15 years ago I bought a pair of shoes. Just last month I lost them. Why is this newsworthy? Give me a minute. 

I bought them in a local Kansas shop, in a town where I used to live: lime green Asics with yellow stripes. At the time, I was just starting to gain traction in my business life, but far more importantly, my son was about to be born. I didn’t intend for these shoes to become so sentimental to me, but they soon did. 

Born after 38 hours of labor, my wife at the time doing the hard work (obviously) and me just pacing back-and-forth, back-and-forth, basically wearing a hole in the floor of the birthing center with those new shoes, it took us days to name our son. For those sleepless days that melded into nights and then days again, as I tied the laces to make meal runs, to bounce him around the yard as his mother got a few hours of sleep, all the while wondering how the hell I was going to do this—be a dad—these shoes held me. On the 7th day, we named him Milo. Looking down at him in my arms and saying, “Hello, Milo” for the first time, those shoes were the backdrop. 

Very quickly they became a comfort for me. I’ve moved six times wearing those shoes, visited dozens of countries, met the people that have become the most important relationships in my life, standing in those very shoes. In every doorstep that I’ve entered as Milo grew from opinionated toddler to opinionated child to opinionated teenager, these shoes have waited on the welcome mats: from hotel rooms to new homes. 

They’ve been through so much with me. 

In Toronto, up until this month, I used the Asics as my house shoes, much to my partner’s annoyance. As you can imagine, they were not in the best state: soles as thin as crackers, threadbare, and stinky. 

Recently I was on the east coast for six weeks, traveling around with my daughter, living out of bags—hotel room to Airbnb—and waiting (probably impatiently) for my son to arrive to join us. You see, I haven’t been his main caregiver since he was that little newborn. We’ve been able to spend time together like a lot of divorced households do—during holidays, in the summer, for vacations, and much-too-short visits. But this summer Milo wanted to live with me. He flew to the east coast and then after a few days of vacation with his sister, the car packed high, Milo and I road-tripped to Toronto, where I got to welcome him to his new home. 

As soon as I opened the door for him and stepped inside, I riffled through my bag to find the shoes, my old comfort. They were gone. 

Because I’d bounced around on the east coast, I don’t know where I’d lost the shoes, but I suspect it was in the house that had bed bugs. Obviously, I’d hightailed it out of that place like, well, like it had bed bugs. Honestly, I’m sure I left more than a pair of shoes there, but nothing as important. Like a passport, credit card, or my green card was missing, I felt panicked. 

As I was freaking out, my partner Steph asked me why. “There’s no sign of my shoes.” 

Steph raised her eyebrows. “You know what I’ll say.” Remember: she wasn’t necessarily fond of them. In that moment, I resented her. Those sneakers, they were significant to me! Sentimental, yes. Smelly, definitely. Significant nonetheless. I got mad. She knew how emotionally attached to those shoes I was. I explained to her that I’d gotten them right before Milo was born and now here he was, living with us, and I couldn’t find them. 

Steph put her hand on my shoulder, shrugged, and said, “Time for new beginnings.” She pointed to a box at my feet. “What’s that? A new box of brand new sneakers?” Recently I’d ordered a pair of YSL sneakers, hightops at half price. “Start a new era—the next 15 years.” Then Steph walked away like what she’d said hadn’t blown my freaking mind. 

Standing there, shocked in my socks, the next fifteen years flashed before me. Milo growing into a man, taller than me, better than me, bigger than me in every way, the seasons changing around us, day to night to day to night, time and time again, successes, failures, movements, and satisfaction. I saw myself taking off these new shoes when I came home. 

I got excited about the next fifteen years, wearing in these sneakers. I thought about how I can be more creative, more inspired. That I could stop grunting through paperwork in a corner and step out onto the pavement. 

I slipped on my new shoes. They felt great. 

Milo came down from his room. “Those are sick sneakers.” 

I told him the story and even he approved, which isn’t easy these days. Then, of course, he used the opportunity to ask for his own pair of new shoes. Fair move, little dude. He recognizes an opportunity in front of him. Of course, I bought him his own pair. It was our small sentimental thing together. It was so beautiful.

My son and I are on a fresh journey together. 

It’s hard to let go of things we treasure and value from the past. And sometimes they’re taken from us. Perhaps it’s at a bed bug house in New Jersey, or perhaps it’s something bigger and much, much worse. 

It’s not about the new sneakers, obviously, but about being intentional about our choices. 

Because I took a moment to grieve about the lost shoes, as silly as it might be, and talk about it with the people that loved me, Steph listened to my sadness, saw my vulnerability, and had some solid advice. This was powerful for me. We had a moment and the richness and decision came from that experience. Perhaps at a different point in my life I would have just been pissed, annoyed, not heard what she said, and we never would have connected. 

The difference is talking about it: with Steph, my therapist, my business partner, or Milo. 

With Milo under my care, I’m questioning myself. What have I gotten into? Am I in over my head? The answer is a definite and resounding yes. But, with help, I’m learning to navigate that too. This too is a lesson. 

If we’re mindful we can teach ourselves lessons, hear it when other people are teaching us, perhaps even pass along nuggets of wisdom to our children. Struggles develop character. This is a platitude that I actually use, really consider, and apply. Even the little struggles teach us big lessons. 

There’s a difference between moving on and walking forward. 

Closing one door before opening the new one, turning to new opportunities instead of stressing out about what might have been: these don’t have to be enormous epiphanies, they can be small journeys. 

Perhaps it’s just boxing up a worn out pair of shoes and unlacing the new ones. This can make all the difference. 

All my best,

Comment, Share, And Inspire On My Friends!


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