This is my second draft. I've been advised that I may be overdramatic in writing this, and I know it's certainly unusual, but I've been disappointed enough by leaders in the tech world lately that I'd rather get out anything that might be disappointing about myself before anyone winds up putting their trust in me than risk being such a disappointment to others later.
I'm going to air here what I consider the two most potentially objectionable things about myself, given the work I'm trying to do and the positions I'm taking. The first is what I personally consider the worst thing I've ever done, and the second is my position in our current socioeconomic structure. These both seem relevant to me, and it will bother my conscience if I let people rely on me without knowing these things.
The first of these I feel uncertain about sharing now because I seem to be the one most upset about it at this point. I've been told I shouldn't bother with it. But I did already promise to share this, and it would bother me if I didn't, so: about fifteen years ago, in order to avoid what I felt would have been an awkard situation, I failed to disclose information to a sexual partner which I might have reasonably concluded they would have wanted to know. I disclosed soon afterward as I felt extremely ashamed of myself. They were not particularly upset, and no material harm was done, but I still, to this day, feel very ashamed of myself for this. Had I heard of this sort of behavior on the part of someone I'd previously trusted, I certainly would think less of them, and I do think less of myself for it. I believe the only thing to do, given all this, is to disclose this information so others may make an informed decision about whether they still want to work with me. If it's something I might care about with regard to others, it's something you might care about with regard to me.
The second of these: I do not have to work for my living. I own my home and am sustained by an irrevocable trust which pays me and my wife the median annual wage for my area. (It will continue to pay her regardless of whether we remain married, as I did not want economics to ever enter in to any such considerations, should they ever arise.) I was previously a software developer working with cryptocurrencies, from which I made a significant sum of money before I eventually came to see cryptocurrency as a fundamentally regressive project (regardless of my own good intentions at the time and the good intentions of a few notable, lesser-known projects). I set up and funded the trust which sustains me with the money I made based on what I estimated it would take to pay me a median wage indefinitely. The money is not legally mine anymore, but the trust is legally obligated to pay me that wage. I put some of what remained into an emergency fund and gave away the rest.
My hope is that everyone might be able to live decent lives in the world I am trying to contribute toward building. My reasoning in setting up the trust was that, in order to contribute most effectively toward that world, I should keep a high degree of freedom without being completely insulated from prevailing conditions. But I am fundamentally insulated in a way most people are not, and my perspective is unavoidably impacted. I feel compelled to disclose this information to anyone who might wish to accurately assess my writing and work, especially as it begins to feel like I am no longer simply shouting into a void but actually may be at the start of building something.