He was only 25.

Last weekend, my wife, Jennifer, and I visited Williams Selyem winery, one of the best-regarded pinot noir producers in California. It was a perfect sunny afternoon for wine tasting, and we were struck by rolling hills covered in grapevines as we approached the estate through a big iron gate.

This is a serious wine producer, and we were thrilled to have a reservation.

As we hopped out of our Uber, a young guy greeted us, introducing himself as our host for the afternoon, Hess. He was friendly and relaxed with a laid-back California “surfer guy” kind of energy.

We followed Hess into the building and made our way to a table reserved with our name on it, covered in maps and charts and wine glasses, of course. Everything seemed to track with the serious vibe we were expecting.

But we couldn’t help but notice that the host at the next table was a much older man than our young host. And I secretly pondered the benefit of being educated by the older gentleman. He looked like he’d been working there for forty years, and I thought that maybe our guy was just an intern.

But then Hess started talking.

Assumptions vs reality

He poured a Chardonnay and explained (rather scientifically) why it doesn’t taste like the oaky, buttery Chardonnays I usually hate. Something about cooler temperatures and slower ripening that lets the acidity develop.

I’m probably not relaying that information exactly right, but I have a long history of not appreciating Chardonnay. But this one was absolutely delicious.

As Hess moved through the tasting, I was locked into his ability to tell great stories. Jennifer asked a ton of questions, and Hess met her curiosities with ease, familiarity, and genuine passion.

Sure, he knows his Williams Selyem history. But he also shared stories about working long days in vineyards, pruning and picking grapes. And he has a pulse on dozens of other wine makers in the area, who trained under who, and what other wines we should try based on things we said. He told us about restaurants we should visit and that he wants to make his own wine someday. He just hasn’t found the time to get started yet.

By the end of our tasting, we were totally impressed with Hess. He was a wealth of information, and not in a scripted kind of way. He knew so much and shared his knowledge so generously. We got so much enjoyment from talking with and learning from him.

I was curious about his age, so I finally just asked him. And he chuckled a little, like he's gotten this question before.

“Twenty-five,” he told us.

Jennifer and I looked at each other in disbelief. We offered self-deprecating jokes about how immature and lost we were at his age, and we encouraged Hess to start making his own wine.

On the ride home, we talked about Hess, and that got me to recalling my first impression of him, when I’d wished the older guy was our host. I’d quietly written him off for no real reason.

And that’s not the first time I’ve done that.

A taxi from New York City

A few years ago, I got an email from a guy named Eric Partaker. When it hit my personal inbox, I was surprised because I didn't recognize the name.

He said he was coming to NYC to meet up with another creator friend of mine who’d recommended Eric reach out to me, too. Eric asked if I could grab lunch while he was in the city.

I looked at his LinkedIn profile, and he had about 4,000 followers at the time. Outside of one or two mutual connections, I couldn’t see anything else we had in common. Plus, I live two and a half hours from the city. So this wasn't a convenient ask. And I assumed it wasn't worth the trip.

So I declined, citing the logistical challenges and wishing him well. But he quickly responded, saying he'd take a taxi up to the Hudson Valley to meet me. That kind of threw me. I mean, who takes a two-and-a-half-hour taxi to meet a stranger for lunch?

I eventually said yes, mostly out of curiosity about someone who was that persistent.

We met for lunch at a place near my house, and within minutes, I knew I'd been an idiot.

Eric walked me through his experience co-founding Chilango, a major Mexican food chain in the UK that he started back in 2007 with a colleague from Skype. Eric had been building real businesses for nearly two decades. When I met him, he just happened to be in the early stages of building his online audience. We had a fabulous lunch, exchanged business stories, and learned about each other’s passion for traveling.

That lunch date was three years ago. Today, Eric has over a million LinkedIn followers, runs a multi-million dollar business, and has become a good friend of mine. Jennifer and I hung out with him and his wife the last time we were in Lisbon, romping around the city, cocktailing, and eating Piri-Piri chicken.

It turns out Eric and I have a whole lot in common. And I almost didn’t meet him because of his follower count.

I cringe at the thought of how foolish that sounds.

What I keep thinking about

Two different people, in two completely different situations, with the same mistake on my end.

The scary thing is how automatic it was both times. I didn't sit down and consciously decide "this person isn't worth my time." The assumption just ran quietly on autopilot in the background, making decisions about people before they'd had a chance to show me who they were.

With Hess, it was just his age compared to his colleague at the next table. And with Eric, it was a follower count and an unfamiliar name in my inbox.

Both times, I got lucky. Hess won me over before I could tune out. And Eric’s persistence made it impossible not to meet up with him.

But now I wonder how many times I haven’t been that lucky.

How many conversations have I half-listened to because I'd already decided what the other party probably had to offer? Or how many should-have-been conversations did I miss entirely?

The thing is, you never know what you missed when you miss it. You just move along, none the wiser.

I wonder how many friends, business partners, and influential additions to my network I've whiffed on by making assumptions.

Catch yourself

The funny thing about self-awareness is we usually don’t know when we’re lacking it. And worse, our brains are wired to make quick decisions and to filter out information that doesn’t feel important.

But what if this evolution is actually filtering out opportunities for new people and new things that we’d love if we gave them a chance? What if our filters are working against us?

So this week, I have a challenge for you. Try to catch yourself in the act of forming micro-assumptions based on unverified information.

And then ask yourself, “What if I’m not right about this?”

Give something a try that you’d usually filter out, just to see what happens. If you have an interesting experience (and you’re open to sharing), I’d love to hear about it.

While I can't write back to everyone, Jennifer and I read every response, and we love hearing from you.

That's all for this week.

See you next Saturday.