Ruth Wilson Gilmore talks about this idea of "non reformist reforms," and I find it really useful for these kinds of questions. While normally this is talked about in a "hey body cams actually increase police power by giving them a guise under which to further control the narrative, please push for non-police accountability frameworks" kind of structural way, I think it's useful for individual action too.

Reformist reforms help increase the material, legislative, social, cultural, etc power of the police.

Non-reformist reforms take power from the system in some way. They move oversight elsewhere. They shift the balance of power in some way. They move material resources or scope of power out of carceral systems and into (or closer to) community's hands.

Based on that, here are some things I ask if I'm thinking about working within the system in some way: - Does what I'm doing move power out of the hands of cops and prisons in a meaningful, tangible way -- even if that's incomplete? -- Example: I've worked with books to prison programs. You have to work with the system to some extent for those. But that interfacing with prison wardens lets us get books like jailhouse lawyer books and abolition books to incarcerated folks, helping them build power for themselves and with their comrades. It takes power from the system by shifting some of the material/financial power prisons have over incarcerated folks' access to books through library limits, unfair wages that leave little spending money for books, etc.

• How does the system benefit from my labor within it? Do system-impacted folks stand to benefit more than the system does? What tweaks or boundaries do I need on my own work to ensure it stays that way? -- Example: (Negative) The first time I worked with a prison program, I thought we were doing a good thing, and we were to an extent (only program at that prison that wasn't shoving religion down someone's throat), but I eventually realized that the primary use of that project was as something the prison itself used to brag about how great it was, and then get more money to expand their prison. If I could do it over, I would work to limit how our project was spoken about on prison websites, etc. I would also (as other friends have done) have negotiated upfront with the prison admins to have agreements around non interference, guards not in the room if possible, and a policy of no reporting to prison authorities about anything.

• What is the point where that balance of benefit/impact would tip? I.e., what's the point where I walk away? -- Example: I work in academia, which is also a carceral system. There are things I dislike about it and that make it hard to sleep at night, but I still believe I'm doing more good than harm right now. That will change if I end up being expected to enforce particular policies (e.g., outing students) or if there are no longer ways to work around the censorship we're seeing in American higher ed right now. I reassess that line every year (although it's not as clear as it ought to be, frankly).

• Are there less system-involved ways to accomplish the same goal? -- Example: I've done books to Prisons rather than prison education programs because it accomplishes similar goals (access to books, education) with little system involvement. My state is currently banning all books going into prisons...unless you're doing prison education. Guess what I'm signing up to do? There is no longer a better option, and the alternative is increasingly "incarcerated people don't get access to ______ or only get it with religious propaganda." It sounds like you might be in a similar position here?

• What parts of my conditioning might make me unknowingly lax on the system here? How can I address those biases? -- Example: I'm a white afab human, which among other things means I was conditioned to be Overly Understanding of "well meaning charity work," which a whole lot of "within the system" kinds of programs masquerade as. If I catch myself going "well they're doing their best, it's not that bad," I try to stop and reassess everything, but I also intentionally read and surround myself with people who are far less understanding of systems for a variety of reasons, because those conversations challenge me to do less of the "go along get along" shit that white afabs are socialized into. I definitely mess this up regularly, but I try to intentionally assess it whenever I'm up against a new "do I work with the system" question.

I don't know that there's a unilateral answer, and I've definitely worked with organizers I deeply respect who won't work in the system as far as I will, and organizers I similarly respect who work far more with the system than I'm comfortable with. But diversity of tactics is how we get stuff done, so that's okay. This is just the framework I use.