How do you practice authenticity?

I'd like to start by mentioning that it sounds like you already know that the way for you to practice authenticity is to simply stop bending yourself to the various social situations you find yourself in. That you need to be more authentic with your gender expression and fear of expressing opinions in unfamiliar groups and situations. This has been my experience as well - that we all need to navigate and learn how to be true to ourselves and ignore the urges to placate or please others for the various reasons we choose to do that. This is the entirety of authenticity, it's simply a choice that people make, to be themselves despite of what others think. It's natural, to an extent, to mirror others and to shape ourselves based on our surroundings. I used to be an extreme social chameleon, as a defense mechanism, but even when it is not defensive there's plenty of scientific literature to show that part of being social is adapting yourself to the environment you find yourself in. The extent to which you adapt yourself is personal, based on some combination of your genetic makeup, your upbringing, and what kind of consequences you'll face by not conforming to society or by sticking out.

Honestly you shouldn't worry too much about any of this, but I would recommend taking small steps - tell yourself that for a week or a month that you'll dress how you want to, your first urge in the morning, and not change your thoughts based on any second thoughts you have. Practice being mindful of when you censor your opinion and then when you are able to recognize it as it is happening, take action to prevent the censorship or correct yourself and share the opinion you wanted to originally. Ramp this up over time and reflect upon how it makes you feel. Chances are, like most people, you'll feel much better being authentic. However, there are times in which we still need to conform to societal expectations such as work. In these realms it can be good to start small to understand precisely what you can share and in what capacities. Your work environment sadly may not be willing to let you express your gender in all the ways you wish without risking your career and taking small steps can help you figure out where you wish that line in the sand to be and how you wish to censor yourself for your own safety and security.

This inspired me to share a brief story on this topic from my own personal history. This history is one I've repeated to many close people in my life, but not something that I've ever shared openly. It's not something that I guard, but it's a fairly long story and it's related to my own personal trauma, so it's merely something that doesn't get shared until I want people to know a bit more about who I am; what makes my clock tick, what shaped my childhood, and why I have some of the ideals I have. If you have the time and are interested, feel free to read on - it's related to my own struggle with authenticity, but it doesn't add anything new to the message above the line so feel free to skip if you're short on time.

When I entered the 3rd grade my parents took me out of public school and placed me into a charter school which was structured in a slightly modified Montessori style. If you're unfamiliar with what a Montessori school is, the general principle is that you don't really have grades, but rather groups of kids placed based on where they are in their studies. Teachers don't give many lectures so much as they are staff on hand to help kids through their studies. Students are encouraged to teach and learn from each other and work their way through schoolwork by investing time filling out packets of exercises. In essence, it's much more self-taught learning than it is structured. At this school there were groups put together based on 'grades' and packets which resembled what should be learned during that grade. So, the 3rd-5th graders were together in one class and the 6th-8th graders in another. This roughly correlated with age, but if you filled out your packets, you progressed to the next group.

My parents were workaholics. Well, my Dad definitely still is, working into his 70s with no clear intent to stop. My mom has since moved on to other hobbies, devoting herself and keeping busy. What this meant when I was a child is that they dropped me off before they went to work and picked me up after. At a public school this meant that I started school with everyone else and then spent another 2-4 hours at some after school area until I was picked up sometime 530-6pm. This new school was a bit further away, so I was there even longer. This timeframe, combined with my natural penchant for absorbing information and learning, an unquenchable desire to understand the world, meant that over the course of a year and two summers (with the extra several hours to work on my packets) I was able to finish the 3rd, 4th, and 5th grade packets. Coming into the next school year I was ready to move to the 6th-8th grade group. I found the school a fantastic fit for my own desired work speed and the free time I found myself with.

Unfortunately, however, the school had some funding issues and had to move to a new location. This new location was further away. I want to say it was something like another half hour or driving, but at this point it's frankly lost to memory. Perhaps it was an hour, maybe even longer. Whatever the cost, however, I was willing to make the journey and I spent some time reaching out to friends at the school to find out where they lived (if I didn’t already know) and to see whether they would be continuing the next year. My plan, you see, was to attend school by carpooling with them. When I had secured such an arrangement, I went to my parents and let them know that I wished to continue this school for another year - I was convinced that I would be able to keep up my speed of learning and be out and into high school very shortly. I dreamed of attending and finishing college as a child - who doesn't have high aspirations?

My parents disagreed. They said that such a long commute would be too hard on me. It's almost as in if they forgot the long hours I spent after school waiting on them to pick me up. Worse yet, they were telling me how I felt about this, without letting me provide my own input. They pulled me from the school and plopped me back into the public school system. I fought as best I could, but as a child I had no sway. When the public school system took me back, they had no idea what to do with the education I had received. You see, even though the packets resembled the 4th and 5th grades, it wasn't transferrable because they didn't follow the same curriculum.

I tried protesting; I didn't want to repeat ‘learning’ the same information I had just acquired for the next two years of my life. Administration did not care and would not make any accommodations. I asked to test out of these grades, and in no uncertain terms they told me no. I was devastated. I searched for allies… I made my pleas to every new teacher I had, any students I was friends with from 2nd grade and their parents. No one would listen. I asked my parents to step up to bat, to fight for my right to test out - to do something, anything to get a cold calculating system to listen to a child. They wouldn't. They told me, in more age-appropriate terms, that life sometimes serves you up a plate of shit and the only thing you can do is to consign yourself to eating it.

I was abandoned. The system wouldn't help me. My friends couldn't help me. Their parents didn't care. My teachers were apathetic. Worst of all, my own parents were too absorbed in their own lives, too unwilling to start a fuss, or otherwise just unwilling to protect me - to center my life instead of theirs; a long conversation, a hug, tutors, a plan to make use of my time… any concerted effort would have helped me to feel supported and loved. Either none of this was offered, or what was offered never stuck with me, because I distinctly remember this as the point in time where I realized that the world is cold and cruel and that when it comes down to it, no one cares about anyone but themselves.

If you've interacted with me on this website, I would hope you'd be struck by the last half of that last sentence. That it would stick out to you as a contradiction to how some of us spend our time on this website and in our lives. It's absolutely a false statement, but you see, I was in 4th grade at the time. I hadn't the depth of experience I have today to realize that there are wonderful, emotionally deep, compassionate, amazing people in the world who would jump in front of a bullet for a fellow human because they truly believe that this mindset is more important than their own life. They live to serve, because they wish to see a world in which others do the same. It took me a long time to get here, but as you can imagine this formative experience is a huge reason behind why I take a similar mindset to a fault - I don't want anyone to ever experience the abandonment I felt, to ever think the world is cold and calculating and that you can't be compassionate or center others. I don't want this so strongly that I've ran into situations where I centered others when I should have centered myself and my mental health, my safety, my ability to help others has been hampered because I gave myself away when I was already broken or in need of help myself.

The 4th grade is when I was diagnosed with chronic depression. You see, I immediately started acting out in class. I was upset about being abandoned by the system. Upset about having to waste my time in a classroom being taught that which I already knew. Upset that I started to resent the act of learning. I lashed out at teachers and swore at them. I got into fights with other children. I walked off campus in the middle of the day because I would rather spend my time doing literally anything else. So, they sent me to a psychiatrist to have me evaluated. Of course I was depressed - look what the system did to me.

However, two incredibly important driving forces in my life began in the 4th grade. The first driving force, which is less important to the context of this post was that of vastly increasing the diversity in which I was exposed to. You see, I became a delinquent, which means that my friend circle started out with other delinquents. I was exposed to people of a much more diverse background as I came from one of white middle-upper class in an extremely privileged area. Ideas which I despise today were drilled into my head when I was younger - don't go to that part of town, it's dangerous there. Those kids are just more prone to violence. Sexism is overblown - look at all the successful women in your life! These ideas broke down very quickly when I started to make friends and visit the ‘dangerous’ parts of town. When I listened to the stories the women told, their mothers told, their sisters told. When I saw how the system actually treated these people and heard what they had to say, it helped me to learn that what I was being taught was actually a lie.

The second driving force was the acceptance and the learning that came from fully understanding that people would not listen to a child. This really solidified in my brain when I was talking with my psychiatrist about this experience and how they ignored everything I said and listened only how my parents reported my behavior, my struggles, and what was happening in class. I learned that if I wanted things to happen, I would need an adult to do them and because of this I started to learn how to get adults to do the things I wanted. I learned to shape myself to fit what the adults wanted to see in a kid. I found out quickly that if they saw themselves in me, they would spontaneously want to protect me and could be an ally which fought on my behalf. If I did small things for them, to show them that I enjoyed or cared for their presence or remembered their birthday, remembered what they liked and offered them small offerings within my means, that I would grow in their hearts and that they could advocate on my behalf. I learned to play this same game with my peers for social points - how I could win their hearts and become social, become cool, or become feared. In many ways this was incredibly sociopathic - I approached social dynamics as an extreme social chameleon. Who I was changed drastically throughout the day and I learned to shape it to be exactly who I needed to be at any one point in time to accomplish whatever goals I had.

Have you ever taken a Meyers-Brigs personality test? I have. I've taken lots of them. I've been administered them too, by therapists and psychologists throughout my lifetime. What's your type? Really?! Me too! You see, I've received all 16 personality types in my life. When I say I was an extreme social chameleon, I mean it to the point at which that I struggled understanding who I truly was. The narrative I told myself is one which fit how I interacted in social dynamics. You see, each question asks you about how you would act or react, but it doesn't set boundaries on context - you're supposed to just create a context in my mind and answer appropriately. Instantaneously in my mind, I'm able to create two contexts in which I am on both sides of the answer - extremely agree and extremely disagree. So how am I supposed to answer? I just put down however I'm feeling that day, or perhaps whatever most resembles a recent experience I've had. This is why I've received every possible personality type. This is the hole I dug myself into - I struggled for years with the idea of an immutable self. There were things about myself which I knew, like my sense of humor and an innate drive to tell jokes even at the expense of myself, but I also knew that I could censor it and would censor it in many situations. I wasn’t sure that there was any immutable self underneath it all as I could always think of situations in which I would modify my behavior.

In my late 20s after I ended a decade long relationship with the only major monogamous relationship I've ever had I realized that I needed to find what would make me happy absent the input of others. Yes, I was extremely social, and derived great pleasure from this extroversion, but I needed something sustainable for when I wasn't social. I needed something sustainable without the presence of a partner. More so, I needed to come away from every interaction happy… not just happy that I had won someone's favor, but happy with myself. It took many years of concerted effort to reflect upon interactions and become conscious of when I was simply doing what someone else wanted me to do to begin to change my behavior or to even understand what I wanted to do. What I wanted seemed so frivolous that in many cases I wasn't even aware that I had any desires. In some cases, I had to simply try reacting in different ways to see how those ways even made me feel to understand my own desires. I had a serious web to untangle, because I had taught myself to be out of touch with my subconscious self.

In my early 30s I also began a journey of becoming more visible. As I spent more and more time in circles which represented some of the identities which I knew I had (bi/pan, gender nonconforming of some sort) and wished to participate in (POC and other minorities which reflected many of my friend’s identities), I began to realize the power and privilege which I had and reflected upon how seeing diversity helped me to recognize who I was. You see, I didn't realize all the ways in which I could be non-binary until I saw other people pursuing the same path and people forging different ones altogether. I vowed that I could use my privilege to make these identities more visible - to show others what one path might look like so they might better understand what is right for them. I also decided that I could do a better job advocating on behalf of others, especially those who may not have the mental bandwidth or emotional capacity to do so themselves, given how the system already oppresses them. This journey helped me immensely in continuing to unravel and stop my social chameleon tendencies. Seeing how others struggled with how they presented themselves to the world helped me realize the ways in which I wanted to present to the world and helped me on my own journey of self-reflection and authenticity.

Today, I think I’ve done a good job uncovering who that person I suppressed as a child truly was. I have rediscovered my love for learning. I’ve accepted and embraced my extroversion. I wear colorful, bright clothing that gets me noticed and leads to some discrimination. I do not shy away from centering the emotions of others even when it conflicts with the needs or wants of an organization or a group of people. I laugh and joke freely, and I spend my time reminding others to live the life that they want to see in the world. Work is fake. Time is fake. Happiness and getting along with other humans are all that really matters in this world, and I will absolutely remind you of this if you dare send me a work email after 5pm. There are better and more important things in your life to be doing, do yourself a favor and unplug and spend that time with your loved ones instead. Is there an even more authentic self still below the surface? Probably, and I wish to uncover them with time, but I’m also compassionate to the struggles I’ve had to overcome to let them out. There’s beauty in a late blooming flower and chastising the flower for taking so long to bloom seems a pointless endeavor – I’d rather appreciate it for what it is, when it gets there, because that’s the kind of person I want to be. Life is too short to not appreciate it.

If you made it this far, I hope the read was pleasing enough. When I started writing this, I didn't realize it would be thousands of words or how deep I wanted to dive into my past, but it is my sincere hope that someone else who reads this gets something out of it - perhaps a little more emotional intelligence, perhaps a little more compassion, a bit more understanding or simply just access to a life experience they've never heard. If I'm lucky, maybe it'll inspire someone else to share a similar story in the future or will touch somebody in a way they didn't know they needed and help them on their own journey. Authenticity is about sharing yourself with the world through your actions and your words, and if you feel inspired, I'd love to hear your story as well.

Really loving the responses to this thread so far! Mine will doubtless rhyme a bit with some of them. This thread came at a good time for me; I have lately been introspecting something fierce and am on the cusp of some major life changes. I have quite a few thoughts that I can hopefully use to craft something resembling a coherent response. Warning: embryonic philosophizing below:

Like @mtset, I find the common conception of the "self" to be of dubious usefulness--particularly as a platform from which one interacts with others. I don't think each of us possesses a set of qualities, immutable or otherwise, that we must be authentic to in order to live well. When it comes to interacting with others, I think we all have a collection of Masks that we don, each one tailored to different people and situations in our lives. It seems to me that many folks do not realize that they are doing this. A little self-awareness, though, allows us to more carefully carve and decorate our Masks to better fit specific contexts. A degree of consistency between these Masks is desirable, in my opinion; it helps minimize cognitive dissonance and prevents the extremely undesirable perception of being untrustworthy or "two-faced". However, allowing for degrees of friction between these Masks can be extremely helpful. At first, each Mask is an exaggeration of practiced and comfortable qualities. Through practice we can add new qualities to each Mask, even those qualities that are more raw and less comfortable for us.

Critically, and perhaps obviously, our Masks are only known to others by the actions we take that affect them. While aligning one's thoughts with one's current Mask is often helpful, it's not strictly necessary--more on this later.

This model, I think, works pretty well to describe how we relate to others. Where it seems to fall apart a bit, though, is when we are alone with ourselves: who are we when there is no
one around to wear a Mask for?

I think, ultimately, we wear a Mask for ourselves as well--and, like the Masks we wear for others, self-awareness allows us to tweak it and tailor it. Just as others only know us by the actions we take, we only "know ourselves" (that is, see our Inner Mask) by the actions we take when no one else is watching. This Inner Mask is what we, without introspecting, tend to think of as the "Self". It seems to be uncommonly realized that this Mask is also quite plastic, if to a lesser degree than the Outer Masks.

As I alluded to earlier in this comment, recent events in my life have given me the opportunity for intense reflection. I have apprehended my Inner Mask more completely than I ever had before (except possibly while under the influence of a certain fungus), and I have found it wanting, badly. My urgent life's project, now, is to whittle at that Inner Mask, add both new and long-discarded materials, and re-shape it into something more to my liking. We tell ourselves stories about our Inner Masks often (usually some sort of self-concept or life narrative), but these are often, bluntly, bunkum. Our Inner Masks are only the sum of our actions taken when no one else is watching.

And no, old scissortail hasn't missed the obvious: whatever part of you that is adjusting the Inner Mask is not the Inner Mask, and has its own values and preferences! What could this be, if not the self?

And yes, I do think this is the Self, or as I like to think of it, our Awareness, or The Decider (see also Stirner's Unique or certain views of Atman). I see this as a cluster of qualities possessing low mutability, wrapped around the same identical spark of consciousness that each of us possess. The low mutability of our Awareness is due to the nature of its construction: it is comprised of our genetic predilections and our deep-seated social imprinting, usually acquired early in our lives. It usually takes a very serious system shock to rapidly change the shape and composition of our Awareness.

However, our Awareness is molded slowly by the Masks it wears; so while one's inner thoughts do not have to line up with one's Mask, as stated previously, Masks change the
Awareness as they are used. This is why one's choice of long-term Masks should be taken with great care. While we should absolutely be playful and improvisatory with the Masks we don in the short term, any we break out more than a handful of times should be crafted with great care. As Vonnegut said, “We are what we pretend to be, so we must be careful about what we pretend to be.”

Our Awareness is not really our traditional conception of "Self" though; its nearly hardwired nature makes it is almost impossible to contravene its values and desires (or, more accurately, its "ways of choosing"), and thereby live "inauthentically". Our Awareness is simply the slow-changing root of everything we are, from which all of our Masks are formed.

Our Awareness, moreover, is known only to us, and can only be guessed at by others through their relationship with their own Awareness. It cannot be communicated in any meaningful way, while some conceptions of the Self can be made known to others. For all of our interactions with the world and its people, we have our Masks. Our Awareness does little but choose the adjustments to make in those masks--a process we become more cognizant of as we learn to become aware of our own Awareness.

@bilbodwyer, to answer your prompt more directly:

Because of the above harebrained ideas, I don't really experience the desire to be more authentic. The desire to lead a more admirable life? Absolutely. The desire to work harder to leave a meaningful legacy behind me? Sure. The desire to live a life closer to some aspirational values? Yep. But I don't really have a "true self" that I feel the need to achieve congruence with. My actions reveal my impact on this world, and I judge and adjust them according to the context and my own Awareness. I will be spending quite a bit of time on that judgment and adjustment in the near future, especially on my Inner Mask.

Now, if you find yourself feeling discomforted by a feeling of inauthenticity in social situations, I think there's a calculation to be made: is your discomfort worth the benefit of the bending that you're doing? Further, if it is worth it, are you bending in such a way that you can avoid duplicity, or at least the perception of the same? If the answer to either question is no, it may be time to stop bending.

After that initial response, though, I'd encourage you to look at it more deeply. What is the root of that feeling of inauthenticity? Which layer of your desires (Outer Mask, Inner Mask, Awareness) was contravened? Would it be worth the effort for you to adjust your desires here? Would it be better to adjust the situation? Is the situation itself one you want to be in?

I hope that made even an ounce of sense. Thanks for starting such a great discussion! I enjoyed writing this out so much that I'll probably flesh it out some more and throw it on my blog.