friend. “I literally just completely caved in front of her.” Lewis is touched by this sort of sentiment from early fans, women who heard her music, she says, “just at the perfect age.” It’s an intense fandom, if limited to a certain demographic.

“I get recognized at Whole Foods,” she concedes. “A lot.”

That last line is just perfection. It reminded me that there was a time when my undergrad dream was to become the kind of journalist who spent entire days with musicians and wrote thoughtful, well-crafted profiles for the likes of SPIN Magazine that vacillated flawlessly from biography and album details to small moments from our day that revealed something readers might not know about the artist in real life. I remember taking a journalism class in college in which we were assigned to a random classmate and had to interview one another and write a profile. I wrote something like nine pages about this woman I’d never met, including details about arriving at her apartment and her daughter greeting me at the door. I think that I got an A.

Spoiler alert: I never became a journalist and I’ve never interviewed a celebrity, but I’m OK with that. There aren’t any hobbies or career paths that I sincerely wish I could have followed. Yet since having children I have seen an unfolding of willingness to try things that, when I was younger, I was too much of a perfectionist or simply too worried about the opinions of others to pursue. I used to believe (and say out loud) that I wasn’t a creative person, and now I consider myself to be pretty crafty. I make things, I write things, I’m a photographer, I know how to sew and knit. I feel an urge to create that was never a thing when I was younger.

Lucas admitted that for his entire life he’s been someone who does not dance, but that in recent years he’s had an unexplainable desire to start dancing (when appropriate – not like, at the office). According to Sarah, he’s a ridiculously good dancer now. He told me that his brother experienced the same flipped switch around the same time. I told him that it makes sense; a blogger I love has referred to it as “zero f*cks forty,” when you just don’t care what anyone else thinks anymore and start doing what you really want to do.

It also occurred to me that this phenomenon, this sudden comfort with dancing in public and wearing things we never thought we could pull off before and maybe just generally relaxing and living life is wonderful, but it also might be the cause of embarrassing mom syndrome. Is that what happens now? We all let down our guard and before we know it we’re those hopelessly and cluelessly uncool moms and dads that young people are slightly embarrassed to be around? So while we’re all feeling brave and throwing caution to the wind, we’re headed down a slippery slope. And while knowing that gives me pause, it also makes me reflect on how totally wrong we were when we were the young people who were cringing at how uncool adults were. Those were just people who had finally figured out that it doesn’t matter at all what anyone else thinks, and that’s actually pretty badass.

So buy that hat and rock it, and start dancing if you want to, and decide that you’re going to become a mediocre sculptor or whatever your milkman thing is. There are always going to be ghost ships, but we might have time to squeeze in a few more things before that ship sails away.

Is there a path you never took that you still wonder about? Share it with me.