Avoid Boring People

At the last big gathering in 1 BC (Before COVID), I saw my friend, Carl, and asked him, “What’s going on?” We discussed nothing of note. 

I later ran into James, a guy I’d see once-a-year at most. “What do you do?” I asked, to which he replied, “I’m a managing director of a hedge fund firm.” It was the holidays and he didn’t want to talk shop and I wasn’t particularly interested in knowing more. We each grabbed a glass of Merlot and moved on. 

On the way out, I finally caught up with my good friend, Ron, whom I’d meant to talk to all night. “How are you doing?” I asked him. “Good. Let’s grab coffee next week.” 

We’ve yet to grab coffee.

I thought about the party later and took stock of the questions I’d asked:

  • “What do you do?”
  • “What’s going on?”
  • “How are you?”


A good question is like a hand-written thank you note. Uncommon, thoughtful and something that forges a connection. These were not good questions.

I was on the wrong side of this useful aphorism:

“The best, most useful advice I ever got was from Jim Watson, [the scientist who discovered DNA], over tea at his New York apartment. 3 words, 2 meanings: Avoid boring people.”

— from James Clear’s 3-2-1 Newsletter

I take time to craft thoughtful questions on my podcast, and I often steal great questions from my favorite podcasts. From this, I’ve prepared my “fast-and-fun round” questions that I like to ask all my guests. I share these questions beforehand and they enjoy that their answers often require more in-depth consideration. 

For example, “What book, movie, story or podcast changed or most influenced your life?” I blatantly stole this question from podcast titan, Tim Ferriss, and expanded the scope from his question — which just covered books — to cover more media. Books don’t have a monopoly on great ideas, and not everyone is a reader.

I’m using this question as the first of the three items I now ask people when we meet:

  1. What book, movie, story or podcast changed or most influenced your life?
  2. What are you looking forward to today (or tomorrow)?
  3. Is there anything I can help you with this week?

I can’t remember the source of the second and third questions. It’s an easy one for someone with whom I’d want to talk to answer. I usually ask the third question after the first or the second. It must sound the least robotic of the items because it must come across as a genuine request.

I’m guaranteed to learn something from the answers to these questions, even if that learning means that I should move on to a different conversation. 

When I meet someone or talk to a passing acquaintance at a party, I face a time choice. This filter simplifies that choice. If someone doesn’t have an exciting answer to one of these questions or thinks they’re not interesting, I should keep the conversation short. 

This approach saves us both time.

Does this approach sound robotic? Sure, at first. But I’m reminded of my business coach when I was developing my “elevator pitch”:

“What’s repetitive to you may be a refreshing change of pace for them.”

We’re all trying to live better lives. This approach does double-duty. It invigorates me and helps me avoid boring people — both by avoiding being dull and bored. As modern-day philosopher and comic strip genius, Bill Watterston, of “Calvin and Hobbes” fame said:

“Creating a life that reflects your values and satisfies your soul is a rare achievement.” 

To this, I would add that living a life that regularly enriches you and the others around you is an admirable goal.


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