Boss Babes: Meet Amy Woodside

Photo via Vanessa Granda

Let’s be real: becoming an entrepreneur just sounds amazing. You usually get to create your own hours and you’ll get to see your ideas come to life. The thing is, being your own boss is not as easy as it sounds and just thinking about beginning your new venture can be terrifying. Although waiting until you’re ready could be an option, today’s Boss Babe did the opposite by taking her career into her own hands to make her dreams come to life.

Just like most of us, Amy Woodside was just trying to figure her life out. At the young age of 22, she flew from her native country, New Zealand, all the way to Canada in hopes of finding the answers she was looking for. While making NYC her home and becoming a successful artist would have sufficed, Woodside knew she wanted to do more. OKREAL was created based on the idea of unmasking the community of strong entrepreneurial women and their stories. From artists to store owners to authors, Woodside interviews and discovers how some of the best leading ladies push through the glass ceiling by molding their careers into the one they’ve always dreamed of. While each interview is unique, they all have one purpose: to help enlighten and inspire other women to take charge of their life and career. And because we’re #teamwo-man, we’re always down for a little bit more girl power in this world.

We got to hang with Amy at Happy Bones for a quick chat about OKREAL, some of her favorite NYC restaurants, and what she misses most about New Zealand. Meet the Kiwi Boss Babe of our dreams, Amy Woodside.

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Photo cred: Vanessa Granda

Photo cred: Vanessa Granda


Auckland, New Zealand

Current location:

New York City

Birth sign:


NYC restaurant you can visit over and over again:

Lucien, Scarr’s Pizza, Dimes

Jewelry line you’re currently obsessing over:

Anna Sheffield and Bing Bang

Photo cred: Vanessa Granda

Photo cred: Vanessa Granda

Best way to end a productive day:

A drink

Ultimate beauty product for the summer heat:

Salt water

Coffee or tea:


Personal motto you always live by:

Get on with it

Photo cred: Vanessa Granda

Photo cred: Vanessa Granda

Tell us a little bit about what you do and how you came up with OKREAL?

I spend my days hearing and sharing the stories of incredible women, gathering up good advice to put out into the world via and @heyOKREAL, and trying to soak it all in as I go. In terms of how OKREAL came about, I’m always trying to sort my life out. And I’ve always been interested in how other women figured their lives out. When it came to women I admired, the stuff I wanted to know wasn’t being told. I wanted to get a deeper insight into who these women were — what they struggled with and how they got through it, what influenced their choices, what motivated them and what freaked them out. I wanted the truth, not some glossy one-liner about balance. I thought other women would be interested in this, too. I wanted to create a resource for women who are striving to take ownership of their lives and want authentic advice to help them do so. OKREAL is about learning from others to help you see yourself more clearly.  

What is one thing you miss from New Zealand?

The fresh air. My family. Many things!

What was one of the most authentic advice you have ever received?

You will never be ready. For anything. For that child, that job, that opportunity. Just do your life. Don’t wait till you’re ready. Get on with it. —My mum

You left New Zealand for Toronto to “find yourself.” Did you feel like that experience made you grow and help you become a better entrepreneur?

Haha. This makes me laugh because it seems so silly now. You don’t find yourself, you build yourself. But I do think that throwing yourself into the unknown is a great way to learn. At 22, that meant arriving in a different country by myself. And now it means creating a career that I’m making up along the way. I choose to put myself in situations where I don’t know what I’m doing, because I know I’ll be better for it. You become extremely resourceful when your only choice is to figure it out.

What is the most important element of your business, and how do you maintain consistency, especially when it comes to creating content?

The most important element to OKREAL is maintaining a relationship with our audience. To always be listening and growing in a way that speaks to them. Consistency comes from respecting instinct. I don’t do anything that feels weird. When I do what feels good, the brand maintains authenticity and consistency. This translates from the women we feature, to our event partners, the language we use, right down to the colors on the site.

Why do you feel it’s important to have a creative outlet? How do you stay inspired every day, especially in a city like NYC?

It’s important to have a creative outlet so that you don’t lose your mind. What’s interesting is when your creative outlet turns into a startup, which is what has happened with OKREAL. Before I began the site I worked as an artist. I still do commissions (and am working on a few fun projects right now), but don’t get as much time to paint and write ‘for fun’ anymore. But I’m still having fun! It’s just different. I’m constantly inspired by the women I feature. Their stories have built the world of OKREAL and I’m forever humbled by their openness and generosity in sharing their experiences for the benefit of others. I also think inspiration comes from process—from actually doing the work. If you lie around waiting for inspiration to come to you, you’ve got the wrong idea.

Photo cred: Vanessa Granda

Photo cred: Vanessa Granda

If you can have a drink with anyone, anywhere, where would that be?

With my best friends from New Zealand, who I see once a year (if I’m lucky). On a boat in the sun would be pretty nice.

What’s so important about surrounding yourself with women that are in leadership roles?

Because it enables you to set higher standards for yourself. It humbles you and reminds you that there is so much to learn. I always want to be around people who are smarter than me. That’s how I grow. You can’t grow if you’re stuck inside your own tiny world the whole time.

Was there a situation that you experience that influenced you to become your own boss?

There wasn’t anything specific that drove that decision. I had always wanted to work independently but had absolutely no idea how to go about it. Gradually I got the guts to take the leap, but I still had no idea what I was doing. At the time, it wasn’t so much ‘let’s see if I can be my own boss,’ but more like, ‘let’s see if I can survive without a steady paycheck!’ Going back to my mama’s advice, I try and kick readiness to the curb. Clarity is overrated.

Where do you see the future of OKREAL in the next 5 years?

World domination!

Any advice for future Boss Babes, especially who wants to create their own business?

I love the advice Elle Rowley gives in her OKREAL interview:

“I think it’s so important to take yourself seriously from the beginning and envision the biggest thing you can. In the early stages of something new, it’s so easy to have this attitude of, ‘Oh I’m just starting this little thing, it’s super whatever.’ Why not say, ‘I’m going to start this mega awesome business that’s going to change the game?’ Let’s do that more. To take anything to the next level you have to be able to see it first. If you can’t see it, how are you going to get there?”

Photo cred: Vanessa Granda

Photo cred: Vanessa Granda

Take a peek at OKREAL to get inspired for your own personal journey by checking out all of their rad interviews and events. And while you’re at it, make sure you visit Amy’s Instagram, too, for some cool behind-the-scenes action.


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Photography via Vanessa Granda 

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