TGIF :: The Authenticity Dilemma

#88 || Do we embrace our "flaws" or "fix" them? A reflection on beauty, identity, and a lesson from Yung Pueblo’s new book: How to Love Better.

Mar 07, 2025

I write to explore living undimmed—present and self-aware of escapist drinking, eating, snark, exercise, shopping, sex, work, drugs—even grooming—so we can truly show up. Prior posts are available here.

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Let’s start with gray hair.

I ran into a longtime neighbor and friend this week. As we walked a block together, making small talk, the conversation turned to the challenges of fundraising.1 After a moment, he looked at me and said, “Is that why your hair is going gray? You always had such beautiful hair.”

Had such beautiful hair.

I joked about being at the crossroads—deciding whether to commit to covering my grays it or let my hair do its natural thing—and we went our separate ways. But the comment lingered—the unspoken implication that non-gray hair is more attractive, that I’m somehow less put-together without haircolor, or something else entirely. Oy.

I sat with it for a moment—why it mattered, why I cared about this friend’s comment. Grasping for counter-arguments, I thought of the #silversisters movement (a digital collective rebelling against the conventional beauty standard that gray hair is “bad” or “shameful”), my 14-year-old son’s recent affirmations: “I like your gray hair, Mom. It makes you look wise,” and the many warnings I read and heard about hair dye toxicity while navigating breast cancer treatment in 2023 (like this one, from the American Cancer Society).

And then later that day, as I often do, I thought of my (late) mother who at this point would certainly be scolding me for not getting my hair “done” already, just like her mother and her grandmother did, all coloring their hair brown up until their last days—great-grandma Nana passing with her auburn curls and painted on brows at 108!

Can we be seen for who we are inside?

This all brought to mind a recent text from a friend:

I’m still pondering the dilemma over antidepressants (whether to “fix” yourself vs feel the feelings) and I feel a parallel dilemma with facial enhancements and procedures (seems like all my convos with some peers boil down to this and menopause 😂).
Should we embrace our authentic appearance and age, or do big or little things to help our soul, self-confidence? I feel kind of stuck on this one.
Not sure if this falls in your categories of dimmers or 8 awarenesses but I’d love to hear what you think on this topic —

I wrote back:

such a good one… authentic connection, authentic beauty, authentic care, authentic orgasms! They’re different!

To which she replied:

It is very unfair we all can’t be seen for who we are inside!

Amen.

A truer version of—everything

There’s something about experiencing beauty, love, enthusiasm, care—and yes, even orgasms—knowing they are authentic. In the age of AI sex robots, a booming beauty industry, and plastic surgery as an increasingly common “investment,” authenticity feels like one of the last things we can deeply sense and feel as humans, and if we choose, hold onto.

So how do we navigate this question of whether we should conceal the signs of our age, “fix” our perceived “flaws,” mask our true feelings, or do any of the countless other things that are marketed to us to appear better? This is such a deeply sensitive and personal question and there are no right answers. But it’s a real topic right now and there are countless voices exploring it for us.

One of my favorites is Elise Loehnen (author of the NYT bestseller On Our Best Behavior, host of the Pulling the Thread podcast and Substack) who explores “culture, and the way it lands in our bodies: Why do we do what we do? What’s us versus the stories we’re told about who we’re supposed to be?” She’s “interested in pulling apart this tapestry so we can re-weave a truer version.”

Can appearances make us feel safe?

I was raised (and coached) by my mother to present in a certain way to be accepted and safe. Clothing. Manners. Car. Makeup. Hair. The implication was that if we didn’t appear a certain way, something bad might happen (I never found out what that might be because we never broke the rules).

Over the years, throughout my own journey, I’ve tried to understand the source of this feeling in her, in part so I could better understand a similar feeling in me. It eventually made enormous sense. She was raised believing that she was flawed somehow as the “unwanted third” child and the “ugly duckling” in the family. So she perfected her presentation, seemingly always fearing that if anyone found out who she really was, what she really (authentically) looked like, she’d be voted off the island of class and privilege she’d navigated her way onto. So of course for her, good parenting was making sure I was equipped the same armor.

Hand on heart. ❤️‍🩹

In unearthing compassion for her and trying to understand the right way to balance investment in appearances and the tender beauty of authenticity in my own life, I’m still trying to figure this all out, while also trying to not be extreme on either end of the spectrum. And, I am still haunted by this question: Can’t we all be seen (and loved) for who we really are?

Appearances as a dimmer

So, going back to my friend’s question: “Should we embrace our authentic appearance and age, or do big or little things to help our soul, self-confidence?”

Of course there is no “right” answer to this question loaded with subjectivities. But we can explore with a few shared tools.

The Eight Awarenesses invite us to not dim out our discomfort, including over-use of products and practices that make us temporarily feel relief. And hell yes, excessive attention and time on how we look can itself be a dimmer. I’m reminded of a time when I went to see an old friend on a layover in Washington D.C. After our airport embrace he looked at me as said “You look fantastic! Is everything okay?” He knew me well enough to know that a super skinny, impeccably dressed, perfectly coiffed version of me might be troubled.

3 questions to explore our (often very) personal why

The Eight Awarenesses framework invites us to consider what lies beneath any “cover ups” or “fixes” we might be curious about in our own lives. These can be just about anything we do or buy to appear a certain way whether it’s a facial treatment, an affluence flex, Spanx, cosmetic surgery, or yet another pair of shoes. Maybe there a discomfort or unpleasant emotion we are trying to not feel? Can we take a few steps back and start there?

Three questions we can (gently) ask ourselves:

What is the underlying motive for a purchase, procedure, or other investment in our appearance? Is it “to feel more like my true self” (I hear this often from my 50-something friends), to look more like someone else (often an idealized celebrity), or soothe an insecurity?
Is there room for some self-acceptance, perhaps more than we feel right now? I was shopping with my partner recently and tried on a baggy dress that I quickly noted “wasn’t flattering.” He commented “Looser clothes have a place your wardrobe too, now that you’re a bit older.” At first, this stung(!), then I took a beat and realized he’s right. I can wear both tight and loose clothes and as I age, it might be more of the latter. There was a breath of self-acceptance in there that felt more like relief and love than resignation or failure.
Are there other ways to nurture our souls, or boost our self-confidence, other than invest time and energy in external appearances? We inhabit a culture that places an expensive premium on physical beauty, but are there things we can all do to feel better from the inside out? Hacks that regularly work for me: good posture, outdoor exercise, meditation/visualization, drinking lots of clean water, remembering gratitude, and eating healthy.

Authenticity and appeal in relationship

Over the years, I’ve grown used to men caring about—or at least noticing—my grooming efforts. It was quite a shock and an adjustment when Soren and I came together and I experienced him repeatedly either not notice or not care about my hair, makeup, or clothes.

At times I loved it, thinking: Phew, he really doesn’t care! Other times I was disappointed wondering: Is he paying attention? Over time I have come to believe that he primarily loves me for other reasons, for what’s beneath the surface. It has been an enormous exercise in reorganizing my own perception of worthiness, adjusting to this new flavor of love.

Do I still take good care of my skin +hair and body, dress well, wear some makeup, and so on? I do, but I do these things primarily for the energy and confidence they bring me whether it’s for a day alone in the office or a night out on the town. (And by all means, do you!) As for why feeling like I appear well actually makes me feel well inside—that is an enormous question and one that the multi-billion dollar beauty industry happily exploits daily. I’m still actively working on this myself with some of the questions listed above.

Accepting our innate imperfection

My good friend Diego (Yung Pueblo) writes about this in his new book, How to Love Better. In Chapter 5, What Love Is and What It Isn’t, he explores the notion of self-love as comprised of three components: (1) Radical honesty with yourself (making sure there are no lies between you and yourself), (2) Positive habit building (how to take yourself to the next level by solidifying good habits), and (3) Self-acceptance which reads as follows:

Self-love is not just about personal transformation; it is also about deeply embracing who you are at this moment where you are in your journey. Self-acceptance helps you develop peace with your emotional history so that you can face your past, understand the hardships, and feel motivated to learn from them so that trauma doesn’t need to be repeated or passed down. Acceptance also helps you appreciate your innate imperfection so that you are not harsh with yourself when you inevitably make mistakes.

I love this expression for many reasons, but one is how broadly we can apply this notion to everything from trauma responses to gray hair. Maybe some of us are being too intense with ourselves, endlessly striving to “be” and “do” good—even make the “right” decisions when it comes to whether we should “fix” ourselves or cover our “flaws.”

Authenticity isn’t just a buzzword—it’s a deep truth, the real version of a person, a moment, a body. Deep down, we all just want to feel love. And maybe, in embracing who we truly are—flaws, aging, and all—we become even more beautiful, more lovable, more approachable to those who want to be close.

And yes, doing certain things to look and feel good have their place too. The invitation is to consider our motivations and stay curious about our “why” along the way.

My Middle Way

Coincidentally, I had a long-scheduled haircut and color this week. As I settled into the chair, I told my longtime stylist about my neighbor’s comment. So, we did what we’ve done for years—a semi-permanent, low-toxicity dye on some strands, leaving the grays around my face untouched.

“My kid likes my grays, at least,” I said. Truthfully, I do too.

For now, this middle ground feels right—a quiet negotiation between past and present, between holding on and letting go. Maybe next year, I’ll choose differently. But for today, I’m learning to sit with the in-between—not perfectly polished, not entirely undone either, just here.

Love. ❤️‍🩹

Miscellaneous…

📚 Yung Pueblo’s New Book, How to Love Better is here—and I love it. The “Eight Lessons from Eight Years of Marriage” part is especially juicy. Deep bow to him and his wife Sara for being so open about their relationship journey and sharing their dharma-steeped learnings with us.

Deep love is not easy because it contains so much. It is full of disagreements, howling laughter, hard conversations, genuine care, plenty of tears, undeniable joy, and the feeling of being truly seen. You don’t get the good without the tough stuff that helps you both grow. - Yung Pueblo

⭕️ One Hour of Community Connection via Zoom. The next Sangha Saturday is tomorrow Saturday, March 8th, 2025 at 9:00 AM PT / Noon ET. We begin with a brief meditation, set a bit of context, and then the space for shared exploration. While not about “sobriety” or “recovery,” we are all actively exploring a life without dimmers; for many, that dimmer was alcohol. Others include food, generosity, pot, appearances(!), and work. Link for invite here.

🎧 Undimmed Podcast Season 2. Pre-production starts next month. Please share guest ideas via response to this email so I can add them to the list. Season 1 here.

🤹🏻 Wisdom 2.0 2025 on “Disruption” is happening in San Francisco May 5-6. Hope to see you there. Info here.