Blogs by InnovatorsBox®


Originally published in: LinkedIn

How do you move beyond your job title in an industry that is risk-averse?

One in 12 residents of Washington, DC is a lawyer. While it is no secret that the nation’s capital is full of lawyers, it is not often discussed how the high concentration of legal matters has an impact on those who choose to work in this industry. Your status, skills, years of practice and gender strongly influences what role you are permitted to play, especially in a city with such a high concentration of attorneys. However, if one’s future is determined by constant measurement and comparison, one’s willingness to try something new becomes a greater challenge.

Why would you explore alternative methods of working when there is the risk of failure that can lead to real consequences? It is understandable why many don’t take such a risk when the stakes are so high.

On August 4, 2016, InnovatorsBox and WeWork co-hosted the third Beyond The Box speaker series to debunk people’s perception on legal affairs. Four innovative attorneys joined us to spark our perception and understanding of this industry that many think lacks creativity. Our goal for #BeyondTheBox is to demystify people’s perception about innovation in five industries, learn from local innovators about how they affected change and innovation, empower participants to embrace creativity, and celebrate small milestones to bring greater change.

I am excited to share the key insights from our conversation.

#3 Legal Affairs, August 4, 2016

At first glance, Sara, Keith, Federico and Skyler’s approach to legal matters looks radically different from the traditional attorneys we see at firms.

  • Sara Guerreiro is a human rights legal advisor and coach who integrates her diverse experience as a navy officer, law teacher, human rights lawyer, and a coach in Portugal, West Africa, Southeast Asia, and the United States to help individuals understand how to bridge international legal gaps in human rights with better questioning and reflecting.
  • Keith Porcaro is the Head of Technology and Development at SIMLab who integrates his passion for startups, technology, web development, and entrepreneurship to find innovative ways to make technology and law practice more accessible at a reasonable price for those in need.
  • Federico Barillas Schwank is the Legal Advisor at American Red Cross where he specializes in international humanitarian law and ‘law of war’ to educate how law can be a guardian and protector to individuals day to day as well as in complicated human rights issues and warfares. He holds two JDs from Guatemala and the United States.
  • Skyler Showell is an attorney and a small business consultant at Showell Venture & Consulting PLLC who bridges product design, industrial design, technology, and entrepreneurship to find creative ways to help small business owners and entrepreneurs understand and resolve legal matters to grow their businesses.

How did they get to where they are today? Interestingly, their paths to success were gradual. All four attorneys, like many others, initially pursued law because their communities, families, and mentors advised them that law is a great career path to make a difference, earn a decent income, and solidify professional status. And they agreed, at first. But, quickly, they realized there was something more they could do despite what society said was possible. Even during their law studies and early years of law practice, they found those challenges to be opportunities to understand what they loved versus what they didn’t. They constantly sought out ways to find possibilities beyond the box where they could integrate their passion for law and their unique strengths in technology, entrepreneurship, education, and coaching.

This is what I learned:


Let’s admit it. Being unemployed, rejected by organizations, failing a class, and failing to achieve your goals are daunting, embarrassing, scary, and even humiliating. When these moments happen, feelings of panic, uncertainty, and confusion can arise. These moments are crucial tipping points from an innovator’s point of view. How you react and recover from these daunting moments is what determines your next steps. For instance, Keith reminded us to get beyond the mentality that ‘anything is better than now.’ When you don’t appreciate what you have now, you are less likely to appreciate the lessons you are learning now and what you can gain from those moments. Similarly, Federico reminds us how no path is straightforward. Because he didn’t take that first job offer in DC when he was unemployed and in desperate need of a job, he was able to say ‘yes’ to a more exciting job opportunity that was in line with his vision and passions as an educator. If he was impatient and didn’t wait, he may still be at an unsatisfying and draining job. Sara also shared how embarking on an unknown transition from navy officer to law and law to coaching without a clear next step has been daunting. Despite societal and family pressures, she took a leap of faith and worked hard on carving out each step, knowing that she will find answers one step at a time. If she waited until everything lined up and for everyone to understand her, she wouldn’t be where she is today as a multidisciplinary human rights legal advisor and international coach.


I get it. It’s hard to stop comparing ourselves when society trained us to think that way. We were told that students with better grades will get better opportunities, and better jobs will lead to more wealth and success. No wonder so many people avoid doing anything wrong for fear of being judged. We fear what others might think of us because it damages our reputation and influences the way others may treat us. This is the point in which innovators are different. As Skyler, points out, to build your career you have to stop worrying about what others think of you and focus on your self-perception. When you care less about what others think of you, you gain more confidence and humility, and focus on honing your craft. Sara reminded us to take life less seriously. Instead of deferring to conventional rules, it’s critical to pause, seek clarity, and develop a plan. Keith echoes the sentiment as someone who speaks two jargons: law and technology. Instead of worrying about how others perceive him, he uses his specialty to help others empathize and work with conflicting positions. Someone is always going to disagree with you. Don’t let that stop you from going where you want to go.


Taking a leap of faith to do something unconventional, takes courage. A lot of courage. Innovators emphasize how being around loved ones plays a critical role.  Federico and Sara agree that family, partners and loved ones were critical for them to recharge, reflect, reenergize and remind themselves why they wanted to travel a road less traveled. For those who like community support, take Skyler’s approach where he meets with his Business Network Company (BNI) group, a gathering of 12 DC professionals in 12 diverse industries every Thursday. For Skyler, this group not only supports him professionally but also challenges him and reminds him that humility is key to learning from the paths others have taken. By surrounding yourself with individuals from various backgrounds, perceptions, and beliefs, innovators understand how these differences help them understand the world and their vision better.


When things get messy, it’s natural for us to feel frustrated and stuck. It’s how you react to these situations that makes a difference. What I learned from all four speakers is that they discovered their unique niches in law because they were frustrated and used the insights learned through frustration to change their professional trajectories. In Sara’s case, that meant leaving her home in Portugal and her job as a navy officer and lawyer to live as a human rights consultant and legal advisor in Timor-Leste. For Skyler, it meant leaving big law firms that did not match his values and start his own firm to support small businesses. For Federico, it meant leaving his home and law practice in Guatemala to enroll in a U.S. law school, gaining admittance to Bar and restarting his law practice in the U.S. For Keith, it meant that he would work for startups and nonprofits that were more aligned with his mission to provide affordable legal service a larger population. If they accepted the way things were when they felt down, they wouldn’t be where they are today. Refusal to accept and follow the status led each of our speakers to professional satisfaction.

These approaches have helped them turn challenges into opportunities. The future is unpredictable but each step toward their goals, visions, and values helped them take a step closer to building the career and life of their choosing. When asked where they would like to be if they can be anywhere, all happily answered that today at this moment is the best time. This simple answer to our SPARK question reflected how much valuing the present moment plays a role in how they navigate their day to day. Even if they started this path because others told them to, it is possible to shift the mindset over the years.

Being a changemaker means reflecting internally and building your inner strengths. Asking yourself questions and reflecting on the answers is key to build the life and career you want even if it looks different from others.

Thank you for reading. I look forward to your thoughts.

I look forward to seeing you at the next Beyond The Box in the evening of August 25, where we will meet four innovators tackling the food industry in creative ways. Tickets are free, but you must RSVP to participate.

P.S. For those looking to build a creative mindset, check out our creative bootcamp for professionals: Creative Jump on August 20-21, 2016 in Washington, D.C.

About the Author

Monica H. Kang

Monica H. Kang

Monica H. Kang, Founder, and CEO of InnovatorsBox® and Author of Rethink Creativity is transforming today’s workforce through the power of creativity. She helps companies rethink culture, leadership, and team development by making creativity practical and relatable regardless of industry or job title. She has worked with clients worldwide including Fortune 500 companies, higher education, government, and nonprofits. Monica’s work has been recognized by The White House, Ashoka Changemakers, National Minority Supplier Development Council (NMSDC), and Women’s Business Enterprise National Council (WBENC). Prior to InnovatorsBox®, Monica was a nuclear nonproliferation policy expert. She holds an M.A. from SAIS Johns Hopkins University in Strategic Studies and International Economics and a B.A. from Boston University.

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