September 16, 2021

Mentorship 1 - Retrospective

This was the first round of an ongoing commitment to mentor ttrpg writers with the goal of growing the space and helping others get published. At the end of each round, I plan to write a retrospective like this, detailing what we did, how I could’ve done better and celebrating successes. This is done to improve my own mentorship scheme, but also to act as a blueprint and encouragement to others with the capacity.

As part of this, the first mentee has provided their own retrospective, provided at the end. Currently, no names are used pending the actual release of the work I assisted with. The plan is to update this page to reflect names once the text is out.

For those interested in applying for Round 2, details will be up on Twitter.

Search & Selection

Prior the mentorship beginning, there was a process of gathering a list of individuals interested. This was mostly done via twitter:

I gathered some basic details (name, project, notes) from each person and stored all of that in a spreadsheet. As can be seen in the thread, the goal is prioritised people with marginalised identities. As such, anyone who didn’t qualify was marked as such so I could quickly filter through - if in a future round no marginalised people are interested, I would begin working with these applicants.

When looking at all the entries, I was incredibly impressed with the quality and diversity of the pitches. From here, it was a case of evaluating how much I can help. This was the hardest step of the process - I wanted (and still want) to see all of these pitches come to fruition.

I focused on projects earlier in their lifecycle, feeling I could make a larger impact - the goal was not to replace any of the traditional publishing cycle steps but to help more in the actual writing step. As such, I discounted those projects with successful crowdfunding campaigns as they would (presumably) have finished manuscripts and (more importantly) have access to funds for developmental editing.

I also considered where my talents and preferences would be put best to use - as many of you are probably aware, I have declared eternal and unending war against systems prefer to work on games content (adventures etc) rather than games systems.

After a weekend spent in deliberation, I selected the candidate - a larger project looking to modernize and improve the city gazetteer’ module. This felt like a challenge, as well as something I’ve worked on in some of my own projects and games.

Format, Management, Content

We structure we settled into was an weekly hour-long Discord call. These broadly fell into two categories:

Show-and-Tell: the mentee would show me what they’d be working on for the past week, and we’d go through it talking about why they had made the decisions they did. This functionally was similar to light” developmental editing, although far more focused on the underlying concepts rather than the functional structure of the actual document. I also took this opportunity to praise elements I really liked - I think highlighting these elements keeps the tone in a good place as well as being a genuine reaction to seeing something cool. These calls were often used to show the principles discussed in the Dissect-and-Analyse calls, as well as identifying additional topics to be discussed. From a technical perspective, this was achieved via GDOCS and the commenting functions. This was useful as I could, prior to a call, go through a section of text, leave comments and then talk through the comments during the call, answering questions and broadening the conversations.

Dissect-and-Analyse: where we had identified a design problem’ or major element of the project, we would try and find some examples of books/zines/blogposts tackling the issue, as well as talking around the subject in a non-games capacity. We would then take the time to read through the game-texts identified prior to the call, and then discuss our findings - often using a screenshare to highlight elements we thought worked well and those elements which we thought sucked. Both were incredibly useful - being able to hold up negative examples and explain why they didn’t work was very illuminating. Even more useful were the near-misses - identifying elements which could be great with a small change. Taking the time (and having a reason) to apply a structured approach to analysing game-texts in this way, and then needing to be able to explain clarified a lot of my thinking on games.
One of the strengths of these calls was the mentee being able to suggest and bring their own examples - both of us having different groundings in games led to some very productive cross-pollination.

Due to real-life existing, we had some weeks were the call was unable to happen - being flexible with this worked for both of us, although having a specific timeslot made planning around the call much easier. This is something I plan to take forward.

Additionally, between calls we often talked over text-chat - both for administration and low-intensity discussions around any tangentially related topic. This was done with the understanding that text chat is responded as suits the other person - there’s no requirement to respond within a certain time. We also used the text-chat pinned messages to store important notes.

We addressed the timeline and progress of the mentorship throughout the process, constructing flexible plans and adjusting as required. From the outset, I deliberately did not set a timeline - wanting to see the project through to the end and to not cause stress. As we approached the finish line, we started talking through when we hit a deadline’ - where the weekly calls would fall away and we’d shift into peers rather than a mentor-mentee relationship. This was done to find something mutually agreeable whilst also having a specific demarcation point to ensure no ambiguity.

Early in the process, conversations focused on the actual craft and technique of writing ttrpg content - how to think about it, how to approach it and how to keep working on a longer project. Much of this can be found here.

Towards the middle stretch of the process, we continued conversations around monitoring progress and structuring how you write a larger document, whilst also spending more time talking about specific design aspects. This is where most of the Dissect-and-Analyse calls happened. We also started talking about end-points - discussing the differences between self-published and publishing through a third party, and the strengths of each. We also spent a lot of time in the Show-and-Tell calls during this step.

Towards the end, we mostly worked on the writing itself using Show-and-Tell calls whilst making firmer decisions around publishing. We agreed to work on writing up a pitch and building some lists of publishers to apply to. Due to various reasons, the mentee pulled the trigger on submitting a pitch ahead of the schedule. As it is, this pitch was accepted - a fantastic result.

With the pitch accepted, we moved the cut-off forward. I’m still involved and there to offer advice and help, but this is strictly as a peer.


  • The terminology and Structure used above is post-hoc - during the actual calls, we just said we’ll talk about THIS using THESE TEXTS.” I think offering a choice between a Structure and an organic scheme of work would make mentees feel more comfortable - some will prefer being more specific with their approach, other prefer a more casual approach.
  • I think having a flexible timeline in place ahead of time could have been useful in the middle stretch - giving us a goal to work towards and monitor progress against might have helped in some areas.
    • This would have to have mentee buy-in to not act as a stressor - the idea is to roadmap the process than to dictate pace.
  • Pre-identifying topics to be discussed at the outset and adding more to a list as we discovered them would’ve helped guide us in structuring conversations week-by-week.
  • Make an explicit offer to have a third party observer’ involved in any DMs and calls. This never came up, but I saw it as a safety consideration made elsewhere and is something I’d like to adopt and normalise.


This has been an incredibly rewarding process for me - not only have I helped someone, I have learnt a lot and gained another peer in the space. I’m very keen to start the next round, and can only encourage people to offer similar opportunities.

10/10 would mentor again.

Mentee Retrospective

I have been Luke’s mentee since February of this year. I’m going to spoil things and say right off the bat that I felt this was a very helpful, rewarding experience and that I enjoyed my time with Luke. I’ll describe below what the process looked like and how I felt about it in as much detail and as candidly as I can so that anyone who’s thinking about trying this can decide whether it’s right for them.

When Luke put out the call for mentees, I had two projects going at the time. One, almost entirely finished, was a zine. The other was something I was still just spitballing in my head which was a big setting book based on materials I’d created for my home game. In my head, I thought it would make the most sense to focus on describing the zine which I thought would be a nice small thing to start with to get some experience in publishing game materials. I was pretty surprised that when he accepted my application he said he was more interested in combining the two and turning them into a bigger project.

It turned out that Lesson One in the Gearing School of Actually Doing Shit was choosing to do the harder thing.


We met once a week over hour-long Discord calls for about 7 months, during which time I went from just an idea of a book with an imagined table of contents to a manuscript that I would put around the 70% mark here in September. I remember the first conversation involved me screencapping my Scrivener outline view to show Luke. Most of the documents had no words in them, and half the ones that did had just one or two lines in them. This made me feel ashamed at the time, like I was showing a guy who’d written several books some unrealistic dream project. Looking back now, I’m glad I started with almost nothing.

This table of contents turned into a kind of framework for what we would discuss during the mentorship. Phrases like Gazetteer”, Market”, Encounters”, etc. all become topics of the week where we would either chat about things I had written in the past week or go over how previous materials had tackled them. Even when I had no new material to show and was unsure what to talk about, Luke would encourage me to have a chat anyway. I’m glad he did; having this check in reminded me that this project was a real part of my life and something I’d committed to. I would say that was one of the most valuable elements of this program.

So that’s what this program looks like from a bird’s eye view: several months’ worth of weekly 1 hour calls with a grumpy veteran writer who loves Clifford the Big Red Dog. You will look at projects similar to yours, you will write things and show it to him and sometimes he will nod and say yes, those sure are some words” and other times he’ll notice you had a good idea or two. That is the meat of the program, and I honestly believe I got a lot out of it. Here are what I think were the most valuable benefits for me:

A Second Set of Eyes

One of the first things Luke did for me was give me some perspective on what had come before my project. I’d read a decent amount of new OSR setting material, but precious little outside of that community or this past decade. Luke helped fill in those gaps. He showed me some old school stuff from sources I hadn’t considered (Warhammer, Glorantha, some Google+ posts from before my time) and helped me solidify what I felt would actually feel fresh about my project so I could lean in to those things.

But this isn’t the only thing a second set of eyes did for me. One of the biggest issues I struggled with in my writing is getting out of my own head and seeing value in my own work. Even when I write a blog post I can’t help but think, does anyone really want to read this? Am I doing anything new? Am I just taking up space? If you are a person with an average amount of self-respect you probably understand that this is a really unhealthy way of looking at your creative output and maybe an excuse not to write. Talking with Luke didn’t eliminate this problem. He wasn’t my therapist. But what he did do was listen to me verbalize these worries and basically say yeah, I’ve been there.” Moreso than assure me that these worries were unfounded, he helped me understand that they are part of the writing process and that it is possible to feel these things and just decide to continue.

Sometimes you just need someone to say yes these are valid feelings, now quit your bullshit and give me something to read for next week.”


In case you were thinking this mentorship is just about a guy who’s written more books than you telling you you’re doing a good job, no! Luke has what I would describe as a much firmer and more specifically described sense of what he wants from roleplaying than I do, and this has and probably will in the future put us at odds in design sensibilities. This is a good thing.

There are things in the book I doubt Luke would ever find personally useful, and things in this book that remain that I’m pretty sure he advised me to remove. I could almost see Luke shuddering as I showed him mechanics I’d written about abstract currencies or progression tracking. I could picture the blank look on his face as I described the Japanese RPGs and Chinese novels that informed a lot of my aesthetic choices. It is safe to say that there are plenty of ideas that Luke helped me develop that are distinctly Not His Jam.

What’s important, though, is that I had access to a very different, sometimes alien lens on writing and design. I can sincerely say that this has inspired me to write things that have satisfied me more than if I had shown my words to someone with more similar tastes. It can be terrifying to expose things you’ve written to someone you’re pretty sure isn’t going to like it, but I would highly encourage trying this. I’m no stranger to critique of my work — I’ve done a lot of writing workshops and a lot of sitting silently as a large group of people absolutely trash my story. But it’s a different thing to write something knowing one person is going to look at it and knowing that one person has very strong feelings about how this is not a fun way to play games. This is an experience you’re not going to get that often if you mostly show your work to people you talk to a lot, and I highly recommend seizing on and treasuring this opportunity.

I have to note that sometimes Luke surprised me in this regard. He would occasionally advocate for mechanizing things I had never considered. He would encourage me to follow my bliss and lean in to what I previously worried would be masturbatory excess. Sometimes I think this was Luke encouraging me to do the thing only I would do, and sometimes I think maybe I just don’t have Luke figured out like I thought I did.


The most important thing this program did for me was to keep reminding me that this project was worth finishing. It’s hard to understate how helpful it is for someone to say every week, hey, you cared about this thing. You still do, right?” As you get months into a long project, it’s helpful to look back at your chat logs, the call notes you wrote, etc. and remember the excitement you felt for it at the start. To remind yourself that this thing didn’t stop being worthwhile just because that new project” shine has worn off. Having Luke there to prod me and remind me that I said I could do this thing was huge. This is obviously something we all need to learn to do on our own, but it really helps to have someone there to get you over that first finish line, to make it part of your personal reality that this ridiculous project you came up with 7 months ago is still possible.

Do it

If for some reason you were reading this entry on Luke Gearing’s blog to figure out whether you want to work together with Luke Gearing, well yeah. You probably should. But I would also implore you to ask yourself if you can do this for someone else. A lot of things Luke helped me with are things that benefited specifically from his considerable experience, but most others are simply Luke choosing to put in the time and invest in his community. Any of us can do that.

When this project is behind me, and when I feel confident that I know at least one way to get a thing started and finished, my hope is to pay this forward and help someone else get their voice heard. The thing that makes Luke Gearing too powerful, as they say, is that he chooses whenever possible to do the thing instead of just talk about it. So do it! Participate in this program, then run your own program. Become Luke Gearing. Then, should you meet Luke Gearing on the road, kill him.

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