31) Courage

Behind-the-scenes building Vambrace AI, a company on a mission to figure out its mission. Please pardon the stream-of-consciousness style. Subscribe to follow along or visit the site here:

(typos are to make sure you’re paying attention)

Introductory Remarks

Dear Vambracers —

In last week’s post, Organizational Structure, I discussed my need for more professional rigor in the construction and development of my business. I’ve been going mostly off of vibes since things started in earnest in October, and I haven’t properly set aside the time to reflect on what I want to build and how I think I can get there.

I’ve been speaking with mentor-like people as the year winds down and this has been a fairly consistent piece of feedback. And it’s not that I need to have some master plan to build a billion-dollar business. I just need to get real about what I want out of this venture and then start taking concrete analytical and professional steps to get there. Which is fun!

Courage

In today’s post, I hope to briefly explore the importance of courage in any entrepreneurial endeavor (and in life more generally). Now I don’t necessarily identify as a courageous person. In fact, I think I’m quite fearful. But I’ve come to understand courage not as the absence of fear and doubt, but rather as the ability to continue trudging forward in the face of immense fear, doubt, and uncertainty.

Starting a company is almost by definition a highly uncertain endeavor—and there are obvious risks associated with that uncertainty; risks that I’m only just starting to appreciate. And on an even more specific scale, committing to do something for some customer or client is also a scary prospect. It’s not so much doubt in my ability to deliver, and more so the fact that the buck ultimately stops with me to do what I say I’m going to do and to deliver for the client.

When you’re the head honcho, you can’t really blame failure on anybody else, or even on learning, or a subordinate, or anything. It really all comes down to (1) your (my) ability to adequately understand the problem I intend to solve for the client, (2) my ability to communicate the solution and the process that allows us to construct that solution, and (3) my ability to build, learn, launch, and repeat, ad infinitum, while maintaining a strong relationship with the client. This is true of pretty much any entrepreneurial endeavor I think.

As a key milestone of my first engagement approaches, namely, the actual production launch of the system I’ve been building, I’ve really been feeling the heat associated with having to deliver. But, the sort of surprising and fun part is that, I really wouldn’t have it any other way. It’s terrifying to think that stuff I’ve built will serve as the backbone for the operations of the company—but it’s also exhilarating. I’m learning to embrace that discomfort and responsibility, because that’s really when I’m at my best.

And so that’s why I keep coming back to the concept of courage, because the fear and uncertainty and doubt and intensity is very real, and are things I face daily. But I’m learning and conditioning myself to absorb that negativity, identify the actual items or underlying causes of that uncertainty, and letting it compel me into greater action and targeted urgency to address those concerns. I want the ball in my hand at the end of the game. And since this is my own thing, it’s up to me to cultivate those end-of-game situations—which is a joy!

This is all probably pretty obvious to many of you—particularly those of you that have started your own companies. But it’s been a fun sort of interstitial aspect of the experience that I wanted to explicitly acknowledge.

Inspiration & Random Snippets

Some random things that come to mind when I think of Courage.

Mike Tomlin

I’m inspired by pretty much anything that has to do with Mike Tomlin—and especially his interview on the Pivot Podcast a few years ago. This is one of my favorite ever pieces of content and it really demonstrates what a strong leader he is. (I’m writing this before we play the Lions, so we’ll see how his leadership is displayed in that game). Specifically, the following quote has stuck with me:

I think this particularly true in the case of entrepreneurship—and perhaps why I’ve been hesitant to pursue too much structural / operational stuff. It’s really easy and pretty comforting for me to spend a day or two researching the roofing market or the pest control market—and to feel really good about myself for doing such erudite analytical work. But where does that really get me?

For me, the concern is that I’m really engaging in performative pseudo-work to cope with fear that I’m not actually doing anything worthwhile to anyone and I’m going to have to wrap-up this silly endeavor and go get a “real job.”

There’s a balance there, for sure, the point I’m trying to make here is that I’ve been in environments where performative work was pursued—and I think a lot of times we create these processes and systems and bureaucratic organizations to diffuse and fracture real responsibility as much as possible across the widest number of people. This let’s us dissociate from real responsibility and focus on our targets or doing just enough to get by.

This is probably part of the reason why I’ve never actually worked in a corporate environment. But I do think there’s a legitimate case to be made that a lot of the bureaucracy stems from a natural-even-evolutionary human impulse to insulate ourselves from danger, fear, and uncertainty.

Courage, The Tragically Hip

This is not expressly related to courage as a concept, but I’m a big fan of the song Courage by The Tragically Hip. The main refrain is pretty much, “Courage, it couldn’t come at a worse time.” And for some reason that really resonates with me. It’s almost as if, by definition, we need courage most when we least want to exhibit it—and so I think that’s what the line captures there. I’ll leave you with my favorite verse from that song (which I think was co-opted from a book):

I suppose in some ways courage is having the, well, courage to embrace the responsibility associated with making decisions and taking action despite an abundance of incomplete information and then living with whatever comes from those decisions. The actual line seems to skew a bit negative, but I think there’s a more optimistic interpretation around some degree of humility in the face of the human condition, and still being able to make decisions and take action despite the certain challenges that will arise and failures we’re experienced.

My Serenity, The Gathering Field

And now I think the last quick piece I’ll share, less about courage per se and more about continuing to try in the face of failure and difficulty. The song My Serenity by The Gathering Field has a relevant refrain:

Looking Forward

I’m somewhat undecided as to whether or not I’ll issue a post next week, given it’s the holiday season and all. So stay tuned. But I imagine my next post will be some sort of annual planning type of thing. Or possibly a year-in-review type of thing and then an annual planning type of thing immediately thereafter. Only time will time.

I hope you have a lovely holiday season!

Sincerely,

Luke