There is a photo of me in the student activities section of my high school yearbook in which I’m wearing a child’s-size thrifted thermal shirt (it was the ’90s) and sitting in the library, leafing through a book. Unremarkable in composition, it stands out in memory—not so much for the nostalgia of youth, but because it was the first time I realized I had been over-plucking my eyebrows. Having recently purchased a magnifying mirror to facilitate the meticulous removal of individual hairs from my genetically high arches, my dark black brows are so thin, so pointy, I look like a visibly evil Disney stepmother.

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The revelation didn’t make enough of an impact to stop me from sculpting two dismembered batwings on either side of my nose bridge in college. But when I moved to New York City in the early aughts, I was given an intervention during an impromptu appointment with Manhattan arch guru Jimena Garcia. “You should grow your brows out,” she said. “Then just brush them up with gel so they look feral.”

I bought in—especially after Jimena introduced me to the game-changing power of vegetable dye tinting. She is the only person who has touched my eyebrows in the last 13 years, which is why she squealed with delight when I recently revealed that I wanted to take our grow-out scheme one step further, and stop cleaning up the small hairs beneath my natural brow line, too—a move inspired by Taylor Hill and meant to eliminate the risk of looking too “done” (my ultimate beauty fear).

“It’s the trend right now,” Jimena confirmed. “Psychologically, where we are as people, we’re just really into that freedom of letting go.” That “letting go” can land you on the right side of Olsen twin—or Kaia Gerber—caliber brows is an added incentive. But it also comes with a painful “grow-out” phase, as I quickly learned, plagued by holes, horizontally oriented follicles, and a whole lot of uncertainty. Looking “feral” is all well and good, until you just look like an unkempt mess.

While real, true grow-out can take a full year, “You can see a huge difference in six to eight weeks—that’s the hardest hump,” Jimena explains. “You just have to find things to maintain your brows while they look unruly.” Things like filling in patchiness with a growth serum, such as RevitaBrow, or a wax-laced tinted gel, like Glossier’s excellent Boy Brow; asking a friend to go through the tweezer withdrawal alongside you; or carrying around a picture of your dream brows (Lourdes Leon!) as a reminder of what all the awkward, hard work is for.

“You have to have a game plan,” Jimena insisted, advising regular check-ins with a brow groomer every month to two months, for continued shaping and tinting, which will “bring out the fuzz” and allow you to see the incremental progress. When the momentary impulse to pluck seems insurmountable, distracting yourself with a bright statement lip habit—or a colored mascara, like Christian Louboutin's Lash Amplifying Lacquer in Sevillana—can be a help.

Trudging toward the seven-week mark, this beauty editor can confirm that the struggle was real. But I eventually turned a corner: At an event one afternoon in Midtown, while playing with different products via the YouCam Makeup virtual cosmetics app, a technician selected one of the preloaded brow filters to “complete my look”—a thin, flat, lifeless line that paled in comparison to the wild but well-heeled thickness I can now proudly call my own.

The resulting pictures—my unaltered selfie on the left, and my digitally enhanced avatar on the right—presented yet another image that will forever stand out in my memory: the first time I actively chose the “before” photo.