Removing Our Masks, Connecting More Deeply

For many of us, Halloween is a time of donning facades, of toying with faces, bodies, and personalities that aren’t really ours. For an evening, we can temporarily play with life as an entirely different being. We may experience liberation and variety in that.

There’s nothing wrong having with this sort of fun sometimes. In some cases, it can even give us insight into parts of ourselves that exist in reality–parts that we may not allow to speak when we’re not donning a mask.

The problem arises when we wear masks of various types throughout life. For me, life’s shifting seasons and winding breezes have been prodding me to lift off the masks, to reveal more fully and authentically who I really am.

For much of my life I tried to bolster myself against various uncertainties by racking up various accomplishments: getting straight As, achieving the top class ranking in a class of more than 400 students, going to an Ivy League school, writing several books, taking on athletic feats such as cycling across the continent and completing a marathon, earning a 4.0 GPA in two graduate programs, and so on.

Granted, some of these accomplishments have been intrinsically fun in different ways, and have also been driven by a sense of deeper purpose and desire to serve others. This includes writing the books. But some were motivated partially by a need to “prove” myself.

Somewhere along the way, I started to feel like I had made many sacrifices to build this fortress of predictability and guaranteed success. I expected the world and universe to grant me this safety and predictability in return.

I should be successful, by society’s most common standards.

Things should go as I have planned.

Because, dammit, I’ve worked hard and earned it.

Often while many of my friends were socializing and having fun, I was studying or planning my future. Even though they sometimes asked me to join them, I’d usually say no.

Deep inside, I thought I was superior in some way. I had it all planned out. And the more I continued down my path, the harder I had to work, because the more I became entrenched in my need to show them that I was right.

I could not fail, as that would suggest I was wrong.

That would be embarrassing.

And so I continued this pattern for a number of years.

But the universe, in its wisdom, did not grant me the stability and guaranteed success (at least not the traditionally defined kind) that I had silently demanded of it. Go figure.

Instead, as I approach 40, I have found myself navigating somewhat of a midlife crisis, following a number of significant changes in my life—some due to my own choices, and some due to factors completely beyond my control. So I’ve been questioning various aspects of who I am, what I wish to become, and how I define myself. How can I live more authentically?

The ways I defined home, family, connection, career, and success have all been blown about like leaves in the autumn breeze.


Many branches are bare, but new sprouts have begun to form.

Alongside the expected anxiety, these shifts have brought some wonderfully amazing people, places, things, and perspectives for which I’m deeply grateful. I do not take these things for granted. Especially the people and the perspectives.

These shifts have also brought me one of the greatest challenges of my life thus far—admitting that I’m just as human as everyone else. Admitting that I don’t always have things figured out and under control, and realizing that this doesn’t necessarily make me any less capable or intelligent. Admitting that, like everyone else in the world, I sometimes need help and support, and occasionally feel scared, lost, vulnerable, and confused.

These are really, really big masks and costumes for me to remove. Sometimes it’s like I’m trying to peel off a 7-layer Halloween outfit, tangled together with a confusing array of zippers, Velcro, and duct tape.

Some of the amazing people and things in my life wouldn’t be there if I hadn’t started to let down some of my facades more. I know that. As I’ve peeled away the layers, it’s become a bit easier to breathe, to move, to sense the energies of the people and world around me.

I’ve also learned that celebrating life’s wins, big and small, is much more fun and rewarding when we can do it with people close to us. And it’s often easier to be close when we’re being real, with many of our facades down so that we’re truly allowing them to know us.

Notice that I said easier to be close, not easier overall. Sometimes relating to others can become more challenging as we let down facades, before we can begin to experience greater intimacy. At least that’s how it’s worked for me. I’m also not suggesting that we be totally vulnerable and naked to everyone, as we all need some masks in our day-to-day lives. But most of us can benefit from doing this with some people.

My midlife struggles and uncertainty sometimes seem especially ironic, as I’ve life coached a few people through some wonderful successes and transitions in their lives, and just this week I passed an oral exam indicating that I effectively practice advanced life coaching skills.

But on a cerebral level I know that being able to guide other people in no way equates to an ability to guide one’s self; and in fact, we all need others to accompany us along our path, which is why I’ve recruited the help of a coach, therapist, friends, and relatives at various points recently. I also know that my own struggles have already equipped me with additional perspectives and tools to empower others.

This all reminds me of some of the original concepts behind this time of year, which have largely been lost amidst practices such as donning masks and trick or treating. Concepts such as the veil thinning between the human and spiritual worlds—whether or not you believe this literally, metaphorically it’s a message about getting in touch with the spirits of our ancestors, the collective unconscious, the larger energy that surrounds and connects all of us, or whatever appellations or concepts you feel most comfortable attaching to it. It’s about quieting ourselves a bit so we can listen.

Some days I find myself feeling disconnected from this broader source of interconnected existence, while at other times I have no doubt it is there. I frequently find myself wondering how I can tap into it more.

At this time of year, the shorter days that cast less light upon the external world provide an opportunity to look within ourselves, and to engage in self-reflection. This includes both who we are behind our various masks and facades, as well as how we’re connected to the rest of the world—both physically and spiritually. Celebrations such as Samhain and Dia de Los Muertos remind us of this.

Amidst munching on the occasional chocolate treat, I’m planning to devote some time to such self-reflection over the next few weeks. Because the fewer layers we hide behind, the more likely we are to experience deep and meaningful connection.

While jogging through a cemetery adorned with beautiful fall foliage this morning, I wondered how many people there had lived their entire lives with their thickest masks still intact, even to those closest to them. I don’t wish to be one of those people. By the day my physical body lays next to theirs, I hope to recognize and shed as many masks as I can.

Coaching, therapy, and supportive loved ones have already assisted me with this lifelong process. And, like anyone else, I also have homework to do on my own.

Some powerful questions to consider: What masks have you already shed? What masks do you wish to shed? How will your life be different once you’ve removed them?

Dave welcomes phone-based life, career, and transition coaching clients from around the world.

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