
This is an adaptation of my weekly newsletter, Adventures Big & Small. If you want to receive emails like these, click here to subscribe.

Before I start. This post BlackFriday+CyberMonday-turned-CyberWeek love letter has nothing for sale, nothing to click. I hope that feels as refreshing to you as it does to me.
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We were recently telling a friend about an idea we have — one that seems completely reasonable to us — to buy a cheap little sailboat and put it on a mooring in Tomales Bay, mostly so we can sleep out there and wake up on the water. We miss the water. Our budget is like $5k. Plenty, right?
She looked at us with a knowing grin and said, “I love this about you guys — you aren’t afraid to do things that make your life harder.”
This isn’t an ethos we’re aiming for, but she might be right. And not surprisingly, I guess. Our parents moved to the Caribbean when they could have stayed in the States. Life there is idyllic in plenty of ways, but it is anything but easy. It’s hot and humid and salty and buggy. We grew up losing power a few times a month. Major hurricanes regularly disrupt life for years at a time.
I was reminded of all this on our most recent visit, as we scrambled to get ourselves to the airport in time for our flight north.
Our departures are complicated by the fact that we own a house in the islands, the one my wife grew up in. We inherited the place much too young to afford a vacation home, but it means too much to let it go. So we rent it on Airbnb, which means we have to finish maintenance projects, clean the fridge, and lock our personal things away before leaving. We’ve done this a dozen times as a family, and we get a little less late each time.
We were doing quite well on this day — only five minutes behind schedule — as I hurried Maggie out to the car seat I’d just installed in our friend’s truck. Maggie had real shoes on for the first time in a week, the energy was high, and in one hand she had a toy airplane, in the other a parrot stuffie.
She was sprinting (she loves traveling) when she tripped. With no hands for catching, she went face down on the asphalt.
First, I checked her hands — nothing, thanks to the airplane and the parrot. Then her knees — a substantial scrape, but pretty typical for our wild child.
Then I looked up and saw blood around her mouth. I checked her face — looked okay. Teeth looked like teeth; none seemed loose. But matching little punctures on the inside and outside of her lip told the story – her tooth went right through her lip. Full puncture. I tell her mom, and the energy hits 11.
At that point, I had two options: give up the flight or get moving. I chose the latter. Healthcare on the island isn’t great, and it’s a Sunday. The wait in the ED would be longer than the flight to Charlotte.
We hop in the truck, I tell our friend Sherie to stop by the trail to Madi’s house, and while I’m on the phone with my dentist dad, I’m sprinting through the bush with a grocery bag, hoping their door’s unlocked so I can stash our leftovers in their fridge. I’m not about to trash a carton of grass-fed milk that travelled four thousand miles to reach the island. Cows deserve better.
Anyway, you’ve made it past the climax. Things got easier from there. My dentist dad said it was fine for Maggie and her punctured lip to travel. Security took five minutes. We departed on time, and our daughter took a rare plane nap. Thank you, universe.
I wrote this letter as an ode to living deeply. We could sell our home in the Caribbean and, with a fraction of the proceeds, stay at the swanky beachfront hotel just three minutes away. We could rent a fancy Jeep instead of fixing up the old beater my parents left behind. It would be infinitely easier.
But then… it wouldn’t be home anymore. We wouldn’t have to bum rides from old friends or rinse salt off windows or scramble through the bushes because I’m not willing to waste milk.
If there’s a line in the sand and we have to choose between an easy life and a rich one, I hope we always choose the rich one.
So cheers to you, parents — the ones who recognize that the last thing you ever want to say when you look back on your life is, “That was easy.”
Anything but.

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