east village

amy woodside


Seven years ago, love led New Zealand-born Amy Woodside to New York City, where she has built a growing community of successful women through her digital publication, OKREAL. Amy talks about starting her own business, her personal artwork and living without excuses.


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When did you first arrive in New York?
I arrived in 2009. I was living in Canada; I was on my way home to to New Zealand and I came through New York. I was here for about a week, then I met an American guy and we were engaged three months later.

What? That’s crazy. Are you still married to him now?
I am! When we married, I was really young. I was only 22—young and crazy.

Before you met him, did you think about New York? Was it on your radar as a place to live?
I'd always wanted to be here. But visas, as you know, are such a nightmare.

It can make things really difficult.
I always had a feeling I'd end up in NYC, I just didn't know how. Funnily enough, when the opportunity presented itself (in very unexpected shape and form), I wasn't actually so sure I wanted it anymore. I wasn’t sure how anybody afforded to live here. It all seemed so out of reach. I was also really looking forward to getting back to my family after being away for six months. I returned to New Zealand for Christmas that year, then came back to the city for good in April. Moving to NYC was the best decision I ever made.

The city is truly responsive to your state of mind. New York listens.

Before you started traveling, what were you doing?
I studied communications at university in New Zealand. You pretty much had two options for a career path, PR or advertising. My first job out of school was at Ogilvy & Mather in their accounts division. I was never on the creative team, but I’ve always been a writer on the side. I soon realized the job wasn’t right for me, but looking back, I had some amazing female bosses. I realize now how much of an influence that was, especially in such a traditional corporate environment.

After a year, I quit my job and decided to move across the other side of the world, to Toronto. I didn’t know what I wanted to do, but I knew I wanted something more. As you do when you’re young, I just kind of turned up in the country. I found a place to live and a few jobs. I worked as a cocktail waitress, which sounds questionable, but it was actually just taking beer on trays to people at a punk bar. [Laughs]

I also worked in retail and as a bartender. I had so much fun. I partied a lot and I had a really great time—maybe too much fun! After about six months I was like, "I've done six months. I’m ready to go back home now." And then my trip home essentially led me to New York in the weirdest, roundabout way. I think things have a strange way of working themselves out if they need to happen.

So what did you do when you first officially moved to New York? It must have been liberating not to worry about visas.
It didn't feel like freedom at the time. It felt like no money and a lot of stress. The visa process involves a lot of paperwork and crazy fees, and I couldn’t work legally. I felt like I was floundering because I didn’t know what I was doing with my life. I was still so young—you don’t really know who you are at that age.

I ended up working as a nanny while my visa processed. I'm the eldest of five, so am really comfortable around children. To add to the visa piggybank, I started a jewelry company on the side. Jason grew up in Florida, so when we’d visit his family we would bring back all these crystals, stones and shark teeth. The jewelry actually sold pretty well. It was featured in Nylon magazine, and photographed for Vogue. I made this janky website for the product. I have no idea how I made that website. I think I googled how to write basic html, then literally went into Dreamweaver and drew boxes around the things that you clicked. Once my visa fees were paid, I was like, "Right, that served its purpose. I’m definitely not a jewelry maker…. Moving right along." It was kind of a weird time. I did a lot of writing, probably angsty stuff about finding myself. [Laughs]


What sort of stuff were you writing?
I was always into creative writing and poetry. I would contribute to zines. I was never interested in writing about fashion. I was always interested in people, but that didn't really come through until a little later. My green card took about a year to come through. A few days after I got it in the mail, I landed a job at RoAndCo Studio as a project manager. RoAndCo is a really great branding / creative agency—the whole world of branding really appealed to me, and again, I was surrounded by women in leadership. After a while, though, I started to feel stifled in terms of creativity. I had learned a lot about the business side of things, but wanted to be more involved in the creative realm. So I started painting on the side. My story sounds so ridiculous when I say it out loud! [Laughs]

Not at all; it’s fascinating.
Jason is an artist and I started painting his studio after work and on weekends. I was like, "Gosh, this is fun." I started selling some of my paintings. I put up a website that said I was an artist, and then once I had a few sales under my belt and a few projects in the pipeline, I quit my job. I worked as an artist for about a year.

What do you mean when you say "worked as an artist"? Were you commissioned work, or you sold your personal work?
Both—I was able to make a living doing it. I think that was the first taste of how rewarding it can be when you take a chance on yourself, do something you’ve never done before, and it works out.

So how did OKREAL start?
I was at a point in my life where knew what I enjoyed and what I was good at, and it was time to properly invest in something that had longevity. Trying new things, whether leaving New Zealand, quitting my job or painting—they might have felt risky at the time, but I think I was just really determined to find out where I fit into the world. It was very important to me to spend my life doing what I was meant to be doing, which I guess is the premise of OKREAL. I’d been thinking about the concept for a while, but I didn’t know exactly what it was. I thought it might be a website, but I wasn’t sure about photos, who I would talk to.… I had never photographed anyone before, I had never interviewed anyone before. But it got to the point where I was like, "I just need to start this, even though I don't really know what I'm starting, and see what happens.” I decided to drop my excuses and go for it.

I got two friends of mine onboard, a designer and a developer. We started building this website without really knowing what it was going to be for. I knew it was going to have articles, and I knew it was going to have interviews. I didn't know which was going to take precedence. I also didn't know what kind of women I wanted to feature.

But you knew you wanted to feature women?
It just didn't really occur to me to interview men. It was like, “I'm going to do a website, and it's going to be about inspiring people who have had an impact on me.” The people who have had an impact on me happen to be women. It kind of turned into this woman's thing without being super deliberate. It's the old advice: write what you know. And I don't know about dudes. [Laughs]

I started interviewing people before the site existed, and that came from having been in New York City for a good few years and working in the creative industries. I really owe a lot to those people who let me interview them at first. Each woman I spoke with would recommend somebody else I should interview. It became about the people I knew who trusted me, and then the people they knew who trusted them. The site launched in August 2014.

How do you feel about where you are now?
I feel good about it. On OKREAL there’s a lot of talk about being OK with where you are, but I also try to be transparent about the fact that I'm struggling along with everybody else. I do recognize that OKREAL has an impact on people and that's really awesome. What I find most most frustrating is that there’s so much more I want to do with the business, I’m super impatient. I am always looking for that balance between being grateful for right now and pushing for more. I think there's beauty in ambition but you never want to be that person who's constantly unsatisfied. I think New York tests you in that way.


What are some of your goals?  
Scaling the platform. It still feels very small, very New York-saturated. It’s a great place to start, but it’s a tiny bubble that could be a lot bigger. I want to expand the  breadth of the woman I speak with. That’s really important to me, to scale not just the audience but our roster of women. Our newest offering is mentorship circles—I’ve been blown away at the response to these. I curate a group of six women and we meet and talk through a specific topic—it’s kind of like a mini group-coaching session with people on your level, a place where you can feel heard and supported. The relationships I’ve had throughout my life with strong, smart women are ultimately what have helped me grow in the right direction, and I wanted to facilitate that environment for others. I’m also starting to offer one-on-one sessions in September called REAL TIME.

What’s the best piece of advice you would give?
Personally, the advice that’s helped me the most is to figure stuff out by doing it. Just start. I think we unnecessarily hold ourselves back with excuses, which are often total bullshit.

Also, try and maintain a sense of humor and lightness. I can easily go into overdrive and stress myself out, and reminding myself that whatever I’m having anxiety about isn’t that important really helps. I take my work seriously but I try not to take myself too seriously. Laughing about things takes a lot of pressure off. Whenever I get stressed about work stuff, I'll stop and think about what actually matters. Like my family or my health. I'll think about New Zealand and all the stuff that really grounds me. The people who love me and the people I love. That always calms me down because it gives me a bit of perspective.

So my advice is to get on with it, stay grounded, don't be weird and keep it light. [Laughs]

What does New York mean to you?
I think New York is really reciprocal. When I’m hating New York, New York hates me back. When I walk down the street and I'm in love with the city, then everything goes my way. The city is truly responsive to your state of mind. New York listens.

I totally agree with that. No one's ever said that before.
New York, like life, is what you make it.

Join OKREAL's mentorship circles to learn and be inspired, and follow on Instagram at @ameohmy and @heyokreal.  


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Photography by Stephanie Geddes ©

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