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

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:&nbsp;handwritten letters, letter writing tips, Toronto Letter Writers Society, army enlistment communication, rediscovering letter writing
Originally aired on&nbsp;2026-02-26

Shane Hewitt & The Nightshift is your late-night companion for real talk, bold ideas, and unfiltered conversations that matter. Hosted by Canadian radio veteran Shane Hewitt, each episode dives into the headlines, human stories, and hidden truths shaping our world—always with curiosity, compassion, and a sharp edge.

From politics and pop culture to mental health, technology, and everyday life, this podcast is where night owls, deep thinkers, and curious minds come to connect. Featuring expert guests, passionate callers, and Shane’s signature style—thoughtful, fearless, and refreshingly real.

If you crave meaningful dialogue, smart perspectives, and late-night radio energy in podcast form, subscribe now and join The Nightshift.

Shane Hewitt &amp; The Nightshift is your late-night companion for real talk, bold ideas, and unfiltered conversations that matter. Hosted by Canadian radio veteran Shane Hewitt, each episode dives into the headlines, human stories, and hidden truths shaping our world&mdash;always with curiosity, compassion, and a sharp edge.
From politics and pop culture to mental health, technology, and everyday life, this podcast is where night owls, deep thinkers, and curious minds come to connect. Featuring expert guests, passionate callers, and Shane&rsquo;s signature style&mdash;thoughtful, fearless, and refreshingly real.
If you crave meaningful dialogue, smart perspectives, and late-night radio energy in podcast form, subscribe now and join The Nightshift.

Shane Hewitt and The Nightshift

Shane Hewitt is known for his engaging and relatable on-air personality, which captivates listeners. His ability to blend insightful commentary with humour and empathy creates a genuine connection with listeners.  Shane Hewitt and the Night Shift provides relatable content, informative discussions and expert insights – along with a balance of anecdotes and entertainment.

Shane Hewitt is known for his engaging and relatable on-air personality, which captivates listeners. His ability to blend insightful commentary with humour and empathy creates a genuine connection with listeners.  Shane Hewitt and the Night Shift provides relatable content, informative discussions and expert insights – along with a balance of anecdotes and entertainment.