A Personal Reflection: On Transitioning & Entrepreneurship

In celebration of the International Transgender Day of Visibility, I find myself reflecting on my own transgender journey; specifically those first few years of my social transition. While fifteen years have passed since those early days, I can painfully remember the careful deliberation, the exploration of all the possibilities, and the persistent fears of rejection, discrimination, and violence. My social transition was one of the most difficult experiences I endured as a young adult, and because of it, I am incredibly grateful for the survival skills I mastered. Interestingly, these days I am leaning heavily upon those skills to strike out as an entrepreneur, and building a business that is transforming leaders and organizations around the country.

My intention of sharing my personal experiences are twofold; 1) to cultivate more trans allies who are entrepreneurs, and; 2) to inspire more transgender people to apply the skills they have gained through their transition and realize their own dreams. If you’re skeptical as to how transitioning relates to entrepreneurship, consider the following themes:

Following Your Heart

Like other transgender people, I had a clear understanding at a very early age that I did not identify with the gender I was assigned at birth. Deep in my heart, I knew who I was and as a young adult I felt the urgency to transition in order to live an authentic life. Similarly, many entrepreneurs come to a realization early on in their careers that they have both a calling to make something big in the world, and that in order to make an impact they need to strike out on their own. For both transgender folks and entrepreneurs, following the heart’s wisdom offers the trusted guidance that leads to an authentic life full of purpose. Let the heart lead the way towards empowerment and movement in the right direction.

Doing What It Takes

I followed my heart, and became clear about what I wanted with respect to my transgender journey. Early on there were many obstacles littering my path, many by people who had good intentions, but failed to respect and affirm me. I did my very best at working around them, and building an intentional community of like-minded trans folks and allies. As a rookie entrepreneur, I am quickly recognizing that like transitioning, obstacles are a natural part of the journey. Creating a clear vision, and doing the everyday work to establish a strong foundation takes an unprecedented amount of discipline, humility, and commitment. Even with the right amount of heart, smarts, guts, and luck, the barriers are real and failure along the way is just a part of the process. Whether it relates to transitioning or entrepreneurship, rooting a vision in authenticity and aligning yourself with a pack of like-minded supporters will enable you to overcome the obstacles that await.

Recreating Yourself

When I first started asking people to use my chosen name and pronouns, it was a big step forward to living an authentic life. It felt really good to introduce myself to new friends, acquaintances, and colleagues. Reintroducing myself to family members, long-time friends, and professors; however, was a much more difficult process, as these folks had long known me by my dead name, and associated me with my assigned gender at birth. This change felt like a lot to ask of others, and when it confused those close to me, it often made me feel misunderstood. As an emerging entrepreneur, the recreation of my professional self feels strangely similar. In a way, I find myself navigating a professional transition of sorts. People have long recognized me as a LGBTQ advocate, fighting for progressive legal and policy changes. These days, I am sharing my expertise as a management consultant helping leaders transform themselves and their businesses. While my skills, expertise, and abilities remain the same, my role has shifted. There is an ease of sharing my new professional identity with new colleagues, while reintroducing myself to long-time colleagues and friends requires more careful conversations and time to share my vision with them.

Facing Your Fears

Despite my racial, class and economic privilege, transitioning posed a great amount of risk, and generated a giant heap of fear. Being raised Catholic, I anticipated the worst - being rejected from my family, getting kicked out of school, not having luck in finding a job, and lacking money to pay rent. I wondered if I could ever live a life where I could be accepted and loved, all while being true to myself. The fears were rooted in the stories I was telling myself at the time, and fortunately with a lot of self-care, patience with my process, and remaining true to myself, I worked through these fears to find peace. Similarly, building a business can generate a lot of unfounded fears related to self-confidence, perfection, failure, imposter syndrome, and money. One of my favorite podcasts, Being Boss, offers an entire episode diving deep into what fear means for business owners, and reminds entrepreneurs that if their work is rooted in passion and creates something of value for existing markets, clients will emerge and help you move past your fears. Much of what we fear are the stories we tell ourselves, and we can move past these fears when we begin to tell a different story.

Embracing Your Resilience

Truly knowing myself, and not accepting any form of compromise with respect to my transition goals gave me the inner strength to overcome my limiting beliefs and fears. Trusting that I was the expert on my identity and directly confronting the health, family and workplace stressors was a liberating moment for my personal journey. I found a source of resiliency in finding my authentic self. Similarly, as an entrepreneur, I recognize that I have so much to offer with respect to my vision, expertise, and passion for the services I’m offering my clients. Most workdays present an interesting challenge that enables me to learn and grow with each stumble along the way. With inward focus and clarity, the outward successes continue to manifest in new and exciting ways that humble me. Resiliency is the name of the game for both navigating the challenges of transitioning, and paving the path towards successful entrepreneurship.

My social transition was painful, awkward, and difficult. Despite it all, I wouldn’t change a thing. It has prepared me for the challenges that lie ahead as I work towards my dream of building a successful business enterprise. It has offered a source of confidence to confront my fears. It has inspired me to continue following my heart, and all of the unexpected twists-and-turns it takes. For the entrepreneurs out there, I hope you can recognize the similarities you share with many transgender folks, and from these similarities, I hope you are inspired to cultivate your ally skills. For my fellow transgender friends, I hope this post offers a source of inspiration to continue the journeys you are on, and recognize all of the life skills you have at hand to make your dreams become reality.

Together let us celebrate this International Transgender Day of Visibility.


Rhodes Perry

Rhodes Perry is a nationally recognized expert on LGBTQ and social justice public policy matters, with two decades of leadership experience innovating strategy management, policy and program solutions for corporations, government agencies, and non-profit organizations. At his core, Rhodes is an entrepreneur, where he most recently established Rhodes Perry Consulting, LLC, a national diversity and inclusion consulting firm that uses an intersectional approach to collaborate with leaders on creating solutions in the practice areas of strategy management, issue advocacy, and stakeholder engagement. Previously, Rhodes founded the Office of LGBTQ Policy & Practice at the New York City Administration for Children’s Services, and prior to this assignment he served as the founding Director of Policy at PFLAG National where he led the policy strategy and advocacy efforts for the organization’s 350 chapters. He cut his teeth serving as a Program Examiner at the White House Office of Management & Budget, where he improved upon federal benefit programs designed to provide assistance to low-income communities. Rhodes earned a Bachelor of Arts in Economics and Gender Studies from the University of Notre Dame, and obtained a Master of Public Administration from New York University.