I’m undertaking a 1000-day reinvention project, blogging here daily to track my progress. In Sunday Planning, I plan for the week ahead.
The road trip planned for last week was postponed, as Ray came down with the flu. I considered making the trip solo but ultimately decided it would be more fun and less grueling to do it with a partner.
Also, I was scared. Even though I’m an experienced road tripper, with many miles under my belt — some of them solo — the thought of traveling 2600 miles with only myself in charge, half of it with a dog, freaked me out, just a little.
I wish I had just done it by myself. But that’s the kind of clarity that only arrives in retrospect.

There’s always a reason to delay. First it was Ray’s flu. Now my dog’s bum has an incision in it he’s recovering from, after a burst anal gland abscess led to minor surgery and, of course, the dreaded, humiliating cone.1
Ray and I have been planning to take Bo along with us to transport my dad’s poodle Kristy to her new home in New Orleans, so his healing and his cone pose a new challenge. Had I gone by myself, I would have left Bo with Ray, and we’d be looking forward to a week of relaxation (though Bo likely would still have needed veterinary care).
As Kierkegaard said, we understand life backwards but we live it forwards. I didn’t know how this would evolve. I didn’t know that Bo would have a hind end issue. I didn’t know that a snowstorm would threaten, though I predicted it in chatting with ChatGPT about whether to go alone or not. I knew we had clear skies for last week. This week, not so much.
Maybe I need to stop planning and just allow this situation to unfold, per my reckless philosophy. Thursday sounds like a good day to plan to leave but even better is to just see how Bo is doing each day. Because neither Ray nor I have regular employment, we can go pretty much any time, weather allowing. There’s snow in the forecast for mid-week, so that’s not ideal. But maybe I don’t need to worry about that.
In my experience, road trips do best when approached recklessly, without reckoning or “recking” (taking heed). Reckless to me means not trying too hard to do what’s “right.” The word reckless derives from the Proto-Indo-European root *reg- which has the main sense of “moving in a straight line.” The word right is derived from it: right as in right angle, right as in the “right thing to do” morally or legally or practically.
In my lingo, doing something reckfully is doing it with careful planning, foresight, analysis, and optimization. Doing it with rectitude (also derived from that same root). Doing it recklessly is approaching it as it unfolds, with adaptability, presence, and even joy. Recklessly, you approach life as it is — nonlinearly — instead of trying to force everything to march along in a straight line.
It might seem like in planning a road trip the right thing to do is to reckon ahead of time where you might arrive, make reservations, carefully plan out your travel route and itinerary. But circumstances change. If there’s going to be snow on Ratón Pass, maybe better to drive through Kansas and Oklahoma instead. If your current driving forecast suggests that stopping in Wichita Falls, Texas will have you starting your next day arriving to the Dallas-Fort Worth rush hour maybe better to press on the first day and get to Dallas that night.
If one of your dogs has a bad bum, maybe that’s no reason to postpone. Maybe his bum will hurt whether he’s stuck in a car for ten hours a day or stuck at home.
If there’s a snowstorm mid-week maybe you can still take the trip. Ray and I are both experienced winter mountain drivers (you have to be, if you’re a ski enthusiast). We can drive slowly if necessary, take breaks earlier than planned, make our way through any kind of weather thrown at us.
I haven’t felt very reckless in this new year; instead I’ve been approaching everything reckfully. I want to optimize my life: take the road trip at the exact right time, with the right set of creatures (me, Ray, Kristy, Bo), with everyone in good health (no flu, no burst abscess) without snowstorms and with the perfect hotel stays, such as Homewood Suites Wichita Falls, on a lake where we can walk the dogs, and with a Wednesday social hour (must leave Wednesday then!). I want to arrive when it’s convenient for my sister, and when she has time to spend with me and the crew of the truck. I want to have all sorts of content ready for Ray and me to listen to — engaging audiobooks, podcasts across a variety of topics, music we both like.
Most of all I want this planned road trip to stop looming over me. It’s just something to be present for, not to get through as quickly as possible. It’s my real life, not an obstacle on the road to that.
What if I lived recklessly and instead stopped trying to control outcomes? What if I accepted the fact that life doesn’t turn out how it should or shouldn’t — it turns out the way it does regardless of my best efforts to bend it to my will.
The road beckons. Ray is ready to go any time. Bo’s feeling good enough that he lunged at the neighborhood turkey this morning, pulling me down with a smack onto the concrete sidewalk.2 I think if he can do that, he’s ready to get himself, cone and all, into Ray’s Tacoma and drive with us to NOLA.