Life Lessons from a Brazen Trans-Woman

When I was about nine, I started to experience chronic pain. After a year or so of going through the UK’s bureaucracy-sodden health system, I got a diagnosis: Crohn’s disease. They told me I’d have it for life.

For the next ten years I suffered doubly: from various levels of recurring stomach pain and other symptoms, and from the various treatments I was subjected to. One treatment probably saved my life; others were as bad as the disease or worse. Once, some nut with Dr. before his name suggested that my stomach be removed and replaced with a plastic bag. No word for it but insanity.

There was more than once that I got pretty close to dying. Spending months in the hospital, wasting away till I was too weak to get out of bed, too sick to eat. I had surgery at least two times. It could have been more; the memories blur together.

High School

I went to boarding school for my last two years of high school. I was still sick but as always I refused for my sickness to stop me living my life. There, I started to wonder what the heck I was doing with my life.

I had always been passionate. I wanted to be a writer, an entrepreneur. I wanted to be free to travel the world. An 8 hour day seemed like prison to me; I wanted to be free.

School seemed like prison to me. I wasn’t learning anything useful. I wasn’t furthering my own goals. It seemed I was only furthering the goals of someone or something else, some entity who had plans for my life and was in no way interested in what I wanted to do.

I was looking for answers. I used my sickness as an excuse to skip class and spent my time reading. I read blogs by entrepreneurs such as Steve Pavlina (“Getting a job is like enrolling in a human domestication program. You learn how to be a good pet.”) and books by John Taylor Gatto which explained how the school system’s main purpose is to teach children to be obedient workers rather than intelligent human beings.

I gained in courage and anger. Bit by bit I pushed against the life that had been planned out for me, first by choosing to homeschool myself and then by ditching the system altogether, just before my final exams.

My parents thought me crazy. To be honest I didn’t have much to support me in thinking otherwise. But I knew what my heart told me.

A New Life

I left home eventually to strike out for myself. Actually, I pretty much ran away from home. And with that gesture of freedom, I chose to stop going to a doctor or use the drugs I had been using. I was sure there was a better way.

I spent three rocky years in my new town, having girlfriends for the first time, trying different lifestyles and making different friends. I supported myself as I could. My only rule was that I was not going to have a 9-5 job with a boss telling me what to do.

I tried the raw food diet to heal my disease. It didn’t quite work. I tried emotional and spiritual healing. I think that helped. I tried fasting for short periods. I found out which foods seemed to trigger me or not.

After a lot of experimentation, I finally found one thing that made all the difference: gluten. I stopped eating it just to see what would happen, and from then on I never had a flare-up of more than a single day. I had my life back.

In those three years I experimented and changed more than I had in my entire life before then. It wasn’t just about healing the sickness. I was determined to question everything, to consciously choose my way of living and have no-one choose that for me.

My Relationship With Money

I experimented with my relationship to money. Most people have this feeling somewhere that money is negative. I had the idea that I’d have to get over that to live free.

So I decided to dive into my problem with money. For a few months, I lived in squats, on the streets, and as a vagabond. I didn’t have to; my money situation was difficult but not that dire. But I did it for two reasons:

  • One, I felt oddly fascinated by the lifestyle and wanted to get it out of my system.
  • Two, I wanted to know what the “worst case scenario” was like so I knew what I was fearing.

See, I hated being bound by that fear that if I didn’t get a job like everyone else… what? What would happen? The most horrible thing in the world, apparently. Well, I found out what that was. And from then on my fear of poverty owned me that much less.

I later tried stealing (from large supermarket chains that I thought could handle it and possibly even deserved it). I found out that it, like vagabondry, was genuinely not worth it. Again, I got it out of my system and started to learn, experientially and not just theoretically, why money is healthy and positive to have.


Later, I kissed my first guy. 🙂

I know I’m challenging people with this article but that’s the whole point. I did what my heart called me to do and I didn’t care what people thought of me.

I kissed my first guy. It was a little weird, and a little good. We had a slightly awkward fling, both of us being basically bi-curious at that time. Eventually we became “just friends”. He decided he was straight. I haven’t come to a definitive conclusion yet, but I’m pretty sure I’m bi.

That’s not the end of that, though.

Nine months ago, after a long deliberation, I decided to say “screw it” and jump into living as a woman.


What possessed me?

I guess I could start with, “Why not?”

I’m sure most people would have something to say about “why not”, but I knew there was nothing wrong with what I was doing. Social pressure makes this way, way harder than it would otherwise be, but I’ve always been determined not to bend to social pressure.

Since finding the courage to try on some women’s clothes three or so years ago, I’d had a low but persistent calling to reinventing myself in this way. I spent that time struggling with self-understanding (Am I transgendered? Am I not? Am I?) before finally deciding to just give it a go. I would try out everything I could which wasn’t permanent, and see where that led me.

It’s been more than half a year now. I’ve experienced stigma and the loss of friendships. And I’ve experienced admiration for my courage and the strengthening of other friendships. I have two romantic partners right now (oh, did I mention I’m polyamorous?). Despite a large part of the world being vaguely hostile towards me, I experience more abundance in love and relationships now than I have done in my whole life.

Happy Ending

Once, when I made my final gesture of rejection of the education system, my parents came to fetch me. On the ride home my father promised me that I was looking forward to a life of complete social ostracism if I kept doing such unconventional things. No one could ever love me. (Thanks, Dad).

The opposite is the case. The more true I’ve become to myself, the more friends and lovers I’ve found, and the truer those friends were, too.

Even with relationships, I’ve seen that despite me seemingly shrinking my dating pool first by being radically unconventional, then by becoming polyamorous, then by transitioning my gender, I’ve become more and more successful as my true self has shone through more.

Financial Awakening

There’s another happy ending, too.

Several months ago, I went through a major emotional/spiritual crisis. I was forced to face up to how much I leaned on others for support rather than trusting myself to be my own strength.

On the other side of that shakeup, I came to find a sense of inner strength I had previously not known. And it seems that then, I had learnt all I needed to learn, spiritually speaking, to make the next step forward in my finances. I got offers from not one, but two well-off friends to back me while I worked on online projects. Within the space of a month.

And at the same time, perhaps as a result of the same upheaval, I had become more sure than ever that being a blogger was my calling.

Everything fit together. It was my time. I moved to a new city again, making a clear separation into a new chapter of my life, and began to live with a new level of purpose and empowerment.

Break Convention And Follow Your Heart

From poverty to empowerment. From estrangement to self-knowledge. From loneliness to relationship abundance.

My purpose in writing this is to tell you: good things come to those that break convention and follow their hearts. Even if it shocks people. Even if you lose friends. Each time you strike out on your own to do something unconventional, you become truer to yourself and stronger.

And as you follow your own inner compass, you reach places you could never have gotten to if you’d followed the path society had set out for you.

So dare to be different today. Do things differently. Be different. Lose friends. Life is bigger than this. You are bigger than this. At the end of your life would you like to say, “I bent to social pressure and did everything other people thought was right for me?” Or would you like to work towards something real, feeling free, empowered and true to yourself?

It’s all down to you.

Article by Sophia Gubb

Sophia Gubb is a transgendered, vegan, polyamorous, esperanto-speaking, bisexual, expat, indigo adult blogger, using her unique perspective to bring home lessons about self-development and inter-responsibility. She writes about all these topics and more at – a blog about living consciously.

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