6 questions I need help answering (+ a call for writers!)

Hello friends! It's been a while! You likely signed up for this after reading one of my essays on Medium, my personal website, or seeing something on Twitter. I send this thing every few months, mostly a wrap-up of stuff I'm working on and thinking about — all ending with a sweet flag. See past issues here. Now, to the newsletter:

And now, an update in the form of questions I’m thinking about.
Do you know any of the answers? Hit reply to this email and let’s be friends:

1 - What makes for a good discussion?

In November, I created Pilcrow House—an event series about important ideas and something I hope can evolve into a physical event space one day. The third event is this week, and I’m trying something new: a sit-down dinner with Tim Carmody, publisher of The Amazon Chronicles. You can get your seat here.

At the previous two Pilcrow House events, I went with a “speaker series” approach. Person in front of room, Q and A, etc. The feedback was positive, but I kept hearing some version of “I want to have a conversation” in the attendee feedback.

The format for #3 is a discussion about Amazon over some good food and good wine. It’s unlike anything I’ve ever done before, and I’m interested to see if it “feels” more on-mission. I’m thinking a lot about how to structure the dinner and the conversation. How much is too much structure? And is it the best way to build community? Have thoughts? Are you good at hosting dinner parties? Hit "reply."

2 - Who are the best online feature writers?

I’ve been at my full-time gig at InVision for six months now, and things are settling in. My big focus: relaunching Inside Design’s editorial strategy. Right now, that means finding a steady team of capable freelance contributors.

If you’re a journalist with feature writing experience and have an interest in writing stories about digital products, design, and designers, let’s talk. I have a budget. Check this contributors guide or reply to this email. You must have feature writing examples to share.

3 - Was this a complete waste of my time?

On Twitter, I take pleasure in pointing out examples supporting my strong belief that we all should own our distribution platform and stop relying on Twitter, Facebook, YouTube, etc. So, I made a single-purpose site to send to people. There may be a rainbow involved.

4 - What makes a "unicorn" startup so special?

I interviewed Notion founder Ivan Zhao for Inside Design and I came to admire his long-term, first-principles outlook. I promise you that it's not the typical founder interview. My favorite part of the interview is Zhao reminding us all that we can do great things with small teams. “Moby Dick was written by one person,” he quipped.

The productivity app is swatting away investors and (until very recently) the press. It may not be the "next" big startup, but I'm interested to see where Zhao and team head next.

5 - What’s the best way to manage a remote team?

I’m entering year three of working remote. I shared some observations on Twitter (which got picked up by Lifehacker). I’ve since had some people reach out to me to talk about remote work, especially managing remotely. I’ve been reading some of the modern management books and find them helpful, but I’ve yet to find the perfect fit for a remote worker. So if you work remote or manage people, I’d love to hear from you!

6 - What’s the best way to grow a side project email newsletter?

The Discourse, my email newsletter about how we talk to one another, has crossed the 2,000 subscriber mark. But more importantly, it has a fun community of people reading and replying, with open rates >50%.

One of the most popular things appearing in The Discourse is my "14 rules for staying sane online", getting picked up by Kottke. So I’ve commissioned a local artist to create a poster of the rules worthy of your office. I’m currently in the process of creating it, but if you’re interested in getting a heads up when it's ready, subscribe to the Discourse or reply to this email.

Etc.

I was asked about design’s role in storytelling by Setka. I’m a bit of a curmudgeon in this one.

🇳🇵Official newsletter flag (for now):

Dear reader, may all of the parts of your life find the precarious unity of Nepal and its flag.

--Sean