This Week on Thinking Is Cool

By luck or fate or some other reason, you’ve found yourself reading an email from Thinking Is Cool, *the* podcast to listen to if you want to have better conversations. If this email was forwarded to you, sign up for regular correspondence from me, Kinsey, right here:

Good morning! I saw Harry Styles play Madison Square Garden last night. I have no thoughts, just this:

Okay I have one thought: It’s October 4, or 10/4. Make a dad joke or something.

And a second thought for the road: I’m really excited for you to hear today’s episode so let’s hop to.

This Week on Thinking Is Cool

I’ve always been fascinated by the idea of speaking freely. Perhaps it’s because I grew up in a home that (and this is not a fabrication) had a framed and historically accurate copy of the Constitution hanging in the living room.

Whatever the reason, the first few words of our Bill of Rights have captivated me for a long time—I wrote my college admissions essay about the lessons the Arab Spring taught us about freedom of speech, and I’m still thinking about that freedom today.

But today, the context for my perception of free speech is vastly different from what it was when I was eight years old, looking up at the living room wall and asking my dad what “the free expression thereof” meant, or 18 years old, pondering for the first time what my independent morals might shape up to be.

Today, my understanding of free speech is fluid. Today, the internet has, as the saying goes, changed everything. With the advent of imperfect but technologically precise social media algorithms, we’ve expedited and magnified expression beyond our wildest dreams. Without uttering a single sound, you can broadcast to millions of people in the blink of an eye—no gatekeeping (or fact checking) involved.

As we’ve taken advantage of the megaphones platforms like Twitter, Facebook, and Instagram have given every single one of us...our behavior—and idea of permissible speech—has changed. We persistently toe the line between constitutionally mandated free speech and hateful, vitriolic mistruth. And the stakes have never been higher.

The reality is this: Not everyone gets to speak freely online, at least not lately. So as we navigate the nuances of deplatforming, algorithmic megaphones, and modern conversational warfare...how is free speech—both in theory and in practice—changing? And how might it be changing us?

This week on Thinking Is Cool, we’re considering as thoughtfully as possible the idea that not everyone deserves to engage in unbridled free expression. We’re weighing the best means of line-drawing in the age of misinformation. And of course, we’re talking about Donald J. Trump.

Listen now: Apple // Spotify // everywhere else

And now, a quick word from our friends at Fundrise:

What keeps you up at night? I have some guesses: climate change, the berries & cream song from TikTok, maybe how long it’s been since you called your grandma? If you’re the financially anxious type, you might worry about big future purchases—like a stationary bike, a car, or a house.

I can’t offer much advice on the purchasing of a car or indoor bike (never been a fan of either, tbh), but when it comes to home-buying, I’ve got the life hack for you: Check out Fundrise, our presenting sponsor for season two of Thinking Is Cool.

Thanks to Fundrise, affording your future home won’t induce restlessness anymore. This first-of-its-kind investment platform gives everyone access to the previously out-of-reach world of real estate investing. With account levels ranging from $10 to $100,000, Fundrise makes real estate investing easy and affordable. Start putting money towards your dream home today and sign up for free online at www.fundrise.com/think.

Thanks for reading. You might not love the conclusions I come to in this week’s episode of the show, but I hope they’ll get you thinking.

I know there are at least two listeners out there (ahem, mom and dad) who together disagree with my episodes on a very regular basis and still continue to listen, debate, and most of all think (even if I get the “someday you’ll change your mind” lecture every time they do). I’m grateful for all the “respectfully, I disagree” this season has inspired. I think today’s conversation will keep with tradition.

Let me know what you think about this episode. Once you’re finished...take some time today to consider:

• What does it mean to freely express oneself online? Does everyone deserve a megaphone?

• How have the imperfections of our perception of free speech principles played out along party lines, generational lines, even platform lines? Do you ever think about how the algorithm might shape your version of reality?

• Does clear and present danger look different from user to user? If so, how often are you consuming content from the “other” side of the conversation?

Finally, two small programming notes:

1. The Thinking Is Cool team had a truly revelatory idea about how we solve free speech online but of course it happened after the episode was finished. So follow me on Instagram to hear us debate said revelatory idea this week, live.

1. I’ll be hosting a live and interactive session on a new video conversation platform called Bright on Thursday (October 7) at 5:00pm ET. I’m breaking down my transition from one dream job to this dreamier job and all the challenge, risk, and reward that came along with it.

After my talk on how to succeed (so far) as an independent contractor, I’m taking any and all questions. Seriously, ask me anything, I’m an open book. I’d really love to have some of my best supporters—y’all reading this newsletter—there to hang out and ask the good q’s.

Grab your tickets now, space is limited: https://brt.live/3u81XhH

See you later! Have a great Monday.

-Kinsey

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