“When you approached me about this interview, I was really worried. Not only worried about what the crowd was going to think, but also about my own inner critic. Am I a good boss? The bosses and leaders I talk to are always trying to figure things out. Whether you’re an employee or a boss, I think we can all have more sympathy for each other.

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Strategy

It took me about a year to go out on my own and start freelancing. I didn’t have a lot of peers out there doing the same thing—whereas now, everyone is going out on their own. I was getting a lot of freelance offers outside of my full-time job and burning out—working my day job, then working nights and weekends. I wanted a better lifestyle, and thought—I’m 25, don’t have a family, don’t have a mortgage, don’t have anything holding me back. It was the best time to do it. It was a risk in some ways, but I could always go back and find a job if it didn’t work out. But it took me a while. I talked about it a lot. I remember going out to a party and telling somebody, I’m going freelance! I’m quitting my job! And they were like, you told me that last year, get on with it.

When I went freelance I had no idea what business strategy was. Over the years I’ve been known to say that I don’t want a business strategy, but I’ve come to understand the importance of one—although perhaps it’s less important to have one at first. You need to figure out what you want within you, then see how that goes over the course of six months, a year, maybe even five years. And then start being strategic.

But at the end of the day, hard work beats strategy.

If you’re not willing to put in the hours, you’re not going to get what you want. It all comes from an inner desire to create something that you believe in… that feeling that you get in the pit of your stomach when you’re like, I have to do this, I have to figure it out, I have to make it happen. You have to listen to that guiding force, put the hard work in and make it come to life. When you get to a certain point, you need to be able to step back and say: are we doing the best we can possibly be doing, and are we doing it the smartest way? I think it’s common for people who have achieved a certain level of success to get comfortable with things working like clockwork. You end up relying on everybody who works for you to snap into that well oiled machine. Then one of your top performing employees might leave, or the industry could shift and all of a sudden you have to pivot your business. And that’s when strategy really comes into play. I think it takes a lot of courage to say, I’m at a point where I’m not as good as I thought I was, and I need to change something to move forward.

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I don’t feel as though I necessarily have balance in my life. I think it’s absurd to assume that every day is going to be balanced. That you’re going to wake up in the morning and meditate and do yoga and find the most beautiful and serene working environment and that every meeting is going to go successfully, that you’re going to get time with your kids, partner and friends. I think that you have to pick and choose on the days that you can. Some days I’m like, today’s my yoga day. Today I have to do it and get it out of my system and I’m going to roll up to the office late and I have to do that, because I was stressed as hell yesterday and I’m not going to be a good boss, wife or mom if I don’t do that today.

I think we’re always trying to find balance, but I don’t know if it’s always there.

Every so often I’ll take a risk, but it’s usually something that I’ve been thinking about for so long, that I’ve actually figured out a way to not make it a risk. If you take one risk, that snowballs into more risks. Whenever I make a big decision, I need to talk to 50 people about it to make sure I’ve covered my bases. But I’ve always been very calculated in my risk taking. It’s taken me nine years to get to where I am right now. In tech world that’s like 100 years. I see some of my clients who are a fraction of my age taking insane risks, and I’m like, ehhh, OK, go for it, I believe in you! Haha. Which in a lot of ways is really inspiring to me, and keeps me on my toes. You can never really settle. You can’t just assume that once you hit a certain level of success that it’s always going to be there.

Try and stay humble in everything that you’re doing. Stay curious. Look to people for help.

There will always be times when you’ll only be able to see what’s right in front of you. When you’re in that stressful place where things are shifting underneath you and you don’t know why or how to control it. But I think you come out of those situations with more clarity, which is the silver lining. It’s hard to get there sometimes when you’re in the muck. But those moments are when you have to be in tune with your intuition and think, what can I learn from this experience? How can I look up? Because when you look up, that’s where the good stuff comes from.

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Money

I think we’re raised in a culture where we hate talking about money. I’ve grown much more comfortable with the subject over the years. Knowing what to ask for, knowing what to get. I think that that comes with experience. My first job, I didn’t know what to ask for, I just took whatever they gave me. I was just happy to have a job! It’s interesting being on the other side as an employer, to see the different personality types that come in and what their expectations are. Some employees always are happy with what they’re given and some are always unhappy with what they’re given. And managing both is an interesting thing. On the flip side with clients, it’s always tricky trying to figure out what our worth is.

Is our worth based on the amount of time we spend doing work? Or is it worth what they’re going to get in return?

That’s very hard to calculate, especially when the industry is shifting. Things that were very valuable not so long ago are not as valuable anymore. For example, web design is very valuable for every business at this point. But now you can get Squarespace or any other kind of template, so the value of custom design decreases. But then people start seeing the same cookie-cutter Squarespace template sites everywhere, and realize they do need custom sites and want our help again. The value fluctuates a lot and that’s something that we have to contend with all the time.

When I first started freelancing, I was always willing to work for a super low rate for friends or people who were inspiring to me. But eventually, as you hire people, you need to pay them in cash. You can’t pay them in like cool points, or whatever. Now, we’ll do free work for a charity, or if it’s something we really believe in. In some ways, that motivates the design team. They want to be able to work on fun exciting projects. Every once in a while I’ll come up with a rule and be like, ‘Mark my words—we’re never going to do an unpaid pitch again!’ Then of course some fabulous fashion brand comes along and they want an unpaid pitch. Damnit! I just said two weeks ago that we weren’t going to do this. And then we do it again.

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In terms of men vs women being better negotiators, I’ve found that it really boils down to personality type and upbringing. For example, I come from a family where my father and mother both worked. My dad worked at IBM for 40 years in an upper management position. So he’s always asking me, how much money are you making, what’s your overhead, what’s your hourly rate? He’s always grilling me on that. But my mom on the other hand is like, don’t be too presumptuous, don’t assume that everyone is going to want to pay you that much. So maybe on one hand that shows gender roles, but it also shows that I’m a result of both of them. I really am right down the middle.

I don’t want to be taken advantage of, but I also want to be fair.

For anyone who’s an employee, absolutely fight for what you think you deserve, but don’t fight your way out of a job. Or don’t fight your way out of the relationship you have with your boss or your manager. That’s one of the hardest things that I deal with—feeling like I’m in negotiation with people who I want as my allies. If you’re always in negotiation with your employees, there’s this underlying feeling of, is this person on my team or is this person on their own team?

New York City is a really competitive environment, and inevitably you’re going to compare yourself. But sometimes I think the beauty of the city is that it fosters competition. The competition is in your face, but it can be a good thing. It drives you to achieve the next thing and reach for goals you may not have thought of otherwise.

I try not to compare our business too much to others, because then we lose sight of what’s special about us.

And Instagram isn’t always necessarily truth. You could see an amazing looking brand on Instagram but they make no money. What is success at the end of day? Is it having an amazing Instagram with your highlight reel, or actually having a sustainable business?

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People

Managing people has been the the most challenging for me. When you’re a freelancer, your biggest challenge is most likely getting clients and dealing with their expectations. Then as you grow a business, not only are you dealing with clients, you’re dealing with your team. At the beginning, when I was starting my business, I didn’t know how to manage people. I kind of assumed that if you employ someone, they’re just going to work for you and that’s all you have to do. They should just sit there from 9 to whatever hour of the night that you’re there, and work their butt off towards creating great work for people. But as the studio grew and the personalities started stacking up, and the needs from employees increased as our demands from clients increased, that’s when it started to get tough. It was very hard for me to understand how to manage multiple levels of the business with multiple personalities—and how to motivate people in different ways to keep them engaged and inspired. In some ways you want to hire people who are self-motivated and will work autonomously, yet sometimes those people can be the most problematic—because they have strong opinions and they challenge you. Yet again, that challenge makes you grow as a leader. It’s a tricky balance.

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I have less one-on-one time with the people on my team, which is a bummer, because I really do enjoy having social time with people that I work with. I love being able to chit-chat and shoot the shit and hear how their weekend was. But the more that you grow and get your business off the ground, the less time you have for that. I spend a lot of time in meetings with clients or my exec team. Whereas I used to really be in the trenches—sitting with the designers and talking to them all day long. In a lot of ways I miss that, that was really fun for me. But as I’ve grown I’ve needed other people to do that, and there are people who do it better than me. That’s always exciting, hiring people who are better at things than you are. I’m very proud and happy to see that.

Achieving autonomy within your team takes time and trust.

You want to be able to trust that person to produce work at a certain standard on their own—that’s the ultimate goal. I don’t like having to sit people down to tell them that they’re not doing a good job. Especially when you like the people that you work with, to have to sit them down is really challenging. So autonomy is very important. On the flip side, if you give employees too much autonomy you can end up feeling like you’re not in control, and sometimes that can lead to friction. I always like to hire go-getters. But how do you keep the go-getters? That’s the big challenge. The ones that want to go freelance or go start their own businesses. They’re there, they’re doing their homework. They’re watching what I’m doing, they’re watching what everyone is doing and they’re feeding off of that and that’s good too. I think it’s good to have a balance of people who are loyal and will stick with you for long periods of time, and people who are like, I’m going to come here, figure it out, conquer it and I’m gonna peace.

Managing people is hard, but managing your own self-critic is harder.

Being the boss can be very unpopular. You’re often thinking, what do people think of me today? I told everyone they had to work late. I’m so unpopular, everyone hates me, this is the worst, I feel like shit. But this is what we had to do to get work done. The inner turmoil is really difficult, but I think that you can find your best management skills through the hardest times. I really appreciate my team, and wouldn’t be able to do what we’re doing without them. At the end of the day, when somebody brings me their personal problems or complaints about another employee, it’s because we’re all human. I also try to remember that the people who work for me are dealing with their own inner turmoil. They’re up against deadlines, my expectations, what their co-workers think of them. They’re dealing with their own stuff, and to remind them that I’m dealing with stuff too is hopefully helpful. Who knows, it may be a bigger burden—they might be like oh shit, the boss is freaking out! Ha.

I think I’m pretty resilient and tend to bounce back pretty quickly. I was at a talk last night and someone said: Getting back up when you’ve fallen down is the greatest measure of success. It’s impossible to show grace and courage all the time, but I try to stay consistent and handle the pressure in stride. Unfortunately my husband probably bears the brunt of a lot of my stress. I come home and the calm facade that my employees see changes very quickly. Over time I’ve built up a tolerance for tough situations—the more I go through the less it tends to phase me. But when it rains it really does pour, and it can suck at times. Sometimes I’m like, nothing is working and my world is crumbling. Often I just think—I have to be absolutely real with everybody here and let them know that I’m not the “fearless leader” they are expecting me to be. I have to be honest and tell them, I’m totally a mess and this is not working and I need your help to make this better. I’ve been really lucky to have people that care enough about what we do to help me figure out how to push things forward when they don’t seem to be working. I definitely have my moments where I butt heads with someone I’m working with, but I always try to come back gracefully and apologize—and let them know, I was in a very stressful and ambiguous place and I didn’t mean to say what I said.”

I think that to be a leader you need to be vulnerable, and I think showing your vulnerability at times is courageous.

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Read Roanne’s online OKREAL interview here.
Photography by Sofia Tomé.