How The Fuck Does This Make Money?

For the last three years, I’ve regularly tried to pitch a recurring feature with the title “how the fuck does this make money?”

The premise was pretty straightforward, as you might imagine from the title.

I’d interview different people in the precarious gig economy, about their overall income, how much time they spent on “work,” what they charged for different products, and their “loss leads,“ or the things that they did because it mattered to them that they didn’t make any money at all on. The things they did that were either part of their vision, represented their values, or made them feel good, and had very little to do with profit/loss statements. I never quite got this pitch off the ground for a few different reasons. 1. Fear of Disclosure — I found it very difficult to convince people to talk to me about their income, even for my own edification, let alone for a public audience.

2 Lack of Knowledge — At the time when I first started pitching this, there was no substack, Patreon was very know, and the global pandemic that made us rethink work in the digital age was the years away, so many publications were skeptical, if not outright incredulous, about the income of the people I proposed interviewing. A newsletter about trains? A Professional cuddler? A Financial dominatrix? They probably got a grant, venture-capital, or a trust fund. Or they were lying. The third reason why I never quite got this pitch off the ground was the most insidious and for obvious reasons, the one most concerning for me personally.

3. I have no idea how the fuck I make money.

I left the nonprofit world last year believing member funded organizing, media, and education was one of the least depressing to imagine a hopeful future, one less dominated by hedge funds and precarity. I had firsthand experience with how effective this model could be, working for a while with Socialist media cooperative Means TV + time spent doing grassroots fundraising (especially online) with LGBTQIA + tenant groups. To be fair, my goals and interests have changed a lot in the last year: I went from doing social media + public speaking trainings for organizers to producing a speculative oral history and writing weird fiction/memoir based on TV Tropes.As I’ve written about previously, I also started treating and taking my recovery from alcoholism (I’m almost 4 years sober but had been “white knuckling it,” to use AA parlance) and treatment for C PTSD seriously, learning a lot about the nervous system along the way. As I am often loath to admit, this takes time and energy, time and energy that cannot go towards building financial and artistic sustainability.

Where I’m Still Struggling, Like Everyone, is $$

A year later, Working 2050’s first season is slowly crawling towards a release date. I publish Notes on Feednet weekly with about a month and a half average backlog, half half a novel draft (Why I decided to also do that this year I’ll never know) and I’ve got a solid plan for next steps on both, barring one critical component. Financial sustainability.  Though I have talked with many people over the years about how to create a meaningful paid subscription model for both podcasts and newsletters, and have even run campaigns for a few myself, when it came time to set this up for Notes on Feednet or Working 2050, inevitably I choked.

Long after my “Brainstorm + start plan subscription model” to do list items had passed their deadline, I have still taken on unrelated work in areas where I had limited expertise, searching for paid work in other areas, and texting my friends at four in the morning, “should I go back to school to be a physical therapist assistant?” (General Consensus: No. What? Why? Go back to bed.) At the slightest fear of pushback, my nervous system conspires with idealist.org to keep me from moving forward.

I’m not that special.

This freeze response, a sense of both urgency and aimlessness in my approach to money is not an uncommon experience right now, during a heinous global pandemic, a completely dismantled economy, and the restructuring of digital labor in the midst of all of this.

But it’s also kept me from doing things in a way that lineup with my values: without a clear sense of my own income, I’ve found it hard to put time and money towards mutual aid. Paying people for participation in Working 2050, especially BIPOC actors, producers, and writers, has proceeded glacially, which is why the launch date has moved from March, to October, to December, and beyond.

Evangelizing about the Passion Economy

What does feel unusual is that this is in spite of my relentless research, my genuine belief in the merits of the “passion economy “as Adam Davidson calls it, I’ve yet to build any sort of path towards financial sustainability for the work I spend most of my time on. I genuinely believe in the values that a member driven model tends to mandate for media — accountability, transparency, and genuine interest in if the people you’re working for are getting any benefit out of what you’re doing. As someone at Autostraddle said in their last member driven fundraiser, “ It’s more sustainable to make things people want to read than to make what venture capitalists want to fund.” I also, naïve as it may sound, genuinely believe that for many people, especially Queer, trans, bipod, disabled, Neurodivergent, and mentally ill people, there is a path towards slightly more financial stability in line with their spoons, executive functioning, and values through digital work. And the people who can’t afford to experiment with this model absolutely should, with as much transparency and accountability about how they build it as possible.

So what gives?

Fear is the Mindkiller. And the Rent Payer. Yesterday, I cashed my last check from previous contract work, paid my rent with it, and cringed. As I found myself preparing for my annual December small business holiday freak out, staring at button making kits with no idea what I would even put on a button, I realized it might be time to do something different. As always, my friends knew what was going on with me even if I didn’t. My friend Zenen texted me “this is my everything you make is about, duh.”

This text message, once I was done being enraged by it, give me a lot to think about.

It reminded me of the non-long discarded pitch I was still thinking about daily, and it gave me an idea. Maybe the problem with previous iterations of “how the fuck does this make money,” wasn’t that the idea didn’t make sense, but that I wasn’t providing the same level of honesty and accountability that I was asking from those I interviewed.  That text also made me be a little more honest with myself: the problem with my member-based model, and my overall financial set up, Was never that it wouldn’t work, that I was the wrong person to do it, or that the people I was talking to were financially strapped enough to begin with (though this may all end up being true!)

The problem is that I am afraid to do it.

Now What? A Four Part Series

So: for the month of December, I’m going to try out something new, as I work to set up financial stability for Notes on Feednet + Working 2050. Notes on Feednet will continue to be updated weekly ( And wow the next six episodes of working 2050 don’t have a lunch date yet, this will not impact their arrival). There will also be a special edition that comes out on Tuesdays, a deep dive into how I am thinking about money, sustainability, and the financial future of the project. In the first week, I will cover my financial set up and how the fuck I’ve made money up until this point.

In the second, I will cover different options for the future, and how I’m evaluating those (Adding a paid day for substack, holding more sci fi journaling workshops, creating longer courses about writing fiction from interviews, a Patreon with extended Working 2050 content, etc).

In the third, I’ll talk about scale, how I think about who I’m talking to, and probably end up sharing some very passionate weirdo thoughts on authenticity belonging and “marketing”. In the fourth, I’ll share updates on how it’s going and a picture of my financials compared to when the series started. I’m hoping I will also talk a little bit about dealing with fear and my overall mental and emotional wellness, which I hope to report has not significantly deteriorated from the start of December.

As this project grows, hopefully, I will also interview other people who have created something sustainable in this new weird digital economy about what works for them, and what they struggle with in the day to day. Here’s Why I’m Doing This:

In many ways, this is a weird personal companion to Working 2050, with some additional skin in the game as I try to figure out my own immediate financial future.

I hope that it’s helpful, not just for me, but also for you, and anyone who is trying to figure out how the hell to manage your brain, emotions, time, and ability to survive under capitalism. It’s really lonely out there, even for the people who are making it work.

I hope that this series will be a way to have more real conversations about the good and bad of how the fuck to make money.

What questions do you hope get covered in this series? Let me know in the comments.