20Something: Diana-May

“I think my fear of regretting something forces me to do it.”

I’m late. No matter how much time I allow myself to get from Lincoln Park to Fulton Market, it is perpetually 5 minutes too little. As I sit in the bumper-to-bumper Halstead traffic, I scroll through Diana-May’s Instagram feed. I’m met with an array of bright colors in the form of clothes, city scenery, and cocktails. She’s managed to find the perfect blend between casual and curated. She’s aspirational in the best of ways - I want her wardrobe, and I want to be her friend.

She greets me instantly with a smile and a hug. True to the impeccable sense of style that permeates her content, she’s wearing a white t-shirt (or maybe it’s a tank?) with a light gray sweater over it, slouching effortlessly off one shoulder. A gold pendant necklace catches my eye, and I’m only now realizing I forgot to ask her where it’s from. Damn!

We’re already chatting as we grab the only empty table in the joint, exchanging introductions and pleasantries. She lives around here (“here” being Good Ambler in Fulton Market), I live in Lincoln Park, she loves Lincoln Park but prefers her spot on the west side of the river, I love Fulton Market but have an undying need to be as close to the lake as possible, etc. etc. By the time we’re both seated with drinks in hand, I know that she’s an Indiana native, has lived in Chicago since 2019, used to live in Wicker Park, and loves the West Loop patio scene in the summer. 

I also know that she recently quit her corporate job to pursue social media full-time and moved to London on a whim. But I make myself wait before unleashing my burning Anglophile questions on her. Instead, I suggest we start at the beginning. 

The story of Diana-May is as follows: born to native Kenyan parents, she grew up in Indiana. Her favorite color is blue, her go-to karaoke song is “anything by the Jonas Brothers,” and her go-to drink is a marg. Can’t fault her. She breezes over the years before college (“I think [college is] when life really started”), though I later learn that she spent grade school and high school playing soccer competitively (soccer : Diana-May :: ballet : Ellie). She went into college as a bio major, planning on a career of anesthesiology, and started a blog on the side to give herself a creative outlet for her love of fashion and lifestyle content. Sounds… oddly familiar?? 

She switched her major to marketing and communications during her sophomore year, setting herself on a path that would ultimately lead to a corporate career in marketing and advertising. It was in 2020 that she started to post more frequently on social media, and in March of 2021, she joined TikTok. “I really didn’t know what it would snowball into,” she says. And by that, she means her 26K Instagram followers and 91K TikTok followers. “I don’t think I ever thought it would be, like, a full time career this early on,” she continues. But a few months ago, her corporate job went back to the office full time and that was that. She quit her job on a Tuesday and moved to London the following Sunday. 

I tell her we’ll get back to London in a minute. Like I said, once I go down that rabbit hole of questioning, there’s no going back. Instead, I want to know what her favorite social media platform is. “I love TikTok,” she says. “I think I’m way more myself on TikTok… it’s way more conversational.” She loves talking through her content and indeed, her energetic, fast-paced videos with quippy voiceovers are what initially drew me in. “You can make Instagram conversational as well,” she continues, “but I do feel like Instagram is more aesthetic.”

“Aspirational,” I offer.

“Yeah,” she says. “I’m not really jumping on there, like, ‘Hey guys, here’s my outfit of the day today!’ I don’t know, it just feels weird to do that on Instagram… I think TikTok is just more fun.” My frequently-ignored TikTok time limit reminder would agree.

But the app hasn’t been around long enough for us to look back on our childhoods and fondly recall our dreams of becoming TikTok stars. “Did you have a dream job?” I ask her.

“In my head I made my dream job an anesthesiologist,” she replies. But on a deeper level, she knew that wasn’t what she really wanted to do. “I was going through the motions, and I was doing everything, but, like, I knew that’s not the career that I wanted… but I was also afraid to disappoint my parents because they’re in medicine, they’re immigrants, and I feel like when you come from an immigrant family it’s like, education is the biggest thing. Giving back to your parents and everything they gave you is such a massive thing.”

When I ask if the thought of relying on social media to be her creative outlet and her career scares her, she says she honestly doesn’t care. She’s content to give it her all now, and let the chips fall where they may. “I just want to let it be, you know… One thing in life that I really, really, really don’t want to do is have regrets. I’m, like, more scared of having regrets than I am of not doing something. So I think my fear of regretting something forces me to do it.” And with that, the conversation swings back to London. 

I ask if it was a spur of the moment decision, or something she had been considering for a while. Based on what I’ve learned about her over the last 20 minutes, I’m guessing it was more the former. “I knew I wanted to live abroad for a little bit, but I didn’t know how, I didn’t know where, I didn’t know when… it just sounded like a good idea.” When thoughts of leaving her corporate job first crept in, she considered London as her next move, but it was mostly a passing thought at the time. When those thoughts of quitting became a reality, things tumbled into place quickly. She found the perfect apartment, packed up her things, and was on a flight across the pond by the end of the week. Oh, to be spontaneous without a crippling fear of failure!

She runs me through her decision making process: “I’ve always said I wanted to move to London, and I didn’t know if I was just kidding, but now I don’t have a choice to back out of it.” And as an afterthought, she adds, “I think if I had time to think about it, I maybe would have not done it.”

“Did you know anyone there?” I ask. She didn’t. But she got lucky, quickly making close friends through social media and happenstance.  I tell her I love hearing about how people make friends post-grad, because everyone seems to have their own methods and comfort zone. For the next few minutes, we volley back and forth a list of ways we’ve made friends in cities that are new to us. A social media friend here, a mutual friend there, a work friend that lasted longer than the job itself.

I ask if moving to a new country where she knew no one made her nervous. I expect her to say yes, not because she strikes me as someone who would be daunted by that kind of thing, but because, well, who wouldn’t be?  Instead, she replies with a simple: “Not really.”

“I just wanted to be there for myself. Obviously, having friends is so nice, but I kind of just wanted to be away… just kind of do my own thing.” She tells me that since graduating college, she’s become increasingly comfortable with being on her own. She has no apprehension about dining out alone, or shopping alone, or traveling alone. “I want to do what I want to do, and I can’t wait for other people to do what I want to do, so I just need to do it myself.”

Her self-assuredness is refreshing, and if I’m being honest, inspiring. I consider myself fiercely independent, but sometimes I worry it’s to a fault. I have this vision of myself in my head waking up one day,  20 or so years down the line, and realizing I hath girlbossed my way too close to the sun for too long, forgetting to let people in along the way. Do I seem too stony to others, I wonder, are my walls of independence built too high. Diana-May does not seem concerned about this. She confidently leans into her independence, and lets friendships fall into place naturally. She doesn’t seem the type to let others sway her to or from her autonomy. I make a mental note to be a bit prouder of mine.

In the following minutes our conversation begins to ramble, wandering from dating (or lack thereof - we agree on the fact that the pickings here are slim, I’m sorry to the Midwest boys), to figuring out how to support our childhood friends as they find their ways down different paths, to how we intend to spend the next few years of our lives figuring out what it means to be Diana-May, and what it means to be Ellie. She exudes warmth and affability, and we quickly fall out of the interviewer/interviewee dynamic. She asks me questions about my life and I find ways to relate to hers - it feels like two friends sitting down to catch up over coffee. 

I ask if she’s always been so stylish. The crux of her content is style, and hers is impeccable. She responds with an anecdote of grade school Diana-May laying out a full week of outfits on her bedroom floor, complete with labels for the corresponding day. And yet, she says it wasn’t until a few years ago that she really found her own style. Inspiration comes to her through experiences and people, especially those in other cities. She tells me that new cities open her eyes to sartorial languages that she may never have found in Chicago.

I bring up one of my favorite debates: European style vs American style. We agree that the Europeans have figured something out that we Yankees have yet to wise up to - there’s an innate sense of intention behind European dressing. It is at once full of purpose, yet effortless. “I think we get a lot of our style from [Europeans],” she says. “I think they get it first. I’ve always thought that.” But she prefers to put the responsibility on herself to figure out what she likes, rather than waiting around for a trend to hit this side of the pond. 

“How would you describe your style?,” I ask. 

“I just figured this out,” she laughs. Following stylist Allison Bornstein’s three-word method, she defines her style as “chic, effortless, and then my third word is interchangeable - it’s either playful or feminine, depending on what I’m dressing for.” One scroll through either of her social media pages confirms this. “You do color very well,” I tell her. As a neutrals-only girl, I am constantly trying to find ways to incorporate more color into my wardrobe. Diana-May has mastered colors in a way that feels cohesive, and doesn’t overwhelm the eye. She says she will always love a neutral outfit, but opts for colorful prints to push her out of her comfort zone. 

I ask if she thinks her sense of style would have evolved so much if her job didn’t revolve around it. She says it would have, because her love of fashion is independent from its presence in her social media. “I want to put an outfit on because I love that outfit, and I feel good about it, and I want to wear it. And now I just get to post about it.”

—————

I’ve all but forgotten about the list of questions I came with, but I do want to try to squeeze a few more in. I ask her what the best and worst years of her 20s have been. She tells me she hated the uncertainty of the months right after college, when the structure of her academic life was gone and suddenly nothing was next. “That was the most uneasy time ever,” she says. I tell her I hate uncertainty too, and she nods. “You know life’s going to go on, but it’s so unsettling,” she adds.

And on the flip side, “I think 25 has been the best age, honestly, because I’ve come into myself the most. There’s been a lot of change, but it’s all been for the best.” She says she hadn’t realized it at the time, but now, freshly 26, she looks back on the past year and appreciates how formative it was. 

Knowing she’s regret-averse, I ask if she has any. “One regret that I have that I always think about is not pursuing soccer as hard as I feel like I could have… It’s a hard regret because I love where I ended up in life without [soccer]. But I do always wonder about that.” 

I ask what led to her quitting soccer, and she says her career naturally ended after she graduated. She played in a few pickup leagues in the months that followed, but the pandemic put a quick stop to them, and she never really picked it back up. “It’s hard because looking back, I’m like, ‘I wish I would’ve done more,’ but in the moment that’s not what I wanted.” Perhaps allowing regret to creep in is easier than sitting with the reality that as we grow and evolve, so do our decisions. We’re quick to blame ourselves for making the wrong choices and slow to remember that at the time, they were completely right. 

She wastes no time in finding silver linings, telling me all of the things she’s grateful to soccer for teaching her: hard work, camaraderie, leadership skills, how to build connections throughout a team. They’re the same things I’m grateful to ballet for teaching me. 

We spend a few more minutes exchanging memories from our extracurricular activities of yore before we wrap up our interview. As we part ways, her philosophy on regrets lingers in my head and the wheels are already spinning - where am I holding myself back out of fear? What am I going to regret not doing in five years? What regrets am I harboring that maybe I shouldn’t? And as I make my way back through the Halstead traffic from Fulton Market to Lincoln Park, I find myself scrolling through Instagram again. I think I’ll add a pop of color to my closet.