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From Mathew to Maddie: Creating space, enjoying the process and uncovering a thriving environment helped me embrace my Transgender True Self.

In 2015, I was a lone American in NTU's MBA program in Singapore. While I shared passion for finance with some of my classmates, my projection of self did not align to my true self. Beneath the surface, I was slowly simmering in my journey and deconstructing many of the values, beliefs and ideologies that shaped my early years

Life can be stacked in a way that does not align with our own identified beliefs. Unwinding these projected ideologies, beliefs and projections is no easy, quick, or immediately rewarding feat. However, the process to align and identify one's True Self has offered me great freedom. No matter your individual journey, the process of self-discovery has many routes and I'll share mine in the hopes that it helps with yours.

Although there is much to my story, I'll focus on three approaches that helped me blossom into from Mathew to Maddie, my True Self!

Space: Values, beliefs and mindsets are deeply rooted in individual communities, cultures and nations. These commonly shared views can be fundamental to driving harmony. However, when mixing in a belief that contradicts an existing belief, you create friction. Most people have a solid understanding about the areas they contradict their community’s belief systems. Creating space, mentally or physical, can be a productive way to explore who you are without your community’s projections. You will have the space to explore and test. By the time you build the individual strength, you can drive positive and constructive conversations in this same community.

My Space: For many months I lived a double life – not like one of those fancy CIA agents. On one side of life I was identifying as Maddie and in the other I identified as Mathew. My Monday through Friday routine would include Mathew and in my free time I would crave to express myself authentically. Although not ideal, it allow two key aspects: 1. Security in my existing space and 2. Playground to expand my identity.


Process: Discovering one's true self is a lifelong, enigmatic and evolving process. To think that tomorrow you will wake up and be 100% your true authentic self is unrealistic (although I wish there were a red pill option for those Matrix fans out there).

My Process: I started dressing in my sister’s clothes when I was 3-4 years old. Fact check against the picture floating around at my parents in a bikini! I always tried to hide this (sometimes maybe wanting to get caught). This process of testing my identity persist into the present moment. I would go through cycles in high school and college where I would buy clothing and then purge to identify what society defined as normative. In 2012 I began the path focused on lowering Testosterone and increasing foods that contained estrogen (Soybean!). I bought hormones when I returned to USA from Singapore in 2016. I planned on taking them but then life happened – like so many times. Things like landing a nice role as a Consultant, to entering a relationship, to reigniting (trying to) old college and high school friendships would pull me back into the normative path. It got to the point where I felt I had everything (relationship, job, friendship, stability, excitement).. But something was still missing. In 2019 I officially decided to start taking hormones and to align my identity. Delicately balancing security and emotionally regulated the innate need to be myself. The journey continues as I further acknowledge my identity in my professional sphere. I’m grateful for my ongoing transition progress, am happy with exactly where I am on that journey and continue to increase visibility to those who might be earlier in their journey toward their True Self.


Thrive: Acknowledging differences is important to help prompt you to find an environment you can thrive. Maybe it’s your existing community, maybe it’s another community or maybe you need to create the community. While the US is more progressive, the ideologies, mindsets and belief are not the same. If you are fortunate, others have already dug a well for you to drink, the water is abundant and you need to find a way to show up. In other cases, there is no well and it then becomes your mission to create a well for others to thrive.

I am Thriving: The six months following my decision to medically transition in June 2019, I began the quest to identify a community where I had the highest odd of Thriving. “Where will I Thrive”? “Where will I find fulfillment?” “Where will I find Joy?” While all of this can be created, fostered and extracted from any environment or community, there are community’s where others have already walked the path.

In my search, I first started with a notepad (OneNote) to outline the countries and cities that ranking high on the Human Rights index. I then began to add other second tier factors like Lifestyle (mindset / active sports), closeness to finance market (career) and access to the rest of the world (global citizen). I was fortunate that I could travel-work in each location for at least two weeks (New York, Miami, Chicago, San Francisco, Los Angeles, Salt Lake City, Phoenix and Denver). As of September 2020, I officially locked my feet in the sand and decided to contribute to the Los Angeles community. While only having been here for 5 days, I have had amazing experiences and feel even more at peace with my identity and journey.

I hope you invest the time to embrace your own lifelong journey to become your authentic self. And in the process make sure to pick-up all the pebble of joy scattered on the path.

Maddie Stenger, born Mathew Stenger, is a 32 year old Corporate Finance professional who enjoys creating solutions to problems.  She loves meeting new people, learning about different cultures, snowboarding, art, music, museums, history, dancing, wine tasting and meaningful conversations. She is experienced as an Investment Analyst with skills in Negotiation, Big Data Analytics, Management, Business Intelligence, and Relationship Development. She holds an MBA from Nayang Business School, NTU, Singapore.


The views, thoughts, and opinions expressed in the article belong solely to the author.

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