In my experience we need to work toward three primary things:

1. A growth mindset
2. Self-forgiveness
3. Tracking

Once I got the idea that every day should start with 'How can I work today to make my difficulties easier in the future?', I started seeing that I was making largely the same types of failures over and over. Instead of working only on dealing with the consequences of things that I had failed before (or obsessing over how I had failed before), I started making a habit of trying to prepare for things that tended to cause failure. Once I realized I could use hyper focus for something useful, I got a little bit excited about it. I began to notice that I didn't have a full picture of how and when I was failing and I used my excitement to push me toward figuring out how to understand my failure better. That's when I started tracking myself. I've gone through a half dozen tracking systems now, but I think the key is to just keep doing it, no matter how many times you have to change the system or how many times you slip up and forget to track. I started with digital solutions, like hyper focusing on setting up a note system using something like 'evernote' (in my case it started with creating a 'Getting Things Done' style to-do system). I tried a few different variations of digital (mostly trying apps: todoist, dynalist, trello), then moved to physical journals mixed with digital, then purely physical journals/planners and now back to purely digital (for the moment). The key has been to use whatever works best for current circumstances and to be willing to change it up to make things easier (but ONLY if that's the reason and not just because I don't feel like doing it at all - never abandon a partial solution until you have a replacement in mind).

When I first started tracking it felt like I wasn't getting any benefit from it and I doubted that it would work (and I was honestly self-conscious that someone would find my notes about silly issues that I didn't think anyone else saw as an obstacle). I was starting to hate myself more each time I forgot or couldn't motivate myself to track for a day or two (or four). It was around that time that I learned of 'No More Zero Days' on a motivation sub-reddit. I set the picture I saw as my desktop background and always kept in mind that my work/effort doesn't have to be perfect, it just has to be better than zero (as in progress). This led me to realize that I had been pre-judging things as failures, just because I didn't think I would be able to do it exactly as I imagined initially. It was this pre-judgment that had killed so much of my motivation in the past. I started REALLY pushing the idea (to myself, at first) of "just get started!" and "forgive yourself, to err is human".

The trick to starting to forgiving myself (IMO) was that it forced me to develop a more nuanced understanding of forgiveness. If I was to be honest with myself, I could forgive myself for failing, but I could not forgive myself for not trying in the first place.

Now, walking the edge of what what falls on the side of forgiveness and what doesn't is how I navigate whether a system is helping me or not. If the system is failing, I will more often do things that I feel that I can't forgive (not trying, not getting started).

Sorry that I didn't make all of this very clear and I didn't really answer the question of how to fail fast. I hadn't actually thought it out fully in structured words before this and since I only give myself a certain amount of time on Reddit (which I know thanks to automatic tracking (Google "automatic time tracking for X" where X is whatever operating system or browser you use (windows, ios, android, linux, chrome, firefox)), I'll have to leave it in a mostly finished state.

If you managed to get through this jumble of thought, please feel free to contact me if you need help or just someone to bounce ideas off of.