The American Music Awards are just another awards show I don’t watch. I likely would’ve remained blissfully unaware of the event, had a tweet by E! News from the red carpet not caught my eye. The post contained a photo of Diana Ross and her family: matriarch at the center, flanked by her children, one of whom, Evan, is married to Ashlee Simpson. Accompanying her husband, Ashlee and her children attended the awards show in support of the Rosses: Diana received the Lifetime Achievement Award and Evan’s sister Tracee Ellis Ross hosted. Ashlee, a child of privilege, had filtered into another family with a familiar name, this time as quiet supporter. Some 13 years into her career, she was back in the shadows.

The role was familiar. Imagine the confusing years of your puberty — then imagine them happening if you were the younger sister of a world famous pop star. As Jessica Simpson’s career took off, Ashlee lived in the background of her sibling, once even serving as a backup dancer on tour. “It wasn’t that I had a sad childhood, but when I was around 14, I hadn’t grown into my face yet and was all awkward and ugly, and I had this beautiful pop-star sister,” she told Cosmopolitan in 2005. “So there was a time when I didn’t feel great about myself.”

Soon, though, she had a reality show, as well as a record deal, because those are the available options when you’re in proximity to fame. The Ashlee Simpson Show, which aired on MTV from 2004-05, was her chance to prove she was someone. The program chronicled Ashlee’s progress on her debut album, Autobiography, the complications that came with her dreams of stardom, and relationship turmoil. Ashlee looked up to Jessica, though had her own dreams of fame that countered the image and style of her sister. Instead of becoming another Britney or Christina clone, she dyed her blonde hair black, and tilted her musical interests toward pop-rock — including a song called “Shadow” about a childhood where she had been upstaged.

Of course, whatever recognition she gained as a recording artist and a reality television star were upstaged by a rather unfortunate incident. You know the one. In October 2004, Ashlee appeared on Saturday Night Live, where she infamously hoedown-ed and walked offstage after the wrong backing track began to play. It appeared as though she was lip syncing; she denied it, but then admitted to the crime. The incident was covered by tabloids, music magazines, and blogs alike; the video, undeniable in its embarrassment, was played over and over again. Even Lorne Michaels threw her under the bus, saying he’d never allow an artist to lip sync on the show, adding more holes to an already sinking ship.

That was the beginning of the end. Ashlee released two subsequent albums, which sold progressively less. The SNL moment paired with an uninspiring musical shift toward empty party anthem pop killed off what was left of her career. “Ashlee's disaster revealed her to be a patchwork pop star,” wrote Kevin O’Keefe for The Atlantic in 2014. “Unlike her sister, she was no longer relatable. She was a product of the machine. Maybe that's why Ashlee's album sales cratered on her sophomore effort; when the wrong track played on ‘SNL,’ America saw the seams. And they didn't like what they saw.”

Ashlee’s emergence from her sister’s shadow began after a few cameo appearances on Newlyweds: Nick and Jessica, the reality show that helped make Jessica a household name. Upon seeing the positive fan reactions to Newlyweds, Joe Simpson, Ashlee's father and manager, pushed his reluctant younger daughter to sign onto her own program in the hopes it would help her establish an audience, and serve as one glorified marketing push before her first album dropped. Debuting at the cusp of the celebreality boom, the Simpson sisters helped — along with The Simple Life and The Osbournes — perfect the narrative of famous people acting in everyday ways on television.

They were extraordinary people, acting in ordinary ways. They appeared to us as somewhat normal, rather than careerist stars, even though pushing the brand was the only intention. It worked, too: Thanks to the “Ashlee Simpson Show” — and the efforts of her manager father who helped craft both of his daughters’ careers — Ashlee’s 2004 breakthrough album Autobiography debuted at No. 1 on the Billboard 200, effectively pulling her out of the doldrums and elevating her unique star power as an individual talent and not one of a larger unit.

It was all constructed, but Ashlee’s plights and heartaches nonetheless felt suitably authentic. Watching her furiously scribble lyrics onto pads of paper, or get her cartilage pierced, provided insight into the life behind the music. When you’re 11-years-old and listening to a song about someone falling in love with their best friend, as Ashlee did in “Pieces Of Me,” you want to witness it — feel as if you were there when they shot a music video together, see his spiky hair and choker necklaces. Ashlee was ambitious and yet innocent, something that resonated deeply with my hopes and fears. She had a lot, and still had to meet her family’s heightened standards for stardom. When Autobiography sold 398,000 copies in its first week — which gave Ashlee something her sister did not have, a number one album — it appeared her father’s plan had worked, until the smooth machinery was interrupted by the SNL heartbreak.

In 2004, we were just becoming familiar with how the internet could accelerate and spectacularly blog any public demise. Now, everyone carries this risk when they attempt self-betterment — you don’t need to be a Simpson sister for the world to mock your downfall. What if it backfires, I wonder when I act. What if my contemporaries glimpse the seams, and deem me unworthy? Ashlee had a management team, but still: She was expending so much energy to carve out a place in a world that was already changing, unaware of what could actually hurt her. She sought recognition, using the available means, and spectacularly overshot.

She was a millennial who failed to get what she wanted. Trust me; I know the type. Let us not recount the myriad ways millennials are apparently to blame for the downfall of a handful of industries, from casual dining to napkins. There’s concrete evidence that the world we live in has left us with the short end of the stick. And it’s not just the time spent on social apps that leads to depression — it’s the constant comparison, the way we filter our lives through the sunniest haze in order to achieve a social standing. If the Kardashians, the reigning royal reality TV family, have taught us anything, it’s that the goal is to live well in public with an audience.

That lifestyle became a benchmark for success. But Ashlee managed to get away from it all. For the rest of us, it’s not that easy. We don’t come from wealthy families who will bend over backwards to get us a reality show if that’s what we really want; we don’t cash checks from mediocre album sales while building a family with rock stars, or the son of a legendary soul singer. We can’t all transform our lives in a petri dish of financial privilege. You don’t, however, need a lush bank account to realize the passions you had in your youth are not everlasting. "I think being a mom kind of took the place of [music], definitely,” Ashlee told Us Weekly in late 2016. She, like many of us in the final days of our waning ambitions, settled down.

On the AMAs red carpet, Ashlee and Evan stopped for an interview with Access Hollywood where she beamed at her husband as he exclaimed, “It feels like a Ross night.” By the end of the conversation, Ashlee had invited the interviewer to the Ross family Thanksgiving. I watched this two-minute clip several times, frequently pausing to catch Ashlee’s reactions. The questions focused on Evan’s family and their roles within the awards show, and Ashlee punctuated her husband’s answers with enthusiastic head nods and grins. But just before the screen faded to black, Ashlee tipped her head up and away from her husband for the first time in the interview, smiling still. Through the layers of bronzer, I sensed an air of genuine pride.

Read the last installment of Very Intriguing Person, on teen star Bhad Bhabie.