Such an enjoyable read! I love the way you structures and phrased it, and it rings quite true.
I think the single most important quality for an entrepreneur is to follow your convictions for as long as you can, but no longer. When reality shows you a different path, grab the wheel and pull, and take it.
Clinging to beliefs for emotional reasons is deeply human, but it seems to be a shortcut to painful failure. Or maybe a longcut, if you’re resilient enough to take a beating or two (or a hundred).
I’d love to hear about specific times when you had to recalibrate and face the truth, and how you decided it was time to do so. That is a hard skill to hone. Because how can you ever know? I think it takes analysis and re-analysis over and over—a lot of our talking heads tell the same stories about the same events, year after year, but are those stories even true? Or did they find a convenient lie that sounds good (I.e., execution is everything), and they get applause for repeating it, for the rest of their tenure?
Sounds like a boring life.
Anyway, I appreciate your post! Definitely excellent food for thought.
"That is a hard skill to hone. Because how can you ever know?"
In general, like Nick said below, I think distance helps a lot, and for many of the times I had to recalibrate it was only in hindsight. In that regard, one practice that Joseph and I have hardened into our discussions is taking a night to sleep on any big decisions. Usually there are heavy emotions and biases, but if the decision is critical enough, sleeping on it will usually nicely reset your emotional barometer so you can approach the decision more clearly. I don't have a specific example that I used this for, because we basically use it for everything -- what language to write our product in, whether to hire someone, how to position our product, etc. etc.
"I think it takes analysis and re-analysis over and over—a lot of our talking heads tell the same stories about the same events, year after year, but are those stories even true?"
You're getting to something really interesting here. I imagine it's a very human tendency to retroactively boil down one's actions into simple philosophies to follow, and in some cases, perhaps these are widely applicable bits of wisdom. But I'd wager that, in general, many of these just happen to be what works for a particular time in history for a particular market for a particular set of people. At some point in my life I've come to believe that, like the old saying re: ML models, all [advice] is wrong, but some advice is useful. But somehow even very smart people fail to internalize this for a very long time (myself included).
E.g. even though I've shared some thoughts on what I believe to be *more* true for the startup world as it exists today, it's also probably only true right now and for the specific set of sub-categories that I've explored.
Thanks as always for the thoughtful comment, Joshua :)
I think that’s a smart approach! I tend to rest too long on decisions, but I think that’s because I’m trying to hold the emotions at bay rather than give them time to integrate and settle. I think sleep is an underrated tool in integration, and it sounds like you’ve really learned to make use of it in that way.
Thanks for elaborating! It’s given me more to think about—and sleep on! 😁
thanks for sharing! I can relate to some of what you went through and not just in the context of the startup experience.
as I've grown older, a recurring realization I've had, so deceptively simple is something like: self-honesty is the bedrock of a good life. it's the main (only?) practice that allows us to course-correct when misled by our lizard brains and fragile egos. but it's also a practice that requires attention and cultivation.
I think one thing that's required is distance. as long as you're deep in the thick of the tumult, it is extremely difficult to have a clear perspective on what you're doing wrong. the more habits you can cultivate to give you distance from your situation - whether mentally thru writing or meditation, or physically through exercise or just being out in nature - the more likely you are to find the space for self-honesty.
Thanks for reading, Nick! This is a really great point, and I completely agree. It's so unfortunate that there is so little pedagogical instruction / structure around how to improve these sorts of meta-cognitive skills. Achieving self-honesty is such an important skill to hone for life in general, and like you, I think I've spent a lot of my life trying to whittle away the patterns that get in the way and learn how to slowly cultivate it, but I don't think this sort of thing needs to be so random walk-y.
Distance is a really important factor. And I imagine there are others that can build into a sort of guidebook for how to do it. Anyways, rambling a bit. Would love to talk more about this some time (also we should catch up)
I wonder if one of our biggest self-inflicted wounds is "start up mentality". I'm talking about that drive to change the world, believe in your vision, be irrationally exuberant. Stepping back, that sure sounds a lot like "great is the enemy of good".
In our lifetimes, we've seen a handful of bold ideas literally change the world. Amazing ideas and amazing execution. But those events are outliers and any good analyst will tell you that outliers are not great predictors of the norm! Instead of looking at how the lottery winners made it (and yes its a lot like a lottery), how did the folks who built a successful business, employed a dozen people and lived a good life do it? What is it like to aim for positive cash flow and profitability in your 1st month and not your 3rd year? Oh, and some of those more modest ideas do get pretty big. Walmart started in 1962 as a discount store. Yes, a big discount store with economy of scale but still, just a discount store
Interesting points, Gordon! On the one hand, I worry about writing off ambition entirely, but at the same time, I do think you have a point here -- it's one thing to shoot high, and another to try to build a business around winning the lottery.
A more general comment here: I imagine, in general, many of the domains that are softer/more ambiguous end up falling subject to this sort of pattern here, where, rather than building off of fundamentals and making steady, incremental progress, outcomes look like magic and so are approached in a way that is akin to making sacrifices on altars and hoping the gods look favorably on your startup.
Such an enjoyable read! I love the way you structures and phrased it, and it rings quite true.
I think the single most important quality for an entrepreneur is to follow your convictions for as long as you can, but no longer. When reality shows you a different path, grab the wheel and pull, and take it.
Clinging to beliefs for emotional reasons is deeply human, but it seems to be a shortcut to painful failure. Or maybe a longcut, if you’re resilient enough to take a beating or two (or a hundred).
I’d love to hear about specific times when you had to recalibrate and face the truth, and how you decided it was time to do so. That is a hard skill to hone. Because how can you ever know? I think it takes analysis and re-analysis over and over—a lot of our talking heads tell the same stories about the same events, year after year, but are those stories even true? Or did they find a convenient lie that sounds good (I.e., execution is everything), and they get applause for repeating it, for the rest of their tenure?
Sounds like a boring life.
Anyway, I appreciate your post! Definitely excellent food for thought.
Thanks Joshua, really appreciate it!
"That is a hard skill to hone. Because how can you ever know?"
In general, like Nick said below, I think distance helps a lot, and for many of the times I had to recalibrate it was only in hindsight. In that regard, one practice that Joseph and I have hardened into our discussions is taking a night to sleep on any big decisions. Usually there are heavy emotions and biases, but if the decision is critical enough, sleeping on it will usually nicely reset your emotional barometer so you can approach the decision more clearly. I don't have a specific example that I used this for, because we basically use it for everything -- what language to write our product in, whether to hire someone, how to position our product, etc. etc.
"I think it takes analysis and re-analysis over and over—a lot of our talking heads tell the same stories about the same events, year after year, but are those stories even true?"
You're getting to something really interesting here. I imagine it's a very human tendency to retroactively boil down one's actions into simple philosophies to follow, and in some cases, perhaps these are widely applicable bits of wisdom. But I'd wager that, in general, many of these just happen to be what works for a particular time in history for a particular market for a particular set of people. At some point in my life I've come to believe that, like the old saying re: ML models, all [advice] is wrong, but some advice is useful. But somehow even very smart people fail to internalize this for a very long time (myself included).
E.g. even though I've shared some thoughts on what I believe to be *more* true for the startup world as it exists today, it's also probably only true right now and for the specific set of sub-categories that I've explored.
Thanks as always for the thoughtful comment, Joshua :)
I think that’s a smart approach! I tend to rest too long on decisions, but I think that’s because I’m trying to hold the emotions at bay rather than give them time to integrate and settle. I think sleep is an underrated tool in integration, and it sounds like you’ve really learned to make use of it in that way.
Thanks for elaborating! It’s given me more to think about—and sleep on! 😁
thanks for sharing! I can relate to some of what you went through and not just in the context of the startup experience.
as I've grown older, a recurring realization I've had, so deceptively simple is something like: self-honesty is the bedrock of a good life. it's the main (only?) practice that allows us to course-correct when misled by our lizard brains and fragile egos. but it's also a practice that requires attention and cultivation.
I think one thing that's required is distance. as long as you're deep in the thick of the tumult, it is extremely difficult to have a clear perspective on what you're doing wrong. the more habits you can cultivate to give you distance from your situation - whether mentally thru writing or meditation, or physically through exercise or just being out in nature - the more likely you are to find the space for self-honesty.
Thanks for reading, Nick! This is a really great point, and I completely agree. It's so unfortunate that there is so little pedagogical instruction / structure around how to improve these sorts of meta-cognitive skills. Achieving self-honesty is such an important skill to hone for life in general, and like you, I think I've spent a lot of my life trying to whittle away the patterns that get in the way and learn how to slowly cultivate it, but I don't think this sort of thing needs to be so random walk-y.
Distance is a really important factor. And I imagine there are others that can build into a sort of guidebook for how to do it. Anyways, rambling a bit. Would love to talk more about this some time (also we should catch up)
I wonder if one of our biggest self-inflicted wounds is "start up mentality". I'm talking about that drive to change the world, believe in your vision, be irrationally exuberant. Stepping back, that sure sounds a lot like "great is the enemy of good".
In our lifetimes, we've seen a handful of bold ideas literally change the world. Amazing ideas and amazing execution. But those events are outliers and any good analyst will tell you that outliers are not great predictors of the norm! Instead of looking at how the lottery winners made it (and yes its a lot like a lottery), how did the folks who built a successful business, employed a dozen people and lived a good life do it? What is it like to aim for positive cash flow and profitability in your 1st month and not your 3rd year? Oh, and some of those more modest ideas do get pretty big. Walmart started in 1962 as a discount store. Yes, a big discount store with economy of scale but still, just a discount store
Interesting points, Gordon! On the one hand, I worry about writing off ambition entirely, but at the same time, I do think you have a point here -- it's one thing to shoot high, and another to try to build a business around winning the lottery.
A more general comment here: I imagine, in general, many of the domains that are softer/more ambiguous end up falling subject to this sort of pattern here, where, rather than building off of fundamentals and making steady, incremental progress, outcomes look like magic and so are approached in a way that is akin to making sacrifices on altars and hoping the gods look favorably on your startup.