Navigating Two Careers. Choosing One Life: Roxy Heapy and life in the Messy Middle

Some people enter your life and leave a lasting imprint. That’s Roxy Heapy.

She’ll turn up to do your makeup, and somehow leave you feeling more like yourself than you have in months. She doesn’t just enhance your features - she mirrors your strength, your softness, your spirit. You leave with great brows, yes - but more importantly, you leave feeling seen.

Roxy has built her life with intention. She’s worked, fiercely and gradually, to shape something steady out of a past that gave her very little to stand on. And yet, here she is. Rooted. Radiant. Stronger than she knows.

Eighteen Years, One Steady Climb

Roxy’s been with Fanatics, a global leader in sports merchandising, for 18 years. It was her first job out of school - a Buying Admin Assistant at Kitbag, which later became Fanatics - and she’s never looked back.

Now, she develops apparel for leading football brands, thriving in a fast-paced corporate world she’s helped shape from the inside out.

But her success didn’t come from a fast-track graduate scheme or LinkedIn strategy. She didn’t go to uni. She didn’t have the luxury of finding herself in her early 20s. After losing her dad at age 10, Roxy stepped into a caregiver role for her two younger sisters while her mum turned to alcohol. The only option was to grow up fast.

So she did. She chose work. She chose stability. She chose building a life - from scratch.

Something of Her Own

Alongside her corporate role, Roxy has spent over a decade growing a part-time business as a bridal and special occasion makeup artist. What started as a course because she couldn’t quite master her own eyeliner turned into a fully booked diary, loyal word-of-mouth clients, and a personal brand rooted in trust.

She didn’t start out knowing what she was doing. She said yes to everything. She underpriced herself. She took on too much. Because back then, she just needed the extra money. And she didn’t want to let anyone down - especially herself.

Now, she knows her worth.

“Pricing your own business comes with confidence,” Roxy says. “At the start, I just wanted to get the work. But in weddings, you’re not just a makeup artist. You’re a confidant, a calming voice, someone who helps people feel beautiful on the most important days of their life.”

Today, she’s selective. She’s balanced. She’s learned to say no — to protect her peace, her time, and the people who matter most.

“I Had to Succeed for Myself”

When asked what drives her, Roxy doesn’t hesitate:

“I had a terrible childhood… I had to build something different. I needed to succeed for myself.”

It’s not about proving anything to the world. It’s about rewriting her own story - carefully, and with compassion.

That’s what led her to counselling after a difficult breakup.

“It changed my life,” she says. “I can’t recommend it enough. It taught me how to cope - but also, how to understand myself and my past.”

It’s what led her to running, too. Starting with a PT, then Couch to 5K, and eventually building a 68-member running club at work. In May, 28 of them completed a half marathon.

“I never thought I’d get there,” she says. “But you can do anything you put your mind to.”

And she means it. Because she’s lived it.

The Conflicts

Even now, even with everything she’s achieved - two careers, a team behind her, a name trusted in two industries - the imposter syndrome still creeps in.

“Am I good enough because I didn’t go to uni?”
“What if I’d made different choices?”
“Why do I still compare myself to others?”

Like so many of us, Roxy feels the pressure - the expectation to have done more, been more, reached more by now. Especially in a world where social media only ever shows the filtered side of the story.

“It doesn’t show the gaps,” she says. “The struggle. The heartbreak. The pressure of being 37 and childless, the fear of not feeling secure… That stuff’s invisible online. Even in my own feed.”

But that doesn’t mean it isn’t real.

Real Strength Looks Like This

Roxy is cautious with her energy. She’s deliberate with her choices. She protects herself now, where once she might have pushed through.

And even though she could go full-time with makeup, she won’t - not unless she has to. Because the truth is, she loves the balance.

“Without the corporate drive,” she says, “my brain would turn to mush.”

Roxy isn’t chasing a dream she can’t define. She’s living a life she’s built, piece by piece. A life that stretches her mind, uses her heart, and honours where she came from — without letting it decide where she’s going.

A Final Note

From the outside, Roxy might seem like someone who’s got it all together. But like everyone we meet here, she’s still got a next step ahead of her. 

She’s still growing. Still learning to rest. Still learning to receive. Still becoming.

“That’s why Notes from the Not There Yet is needed,” she told me. “A place away from AI… a place for real conversations. About the struggle. The reality. What it actually takes to get here - even if you’re not fully there yet.”

So if you’re in your own middle - unsure, comparing yourself, doubting your path - let Roxy be your reminder:

You don’t need a degree to be brilliant.
You don’t need permission to begin again.
You don’t need to be “there” yet to be proud of how far you’ve come.

You just need to start.
And keep going.
Exactly like she did.

Listen to Roxy Heapy's Story 

 

Find Roxy Heapy

You can find Roxy on Instagram.