The new Wait but Why post, purporting to understand Elon Musk’s “secret sauce” in being so innovative is a very long, but great, read. And what Tim Urban suggests is that Musk is proactive in updating his mental software to reflect reality, and the real question he gets into is: why aren’t the rest of us? The rest of this post will be thoughts inspired by reading that post, so this post will make more sense if you first take the time to read that post.

He describes one’s mental software at a simple level as a person having a set of desires and an understanding of current reality, the potential intersection of which is that person’s set of goals (what they want that is achievable in the current reality). Based on that set of goals, the person comes up with a strategy for achieving those goals.

What Tim spends the rest of the post asking is why most people do not really question any of those three boxes (their goals, their understanding of what’s possible, and how to achieve their goals). People tend to accept what they’re told when it comes to what’s possible, or what are acceptable ways to achieve their goals, or even what their goals should be. One example he gives is that people who grew up in the Great Depression have mental software about career selection that says that reality is scary and you might starve, so your primary desire should be job security, and your strategy should be not to get fired (never rock the boat). And that would be fine, except that those people passed that software and reality onto their children who passed it on to their children, and it’s outmoded in the 21st century, where security can also come from embracing a growth mindset and challenging oneself. He posits that Musk is exceedingly good at hacking his own mental software to keep updating what’s possible regardless of what “conventional wisdom” tells him, and to focus on the biggest impact he can have within that expanding realm of possibility.

[Note: I understand that this is a privileged view for those of us who are not struggling to survive and have the mental space and financial security to explore our thinking. That being said, I find the topic interesting so I’m going to be reflecting on how I think for the rest of this post. If you’re not interested in omphaloskepsis, this would be a good post to skip.]

Tim’s proposed model resonated with me, given that I’ve been spending the past few years hacking my own mental software. I’ve been getting better at actually testing and pushing my own limits and realizing those limits were phantasms of my mind rather than actual limits. An early success was moving to New York – at the time I moved, I had no close friends in New York and was apprehensive as I thought I didn’t know how to make friends. I had made only a few good friends in the ten years since college, which meant that most of my close friends still saw me as a socially awkward teenager, which reflected my own self-image. Moving to New York helped correct that, as I made new friends who first met me as a competent adult, which helped me update my own self-image to reflect that reality.

In 2012, I made another big push forward on updating the assessment of my own capabilities. I had been in a rut of continuing to do only my existing activities (skiing, volleyball, singing) rather than taking up anything new because I was scared I couldn’t learn to do new things any more. But that winter had terrible snow, so I was bored on my skis, and decided to try snowboarding. And by the end of that spring of 2012, I was an intermediate snowboarder, which was really empowering. That summer, I decided to try something else I had never tried – the previous summer, I had bought a Surly Long Haul Trucker, an indestructible bike designed for touring, to be my all-around bike. I had been using it as a road bike, but felt that it wasn’t getting used to its full capabilities. I had time off for the week of July 4th, and decided to do an impromptu six day bike tour down the California coast to Santa Barbara, despite having no experience – I literally went to REI the week before to buy a bunch of camping gear, did one overnight bike camping trip the weekend before to see if the gear worked, and took off. And it was awesome. Lastly, at the end of 2012, I decided on a couple weeks’ notice to go to India for three weeks – the first time I had ever traveled internationally alone, the first time I’d been to a developing country – and it was a fantastic experience.

So on the way back, I was writing in my journal and realizing that I had developed a new “superpower” – if I decided to do something, I could do it (snowboarding, bike touring, traveling to India) – and the question was, what was I going to turn that new “superpower” on next? And the obvious answer for me was dating and being social. I had always convinced myself I was a shy introvert, and wasn’t interested in going out and being social – I was happy staying home all weekend, reading and writing (I used to read and update my blog a lot more). But part of me wondered whether I could become more social just by deciding to. And it turned out I could – I was more social in 2013 than I have ever been, and have been building on that ever since, to the point where it’s common for me to have a packed social schedule. As I write this, I’ve had social plans for 6 of the past 7 nights, which is a schedule that I previously would have thought would kill my introvert self.

I continued this process by remaking my physical self in 2014 and 2015. I had started doing longer bike rides in 2012 and 2013, but I really ramped it up in 2014 so that I could do a mountain bike tour from Durango to Moab in the summer, and a couple centuries in the fall. Completing those made me wonder how much further I could push it, which led this year to riding the Death Ride and Leadville, mythic rides that I once thought were impossible, and running my first marathon. These accomplishments (getting in the best shape of my life after my 40th birthday) have helped cement the idea that the primary limit to me doing something is the mental limits I place on myself (again, noting that I am blessed with good physical health and the financial security to explore those limits).

So now the question is what’s next? How can my goals have more of an impact than just updating my own mental software? Let’s get back to that in a couple minutes.

The other aspect that I like about the Wait but Why post is that it explicitly models an understanding of the current reality as part of our mental model. In other words, it doesn’t posit a single unshakeable Truth – there is only our current understanding of reality. I have previously reflected on this blog on the contingent nature of truth, and that questioning of “truth” is something I’ve done throughout my life. I want to understand things from first principles, as he suggests that Elon Musk does. In fact, when I was in fifth grade, I wrote an essay describing “The Religion of Science”, where I wrote that the only faith we should have was in the scientific process, which would guide us to truth.

This tendency to question what I’m told about reality and to want to derive my own understanding from first principles is something that goes back to childhood. While most people are taught to respect dogma and have faith as kids, I was taught to be a scientist. And because I grew up in a Republican, fundamentalist Christian town, I didn’t fit in, so I had to question whether I should trust my thought process over what everybody else believed. I did, but I often wondered whether I was actually insane because I was so out of step with those around me – I can’t tell you what a relief it was to go to MIT and realize I wasn’t alone in thinking like that. That being said, I think religion has a lot of value – it just wasn’t the right fit for me.

But that upbringing where I was always questioning everything has served me well in many ways throughout my career. I don’t believe things just because others do, and that often helps me debug technical or organizational problems because I can see where an assumption has broken down that others are taking for granted. I’ve developed the ability to derive, in many cases, why systems work the way they do from first principles, which is part of my ongoing interest in organizations.

But I haven’t yet figured out how to always take action to fix the problems that I see. I’m stuck at what Tim Urban calls the “Self-Loathing Cook” stage, where I see that things are broken and other people don’t necessarily know what they’re doing, but don’t have the will to change things myself.

And this is where the two threads of this post connect – the hacking I’ve been doing on my mental software to expand my understanding of my own capabilities is perhaps a necessary prerequisite to expanding the set of goals I have to ones that could have more impact. This is a theme I’ve been exploring this year – I went to a retreat earlier this year with the theme of “Playing with Purpose” where I had to admit I wasn’t sure what my Purpose was.

So I don’t really know what’s next and where I’m going to go with this. But I really liked the Wait but Why post, as it reflected a lot of my own recent journey. I wanted to share it and some of my own recent thinking on the subject – I’ll be curious to get your reaction.