I didn't feel ready. It didn't matter.

It has been almost three years since leaning into working the Colorado ranch. For the decade or so before that, my Dad had been adamant that “someday, all of this will be yours, Jessie.” Mom was convinced that she had another twenty years to tend to things and that if she were to pass, I was to take care of the horses and the dogs. Full stop. Nothing more on her list of estate planning. (Who needs to plan when you are 76 and certain you have 20 great years left?)

I had spent those years hardened by a stabbing sense of abandonment that arrived when the two of them pulled up stakes and headed westward. I wanted as little to do with the ranch as possible—albeit somewhat irrationally and dramatically for a happily married, forty-something mother of four and small business owner.

My stance held firm for years. Then, in the wake of Mom’s passing, it slowly occurred to me that the land, horses, cattle, tractors, and dusty array of tack were indeed mine. We can know something rationally while concurrently maintaining the illusion that it belongs to a separate life. Heading off on a raid with a deputy and a Colorado brand inspector—both wearing bulletproof vests (nope, they didn’t offer me one)—to retrieve a stolen horse may have accelerated the dissolution of that illusion. 

At the time, the refrain of SOMEDAY ALL OF THIS WILL BE YOURS was on repeat. The only way out was through: the probate of my father’s will (which Mom and the courts had failed to attend to five years earlier) was just one of the challenges suddenly bestowed upon me. 

Over the months that turned into years, those challenges began to take on a different hue. Beyond the interactions with courts, lawyers, and county clerks (both in Colorado and New Jersey), and amidst the unexpected crying jags that grief hoists upon you with absolutely no warning, came the daily task of keeping the animals alive, the hay field watered, and the homestead from being robbed. Again. 

It was within those tasks that I found something I had no idea I desperately needed. 

The small ways I surprise myself while tending to the goings-on at the ranch are decades removed from my former endeavors as educator, parent, chief cook, and bottle washer. Yet, there are similarities in the attention required for the well-being of those under my care—emotionally, mentally, physically, and spiritually. 

Beyond that fundamental component of nurturing, which comes so naturally to me, is this other piece: doing things that scare me, surprise me, and simply need to be done. 

Pushing a calf that slipped through a fence back in with its mama without getting kicked. (And, without spooking the mama.) Finding the wherewithal to turn on the air compressor and fill up the side-by-side’s tires before heading out to check the measurements on the Parshall flumes along the ditch. Telling Trey, our grey rescue horse, to back it up and settle down until I say it’s okay to resume pursuing his unrequited love over the fence with our mare, Keenie. And climbing back on Lad, our 29-year-old half-Arabian, born back on the farm in New Jersey, after a ride the year before when he had pranced and hopped so badly that I had to get off mid-ride. 

These experiences require a willingness to do something that feels both vaguely familiar from childhood and entirely outside the bounds of comfort. 

Our farrier once put it well when he said,  “Sometimes when I ride a horse, I just want to be a passenger, but most of the time horses will demand that you ride.” 

None of the aforementioned tasks are particularly groundbreaking, nor do they require advanced knowledge of constitutional law or quantum physics. Yet, each small accomplishment buoyed me in a way that felt so unexpected it startled me. 

The pure joy of thinking, “hey, I just did that,” felt like a shot of espresso, only better. Less jittery. Fewer compulsions to magic eraser the refrigerator door seal.

I hadn’t yet found a word for what had been quietly changing in me. Then, as it tends to do, the right one arrived uninvited, tucked inside a podcast I happened upon, which led me to one of those commencement speeches that resurface every spring, right around graduation season.

In 2005, Steve Jobs delivered a notable commencement speech at Stanford. Near the end of his address, Jobs circled back to a scrappy little countercultural magazine he adored as a young man: the Whole Earth Catalog, created by Stewart Brand. 

The Whole Earth Catalog was a generous grab bag of tools, ideas, and prompts for people who wanted to build a life on their own terms. On the back cover of the final issue, Brand printed a photo of an empty road at dawn alongside a simple goodbye: “Stay Hungry. Stay Foolish.” 

Jobs explained that he’d quietly carried those words as his own north star for years before passing them along to the graduates as his last piece of advice: keep your curiosity sharp, keep your experiments a little unreasonable, and don’t let “playing it safe” be the whole story. 

The small accomplishments that come from figuring things out, whether in a struggle of wills with an 1,100-pound animal or by using YouTube to find the “on” lever for the air compressor, have made me more of a rider and less of a passenger not only on the ranch, but in my roles as wife, mother, and college counselor. 

In small but meaningful ways, they have strengthened my sense of agency in a world changing rapidly before our eyes—a world whose uncertainty is increasingly difficult for the next generation to ignore.

I didn’t go looking for agency on a ranch in Colorado. But it found me there in the smallest, dustiest, most unglamorous ways, and it turned out to be exactly what I needed. 

That’s the thing about staying hungry and a tad foolish: you don’t always get to choose the classroom. 

Still, there’s real power in keeping Brand’s advice close to heart. Be a rider in your own life. Do whatever it takes to step into that role, because the world—and the horses—will not wait for you to feel ready.

P.S. If you’re curious about the still very active mind behind the Whole Earth Catalog, and why his ideas about agency and the future still feel relevant to Boomers and new graduates alike, this conversation is worth a listen: “Stewart Brand, Silicon Valley’s Favorite Prophet, on Life’s Most Important Principle.”