https://myletterstoleo.com/lettersWeekly letters from Ryan Libbey to his son, Leo.https://myletterstoleo.com/letters/the-boy-in-the-blazerhttps://myletterstoleo.com/letters/the-boy-in-the-blazerTue, 08 Sep 2026 06:00:00 GMTA letter about the first day of school, learning to let go and how love is often spelled T-I-M-E.https://myletterstoleo.com/letters/the-people-before-youhttps://myletterstoleo.com/letters/the-people-before-youTue, 01 Sep 2026 06:43:46 GMTA letter about the people who came before you, the memories they gave us and the parts of them we carry forward. As I prepare to run the New York City Marathon for Alzheimer’s Socihttps://myletterstoleo.com/letters/the-school-gatehttps://myletterstoleo.com/letters/the-school-gateTue, 25 Aug 2026 06:00:09 GMTAs Leo prepares to start big school, I confront the fear beneath this milestone: that helping my son grow also means slowly learning to let him go.https://myletterstoleo.com/letters/unlockedhttps://myletterstoleo.com/letters/unlockedTue, 18 Aug 2026 06:00:09 GMTA first length of the pool, a summer filled with new skills, and a few precious weeks together before big school begins.https://myletterstoleo.com/letters/refillhttps://myletterstoleo.com/letters/refillTue, 11 Aug 2026 06:00:00 GMTFrom the waters of Zakynthos, a letter about cousins, family holidays and how confidence is quietly rebuilt through play, patience and having somewhere safe to swim towards.https://myletterstoleo.com/letters/do-you-have-to-be-selfish-to-be-successfulhttps://myletterstoleo.com/letters/do-you-have-to-be-selfish-to-be-successfulTue, 04 Aug 2026 06:00:00 GMTIt’s my 36th birthday today, and it happens to coincide with my 40th letter to Leo. So this week, I’m looking back at what nearly five years of being a dad, and 40 Tuesdays spent whttps://myletterstoleo.com/letters/before-you-re-readyhttps://myletterstoleo.com/letters/before-you-re-readyTue, 28 Jul 2026 06:15:05 GMTIt's been a couple of weeks since I last wrote, and a lot has happened. Three family holidays, Leo discovering confidence in the water, on a surfboard and in a skate park, and me ahttps://myletterstoleo.com/letters/the-safe-placehttps://myletterstoleo.com/letters/the-safe-placeTue, 07 Jul 2026 06:01:54 GMTLast week I asked for advice, and hundreds of you wrote back. One message, from a grandmother, stopped me in my tracks and completely changed the way I've been thinking about fathehttps://myletterstoleo.com/letters/borrowed-pressurehttps://myletterstoleo.com/letters/borrowed-pressureTue, 30 Jun 2026 06:00:00 GMTI thought this letter would be about Leo's final sports day at nursery. Instead, it became a reflection on something far more uncomfortable: the invisible expectations we place on https://myletterstoleo.com/letters/built-slowlyhttps://myletterstoleo.com/letters/built-slowlyTue, 23 Jun 2026 06:15:00 GMTSometimes the most meaningful moments aren't created overnight. They're built slowly, through years of conversations, relationships and small decisions. Last week, many of those thhttps://myletterstoleo.com/letters/echohttps://myletterstoleo.com/letters/echoTue, 16 Jun 2026 05:55:27 GMTI wanted to write to you about my own father in this letter, so I got up at 5:00am thinking I could sit in silence with some coffee and my thoughts.https://myletterstoleo.com/letters/around-the-firehttps://myletterstoleo.com/letters/around-the-fireMon, 08 Jun 2026 23:00:00 GMTNext week, something very special is happening.https://myletterstoleo.com/letters/the-one-eyed-manhttps://myletterstoleo.com/letters/the-one-eyed-manTue, 02 Jun 2026 06:00:00 GMTMost people are making it up as they go. This letter is about uncertainty, curiosity, and the freedom that comes from realising you don't need all the answers.https://myletterstoleo.com/letters/learning-to-seehttps://myletterstoleo.com/letters/learning-to-seeTue, 26 May 2026 06:27:31 GMTAfter sixteen days offline, a reminder that the amount of good in our lives often depends on our ability to see what's already there.https://myletterstoleo.com/letters/contexthttps://myletterstoleo.com/letters/contextTue, 19 May 2026 06:00:00 GMTThis week, I was reminded how quickly context can disappear in the modern world. A conversation reshaped online became a reflection on judgement, empathy, and the importance of seehttps://myletterstoleo.com/letters/the-songs-men-singhttps://myletterstoleo.com/letters/the-songs-men-singTue, 12 May 2026 06:00:00 GMTA reflection on the quiet ways men communicate through music, behaviour, silence and emotion. I talk about how songs became emotional signposts throughout my life, from childhood mhttps://myletterstoleo.com/letters/what-life-is-trying-to-show-youhttps://myletterstoleo.com/letters/what-life-is-trying-to-show-youTue, 05 May 2026 06:11:45 GMTA reflection on the people who shape us, the conversations we avoid, and the quiet signals life places in front of us. A reminder to stay open, pay attention, and trust what feels https://myletterstoleo.com/letters/we-ve-made-the-wrong-men-famoushttps://myletterstoleo.com/letters/we-ve-made-the-wrong-men-famousTue, 28 Apr 2026 07:00:00 GMTMy reaction to the “manosphere” becomes something more. A reflection on modern masculinity, the quiet presence of good men, and the standards I hope to pass on to my son.https://myletterstoleo.com/letters/just-us-for-the-first-timehttps://myletterstoleo.com/letters/just-us-for-the-first-timeTue, 21 Apr 2026 07:00:00 GMTA first solo trip to Morzine becomes something more — a chance to rewrite old memories and begin a new chapter with Roarsome, where your childhood meets my dreams.https://myletterstoleo.com/letters/do-what-feels-right-for-youhttps://myletterstoleo.com/letters/do-what-feels-right-for-youTue, 07 Apr 2026 06:30:00 GMTA visit that didn’t feel right, a memory that now can’t be unseen, and the quiet realisation that sometimes the hardest decisions are the ones we make against our own instinct.https://myletterstoleo.com/letters/you-don-t-get-more-timehttps://myletterstoleo.com/letters/you-don-t-get-more-timeMon, 30 Mar 2026 23:00:00 GMTFour weeks passed in the blink of an eye. This letter is a reflection on how quickly time moves, the responsibility of fatherhood within it, and the quiet urgency to fill life, nothttps://myletterstoleo.com/letters/you-decidehttps://myletterstoleo.com/letters/you-decideTue, 03 Mar 2026 07:00:00 GMTThis week, I passed the pen to Grandad. A letter about pride and some of the values we as a family stand by.https://myletterstoleo.com/letters/can-you-win-without-losing-yourselfhttps://myletterstoleo.com/letters/can-you-win-without-losing-yourselfWed, 25 Feb 2026 06:30:00 GMTIn a world that often rewards sharp elbows and relentless ambition, it’s easy to confuse visibility with value. This letter is about discernment, about building something meaningfuhttps://myletterstoleo.com/letters/delivered-differentlyhttps://myletterstoleo.com/letters/delivered-differentlyTue, 17 Feb 2026 07:00:07 GMTSometimes life doesn’t unfold the way you imagined.This week, I’m writing about family, fear, second chances and the different ways love can arrive.https://myletterstoleo.com/letters/the-lighthousehttps://myletterstoleo.com/letters/the-lighthouseTue, 10 Feb 2026 07:00:07 GMTWhy I keep writing these letters, even when life is full. And what these letters have become for so many others.https://myletterstoleo.com/letters/the-quiet-cost-of-being-a-parenthttps://myletterstoleo.com/letters/the-quiet-cost-of-being-a-parentTue, 03 Feb 2026 07:00:07 GMTA reflection on parental guilt and the quiet choices we make so our children get us at our best. Like getting up at 4 am to train before Leo wakes up…https://myletterstoleo.com/letters/what-matters-most-to-your-child-security-or-adventurehttps://myletterstoleo.com/letters/what-matters-most-to-your-child-security-or-adventureTue, 27 Jan 2026 07:00:10 GMTI was sat with a friend earlier this week. We’re both dads, same age, similar stage in life.Both tired in the same way, aching in the same areas, starting to pose similar questionshttps://myletterstoleo.com/letters/how-do-i-protect-my-sonhttps://myletterstoleo.com/letters/how-do-i-protect-my-sonTue, 20 Jan 2026 07:02:59 GMTThis week your teacher told me that you run too much in the classroom. That you find it hard to sit still. That you don’t always make your own decisions.https://myletterstoleo.com/letters/why-i-chose-hard-thingshttps://myletterstoleo.com/letters/why-i-chose-hard-thingsTue, 13 Jan 2026 07:09:28 GMTA letter about becoming. About choosing depth over comfort, resilience over ease, and the kind of man I hope my son grows up watching.https://myletterstoleo.com/letters/false-starts-still-counthttps://myletterstoleo.com/letters/false-starts-still-countTue, 06 Jan 2026 07:00:08 GMTA short letter about false starts, quiet pauses, and learning that preparation is progress, even when nothing visibly moves forward.https://myletterstoleo.com/letters/what-we-carry-into-the-new-yearhttps://myletterstoleo.com/letters/what-we-carry-into-the-new-yearTue, 30 Dec 2025 07:00:14 GMTWe’ve got exciting updates, fresh faces, and some serious miles ahead. Whether you’re training for your next race or just getting started, we’ve got something for everyone.https://myletterstoleo.com/letters/the-night-before-the-magichttps://myletterstoleo.com/letters/the-night-before-the-magicTue, 23 Dec 2025 07:00:11 GMTWritten late at night, wrapping presents and remembering my own childhood, this letter explores the magic of Christmas through the eyes of a parent and the unseen effort, love and https://myletterstoleo.com/letters/before-the-new-year-arriveshttps://myletterstoleo.com/letters/before-the-new-year-arrivesTue, 16 Dec 2025 07:00:09 GMTA reflection on why we shouldn’t wait for a new year, a clean slate or the “right moment” to change who we’re becoming. Think ‘direction’, not resolution. What direction are you mohttps://myletterstoleo.com/letters/the-christmas-you-ll-rememberhttps://myletterstoleo.com/letters/the-christmas-you-ll-rememberTue, 09 Dec 2025 07:00:20 GMTThe moment you see Christmas through your child’s eyes, everything changes. Here’s how I’m trying to make this one unforgettable for Leo.https://myletterstoleo.com/letters/5-things-i-want-you-to-knowhttps://myletterstoleo.com/letters/5-things-i-want-you-to-knowTue, 02 Dec 2025 07:00:25 GMTA contemplative letter, sharing five lessons learned about time, trust, creativity, energy, and the people we choose to surround ourselves with. A gentle reminder to Leo to stay prhttps://myletterstoleo.com/letters/lead-with-lovehttps://myletterstoleo.com/letters/lead-with-loveTue, 25 Nov 2025 06:00:21 GMTA tender look back at sleep training, midnight smirks, and the sacred chaos of sharing a bed with a little one. A letter about boundaries, parenting styles, and the realisation thahttps://myletterstoleo.com/letters/the-quiet-things-that-matter-mosthttps://myletterstoleo.com/letters/the-quiet-things-that-matter-mostTue, 18 Nov 2025 07:05:06 GMTA reflection on stepping out of your comfort zone, returning to what matters, and the simple truth that kindness and gratitude outlast everything else.https://myletterstoleo.com/letters/the-moment-i-realised-my-son-was-teaching-mehttps://myletterstoleo.com/letters/the-moment-i-realised-my-son-was-teaching-meTue, 11 Nov 2025 06:00:24 GMTWritten from a quiet hotel in Copenhagen, this letter looks back on four years of love, growth, adventure and what it really means to grow up together.https://myletterstoleo.com/letters/big-schoolhttps://myletterstoleo.com/letters/big-schoolTue, 04 Nov 2025 07:00:23 GMTToday your mumma and I received an email from a school. Your first official offer for a place in big school next year.The good news is, it’s one of our top three choices, from the https://myletterstoleo.com/letters/a-rising-tide-lifts-all-ships-even-when-comparison-comes-knocking-8a8ahttps://myletterstoleo.com/letters/a-rising-tide-lifts-all-ships-even-when-comparison-comes-knocking-8a8aTue, 28 Oct 2025 07:00:06 GMTAfter seeing an actor launch a campaign just like Letters to Leo, I felt that sting of comparison - until a friend reminded me what it really means to lift together.https://myletterstoleo.com/letters/in-a-world-that-loves-to-talk-i-want-to-teach-my-son-the-quiet-art-of-listening-because-real-connecthttps://myletterstoleo.com/letters/in-a-world-that-loves-to-talk-i-want-to-teach-my-son-the-quiet-art-of-listening-because-real-connectTue, 21 Oct 2025 06:00:24 GMTThe older I get, the more I realise that listening, really listening might be the most underrated skill we can teach our children.https://myletterstoleo.com/letters/letters-to-leo-personal-legacy-community-building-0430https://myletterstoleo.com/letters/letters-to-leo-personal-legacy-community-building-0430Tue, 14 Oct 2025 06:00:00 GMT2000 new readers overnight. Proof that the world is still hungry for something real.https://myletterstoleo.com/letters/letters-to-leo-personal-legacy-community-building-621dhttps://myletterstoleo.com/letters/letters-to-leo-personal-legacy-community-building-621dTue, 07 Oct 2025 06:00:00 GMTIt’s been an exciting time for your dad lately. A lot of change, new opportunities, a new agent and management, and even a personal assistant to help keep the plates spinning. Betwhttps://myletterstoleo.com/letters/letters-to-leo-personal-legacy-community-building-191chttps://myletterstoleo.com/letters/letters-to-leo-personal-legacy-community-building-191cTue, 30 Sep 2025 06:00:00 GMTThis letter is about small wins, like sitting across from the hospital that once consumed me with fear, and realising time has softened its hold. What felt unbearable back then nowhttps://myletterstoleo.com/letters/letters-to-leo-personal-legacy-community-building-c674https://myletterstoleo.com/letters/letters-to-leo-personal-legacy-community-building-c674Tue, 16 Sep 2025 06:00:00 GMTA rainy cycle through Brompton Cemetery sparks reflections on mortality and living fully. In this letter, I share truths on youth, love, purpose, and kindness, lessons I hope Leo chttps://myletterstoleo.com/letters/letters-to-leo-personal-legacy-community-building-72a4https://myletterstoleo.com/letters/letters-to-leo-personal-legacy-community-building-72a4Tue, 09 Sep 2025 06:00:00 GMTA hospital trip for Leo’s second ear infection reminded me how hard it is to see your child in pain. The lesson? Small habits, like hand washing can be powerful acts of protection.https://myletterstoleo.com/letters/letters-to-leo-personal-legacy-community-buildinghttps://myletterstoleo.com/letters/letters-to-leo-personal-legacy-community-buildingMon, 01 Sep 2025 13:43:59 GMTLeo turns 4 soon. A look back at the scars of his arrival, the lessons of fatherhood, and the gratitude I carry for the version of the story that gave us him.