What Matters to Ash Oliver

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Debbie Millman has an ongoing project at PRINT titled “What Matters.” This is an effort to understand the interior life of artists, designers, and creative thinkers. This facet of the project is a request of each invited respondent to answer ten identical questions and submit a nonprofessional photograph.


Ash Oliver is an Amsterdam-based designer, entrepreneur, and founder of the solo design practice, Foster. Ash is a passionate multi-disciplined creative, proud trans guy, book nerd, plant parent, and dog dad.

What is the thing you like doing most in the world?

At the risk of sounding totally cliché, I’ll say travel and expand on why it absolutely does it for me:

Moving around a lot as a kid (like, five different schools before grade two kind of moving around) meant I got pretty good at the pick up and go, and can get my bearings in new places quickly. For this, I’m exceptionally good at leaning into the unfamiliar. Though I’m also a fairly big homebody, and incredibly habitual in my day to day, so travel really shakes up my routine, on top of being an enormous surge of inspiration and creativity. There’s nothing I love more than exploring somewhere I’ve never been. Travel invigorates my senses, and always leads to some new connection, idea, or story.

What is the first memory you have of being creative?

Growing up, I spent a lot of time at my grandparent’s house. All my earliest creative memories seem to have taken root there.

I have distinct memories of sitting at their kid desks (the old wooden types that have opening lids and an attached swivel seat) focused for hours, toiling away on some creation.

When I was six or seven years old, my grandmother encouraged me to enter a coloring contest. I remember winning, and having my name featured in the local newspaper. Later, a poem I wrote about her (an acrostic poem spelling Treasure) would win in a school poetry contest. It’s still framed, hanging in the same spot in her hallway, likely with slightly less faded wallpaper behind it.

I find it interesting that these are some of my earliest memories involving creativity. Ones that not only include my grandparents, for which I’m not entirely surprised – there were countless factors at play there, all encouraging my imagination. Among them, a fully operable,
insert-token-to-ride Chuck E. Cheese space car my grandfather got at an auction for us grandkids, along with a freestanding Tic Tac dispenser, all situated in their living room. But I’ve also contemplated how these early creative memories are also ones that included a competitive component, and some form of validation. I think this says a lot about me personally, and some about creativity in general.

What is your biggest regret?

Fortunately, I don’t have any looming regrets. I live by a motto (also a tattoo of mine) that stands for Trust In The Unfolding.

Of course, there are things I might change given the chance to go back, but mostly only to have gotten started sooner. This is more about me getting out of my own way earlier than it is a regret. Some things just take their own time.

How have you gotten over heartbreak?

I’ve certainly had my share of heartbreak. I’ve experienced the hardest of them like purging; crying so hard it feels like the sadness is coming up and out from the depths of your stomach. I’ve broken down, cry-heaved— you know, the kind of gut-wrenching sadness that only comes if you’ve loved deeply enough.

The things that have been both companions during these times— as well as offering a lending hand in getting to the other side— have been both music and making.

When my partner and I separated, I took all the postcards I had sent her over the years and turned them into a printed lookbook. I may never look at it again, but there was something cathartic to sitting down with all of those memories and creating something from them.

What makes you cry?

Nature. Music. A toothpaste commercial once. I consider this sensitivity a strength, one I feared I’d surely lose if I transitioned. Indeed, testosterone shifted a lot, but I can still get brought to tears by the trees.

How long does the pride and joy of accomplishing something last for you?

Not long enough! I’m trying to get better about this, but I have a real predisposition for charging ahead. Always pushing for better, and keen to get a jump on the next thing. It’s part of my wiring.

Do you believe in an afterlife, and if so, what does that look like to you?

Absolutely, I do! I’m not a religious person at all, and I think organized religion has caused more harm than it’s worth, but I’m a perceptive and sensitive person, and find spirituality interwoven with leading a good life.

I definitely believe in an afterlife, and feel that I have been here on Earth before. There are just too many connections to ignore that inner knowing, even if it’s not provable to someone else. In this belief of past lives, I think there might be many destinations within afterlife— ones we might experience in a physical realm, and others we may only experience on the energetic. What I hope it always conjures, however, is some inner state of being exactly where you are meant to be.

What do you hate most about yourself?

I have had to tame a pretty harsh inner critic, and operating with the same critical eye that’s been an advantage in my design work certainly has its drawbacks when you are the subject of your own critique.

I guess it’s both a positive and negative that the things I hate about myself are only physical characteristics. I’ve come to know and love who I am, but dysmorphia really warps the path towards loving your body. As a trans guy, I’m only four years into getting to know my changed body, but my mind’s eye has always had a strict measure towards the chiseled, James Dean archetype. I’m trying to soften the way I think about my body and do things out of appreciation towards it, rather than ridicule.

What do you love most about yourself?

I do not lack passion or ambition, a combination I’ve learned can take you very far, and be exceptionally rewarding especially when paired with consistency, another characteristic I’m happy I’m not short on.

People have also frequently commented on my courage. Although courage has been harder to apply to some areas of my life over others, in the end, I’m just not the type to shy away from big things.

What is your absolute favorite meal?

For as much as I loathe the term, I’m a pretty big foodie, and deeply enjoy cooking. One of the meals I’d go back and recreate over and over again is moules-frites, accompanied by a fresh chilled French wine! But as lush as that sounds, there is an equal desire for a classic slice. I can’t deny my New Yorker roots— there’s just something comforting about pizza.