The Creative Files with Holly Chapman: On Building Brands, Big Careers, and Finally Pressing Publish
Welcome to The Creative Files, spotlighting the writers, photographers, community builders, and creative thinkers who are daring to shape their own path. These candid conversations spotlight the non-linear careers, the unexpected pivots, the side quests and passion projects — the kind most of us rarely see on LinkedIn. Discover which rituals and daily habits inspire their best work, what anchors their approach to creativity and where these women turn to for inspiration.
Holly Chapman knows how to build something worth talking about. After spending over 13 years working with global brands, VC-backed startups, and fast-paced agencies, she’s honed her craft operating at the intersection of creativity and commercial impact.
A Londoner at heart, Holly spent years at category-defining stationery brand Papier, eventually moving to New York to scale their US presence (leading high-profile collaborations with The Met, Headspace, Reese's Book Club and Goop along the way).
Most recently, she's picked up her life and landed in Sydney, building a portfolio career as a brand and marketing consultant and finally, after three years of sitting on the account, pressing publish on her Substack, hi holly.
In this edition of The Creative Files, Holly explores the privileges and pressures that come with pursuing a portfolio career, why she's changed her mind on how brands should build community, and what it finally took to stop waiting and start writing.
Q. Tell us who you are and what you do, but skip the LinkedIn version. What's the real story of how you ended up here?
“I'm a brand strategist and consultant based in Sydney, via London and New York. I've spent my career building brands.
I always wanted to be a magazine editor, but ended up in PR and comms. For a long time, I thought that made me sound fluffy and like I was hosting a lot of dinners (I actually do love to host). But I now reflect back and think creative communications is one of the most underrated strategic backgrounds you can have in brand and marketing. I'm always asking what's the story, why now and then the how.
I spent years at Papier, took them into the US and Australia, built partnerships with names across fashion, wellness, art and culture (like Headspace, Rejina Pyo, Reese's Book Club, The Met and Goop), and built out their influencer ecosystem, organic social and integrated marketing and planning architecture from the ground up.
I also write a newsletter about culture and brand strategy, which is mostly just a reason to read obsessively and call it work.”
Q. You left a senior role at Papier to build a portfolio career while moving countries with a toddler. What's the version of that decision you don't usually say out loud?
“We moved for our family. My husband felt it was time to come home to Sydney (he's Australian), and we arrived with our toddler and have since had our second baby here. I'm a Londoner at heart and think it's the best city in the world, so it's been an adjustment, and I'm still finding where I fit.
Ambition looks different here than in the cities I've lived in before. New York is overt hustle, networking at every interaction. London has a quieter builder's energy but a lot of cool creativity. Sydney feels like you can have a really nice life working less, with more balance, and stability is valued here in a way I've come to respect. It's just not quite how I'm wired. I'm still working that out.
“The portfolio career has been interesting. I think people skip over the part where it only works if someone else in your house has a stable job. My husband does, and that's what allows me to be selective, to explore ideas and build things beyond client work.” — Holly Chapman
That's a privilege I don't want to gloss over, but it's also pressure. We're essentially betting on me long term. I still want the big, exciting career. That part hasn't changed at all.”
Q. What does a creative day actually look like for you: the conditions, the rituals, the habits and the way you do your best thinking?
“I don't really have one. My best thinking happens the moment I wake up, before anyone else needs anything from me. But I have two small children, so those conditions are fairly difficult to control. I grab time when I can.
I read a lot. Print magazines, fashion, news, culture, business. I love when my husband and friends send me things I'd never choose myself, and I find myself often in Substack rabbit holes. Something I read weeks ago will suddenly just click into place with something else; I love making those connections.
“I do write something every day, usually in a notebook. My desk is covered in books and paperwork, but looks tidy on a Zoom call, which feels like an accurate summary of how I work.” — Holly Chapman
And if I can get tea in the morning with a friend or someone whose ideas I love, I'll use that energy for hours after. People are a big part of how I think, and I find it underrated to have conversations that aren't about catching up and about life but about ideas. The honest trade-off right now is that I've let exercise fall away completely. I know I need to fix that by getting back into running again or, even more terrifyingly, joining a barre class.”
Q. What's something you've completely changed your mind about in the last year?
“Community. I spent years thinking about how brands build their own communities, own the audience, and own the relationship. I've changed my mind on that.
“The most interesting thing happening right now is brands building with existing communities and adding value there rather than creating from scratch.” — Holly Chapman
The audience is already there, already talking, already loyal, and there's a huge opportunity for brands to integrate in ways that build real relevance, tap into smaller niches and feel cool and of the moment rather than manufactured.
The other thing I’ve changed my mind about is working mum guilt. I listened to a podcast with Emma Grede and Dr Becky that completely reframed it for me.
The idea is that real guilt only shows up when you act out of alignment with your values. Most of what mothers call guilt isn't guilt at all; it's absorbing other people's discomfort and taking responsibility for feelings that aren't yours to carry. I'd been doing that for two years without realising it, and it stuck with me because it forced me to get crystal clear on what my values actually are.”
Q. You published your first Substack four hours before your flight to Sydney, movers packing up the house, hiding in a café with your laptop. What finally made you press publish after three years of sitting on the account?
“I was sick of myself. Three years of sitting on it, I was writing LinkedIn posts, speaking on panels, cultivating a point of view in public, but never committing to the thing I actually wanted to do and at some point that became embarrassing to me.
There was something about leaving, too. When you're packing up your life and about to get on a 24-hour flight, you reach a point where you have nothing to lose. The movers were in the flat, I had one spare hour, and I was in my local café. I wasn't going to see friends or family for a while, and I knew I had a window of reinvention ahead of me. There was a sense of possibility, too. Nobody in Sydney had a fixed idea of who I was yet, so I think I gave myself permission to just try.
“It goes back to always wanting to be an editor and work in media. Everything I wanted to say was already there. I just wish I'd been brave enough to do it three years earlier.” — Holly Chapman
Q. What are you obsessed with right now?
“I'm obsessed with so many things right now, where do I even start.
I've gone down a full rabbit hole with running brands (so now I need to get out and do some running!):
UNNA is a Swedish brand built around joy and wellbeing over performance, the anti-hustle running brand.
Alex Zono makes the coolest t-shirts, and these shorts are the kind of thing you'd want to run in and then not take off.
I'm also about to sign up for a ceramics class, partly because I haven’t found any plates I like and was inspired by KS Creative Pottery, and partly because I just want to spend time doing something without my phone.
I just finished Strangers by Belle Burden, a stunning memoir. I'm also very into Solvej Balle's On the Calculation of Volume, a novel set on the same day repeating over and over. What gets me is that the repetition isn't just the concept, it's the style too. The prose does the same thing, and somehow that makes it more hypnotic. I’m eagerly awaiting the last installment.
Mother Tongue is the print magazine I keep pressing on people. It's about modern motherhood, but not in the way you'd expect at all.
I love what Bella and Remi at Ponnd are doing, building a new kind of professional network and being really transparent about the journey. And Rolodex Media for smart culture and business writing.
The snail mail club moment feels significant to me; I’m seeing the move back to physical, tactical things people want to hold everywhere. Also, this piece by The Cool Kids Table on why the DTC cheat code is dead felt very of-the-moment.
Currently, I’m coveting:
This T-bar necklace from Tilly Sveaas that's been on my wishlist for months
Miu Miu stripe tops; I keep screenshotting, but settled for a more purse-friendly version from Bassike
Ffern for fragrance, which I look to constantly for inspiration on how a brand can build something really considered and slow
Plus, I’m listening to the new Courtney Barnett album on repeat, and the BoF podcast episode on Nike's Reality Check, which is interesting too if you work in brand.”
Want to follow Holly’s journey?
If Holly’s story resonated, here's where to find her:
Work with her at hiholly.co.uk/
Connect with her on LinkedIn
Read her latest writing on Substack