Ok Real founder Amy Woodside

Women compete, compare and undermine one another – or least that’s what the prevailing rhetoric would have you believe about the way we interact. Famous women like Jennifer Lawrence, Beyoncé and Taylor Swift are heralded as feminist heroes, in part, because they belie that stereotype. Being beautiful, talented and absolutely nailing their respective fields while actively celebrating the achievements of their peers and not being catty about their successes is portrayed as something novel. It doesn’t sit right with me but I’d be wrong to say that feeling on guard around other women isn’t a reality I’ve grappled with. It’s something many of us have experienced at one time or another – and it’s exhausting. Particularly when interviewing women further along in their professional journeys for our careers section, I’m often told stories about having to tackle that ‘there can only be one’ mentality with other women, so there is definitely something in it.

There’s countless research about female competitiveness – mostly laughable but there are some interesting takeaways. A literary review piece by Tracy Vaillancourt in 2013, for example, found that women express indirect aggression to other women as a means of “self-promotion” to make themselves look better but also to derogate their rivals by being catty.

Ok Real founder Amy WoodsideI remember going through school and seeing my relationships with friends change from being a mutually supportive network to one that was quick to point out its members’ flaws in painstaking detail. Starting The Lifestyle Edit and being part of this new generation of female founded businesses has completely transformed my relationships with women though. My clients are all women. My mentors? Women. The people who have wilfully connected me to the right people or who have read and shared my work as soon as it’s gone live have always women. Dinners now are spent constantly affirming one another – women congratulating women about on their books, keynote talks or a nice outfit – and when I mention that I’m having a shit time, they’re the first to rally round. Yes, I want to succeed but I want all the women around me to as well, and I genuinely believe that they want the same for me.

And that’s what brings me to OKREAL’s founder, Amy Woodside. In many ways we occupy a similar space. OKREAL was launched with the MO to help women be real about the issues that matter most. Think of the site as the ultimate no BS guidebook. Not only does she share the candid stories of women in the fashion and lifestyle community on a range of topics from managing our expectations to harnessing confidence, she’s also created a space where likeminded women can connect in a relaxed environment over wine for informal panel talks and mentoring circles. Speaking honestly here for a second, I was initially in two minds about running this feature to begin with. Surely it wouldn’t make sense to spotlight a publication with a similar mission as my own, right? Well, the short answer is, of course it does. And interestingly, it goes to the heart of this whole idea of female competitiveness. Competitiveness is often shrouded in secrecy and often results in guilt. It’s one of those things that takes growth to overcome. The reality is: we really competing with other women but with ourselves – and often the gap between where we are now and where we feel we ought to be. For many of us, we look at the accomplishments of others and see a better version of ourselves. We don’t see the other women and her story at all. Instead of being threatened by the presence and successes of others, wouldn’t it be great if we allowed one another the space to succeed in a healthy, collaborative way? It’s watching the incredible community Amy’s created with OKREAL and the way she continues to support that community that inspires me.

I spent an afternoon with her recently, strolling around her neighbourhood in New York’s East Village sharing our stories about how life brought us to this point and what our missions were when we set out on this scary start-up journey. Unsurprisingly, she’s now one of my favourite people and after reading her story, I’m sure you’ll feel the same.

THE BIG IDEA: I think there are fantastic digital resources for women in the career, relationship and wellness realms—but when it came to understanding who someone was, what influenced their choices, how they got through challenges—I couldn’t really find this out there. Something that was more about someone as a whole, whose story I could learn from. I also thought a really down to earth and honest voice was missing about what life was really like for women. OKREAL is sometimes referred to as a kind of modern self-help, which I guess it is, but more from the angle of sharing personal experience as opposed to telling someone what to do. We also talk about the hard stuff in life as much as the good stuff—we keep things real. OKREAL is about learning from others to help see yourself more clearly. 

ON OPTING AGAINST INVESTMENT: My advice is that you will need more money than you think! I used my own money to launch OKREAL. This is not the solution for everyone, but this is what worked for me. I was always deliberate about the site being sustainable, but I wasn’t in a rush for it to happen. It was more important to me to establish the platform, create and harness a community, then develop a business model from there. Investment requires very clear data driven projections, which at the time of launch, I didn’t have. I mean, I launched a content website. Hardly a money maker! But I knew that if I put in the time, opportunity and money would come. And slowly but surely, it has. I was never going to be someone who created a product out of nowhere and sold it. It’s just not how my brain works. Events were a natural next step for us, as was ecommerce. I ignored the people who didn’t understand it at first and thought I was an idealistic weirdo, and said in my own head ‘Just you wait and see.’


OKREAL founder Amy Woodside


ON CHOOSING WHOM TO INTERVIEW: I try and feature a range of women who are at different stages in life, some more established, some less established. If I’m speaking with someone who has had a lot of publicity, I try not to ask them the same questions I’ve read them answer time and time again. In terms of being on brand, everything we do has to be of value to the reader, has to teach them something in one way or another. I think being on brand and staying consistent is a gut thing. I don’t do anything that feels weird. 

ON THE EVENTS LIMB OF OKREAL: We have such a radical, supportive and smart community, who are really using OKREAL as a resource—they’re using these women’s stories, lessons and wisdom to help inform their own choices. Facilitating an environment where they can connect with each other and learn together was a no-brainer. Women want to engage with each other—it’s how we feel connected, right? To see women take notes throughout the live interview process, to hear stories of how they’ve gone on to collaborate with women they’ve met in the audience, or how they were motivated in a mentorship circle to leave a shitty job—that is so rewarding for me. I think it comes down to really knowing what your audience needs—always listening to them, understanding what people respond to and what they don’t—the more in tune you are with your audience, the better you can serve them. 

THE POWER OF COMMUNITY: Women in my own network were so important to the growth of OKREAL. I think everyone deserves to be surrounded by people who will lift them up, and that’s what our mentor circles are about. They’re curated, concentrated groups of women in the OKREAL community, led by myself and sometimes a special guest. Sessions focus on enabling participants to overcome obstacles and reach their goals through group discussion, network connections, and leveraging relationships within the group circle. Basically: we talk about what we’re going through over wine, share what works and what doesn’t, come to solutions together, and hook each other up with contacts. I’ve also just introduced REAL TIME, which are one-on-one sessions with me and a member of our community. I’m really interested in helping women define what their version of fulfillment is, and figuring out what they need to do to get there. Mentor Circles and REAL TIME are great ways to do that. 


OKREAL founder Amy WoodsideDEALING WITH MOMENTS OF SELF-DOUBT: I think the fear of making a wrong decision is often worse than the outcome. I prefer to make a decision, decide to make it work, and if it doesn’t, I’ll figure something else out. I don’t believe in wrong decisions (within reason!) I think mistakes are perfectly natural and necessary, and that your recovery speaks more of your character. If I let doubt rule my choices in life I’d probably be back in New Zealand, working a 9—5 that wasn’t right for me. I doubt myself all the time. I’m never sure. But I’ll close my eyes and jump, see where I land and go from there. Clarity is overrated, get on with it and iterate as you go. 

ON THE IMPORTANCE OF SELF-CARE: Some people pride themselves on how little sleep they get, like it’s a badge of honor. Not me. I need sleep, I need to work out regularly and I need to eat well. Otherwise I’m a total mess and can’t do my job well. Most of the time I’ll have two out of the three going well—it’s definitely not a perfect balance, and I probably work way too much, but whatever, I’m trying, and I’m happy! Something I’m learning all the time is how to set boundaries for myself. I think as women, that’s a particularly push-pull process. What do you stand for? What are you going to speak up about? What is important to you? What are you going to say yes to, say no to? I think we can be preoccupied with the people around us, and are left with the smallest sliver of energy for ourselves. Imagine if you used some of that giving, loving energy that you pour into other people on yourself? Even just 10% of it? I think we forget how precious our energy is and can spend it on the wrong thing. I often make the mistake of taking things too personally, taking responsibility for more than I should, placing way too much pressure on myself. I’m constantly toeing the line of having high standards for myself and self-kindness. I find that very difficult. It takes a lot for me to say: That is not my problem, I am not worried if you do not like me, I am enough as I am. 

ON THE FUTURE: I think the core of what OKREAL is—a platform that lifts women up and helps them figure their lives out through storytelling and conversation—will remain. But I see our offerings scaling… we’ve really concentrated on our New York City core over the past year, and bringing OKREAL to different countries and women around the world is something we’re working towards. So… world domination?! I am super organized and a bit of a control freak by nature. I am very future-oriented and am always thinking about what’s happening next. But what I have learned is that flexibility is my friend. I have my plan, I know what I want, but I’ve also learned to loosen my grip a little. Sometimes you can hang on so tightly to a plan that you end up self-sabotaging. There’s no grace in that high-strung, stressed out way of operating. You also have to be able to respect and enjoy the process—as my friend Bonnie said in our live interview: “We often think, when I achieve this then I’ll feel great, or when I reach that goal I’ll know my work is worthy. From my experience, if you don’t like the process—right now, today—of doing what you’re doing, then the outcome is not going to be any better.”