Cheap Wine: The Power of Authenticity and Humility

Mon, Feb 12, 2024

It was one of the most important dinners of my professional life up until that point.

I was at a private event and had unexpectedly been invited out afterward to have dinner with a dozen of the heaviest hitters in the space.

It was a “Who’s Who” + me as a tag-along.

The dinner was in a private room at an upscale steakhouse—as bougie as it gets. I wondered if the round table was serendipity or foresight on the part of whoever did the planning. It’s tough to sit in a room full of people who are all used to being the center of attention.

The small talk was anything but. It was so much fun to sit there and listen to the behind-the-scenes stories of people I had been following from afar for years. Everyone took turns chiming in on what they were working on and all their success that year. It was inspiring.

It was also tense with the obligatory posturing and semi-veiled ego flexes that come with the territory of professional marketers.


Imagine a room full of fencing champions who had sheathed their weapons to eat. They all still keep a hand on their hilt, ready for the first sign of a challenge.

The waiter was a little late in taking our drink order. He stood at the opening of the room while everyone more or less shouted their requests. This was yet another moment of mild flexing as each person took turns ordering eclectic mixed drinks or too-expensive wines.

I was the last to go. The waiter pointed at me for my order, and I half-shouted I’ll take your cheapest glass of Pinot Noir.” The room froze. Everyone turned toward me to gauge my seriousness (the waiter included). I didn’t crack; the waiter wrote it down and left the room.

The entire room broke at once. Everyone laughed at my brazen shamelessness. It’s hard to explain why it was so funny. A room full of world-famous marketers, all geared up to spend the evening posturing, and I played a trick card that only a professional magician could respect.

Everyone (including the waiter) took turns ribbing me for the rest of the night for my complete lack of decorum.


At the same time, everyone dropped their guard.

Not entirely, but enough. By making myself something of a human punchline, I’d given everyone permission to loosen up.

I’m often scolded about my self-deprecation by the people who love me. It’s a default setting of mine and, admittedly, something I need to rely on much, much less. However, sometimes it’s the only tool for the job.

When those times come, it feels like a superpower.


Letting yourself be seen in less than a perfectly cast light can soften people to you.

That becomes more true as you climb the ladder of whatever social hierarchy you participate in. Authenticity and humility become a form of currency that people are attracted to.

I’m not saying you must purposely embarrass yourself or make yourself look silly. I might take that tact a little too far sometimes. However, it doesn’t hurt to make it a habit of not taking yourself too seriously. Plus, if we’re being honest, cheap wine tastes just as good.

What’s something you do to help grease the social wheels?