They say inside you are two wolves. But not me. I just have a sheepdog.

In which I try to explain my reason for everything.

About five years ago, I left a promising career path as a lawyer to become a full-time parent. (For more detail, check out my first post, If you've considered quitting work forever, my story may interest you).

When people hear about this, they often wonder why I did it. There are a few common conjectures, and each has a claim to part of the truth.

Did you get tired of the grind? I think this is the prevailing theory. It’s certainly a feeling many can relate to. And yes, it was a factor: leaving behind billable hours and stultifying research projects was a relief. But it wasn’t just that.

Was it your dream to stay home? While rare in professional circles, this sentiment is not unusual in the traditionalist culture I come from. I know plenty of folks who feel called to full-time parenthood. And yes, there are things about the stay-at-home life that suit me well, and some that I truly treasure. But full-time parenthood was never my dream, and this wasn’t the central motivator.

Did you feel a duty to your children? For sure. My mother raised us full time, and her decision to do so meant the world to me. My wife wanted to work, so if I wanted a parent at home, it was going to be me. This was a certainly part of my decision. But there was more to it.

Was it influenced by your faith? Oh, definitely. Everything I do is. I’m a follower of Christ, and I believe he teaches us to focus on personal and unseen service rather than chase the glitter of money, influence, or recognition. This would be a very noble reason if I could fully own it. Alas, I can’t say I’m so good or selfless. There was always more.

Together, these explanations account for much of my choice. But there’s yet another reason—one that might be at the center of it all, though it’s harder to explain and far less apparent. And oddly enough, it’s the same reason I pursued law in the first place. It has to do with a restless force deep within me—one that has shaped much of the arc of my life.

You see, inside of me lives a sheepdog.

A Brief Detour to the Scottish Countryside

If you’ve never seen a dog herding sheep, then do yourself a favor and watch this short video of a border collie named Storm. It’s a mesmerizing little vignette: the master’s command, the canine’s cartoonish sprint, the scattered flock’s instant compliance. It’s an instinctual dance between an ancient predator and prey who have evolved together to serve humanity’s purposes.

I want to draw your attention to two moments in that video that are easy to overlook. The first is the split second before Storm’s owner issues the order. Her physical work hasn’t begun, but you can tell that for her, this is the hard part. She’s keeping an arrow pulled tight on a bow string, and she quivers with the effort. Aching with anticipation, it’s clear that she yearns to explode into her work, into her nature.

The second moment happens right after the herding is complete. The shepherd calls Storm back and commends her for a job well done. She seems to enjoy the praise, but you get the sense that she doesn’t really need it. Because you can tell that the herding—it felt good. Real good. It was probably exhausting, muddy, and cold. But it was also just right.

Those two feelings—one that I know all too well, and one that I yearn for—are the key to all this. If all those reasons that I listed above were the gunpowder that blew up my career path, my inner sheepdog was the burning match. My sheepdog made me do it.

So Tell Me About This Sheepdog

This is a dog that I once found on the street and helped find his humans. It’s not the actual dog inside me.

There are a few things you need to know about this sheepdog inside me. The first is that he is very energetic—sort of like how you might call a power plant “energetic.” He does not like to rest. He hates to be bored.

I have spent a lifetime trying to train this dog. But while he is mostly obedient, he is also a confident dog who has his own ideas. There’s a lot that he wants to do, and heaven help you if you’re in his way when he’s doing it. And if you’re going to set a goal for him, I’ve found that it’s important to get him on board first. Otherwise, you might have a hard time.

I learned a long time ago that my sheepdog can be a huge asset. With him nipping my heels, I can accomplish a great deal. He pushes me out of my comfort zone and brings out the best in me. And I believe that with him at my side, we could do just about anything. He is, as they say, a Good Boy.

But he can be a challenge. If I don’t channel his energy, I can end up with a lot of shredded furniture. Over the years, I’ve given him countless toys, taught him every trick, and walked him all over Creation. But it never feels like enough.

Because for all that, every night, my sheepdog dreams. In these dreams, he sees white shapes—indistinct blobs, milling around aimlessly, making sounds that are both foreign and familiar. And every night, he spends hour after unconscious hour organizing and arranging these shapes, his paws twitching.

He doesn’t understand—how could he? Of course, I know what he needs. He needs the right flock to herd. And I want badly to give that to him. Those twitching paws get me every time.

But there’s a problem: I don’t know how to find a flock like that. In fact, I’m not even exactly sure what that flock would be.

Dog’s Search for Meaning

My sheepdog and I have tried all kinds of things in the name of finding our flock.

For instance, we’ve delved deeply into music. This is a beloved occupation, a godsend for my restless companion. He can practice happily for hours. But even after expending all that effort, he will lie down and dream of sheep.

I’ve noticed that he loves creative work, so we’ve started countless projects. We’ve created videos, games, articles, albums, and more. Each was a rabbit to chase, a field to romp in. But not, ultimately, a flock—our flock—to care for. He dreamed of sheep.

What about law? Well, he turned out to be pretty good at it. It certainly used up a lot of his energy. And it afforded him many a “good boy!” and plenty of treats, all of which were very nice. But dressing up in business casual and researching discovery rule exceptions to statutes of limitations in Delaware didn’t quite do the trick. All throughout that era of our lives, he dreamed of sheep.

So what about fatherhood? My sheepdog is a family man now, with a partner and little litter of his own.¹ It’s a topic that needs fuller treatment elsewhere. But suffice it to say: family life is the ultimate source of meaning and joy in my sheepdog’s life. But there is family, and then there is a flock. And so still he dreams of sheep.

It Is Wool with my Soul

At the core of my being is the hunger to get life just right. I want to live a life that is objectively good and also true to who I am. In that, my sheepdog and I are aligned. He holds me to this desire, nipping me when I get lazy or complacent, or when something isn’t quite right. While I’m ostensibly in charge, he’s often the one herding me—driving me forward, pushing me toward a life well-lived. A life I can be proud of. One that, when all is said and done, I can be satisfied with.

I think part of attaining life will be finding the right flock of sheep for that sheepdog.

I don’t think I’ve found it yet. And that’s hard to think about. I turn 35 next month. It feels like my cohort is entering the illustrious era after you’ve accumulated significant experience but before you’ve left your prime. It’s an age when reins are handed over, when legacies are begun. It should be my turn on the stage—and I haven’t even found my sheep yet. I’m still trying to answer so many questions, and every time the sun goes down, I know I have one fewer day to figure it out. I won’t say I’m old yet, but how many times can you start over and still achieve something exceptional before the buzzer sounds?

When I think that way, I wonder: was I right to leave the law? It’s such an esteemed outlet for one’s talents and energies. Maybe my sheepdog would have adapted, could have made it work.

But then I think of those twitching paws. And I know that I owe him better.

I’m committed to taking radical action to find our flock. I’ll write off heavy sunk costs. I’ll try something and fail, publicly, a hundred times. And if I need to leave the safe, sensible thing and start from square one, I’ll do it. Wouldn’t be the first time.

As far as I’m concerned, until you find your mission, your mission is to find it. So for me, the search continues.

And that brings me to the Fare Well Files. It’s not just a chronicle of my experience of saying farewell to my career. It’s also about the dogged pursuit of truly faring well. I hope this project will help me work through my own questions about my deepest ambition: to be exceptionally good and live extraordinarily well, whatever that actually means. I also hope that it will be a useful data point for anyone trying to be deliberate about the path they are forging—whether family, friends, or friends I haven’t met yet.

Or maybe I’m just writing this for my sheepdog. This project hasn’t fully emerged from the fog yet, but it seems promisingly white and sheep-shaped. At the very least, it’s one more thing to try. Writing an essay, even a bad one, every single week is a daunting prospect. But we’re up for it. My sheepdog does love a good creative project. In the process, I’m sure he’ll get muddy. I hope to see him panting hard. And maybe if I’m lucky, after we post, he’ll curl up to sleep, and his paws will be still.

1. Astonishingly, this development coincided precisely with me getting married and having children.

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