A 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 that love and kindness are the foundation we return to, even when we disagree. A story of learning, together.

I can still remember the torture of sleep training you.
Me sitting on the floor outside your bedroom door, resisting every instinct to rush in and scoop you up… letting you wrestle with your emotions, searching for that tiny moment of calm, that quiet realisation of, “Oh… I’m okay.”

Your Uncle Carlos is going through this now with Charlie. And your Uncle Scott, had to live through this, just next door to us here at home. I think he lost out some sleep as well as us, poor guy. 

It was a long, hard week. Maybe more than a week in reality. Your development, along with every other childs, moves in waves, cyclical moments of progression and regression. Just when you think you’ve cracked it, you realise you havent at all. Then one day, it seemingly all fits together and every parent asks themselves the very same question, “how did that happen”.
Any parent reading this letter will have empathy to this time in a babies life. Hearing the little cries tugges at every heartstring, but learning to self-soothe, results in a 7–7 sleep, for everyone. 

And then somewhere along the way, it all went to pot.

It must have been around the time we moved you from cot to bed, when the sides came down and, in your mind, it became fair game to hop out of your room and into ours. At first your mum and I tried to fend it of and yes it was always me who carry you back to bed, barely breathing and creeping up the staircase trying my hardest to cushion any sound or impact that might wake you. 

Clearly, we lost that battle because youre back in bed with us haha. 

But is it really a loss?

We both share the same opinion on this: the day will come when we’ll miss having you in our bed.

Last night, as I came upstairs to get into bed myself, I heard you crying out for, “Daddy.”
I’m not sure if it was a nightmare, or the room was too cold, or too dark. I asked you a few questions to figure it out, but didn’t get much from you. So I scooped you up and asked if you wanted to sleep in our bed.

And then you smirked.

Up until that moment I thought you were still half-asleep, seconds away from drifting off. But that little smirk, that tiny spark of mischief, made me laugh. As if to say, “Got him. Again.”

The reality, of course, is that this means I get the boot and end up in the spare room.
You have Jedi-level accuracy with your flapping arms and legs and almost always manage to tag me in the face or the crown jewels. So i conceded, the bed is yours, for now. 

Before I moved rooms (which is becoming more regular than your mum would like), I lay there watching your tiny features: your plump cheeks, long eyelashes, that cute little nose. Your mum caught me staring.
There’s something about those moments, the weight of you next to us, that feels a bit like waking up on Christmas morning with a stocking resting on your leg. 

I suppose the wider theme of this letter is discipline and boundaries.
What is our role, really, as parents?

At the weekend your mum requested a movie, which is very rare thing for her. Mum wanted to watch ‘Cheaper by the Dozen 2’, craving a Steve Martin fix. The movie shows two very different parenting styles, the Murtaughs vs the Bakers and how the kids mirror the energy of each home.

The takeaway?
Lead with love and kindness. Raise your children with those first, and everything else can be figured out along the way.

This morning I was reading a passage in a Ryan Holiday book. It offered another way of seeing tantrums or what adults like to label as “bad behaviour.”

Is it a lack of discipline or boundaries?
OR is it a sign that a child feels safe enough, loved enough, to fully express their emotions?

Your mum and I sometimes clash on the how of parenting you. That’s normal.
But we remind ourselves that the ideal recipe is input from us both, different energies, different perspectives. Mum and dad. Female and male. Not one more important than the other.

Together, we make the whole.
And you, are learning your way through the world with both of us by your side.

Always,
Daddy xxx

I wanted to share just one of the emails that I received to last weeks letter. I am so thankful to everyone that writes to me and it fills me up with huge love and pride seeing the community we are building and how far and wide these letters are reaching.

Here is a email I had from Kate, please read.

Dear Ryan, 

I’m writing to you from my home in a suburb of Kansas City, Missouri. My day is just getting started and your email was the first I read today. I’ve thought of responding to you before but today felt compelled to put my thumbs to work before the urge passes. I could easily launch into a lengthy email about the many ways and reasons I have enjoyed your letters but time constraints will keep this short. Each of us who reads your letters benefits from them, their sentiment and the reminders you provide, but I mostly want to encourage you to continue for Leo. My father turned 80 this fall and I have boxes of letters he’s written to me during my life. I also have boxes of letters from my grandfather, the first one written on air mail paper two months after I was born after our first meeting. Conversations are special, but written words, observations, lessons and feelings, they’re invaluable. I don’t read my father’s letters often and I know he would shake his head and question why I kept them, but knowing I have his words to turn to and will when he is no longer with us (hopefully a long ways off) means the world. I can hear his voice as I read them, as Leo will hear yours. Your letters are a gift and I’m appreciative that you share them with us, but I’m immensely grateful to you on Leo’s behalf. He’s a very lucky boy.

Best wishes for a beautiful holiday season. 

Sincerely, Kate

Including a post from Leo’s 4th BIRTHDAY!!!

If this letter resonated with you, i’d love for you to share it with someone who might need it too - or better yet, invite them to subscribe to "Letters to Leo’.

Here is your magic link to pass on to the people in your world.

P.S.

Thank you so much for taking the time out to read these letters. I really hope in some small way, it helped you pause, reflect and feel a little more connected.