Handwritten letters sitting in a drawer right now, you know exactly which ones they are. You have not thrown a single one out. Your inbox from the same period is gone. Ryan's army-enlisted friend couldn't take a phone into five months of training, suggested writing letters instead, and Ryan realized he hadn't sent one in eighteen years. The last time was summer camp.

The Toronto Letter Writers Society co-founder says there is no wrong way to write a letter, treat it like any other conversation. Shane's approach goes a layer deeper: sit with the person in your mind first, identify what you are actually afraid to tell them, and start there. Don't rewrite mistakes, scratch them out and keep going. Timestamp it. "It's late and I had you on my mind" is a sentence that lands differently than anything you have ever typed.

The instinct to delete that and send a text instead is exactly the problem. The letter from someone who took the time is the one you keep.

Topics: handwritten letters, letter writing tips, Toronto Letter Writers Society, army enlistment communication, rediscovering letter writing

Originally aired on 2026-02-26