Learning From Mistakes

The purpose of this blog, as I’ve stated elsewhere, is twofold. The first purpose is to serve as documentation and guide for those seeking to understand my own thinking and the experience of building a startup; the second is as a record of my beliefs from which I can learn. Today’s post regards the second purpose.

In order to learn, simply identifying one’s beliefs is insufficient. One also must test those beliefs, and accept the lesson if necessary. (I could describe further or more complex steps, so as to not make it sound too easy, but I think this is sufficient detail for our purposes here.) The test is often execution – that is, actually working at Modulate and seeing if my ideas succeed – and in other occasions comes simply from discussion, both here in the comments or elsewhere, about the ideas I’ve presented. The benefit of working at a startup is that I have the opportunity to engage with a huge variety of challenges and situations, meaning my beliefs can be tested widely and thoroughly. But this benefit is useless to me – and less than useless to Modulate – unless I can also accept the lessons when I discover I was wrong.

I like to think I’m decent at this already. One doesn’t work at Bridgewater very long without being able to endure being told they are wrong, and coming to recognize it for themselves. But I don’t always have the luxury of a wise mentor noticing my mistake and taking the time to help to understand it, these days, so I think it’s important to build my own systems to hold myself accountable to not just acting like I’m willing to learn, but actually learning.

This is hard to do well (and that’s an understatement.) But one tool which I believe can help is to own my mistakes publicly, not merely internally. There’s a few reasons why this is true:

  1. I already have a habit of reinforcing my willpower through explicit “promises” with myself, which is driven by my (repurposed for good) sense of pride in myself as a man of my word. This taps into that same mechanism of putting my pride on the line, making it both familiar and somewhat battle-hardened for me as an individual.
  2. Writing about my mistakes publicly forces me to think about how to communicate them, which, as any good teacher will tell you, forces me to first understand them. This only helps if I can get far enough as admitting I made some mistake – in which case it ensures I don’t cheat by letting myself pretend it was lesser than it was – but is still a useful tool.
  3. Putting my mistakes out there prompts others to provide feedback about how I ought to improve, whether I’m misinterpreting my mistakes, etc. Even if this doesn’t directly happen in the comments of the post itself, at bare minimum having the content already ready to share makes it easier for me to request such feedback from specific individuals later.
  4. This isn’t directly valuable for my own growth, but hopefully my candor and (dare I say) humility in acknowledging these errors will help people to better understand me, and perhaps even set a useful precedent for others hoping to accelerate their own personal growth.

Based on this reasoning, I’ve decided to start tracking my mistakes on this blog. I’m not going to go through the effort of trying to list past mistakes – there’s frankly too many – but moving forward, I intend to make an effort to track here any mistakes which I consider to be suitable large or interesting, especially those relating to other content on this blog. For now, I’ll be adding them below on this post, to ensure the above background is always available and to make these admissions easy to find as well. As this post grows over time (and I’m sure it will), I may fall back to an alternate approach, in which case I’ll edit this post to explain at that time.

One final note: I want to really reinforce that the mistakes I outline below are, to me, the process at work, and not a moral condemnation. I’m not attempting to self-flagellate, nor to claim that it would have been better to do nothing than to make (and get the chance to learn from!) the mistake – only to ensure that I actually collect the wisdom I’ve earned by taking those risks in the first place.

I hope this proves useful, and look forward to your thoughts and feedback about this strategy. And, if you know me well enough to recall one of my past mistakes; or have identified a clear error in one of my posts here, please don’t hesitate to share your suggestions for errors I should add discussion of below!


My mistakes so far:

  • [8/11/2019] My blog post titled “Why Discord Is Wrong” cheated by limiting its perspective too narrowly. Specifically, the content of the post argued that Discord was wrong because its current strategy was likely to lead to a loss of its leadership in the voice chat space in gaming. As of this writing, I stand by the arguments made in the post, but where I erred was the implicit assumption that, because Discord started as primarily a voice chat tool, it must be taken for granted that “winning voice chat” would indeed be a major goal of Discord’s. In speaking with many friends throughout the gaming industry after writing my post, I’ve come to gain a much clearer picture of Discord’s expansion into community management which my post completely neglected. I’m not, at this time, prepared to say that this separate focus definitively means it’s okay for voice chat to be neglected by Discord to the degree it seems to be – but I’m definitely no longer sufficiently confident that they are making an error in neglecting it, either. Hence my claim that I cheated – not to say that I lied willfully, but simply because I was too enamored with my conclusion to listen to the niggling voice in the back of my mind wondering if I was missing something.
    • How I learn from this: At the fact-level, I’ve already learned new context about Discord, which is how I came to understand I’d made an error in the first place. More generically, though, I think the primary reason I made this mistake is that I am so focused on the importance of voice chat due to my own work that I was biased into ignoring the possibility that they would not be interested in it. This likely came from a sort of “protectiveness” (I’m often asked by those outside gaming if voice chat is really important – to which I continue to maintain the answer is emphatically yes – but the ability to cite billion-dollar companies focused on this exclusively is a convenient way to reinforce this claim), so I’d say the broader lesson I need to take is to recognize when I’m making an argument whose conclusion is convenient to me, and push myself particularly hard in those cases to really explore the alternatives.

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