From The Freedom in Leaving
Every new piece, published on Substack, collected here. Click through to read or listen on Substack.
Essay · October 18, 2026
Cape Town Trip Zoom Call Sunday Meeting at (EST) 3-3:40 PM. | (PST) 12-12:40 PM | Please forward to your Friendship CircleTopic: Freedom Journey to Cape Town In…
Essay · October 16, 2026
Elias Whitfield is inviting you to a scheduled Zoom meeting.Topic: Freedom Journey to Cape Town Information Call | Sunday Oct. 18Time: Oct 18, 2026 03:00 PM Eas…
Essay · October 15, 2026
**BOOKING IS NOW OPEN**https://traveljoy.com/bookings/tkoGnhKMEC52knCpe4Ukm9AHFreedom Journey: Cape Town Pride 2027 is not just a trip. It is a shared experienc…
Essay · October 13, 2026
https://thefreedominleaving.com/travel/cape-town-trip/ Sign up for latest news on the Cape Town trip!You’re INVITED to 10 days, 9 nights of Pride, Culture, Co…
Essay · October 12, 2026
You're INVITED to 10 days, 9 nights of Pride, Culture, Community, Nightlife, Amazing food and discovery in Cape Town, South Africa!! February 25 - March 6, 2027…
Podcast Episode · August 12, 2026
He told me I was too old, too broke, and a coward for leaving America. Weeks later, he told me he was buying a condo in Brazil. He’s 5 years younger than me.T…
Essay · August 11, 2026
Thanks for reading Letters on Leaving! Subscribe for free to receive new posts and support my work.Not only was I shouting back, but I also wanted to physically…
Podcast Episode · August 7, 2026
The New Great Migration is on!! The book comes out in October 2026!! Find out how and why nearly 700,000 Black Americans have left already!!
Podcast Episode · August 6, 2026
Why Black gay men research every trip like reconnaissance for part or full time refuge from the toxicity of the United States. How race, sexuality, and safety s…
Essay · August 5, 2026
One thing about gay men. We love to travel. We love to travel internationally. Call it a stereotype, but it’s my own personal experience and that of my gay fr…
Podcast Episode · August 3, 2026
Congratulations on relocating from the United States to the country of your choice. Here’s what to do in the first 90 days of your move. Some of it you can do…
Podcast Episode · July 29, 2026
There’s a restlessness that lives inside Black America. It’s been there before. Between 1910 and 1970, The Great Migration happened when 6 million Black Ame…
Podcast Episode · July 28, 2026
It’s sad to say that out of the 54 countries on the continent of Africa, there’s really only one I feel comfortable living and thriving in as a Black Gay ma…
Podcast Episode · July 28, 2026
My partner and I are in the middle of emigrating from the US to South Africa. So we’ve had to face the question head on: is South Africa safe for Black expats…
Podcast Episode · July 27, 2026
The headlines are horrible. The protests violent. The looting and deaths very real. No need to sugarcoat it. The South African xenophobic attacks spanning the M…
Essay · July 27, 2026
It’s sad to say that out of the 54 countries on the continent of Africa, there’s really only one I feel comfortable living and thriving in as a Black Gay ma…
Podcast Episode · July 25, 2026
South Africa. First — and still only — African country where gay rights is written into the constitution, signed into law 30 years ago this December and whe…
Essay · July 23, 2026
There’s a restlessness that lives inside Black America. It’s been there before. Jacob Lawrence painted it in 1941. Across 60 panels, no titles beyond a sing…
Essay · July 21, 2026
My partner and I are in the middle of emigrating from the US to South Africa. So we’ve had to face the question head on: is South Africa safe for Black expats…
The Freedom in Leaving