It may feel outdated now. But in the early 2010s, back when I was first immersing myself in social justice activism, one of the most common phrases you’d hear social justice activists say to one another was: “Check your privilege.” The phrase “check your privilege” has since fallen out of fashion, of course, along with the phrase “social justice activist” and its more disparaging variant “social justice warrior.” It’s all been reduced to the simple catch-all “woke” — a shift that reflects the Right’s success in reframing and reclaiming the language we’d built a decade-and-a-half ago.

In the early 2010s, while “check your privilege” was occasionally employed as an accusatory call-out, more often than not its primary intent was collaborative and inviting. In fact, 2010s-era social justice activists would often self-“check” themselves unprompted — as in: “…and I have more thoughts on the matter, but I’ve already been taking up lots of space in this discussion about feminism. As a man, I need to check my privilege here. I’ll stop there.”

At the time of this writing, it is February 17, 2025. We are nearly a month into President Trump’s second term. To say the last month has been dramatic would be an understatement. The new regime has already sent tens of thousands of immigrants to Guantanamo Bay. The executive branch is attempting to shut down entire government agencies without congressional approval. President Trump has been cozying up to other authoritarian world leaders such as Vladamir Puttin. The world’s wealthiest man and mega-weirdo Elon Musk has been seizing control of vital government functions. And, perhaps most relevant to the introduction of this essay, much of the progress my fellow social justice activists fought for has been not only rolled back but in some cases outright criminalized.

Having spent my formative years deeply immersed in the social justice world, and now watching the progress we’d made go up in flames, it is hard for me not to feel at least a little bit nostalgic for those early days, back when I first got involved.

And the truth of the matter is that as I check my privilege in 2025, I am doing OK. I am doing far more than OK. I am doing far more than OK  — precisely because of the privilege I enjoy. Privilege I’ve secured — ironically — through my work in social justice.

***

I have a friend who, for obvious reasons, I’m not going to name here. He’s an undocumented immigrant. He’s made an extremely successful career out of advancing labor and union rights. He’s very effective at what he does. And in his time in politics, he’s been extremely, extremely public about being an undocumented immigrant — it’s a matter of pride for him. As ICE raids continue to escalate around the country, he’s become much more mindful of how he conducts himself publicly (to say the least).

An estimated 11 million undocumented immigrants live in the USA, a population now facing unprecedented threats from the current regime — unprecedented certainly in its dramatics and scale.

And that’s just undocumented immigrants. The current regime has targeted countless other communities across this country — and beyond its borders, it has also sown fear and instability worldwide. How do we even begin to wrap our heads around the sheer scale and depth of the Horror?

***

From February 2013 to July 2023, I worked as a field organizer for progressive labor unions. I helped thousands of workers form unions — from hospitals, to nonprofits, to community colleges, etc. I am extremely proud of this work. Of everything I’ve done so far in my life, union organizing remains the most meaningful.

I was also miserable. I was exhausted. And toward the end of a decade of union organizing, I was increasingly resentful. I spent the majority of those ten years living in hotels, unable to predict when and where I’d be sleeping and working from week to week. It is fair to say I worked a lot. I missed personal events. I could not reliably pursue personal projects. And when I was faced with increasing professional disagreements that I won’t detail here, I knew shortly after my ten-year anniversary as a union organizer that I had to step away from it for my mental and spiritual well-being.

It is so strange looking back — the unbelievable disparity between being deeply unhappy and knowing deep into my nerve-endings that the work I was engaged with was maximally meaningful, aligned with a purpose way beyond myself. How could I have been so unhappy yet filled with so much meaning?

In July 2023, I made a jump. I’ve spent the last year-and-a-half working in union communications while also building up a political media business. I no longer feel the deep unhappiness I once felt — in fact, if anything, it is fair to say that I have been stupidly happy. Of course I experience the banal frustrations that come with life, but for the most part, I get to spend most of my days engaged in creative pursuits. I am good at these creative pursuits; I am appreciated and well-compensated for these pursuits; and it could be easy to rationalize to myself that these pursuits all contribute to higher values and a larger politics that I agree with.

Yet, deep down, I know that the political media I have made in the last year-and-a-half has not been as meaningful as my organizing career. Political media, especially political media my clients have paid to publicize, can reach far more people than any field organizer can dream to talk to in his lifetime — but it is the deep, hard skill of piercing, vulnerable, authentic conversations that transforms people. It is those deep conversations that can help masses of ordinary working people rise up and make transformative political change.

As I search my soul, I’ve come to accept a truth: even as the state of politics in the USA implodes, I have little desire to return to field organizing full-time. I understand the urgency, the shortage of seasoned field organizers who deeply understand what they are doing, the weight of the work left undone. And yet, I find myself drawn elsewhere — I like writing these silly essays, and creating songs, and making films and photos. A life dedicated to creative pursuits would not be deeply meaningful to me, but I suspect it could be absurdly joyful.

Conceptually, I don’t know how to bridge that gap. I’ve tried.

Here are three main ways I’ve tried to rationalize this gap to myself. (1) I’ve made it a practice to lobby my media clients to incorporate field organizing into the media campaigns I produce for them. I tell my clients stuff like, “If you’re going to blast a campaign ad, you might as well use that campaign ad to collect emails and phone numbers, and we have the potential to continue to build from there.” It is true, albeit ironic, that I’m beginning to see more success advocating for field organizing as a political media guy than as a full-time field organizer. This irony could be a whole separate essay. (2) I’ve been volunteering for and helping shape field organizing campaigns — admittedly on a very part-time basis. (3) I tell myself that my impact as a social agent is only as strong as the authenticity of my pursuits.

That last one — “I tell myself that my impact as a social agent is only as strong as the authenticity of my pursuits” — probably needs a bit of unpacking.

***

I wrote in the first section of this essay that “having spent my formative years deeply immersed in the social justice world, and now watching the progress we’d made go up in flames, it is hard for me not to feel at least a little bit nostalgic for those early days, back when I first got involved.”

I feel nostalgic. I feel uneasy about the privileged life I’ve created for myself through social justice. And looking back, I also feel quite critical of the 2010s-era social justice movement I’d immersed myself in.

In 2011, I was 18 years old. My social justice warrior friends and I were kids just starting to plant the seeds of our convictions. Fourteen years later, I’ve seen how the seeds of our choices in life have grown and taken shape.

Certainly, the great majority of my social justice warrior friends from the early 2010s are simply no longer involved in politics and activism in any sort of way — which is to be expected. People’s interests fade — in a general sense, and particularly for those young adults who were never very committed in the first place. There is also a very small minority of folks who were hyper committed back then who are still hyper committed in a genuine and increasingly useful way today.

And then there is the majority of the minority of folks still around from back in the day.

***

One of my closest friends I met through a radical leftwing political group is now well into her mid-thirties. She has never held a job for longer than six months. I’ve witnessed her attempt to end her life. She has an abusive boyfriend who has sexually assaulted multiple women. She is depressed and isolated as she has been extremely verbally violent to nearly everyone she is close with. She is an alcoholic who used to beat her ex-husband. (That’s why they are no longer married.)

Back in the day, she was seen as a leader in left-wing spaces. But I now realize that much of her influence stemmed from a need to manage an internal void rather than from genuine leadership. Looking back, I question whether her politics were driven more by resentment than by a true commitment to justice — a means of externalizing frustration instead of taking responsibility for her own life. While her anger resonated with other radicals at the time, it ultimately hindered her ability to organize everyday working people. (In her one full-time job in what I would consider real field organizing — a job that I pulled strings to get her — she was fired within 3 months.) In my ten years of field organizing, I’ve learned that working people only begin to trust self-proclaimed organizers when those organizers are thoroughly competent, when those organizers are transparent about who they are and why, and when those organizers wield a genuine curiosity and willingness to connect with them. Without these qualities, an organizer cannot be effective — especially not in the long-term, and especially not if that organizer is pushing groups of folks to take the major life risks necessary for transformative political change.

In addition, as she got older — and as she increasingly hid behind political ideology — her words became more predictable. Conversations that were once genuine and surprising, blending her personal experiences with what others shared, started to feel scripted. Through my decade as a field organizer, I also learned this crucial lesson: the fastest way to lose the trust of ordinary working people is to speak in a way that lacks the type of spontaneity and authenticity in which even you yourself are surprised by what you’re about to say.

Of course, the friend I’ve described here is an extreme example of “the majority of the minority of folks still around from back in the day.” But 14 years later, observing how the seeds of my fellow social justice warriors’ choices in life have grown and taken shape, it is undeniable to me that the majority of the minority of folks still around from back in the day either (1) speak in a scripted, ideologically possessed manner when speaking to others about politics, or (2) remain way, way disproportionately unemployed or under-employed while still going through the immense social and emotional hardships people typically reserve for their early 20s. (Mind you, the majority of my social justice warrior friends are not elderly immigrants with multiple jobs and children — admittedly, most of my old friends are white and come from middle class parents.)

As a social justice movement, I wonder if our collective individual weaknesses back then help explain our failure to prevent the Horror of now. (This is why “looking back, I also feel quite critical of the 2010s-era social justice movement I’d immersed myself in.”) If the majority of the minority of the social justice movement that stayed around either failed to fully integrate psychosocially or failed to narratively develop their lives in a way that most ordinary working people would respect, what chance did the social justice movement as a whole have to develop the capacity to successfully pushback against the current fascist regime?

***

Earlier I wrote, “In my ten years of field organizing, I’ve learned that working people only begin to trust self-proclaimed organizers when those organizers are thoroughly competent, when those organizers are transparent about who they are and why, and when those organizers wield a genuine curiosity and willingness to connect with them. Without these qualities, an organizer cannot be effective — especially not in the long-term, and especially not if that organizer is pushing groups of folks to take the major life risks necessary for transformative political change.”

So, a maximally effective organizer must be transparent about who they are and why. But what if in being vulnerable about who I am and why, I authentically lead myself out of a field organizing career? What then?

Moreover, what do I do if I believe that “my impact as a social agent is only as strong as the authenticity of my pursuits”?

***

As the state of politics in the USA continues to go up in flames, I wish I knew what to do. As cynical as I’ve been about my political media pursuits in this essay, I do think political media can help — especially when combined with field organizing. I also want to continue volunteering for and helping shape real field organizing campaigns when I can.

At the moment, those are my best guesses about what to do.

It all feels like not enough. I feel sad about the state of politics in the USA. I feel guilty that I’ve been able to build a successful and financially rewarding career off of the social justice movement. I feel deeply critical of the 2010s-era social justice movement I was a part of, and I wish I had the fortitude and foresight back then to speak out against the toxic resentment that not only prevented our movement from growing stronger but contributed to many of my old friends’ lives being stunted.

I feel horrible that this is my truth. I feel that I do not know how to feel in these times.

In the early 2010s, I learned that when you’re uncertain how to feel, it may be a good moment to check your privilege. So thank you for allowing me to reflect and ramble.