A few years ago, when my now-wife and I had recently started dating, we went for coffee with a friend of hers. It was my first time meeting this friend — I hoped to make a good impression so that my wife would be allowed to keep dating me.

(I’m not an expert, but I’m pretty sure that’s part of the Lady Code.)

At the time, I was maybe a year into a new chapter of my life. In late 2016, I had walked out on the corporate world, abruptly. I’d had enough — the mundane work, the office politics and the meaninglessness of it all. I was sick and tired of feeling like my work helped no one but myself. So I quit the corporate gig and started a non-profit. From then on, my work in this world would be dedicated to helping others.

(The details are a story for another day, but loosely — the vision was for financial advisory services as a social enterprise. Sell financial services to people, redirect the profits to local charities. Just add water, and voila — a better world. Spoiler alert: it wasn’t that simple.)

For the purposes of our story here, just know that the coffee intro happened during a period where my optimism and enthusiasm were at all-time highs, in terms of both my work and my general outlook on things. You can imagine, then, that my get-to-know-ya spiel over coffee played like an effusive LinkedIn post. (“So excited to have the opportunity to…” — *shudder*)

I don’t remember exactly, but I imagine I dominated the hour of conversation — going on and on about all the people I was aiming to help and all the problems that my new venture would solve. (Paraphrasing, but probably not far off:) I had figured out what was wrong with the world and I was going to fix it. And let’s be clear: I meant every word of it.

I left the coffee date feeling energized about the conversation and about having made a new friend. She seemed great!

My wife later got a concerned text: how... umm... had she settled for me? This new guy’s arrogance was off the charts.

My wife kept this from me at first, but I eventually learned of it — and when I did, I felt like the kid who gets his ice cream cone swiped and smooshed on top of his head. I was mystified (and hurt). How could I have made a bad impression now of all times in my life?? I was clearly a better person than ever before.

Here in 2021? I get it.

This is the deal: you can have great intentions and still be arrogant as shit. The two are not mutually exclusive. (I have the dried ice cream in my hair to prove it.)

Arrogance, when you break it down, is unwarranted certainty. And in those days, I was full of it.

I was so sure of my worldview and that had been on display in the coffee-shop conversation. In those days I couldn’t talk about my great intentions for humanity without talking about my view of the problem(s)… The corporation (in general) was always out to screw people. The people inside the corporation were always out to screw each other. Nobody gave a shit about anything. And I had all the answers.

So what then? Was I a bad person for wanting to help others?

Nope. First of all — “good person”, “bad person”… that’s not really a thing. Secondly, arrogance has nothing to do with your intentions. It’s about presuming you know better than the next person, period. In my case, it was about being certain of things like other people’s motives or why the world is the way it is, in so many ways. 

Sure, I had good intentions — maybe even strong morals. But when you mix those things with blind certainty, you just get access to a special section of the Arrogance Club… Welcome to the ranks of the self-righteous and sanctimonious. (Bathrooms on your left, tiny sandwiches over there on your right.)

So in the coffee shop, gushing about my newfound purpose in life, I had the passion of a great orator in front of a crowd of thousands. To the friend, I was just some guy on a soapbox downtown, preaching to hurried pedestrians. She was right to convene a Council of Concerned Ladies to talk my wife out of keeping me around.

(Again, not exactly sure if that’s how things work, but I have my suspicions.)

The generalizable lesson here is summarized nicely in David Foster Wallace’s commencement address entitled This is Water (which also happens to be one of my favourite works of any kind, ever):

The point here is [...] to be just a little less arrogant. To have just a little critical awareness about myself and my certainties. Because a huge percentage of the stuff that I tend to be automatically certain of is, it turns out, totally wrong and deluded. I have learned this the hard way…

I’ve also learned this the hard way — through flubbed coffee intros and a thousand other examples like it. Good intentions and all.

By the way, I’m happy to report that the friend and I are indeed friends these days. We’ve never actually talked about that first meeting... it probably made more of an impression on me than it did on her. 

Plus, hey, I got the bride. So at least I nailed that audition.