Five years ago, scrolling social media, Courtney, a marketing strategist and the eldest Hollander daughter, had an epiphany.

She’d long known her youngest sister Tessa, way before becoming an award-winning, record-setting javelin thrower at Marquette, was really, truly, deep down, an artist. In every sense of the word.

Growing up, Tessa’s go-to gifts were handmade paintings, primarily on rocks. Tiny, flat stones she’d find in her front yard or at the river near her home, no bigger than a couple square inches. She would cover the dull, credit-card-sized mineral slate with bright, elaborate, meaningful designs.

Tessa’s cousin got one as a wedding gift, which showed the lovebirds in front of the church where they got married. Her grandparents have received many, including one of their family home in Montana. All her sisters have them.

She poured her soul into each one. And she wasn’t doing that for just anybody.

“She was pretty stingy with them,” Tessa’s mom, Kristen Hollander, says.

Soon after Tessa started, word began to spread about the girl who put life into stone, and her reputation as an artist expanded outside of the family. When Courtney, now 30, was a guard on the Seattle Pacific women’s basketball team, her coach, Julie Heisey, commissioned Tessa to paint rocks the school’s deep maroon with their falcon logo in the center. Each cost $1.

“Little 12-year-old me was so, so stoked,” says Tessa, now 21.

As nice as Courtney knew this was, she also knew her little sibling could do more. Gifting rocks was a good start, but not enough. Tessa had the potential to create real demand for her talents outside of her orbit. Perhaps even turn her skill into a legitimate business. All she needed was to paint something everyone could get excited about, but Courtney didn’t know what.

Until one random day, browsing her feed, she was let down by what she saw. Tons of posts flaunting the very trendy custom shoes, but none all that impressive. That was her ah-ha moment, when the clouds parted to reveal a clear path forward.

“I was like, [Tessa] could do a better job than this,” Courtney says.

So, Courtney had her product. Now came time for the rest. She created a private Instagram account, naming it @tailormadebytessa. She ordered leather paints and a pair of Nikes. She caught her two other sisters, Haley and Tara, up to speed. With everyone on board, all that was left to do was inform Tessa.

How do you tell someone they are running a business they don’t know exists? Duh. You make it their 16th birthday present. Obviously.

The three sisters hatched a plan. They coaxed Tessa to a hotel about an hour from their house in Lynden, Wash., masking the trip as nothing more than a birthday getaway. A staycation, Courtney called it. Their mom, Kristen, drove Tessa down while they decked out the room. Tessa walked in for the first time, saw all three sisters standing, sweet 16 birthday decorations hanging — and became an entrepreneur.

The bedroom’s walls were once blank, its furniture empty. Then Tessa moved in, and made it her own. The space pops with color and teems with life.

Paintings, plants, pictures. A map of the world, punctured by 58 pins in all the places Tessa has visited. Well, the ones she’s remembered to mark. Medals from track meets hang over ribbons from track meets. A vintage camera from the early-1900s, unearthed from a random box in their house last summer, sits on an end table.

Her desk epitomizes organized chaos. Set up to show the visiting ink-stained wretch what it looks like when she’s painting, art supplies cover everything. Brushes of all sizes complement paints of all colors. Bottles of leather deglazer sit next to bottles of acrylic finisher, the alpha and omega of the shoe-painting process.

In the center of it all is a completed pair of Nike Air Force 1s with Marquette’s logo and outlines of javelin throwers mid-launch, situated to look as though the equipment forms a protective ring around the shoes. The prize guarded by its gear.

This is where Tessa Hollander is herself. Her real self. Not the junior Marquette athlete who has thrown a javelin 43.74 meters — a mark that used to be the farthest in program history — or the civil engineering student stressfully cramming for tests. Rather, the artist at peace. One wearing noise cancelling headphones, playing a television show in the background, the low-stakes kind you don’t really need to pay attention to, and tuning out the world — while adorning leather with paint.

“That’s my relax time,” Tessa says.

She’s most comfortable with the brush in her hand. It’s when she can finally breathe. By the time she sits down at her desk, Tessa has been constantly moving. Her morning alarm blares as the sun rises for team lift at 6:30 a.m. After breakfast with her fellow throwers, she is off to class — one of her seven this semester. Then comes actual practice and more class. Followed by dinner and hours of homework and studying, she often doesn’t find herself back in the comfort of her room until 10 p.m.

Over 12 hours on the go would drain most people. Make them susceptible to mistakes, especially with the finer details. Not Tessa, a self-described night owl who prefers to paint while her world rests. She thrives in the nitty-gritty. Her hand is surgeon steady. No margin is too tight, no space too small. Minor brushstrokes trump major. Always.

Flanking the map on her bedroom wall are 12 small canvases — only 4-by-4 inches in size. The ones with people show creases in shirts and striations on bodies. Others have shadows and reflections. All the little nuances almost imperceptible to the untrained eye, but what elevate each in some obvious yet simultaneously ineffable manner.

Every speck, like on each of her shoes, is placed entirely by hand, unassisted by tools. You can find a lot of gizmos on Tessa’s desk, but not a stencil. Using one would defeat the purpose. Aides prevent her from escaping the craziness of Earth and finding peace in another dimension of leather, acrylics and bristles.

By freehanding the work, she goes for twice as long as originally planned.

“I’ll just lose track of time,” Tessa says. “Just because I get so into it and I love it so much that I’ll be painting, and then I’ll check the time, and I’m like, ‘Oh, I have to wake up in four hours.'”

Painting sessions that start at night frequently end in the wee hours of the morning. Kristen has repeatedly walked in on her daughter, head tilted, examining what appears to be — what should be — a finished product, in search of something to improve. Anything.

“Her mind is like, ‘What can I do? Something’s wrong, something’s missing. What is it?'” Kristen says. “Her mind, I don’t know how that mind works, but she sees something in her mind, and what she’s looking at is not it. So she’s got to keep trying.”

It quickly reached an inflection point, as shown by a certain Snapchat video.

In it, Tessa’s pupils are invisible, hiding behind droopy eyelids. The same cannot be said for her art supplies, as she holds her brush in one hand and phone in the other. It’s 4:38 a.m. and a 16-year-old Tessa is semi-awake, working at her dinner table. She started Tailor-Made by Tessa 11 months ago and business is already booming. So much so, she is still up, painting.

Little did Kristen know. Hours earlier, Tessa went upstairs to go to bed, only to complete a rite of passage for every high schooler in America. She snuck out. Not to party or drink in the woods, but to keep painting.

Finally calling it a night just before day, Tessa got maybe an hour of shut-eye, woke back up at 6 a.m. to finalize and box the shoes, went to school late and left at noon. She skipped cross country practice and slept for 10 hours.

Leaving orders unfinished until the last minute became a habit of Tessa’s. Kristen has had to overnight ship many shoes so they got delivered on time. Once, she even flew to Colorado to get pairs in a customer’s hands on schedule. Perfection has a price, and that time, it was a plane ticket. More often than not, though, the biggest cost is sleep deprivation.

“I love how much it tests you, and how hard it can be at times,” Tessa says. “It’s interesting, but it’s also so, so rewarding.”

One of the payoffs is real, physical, money. But, beyond that, opportunities and experiences. She did a cross promotion with her local bank her first year in business. Shortly after, she traveled to New York Fashion Week with the Australian shoe company Frankie4 — where Courtney worked — and painted customers’ initials on pairs they bought.

At Marquette, Tessa completed a pair of kicks for former men’s basketball guards Kam Jones and Stevie Mitchell for their podcast, “The K1 And Stewie Show.” She also painted ceramic, 3D-printed minions for the men’s lacrosse team in honor of Noah Snyder and Scott Michaud, who died in a car crash last September. For men’s lacrosse head coach Jake Richard specifically, she surprised him with a special pair showing the late sophomores’ names and likeness.

He wore them to every game last season.

Every opportunity has helped Tessa gain more confidence. Owning a business is scary for anyone, let alone a teenager. Starting out, only getting orders from friends and family, was great. But a pit sat in her stomach. Self-doubt crept into her mind. Do people want my art because I’m Tessa or because I’m a Hollander?

People say comparison is the thief of joy, and Tessa began robbing herself. 

“I’ll see other people painting out there, and I like to compare my design to their design,” she says. “‘Wow, I would love to be at their level,’ thinking that mine isn’t as good.”

Then people trust her with important projects. A company flies her out to work one of the world’s most premier fashion events; athletes go to her to commemorate their college playing days before turning pro; a team relies on her multiple times to honor their fallen brothers’ legacies.

“And then I do realize how much even my skills are appreciated,” she says, “and my specific style is appreciated by these certain people. So that helps to get rid of the imposter syndrome feelings.”

But not all of them. Tessa still deals with these thoughts. Maybe she always will.

To this day, after five years and dozens of deliveries, when dropping off a completed pair, Tessa still worries whether the customer will like it. She knows she put as much skill and effort into the design as possible. What if it’s not enough? What if they’re still disappointed?

“But…,” she says reassuringly, half to a reporter and half to herself. “…Everyone has liked them so far.”

A Chicago Cubs worker wanted shoes with her employer’s logo. A Dayton volleyball first-year asked for her school’s winged-D symbol on the pair’s sides, with outlines of her setting and serving on the heels. An Irish Dance group ordered shoes with their castle logo and abbreviation.

Someone at the Wisconsin Interscholastic Athletic Association wanted 12 pairs for their entire staff, all with the WIAA logo. A grandmother gave her family for Christmas 10 unique pairs — Tessa recalls one had camouflage, another basketball-themed, two with butterflies (with different colors), a fifth was Burberry-inspired and the last one she remembered had a Georgia Bulldog.

These are just some of the orders Tessa has received. She does not know the exact number, but she estimates she has completed 80-100 pairs of shoes for her business, for people in places as far away as Texas and as close as home. All with different designs for different people of different ages from different walks of life.

Each taught her certain things. Some about painting, some about life.

She knows how to prioritize her time better — there are fewer 3:30 a.m. bed tucks now than in the past. On the shoe, paint will chip off the rubber midsole first. It’s okay to advocate for fair compensation. The hardest part of an Air Force 1 to paint is anything around the Nike swoosh — it’s putting a 2D object on a 3D surface. Reaching out to people is not as scary as it sounds — in fact, it’s become one of her favorite parts of the business.

“I love communicating with people on designs and meeting all these new people,” Tessa says. “Then, slowly, I’ve become more confident in my skills, and I know how to value my skills now a lot better.”

She started her business with the small set of brushes she had since she was a child, long before her art cost money. Now, she has 36, ranging from big enough to cover entire sections with a single stroke to small enough for individual stitches. While she was given a few leather paints on her 16th birthday, she is up to 32. She recently acquired an airbrush and X-Acto knife.

Tessa used to buy the shoes with Kristen’s money and pay her back later. Now, she does it all on her own, keeping track of her own expenses and profit margins. In the early days, Courtney would guide Tessa through deals and troubleshoot hiccups as the adult voice of reason, being CC’d on emails and added to text messages. Not anymore.

Some things do remain the same, though. Like the motivations of the person wielding the brush and crunching the numbers. While the supplies and ability have improved over the years, the drive hasn’t needed to. Tessa is as lost in the gloss as she was over a decade ago, when she was not yet fulfilling customers’ orders with professional equipment, but painting whatever her heart desired with her fingers.

She’s still that same person at heart. If you think a little money jaded her perspective, you’re wrong. Tessa has and continues to wear the first pair of shoes she ever painted — with purple tips and butterflies. She shed tears to Kristen about perfecting the men’s lacrosse shoes for Richard because they mattered that much to her.

When Courtney had a son last year, Tessa made him a pair of shoes before he was big enough to fit in them. She covered the inner edge with basketballs (for Courtney, the former college hooper) and the outer edge in mini fishes (for Drew, Courtney’s husband, an avid fisherman).

The passion remains in every pair, paid or not.

“She’s giving you a piece of her heart, because she just really is trying to think of you and what would make you happy,” Kristen says. “Each shoe is made specifically for you. She wants to know who you are. She wants to know what you like. She wants to know everything so that the shoe is perfect, just for you.

“It just makes you feel special.”

After two hours spent talking about the many things Hollander holds — brushes, javelins, her bright pink graphing calculator — it was time to address perhaps the biggest question. What is she reaching for first, metaphorically and literally? With which does she most identify?

“For sure, artist first,” Tessa says.

It does feel relevant that, in the same answer, she also said she “loves” telling people she’s an engineer and a student-athlete. However, art preceded the other two. She didn’t throw a spear until middle school and, even in high school, she didn’t know she wanted to be an engineer. But she’s always been crafting, composing, fashioning, designing. Painting.

Her art is how she differentiates herself. Flexes her creativity. It’s why she inscribed her signature on her old javelin spikes, because it adds her personality to contrast the uniformity of uniforms. There are a lot of Golden Eagles, but only one Tessa Hollander.

And if art is how she distinguishes herself, doing it for others is how she is herself.

There’s a reason shoes stuck in a way other mediums didn’t. Shoes have a purpose. Not just to protect feet from blistering pavement, but more. They are a form of expression. A window into a person. Their likes, dislikes, general vibe. Rocks don’t do anything close to that.

To Tessa, the best feeling in the world is seeing her art utilized. On people’s feet, transporting them from one place to the next. A part of their daily lives.

“How many people want [shoes] really helps keep me motivated,” she says. “I love shoes because I know they’re being used, that people are actually wearing my shoes versus some other artwork.”

When Courtney gave Tessa that 16th birthday present, she had no idea if her little sister would see it through. That wasn’t the point. The gift was more than a shoe-painting business. It was an outlet. As a professional marketer, Courtney gets paid to find potential channels for people to capitalize on their abilities.

She just happens to be good at her job.

This story was written by Jack Albright. He can be reached at [email protected] or on Twitter/X @JackAlbrightMU.