Preparing for the darkest days

Welcome to the end of the (calendar) year — solstice, Hanukkah, Christmas, whatever that looks like to you. Now that we've passed the shortest night of the year, we're ready to welcome the light again. Right?

Actually, I want to invite you into deeper into the dark in this murky period before 2026. Light casts shadows and puts everything into relief, but darkness holds vastness and nuance without shying away—something I believe you can do, too, if you aren't too busy clamoring for the light.

Who do you share the darkness with?

Last week, Andrea Grimes wrote a short, thoughtful piece over on The Flytrap in reaction to this absolute trash the NYT published back in November (with Mel Robbins as a co-author) about how much we'll all regret fighting or cutting off ties with family who politically or socially misalign with us. Grimes breaks down the key assumptions that Robbins and Pillemer leverage, including the guilt-tripping and false imagining of what "hard work" in relational dynamics should entail (largely, tolerating intolerance for the sake of supposed connectivity, even if we never explore how that connectivity could barely reach an inch in depth with this approach).

Far from forcing ourselves through the awful holiday-time ritual of putting up with people in our lives whose bigotry and regressiveness revile us, Grimes writes that, rather:

It should be expected, even considered natural, that people who say and do harmful things are, as a result, put in limited contact with, or even ostracized from, people who dispute, rebuke, or abhor those beliefs and behaviors. It’s not that complicated, even though it is very fucking serious and can indeed be devastating for families and communities.

Sure, there's something to this idea that we should choose and invest in relationships that center the values we want to uphold. That we should reject superficiality in our connections. That there's no special benefit to "togetherness" when it rests on such tenuous foundations. Of course I'm sympathetic to this argument, not only because of personal choices I've made in my own relationships or because I'm skeptical of the self-help industry or because I think the "let them" theory is rank bullshit dressed up as zen radical acceptance.

I'm sympathetic because I believe that actions should and do have consequences. I believe that living in relationships and communities and societies requires us to contend with and navigate conflict (notice I didn't say resolve conflict). I believe that living in accordance with values and principles requires shifts in our behavior, and that can include who we choose to spend time with and how.

But I'm also sympathetic because I believe that part of what's at stake is how we're constructing a reality together. In the last year, so many of us in the so-called United States have experienced the never-ending deluge of bad political news as an enveloping darkness and heaviness.

For some of us, that wasn't a new feeling; for others, it felt like a sudden onslaught. Either way, acknowledging the darkness and the state of our reality is the only way to build strength, power, safety, and security. Ignoring it, letting people in our lives espouse its banality or treat it as inevitable, keeping one foot in the doorway of denial—all of those prevent us from grappling with the reality of the darkness itself.

What's at stake in that failure to confront our current circumstances isn't just some manufactured loneliness crisis or generational divide or risk of family estrangement. What's at stake is survival.

"Accepting people for who they are," as Robbins and Pillemer write, does not at all require that we validate their worldviews or honor them with our presence and connection. But neither is it the case that merely withdrawing that connection to protect our peace (as Grimes seems to advocate) fully supports our political ownness and power.

Going with the flow versus standing in the stream

I can't speak in a prescriptive way about how any or every individual should conduct themselves around family and friends—I believe you are a better judge of what circumstances require than I could ever be. But I do want to offer that your only options need not be:

(a) Withdraw your presence entirely
(b) Pick a fight (and win it)
(c) Give in, remain silent, play along

As human beings we have finite energy, and I personally strive to not give up too much of my own to people who just swallow it whole unabated with no conversion to anything that matters. If for you that means withdrawing your presence from people who can't receive or benefit from your time investment, then proceed accordingly.

If remaining silent and smiling along for the sake of "unity" doesn't cost you pieces of your humanity (or you have great support structures in place to help you weather the interactions, and have solid reasons for proceeding this way), more power to you.

I want to focus on that middle category, which supposes that if we are coming into our holiday interactions in values conflict, we have a responsibility to argue our policy positions and combat the bigotry of our kin. This sense of obligation is borne of a very common (liberal) assumption that the primary front for political battles is in the marketplace of ideas—that if we simply "win hearts and minds" we will also naturally produce the society we want and deserve. If only your conservative relatives were confronted with the Truth™, you imagine, they would see the error of their ways and change "sides" in the debate, ipso facto democracy prevails.

The fantasy undergirding this idea is one in which we as human beings don't have fundamental or reasonable conflicts about policy, or about how our society should be structured, or about what means achieve the ends that we supposedly agree on. And in some ways it's a fundamentally coercive vision in which our utopian arrangement first requires total consensus.

But there's a difference between engaging in passionate argument and spirited debate in attempt to best your ideological foes... and simply remaining a stalwart, fixed, immovable force in the face of someone else's ugly beliefs and repugnant actions. Even if they cannot agree with your principles, for whatever emotional and historical reasons, others can feel moral clarity and fixity. And building that feeling within yourself can take you outside the adrenaline-fueled debate sphere and back into your own sense of purpose.

More on the practicalities of this shortly...

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What does it feel like to confront the darkness?

I was watching footage of Evanston Mayor Daniel Biss face off with CBP this past week and thinking, how many average people would feel bold enough to stand 6" from a fascist's face? And does Biss come to that place from ignorance and entitlement (as a white man and holder of political office), a sense of obligation to his constituency, an incomplete calculation of risks, or a true moral certitude?

The thing to note here is, for some rare small subset of people, this kind of confrontation can happen instinctually. For many more, it can only happen as a function of practice. If you've never directly confronted the darkness and sat in its envelopment, if you are always immediately and frantically fumbling about to find the light, how can you trust yourself to stay resolved and clear even when no light is available? Or when you are asked to be the light yourself?

I'm not saying, put yourself in harm's way and/or endure an onslaught of abuse from family for the sake of building your own moral character. What I am saying is, practicing your politics even through quiet acts of resolve and refusing to cede rhetorical ground teaches you that you do have resilience to meet the darkness. It doesn't require that you have the perfect words to say to best an intellectual foe, or that you don't have any emotional fallout from negative interactions with bigoted or dangerous people, either.

Practicing this fortitude in familiar environments, around familiar people, is its own act of self-preservation and political power-building. And. It builds the skillsets you need for deepening your political relationships elsewhere: patience to withstand misunderstanding and misinterpretation, clarity in your principles and values, practice articulating your views and beliefs for different audiences, courage to disagree and differentiate yourself, discernment to see the planks that form the necessary foundations for your deepest relationships.

Some practical actions and hopes for your holiday season

As promised, this isn't just a philosophical intervention. I genuinely believe that confronting the darkness we're surrounded by (in others, in ourselves, in our political climate) is a tool we can wield to refine our own values and commitments, to learn what we're made of, and to (eventually) bring our values into reality.

And as such, I want to offer just a few practical thoughts for how you might proceed this holiday season if you're one of many people navigating our current darkness and feeling called to confront it head-on. These aren't just skills for a few weeks as you navigate friends and family—they're the building blocks to meet our political darkness with strength and resilience no matter what season.

Get clear

Before approaching any interactions with people outside your political milieu this season, get clear on your own beliefs, red lines, and basis in fact. Check:

• What do I believe to be true? How do I know?
• Where am I willing to update my beliefs in the face of new evidence or perspectives?
• Where or with whom do/can I seek out clarity and refinement in these beliefs or the implications I draw from them?
• What are my red lines, and what will I do (e.g., withdraw my presence) if they're breached?

Get strategic

Not every interaction needs to be treated as a battle to be won, no matter what your intellectual commitments or nervous system tell you. Approach holiday gatherings with a sense of strategy:

• What do I want my medium- and long-term relationships with these people to look like, and are my current actions in service of those visions?
• What context are we in and is that supportive of the conversations I want to have? (i.e., maybe don't start a detailed negotiation about asylum policy while 16 of your cousins are screaming at the football game...)
• What needs exist in this dynamic or relationship, and how can I honor or attenuate those? (e.g., if you are financially dependent on someone, you may need to moderate your engagement)

Get support

More than anything else, remember that you don't have to navigate tough interactions alone—not over the holidays, not ever. If you don't yet have chosen family and a support system that is helping you grow in your values and politics, let this be the flashing neon sign that makes you prioritize that need in 2026.

But in the near term, seek out support wherever you can:

• Talk to people you already trust. Pre-game interactions with them, invite them to a post-mortem of your holiday dinner argument, engage them as a sounding board to refine your own beliefs and commitments.
• Seek out media (books, shows, news outlets, social media, whatever you need) that helps you feel grounded and not alone. Critically, this isn't about burying yourself in mind-numbing short-form video content (although sometimes that's cathartic)—it's about showing the you that is practicing resolve in the face of darkness and adversity that others are building their resilience too, and we're in this together.

Staying connected and engaged til the end of 2025

No matter whether and how you're approaching your interpersonal dynamics this season, staying politically aware and engaged is part of preparing for seasons of darkness. So here's your slightly overdue weekly round-up of news you may have missed, and some ✨good things✨ too, as a treat.