Good Questions to Ask Your Friends

Hey,

Welcome back to Stay Curious — a newsletter I write once per week to riff on a few things in the world of startups and day-to-day life keepin’ me curious.

Today’s deep dive is sponsored in part by last night’s wonderful sauna session.

Let’s get to the goods.

On deck this week?

  • Email intro your friends to dream meetings

  • “If success didn’t matter, what goal would you go for?”

  • The World’s toughest row: 2800 miles, 45 days

  • Ben Franklin’s 24 Junto questions

Let’s dive in:

1) Email intro your friends to dream meetings

Yesterday I was on a trail run.

Midway through, I thought of a friend I hadn’t caught up with in a while, so I dialed him up and got chatting. His name? Nicolas.

He’s a filmmaker and loves fishing, and getting lost in the mountains. 10 mins into the catch-up, I asked him: “who’s your dream meeting this year?”

He told me, “We’ve always wanted to do a collaboration with Yeti.”

As he’s explaining his next big film project and why they’re the perfect fit, I checked my LinkedIn, saw I was connected with their head of marketing and saw we even swapped messaged 2 years ago.

Sure enough, I sent him a note after the jog, and in 30 mins I got a reply saying he loves what Nic’s doing and he’d love to chat.

Crazy to see my old dormant work connection was able to be reactivated for my friend’s top dream reality.

It took me 5 mins and could mean the world for his next project.

Here’s to doing that more for our friends.

This is my friend’s last video project if you wanna watch it.

2) “If success didn’t matter, what goal would you go for?”

This last weekend I hosted some university friends for a golf getaway. We’ve known each other for almost 10 years.

Over lunch, one of them asked: “If success didn’t matter, what business would you go for? and I loved the reframe.

It put me in a new zone of creativity because success wasn’t part of the equation.

When success isn’t on the line, it reveals what we truly want to put our time and energy toward.

3) The World’s Toughest Row: 2800 miles, 45 days

I had a good chat with a friend named Connor the other day and he was telling me about his next big goal. And when I say it’s big, I mean it.

He’s training for 2 years to complete the world’s toughest row - a 45 day row from California to Hawaii.

My eyes exploded. I couldn’t imagine being in a boat that long.

There’s something about hearing my friends chase big dreams that gets me so fired up.

The fact he’s taking 2 years to train for it and build his team is admirable. It makes me think — what life goals am I working toward that would require 2 years to train for?

If not, are we daring to dream big enough?

4) Benjamin Franklin’s 24 Junto Questions

I asked a close friend what he was reading the other day and he told me it was Benjamin Franklin’s biography.

He went on to tell me some surprises the book shed light on and one of his favourites was a Friday evening discussion club Franklin put together in 1727 called the “Junto Club.”

It was a group he assembled each week to discuss 24 questions that ranged from morality to society.

In my mind, this was the YouTube/Netflix of the day.

People wanted to catch up, be helpful, and learn what was going on in their city. These 24 questions are full of gold if you’re curious.

Thanks to Braden for putting this on my radar.

What was your favourite riff from today?

Reply and let me know.

Also, if you liked today’s deep dive, forward it to a friend.

Joel

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