View this email in your browser

You are receiving this email because you signed up to Caffeine for your Inbox, a weekly newsletter about living a more intentional, innovative life. It’s kind of like caffeine for your life. If you were forwarded this email, you can get your own here.

🥛Cream & Sugar

Ideas and current events about living a more intentional, innovative life. The kind of stuff that makes the internet (and coffee) good.

As many countries are looking to reopen by the summer, people are grappling with the strange reality of socializing again. While it can definitely feel anxiety-inducing, there is also something exciting about being able to connect with people again.

This week's Cream & Sugar is a celebration of that with a few distinct ideas from some of my favorite thinkers around having good conversations. I hope it plays a small part in making your future in-person connections more meaningful (and your current Zoom connections slightly less painful).

Where to Start

Whenever someone asks me a question, my brain defaults to beginning with "So, yeah..."

Unsurprisingly, this is one of the worst ways to start a conversation. It sets the tone of the dialogue as awkward, or worse, uninterested.

I recently stumbled upon this Twitter thread by Joe Ferraro, founder of Damn Good Conversations, who suggests alternatives to opening a dialogue. So, let's say someone asked me how my weekend was. Here are some routes I could take:

• Micro-Macro: Begin with a concise, direct answer. Then, dive in and elaborate. "Completely wonderfully ordinary. On Saturday, I slept in..."

• Framing: Start your answer by outlining what you're going to talk about. "I hung out with friends on Saturday and worked at a coffee shop on Sunday. On Saturday..."

• Story Launch: Go straight into telling a story. "Friday night we were at the lake when..."

These might seem a little formulaic at face value, but play around with them to find the balance that works best for you.

Be Unpredictable

Dialogue can quickly become redundant. So much so that we begin anticipating what is coming before people even speak.

As the dialogue tree (source) below highlights, certain conversations have finite ways to progress. I imagine this will be especially true after the pandemic, when we'll be having a lot of similar-sounding "So, what have you been up to in the last year?" conversations with old friends and familiar strangers alike.

But great conversation happens when we are excitedly anticipating what the other person is going to say because we have no clue what it will be. They are less like checkers and more like chess.

In order to make conversation chess, let people speak without thinking about how to respond. It's okay if that means there is a little bit of "dead air" after they finish while you take some time to process.

As Steve Martin once wrote after he was interrupted onstage, "I can’t help wondering what we might have said if we hadn’t been stopped. Maybe we were just around the corner from something thrilling. Isn’t that the nature of a live conversation? It halts, it stutters, it doubles back, it soars. We might have found a small nugget, something off topic or unexpected.”

More from Austin Kleon here.

Break the Ice

The first question asked in a conversation sets the tone for the rest of the dialogue. That's why I wish less of my small talk with strangers started and ended with "So, what do you do?" Instead, I'll leave you with 7 of my favorite icebreakers from Rob Walker, a writer who reflects on The Art of Noticing.

• How does your family / your culture cook rice?

• What are you looking forward to right now?

• What is a boring fact about yourself?

• Have you been pleasantly surprised by anything recently?

• If you could do something that you don’t do because it’s bad for you, but you could do it without any repercussions — what would you do?

• What question do you wish people would ask you?

• And lastly, if you are really that curious about what someone does: Without using the title of your job, tell me what you do.

💥Jitters

For that moment when the caffeine hits: a random assortment of resources, articles, and other fun things.

• The Quarantined Comedian: A fascinating look at Seth Rogen's routine in quarantine.

• The Rise of Naked Brands: A deep dive into how what makes a brand popular has evolved over time to what it is today.

• The Evolution of the Moon: A picture of the moon photographed at the same place at the same time over 28 days.

💻What's Brewing at My Desk

Updates on Think Outside the Odds and other projects.

Last week, I met with my new editor, who will be working with me for the rest of my publication journey. He's the third person who will be looking at my manuscript, and I could not be more grateful to have so many diverse perspectives helping me make Think Outside the Odds a reality.

☕Espresso Shot

All the actionable insights from this newsletter condensed into a few bullet points.

• Be purposeful with how you start dialogue, as it can set the tone for the rest of the conversation.

• Rather than anticipating what someone is going to say in a conversation and then preparing your answer in advance, listen to them with your full attention as they speak.

• When building your personal brand, highlight what your life is like on an everyday basis and use that as a point of connection with your audience.