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HomeTravelWhat Lena Dunham Taught Me About Ambition, Identity, and Starting Over

What Lena Dunham Taught Me About Ambition, Identity, and Starting Over

Home » Travel Tips » Rewatching Girls at 40: What Lena Dunham Taught Me About Ambition, Identity, and Starting Over

There’s something strange about revisiting a TV show that once helped define your twenties—only to realize it now has something even more to say in your forties.

Recently, I started rewatching Girls, the HBO series that made Lena Dunham famous among my generation. I remember watching it when it first aired: a messy, raw, often ridiculous show about that 20-something life that somehow felt like a mirror, even when I didn’t want to look. But now, watching it again while living in Brooklyn, a decade older, a bit more jaded and a lot more self-aware, it’s hitting differently.

I didn’t expect to relate so deeply to Hannah Horvath (Dunham’s character), a would-be writer with a chaotic love life and a deep well of self-delusion. But there’s something undeniably familiar in her creative yearning. The desire to make something, to be heard, to live a life shaped by her own voice. And more than that, her constant confusion, paralysis, and the shame that comes when you don’t quite get there.

What Lena Dunham Taught Me About Ambition, Identity, and Starting Over

Lately, I’ve been having what I can only describe as a mild identity crisis. Professionally, I’m known as a digital marketer, particularly in the SEO space. I’ve worked hard to build a career around content strategy, data, and digital growth—especially since the pandemic shifted my career focus out of travel & tourism and into the corporate world.

It’s work I’m good at and it’s helped me build a life here in Brooklyn that I really do enjoy. But at the same time, I’ve started to feel unmoored from that label. The SEO industry is shifting rapidly, with AI reshaping the way people find and consume information. And there have been several reports and studies out showing how AI is going to impact marketing jobs specifically.

And so I’ve been asking myself: am I still doing work I love, or just work I’m used to?

More and more, I find myself thinking about writing again—not just blog posts like this one or travel guides or “content,” but real writing. Personal, honest, sometimes uncomfortable stories. Like the kind I’ve filled my Moleskine journals with and the ones I used to tell during my travel writing days. And, yes, like the kind Lena Dunham wrote and continues to write.


When Girls first came out in 2012, Lena Dunham’s Hannah Horvath character resonated with a generation of people trying to figure out who the hell they were and how to get through it with some sense of meaning. And it still resonates with that same group of people—including the newer generations first discovering the series now.

And here I am, a 40-year-old gay guy living in Williamsburg, looking back at my 20s and 30s with a mix of pride and regret, wondering what’s next. I’ve built a lot of things I’m proud of. But I’ve also shelved parts of myself that used to feel essential. The part of me that told stories for no reason except to feel alive.

So I’m starting again. Not with a definite play, but with a decision: to write more. To pay attention to the things that move me, scare me, make me laugh or want to cry. To be less afraid of being misunderstood, or not going viral, or not being good enough.

I don’t know where this will take me, or what it might bring. All I do know is that I’m not done yet. With whatever it is. If, like me, you’re also feeling that weird mix of nostalgia, ambition, and creative restlessness—maybe it’s time to start again, too.

Write the thing. Start the show. Tell the story.

Even if it’s messy. Especially if it’s messy.

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