Moving West in a U-Haul
Gifted by Mike Kennedy
Gathered by Nancy Small
Gillette, May 2026
Mike Kennedy remembers the decision to leave a successful advertising career and move his family from Connecticut to Jackson, Wyoming. For him, the move was about choosing time over money and building a life around the things he wanted to do. Along the way, a broken U-Haul in Iowa City turned the family’s westward move into a hot, chaotic, and unforgettable adventure.
Mike: So by now, you know, backing up just a little bit, I'm out of school. I meet Jane, I get married, we have three children right away. I become a little concerned about the cost of education in New York City. So you do what everybody does, you move to the suburbs.
And we found a nice home in New Canaan, Connecticut. New Canaan was a one-hour train ride from New York. We buy that house. Once again, the house was very much a fixer-upper. It had been built, I think, about 1880 or so. It had central heating, but barely. It only had one bathroom, did not have a shower. Just had a tub with a hose in it, but it was in a perfect spot. It was on five acres of land. It was in the woods. It was very colonial. It was antiquey. And so it was just right for us. So we buy that, move out of New York City, and once again, on weekends, I'm a very different person than the guy in the pinstripe suit that goes down to Madison Avenue every Monday morning on the train.
And that lasted from 1970, I think, is when we bought the house. And so the kids were aged five... No, I'm gonna say seven, five, and three. Or four. But we get 'em into school, and my career prospers. And after several years, one day, country boy says, the city boy says, "Hey, Mike, you know, you seriously want to continue doing this?" Now, I had discovered Colorado and mountain climbing.
I had gone hunting, thank you to Jerry Van Wagner. He invited Casey Donovan and I to go into Montana. I had, on a business trip to San Francisco, on the way back routed myself through Jackson, Wyoming because a friend of mine from Becky's had moved to Jackson and he and I are exactly the same size. Same gloves, same shoes. And I said, "Yeah, maybe I'll just stop in Jackson and see my buddy Bob and borrow some of his stuff and go skiing."
So, which I did, and that is another day that changed my life. 'Cause after one day I said, "I'm winding up here. "You know, I got home, I said, "Jane- Jackson, Wyoming, ever hear of it?" "No."
And Jackson's actually a fairly famous place. Okay? So I started redirecting everything in secret. This is nothing you would divulge to top management at the agency. But now every year I went back to Wyoming to go hunting in November, and then I bought some land in Jackson, Wyoming, some building lots. And then when Country Boy said, "Are you really serious about this?" I did the following analysis.
I am paying federal income tax. I am paying New York State income tax. I am paying New York City income tax, and I am paying Connecticut property tax. And this all adds up to about 55% of what I make. I said, "A joke's a joke."
And I was still, I was only a senior vice president. Well, the next thing was executive vice president and the next thing was the agency, which would've been really a lot of money. However, the price of making money is you really gotta work your ass off.
And you're never home. And you're never doing the things that you wanna do. And you get into this trap, I felt, of your number. Well, how big is your number? And you evaluate yourself against all the competition of their number and your number. But my attitude became, it's time [that] is the most valuable thing you have. The problem is, you don't know how much time you got.
And you have to spend time every day. But if you can have your choice of how to spend that time, that's real wealth. Now, this is not an original thought with me. This is one of the philosophy courses that I took when I was in college.
And I will acknowledge that this all occurred once I had saved enough money in the bank that I could do the following. I could put all three kids through college. That's an obligation. I could have a home with no mortgage, no debt.
And still have some left over for kicks and giggles. So I announced to the family, "We're moving to Jackson, Wyoming." And they said, "Okay, where is it?" And I quit my job, and I did this when the oldest two children, Brian had just graduated from high school and Michelle was graduating from high school. So I said, "This will be the least disruptive time 'cause they're about to go off to college anyway, about to leave home."
It was kinda tough on Sarah, who was a sophomore in high school. And we're just ripping her out of all of that. But anyhow, since I like to do things myself, I hire a U-Haul truck and a trailer, and I pack up everything we own, and I make one trip out to Wyoming in my Land Cruiser, which is, you know, an overgrown Jeep, and it's, you know, no air conditioning or anything, but I didn't care.
So I drove the 2,000 odd miles from Connecticut to Jackson, Wyoming, stashed some stuff, flew back, got in the U-Haul truck with everything we owned, and off we went on a new adventure. In Iowa City, Iowa, on July 3rd, I think it was 1982, we blew the engine in the U-Haul truck. And came coasting to the side of the road with everything we own in the truck.
A super hot day in Iowa. The children were driving our Suburban. Plus, as a bribe to get my three kids to come out to Wyoming, I said, "You can bring a friend for the summer on me." And one other neighbor's kid heard about this, and he came and asked us, "Would you take me too for the summer?"
"Yeah, sure. Why not?"
So we had seven teenage children in the trail car, Jane and I in the U-Haul truck. It's 100 degrees out, and the darn thing won't move. So I make a phone call, and this is back before cell phones. Right. Okay? Well, we get the U-Haul truck towed to the nearest U-Haul place.
I didn't know at the time that there was a huge element of our population that follows the professional golf tour.
These people live in their RVs, their motor homes, and they follow the tour around America, and they usually get to the next town on the tour, which in this case was Iowa City. There was going to be a tournament that weekend. Well, it's Tuesday. And the U-Haul truck is now in the U-Haul yard, and they give us a new truck. But here's the problem. When you pack a big moving van everything is very precisely done.
Well, you can't just take it out and put it in another truck. You gotta take it out and then put it back in the same way it came out. Right. The point being that at one point on a sunny summer afternoon, everything we owned was out on the ground. Now four or five Persian rugs. Sofas, my gun collection of some 80-odd rifles and things, just laying there. And we're working our asses off. We're hot and sweaty, but these people that follow the golf tour are walking around the town, and they see through the trees this spectacle of two U-Haul trucks, and these seven teenage children and these two adults. And they come, and they start looking around.
And one of the teenagers, who's a real character, 'cause somebody says, "What's happening?"
And the teenager says, "Well, you see, sir, we're moving west, and we're running out of money, so we're gonna have a little sale."
And these people go nuts. And I say, "No, no, get away."
So we weathered that storm. I rented a motel that had a swimming pool so we could cool off. Took us two days to get reloaded, and we make it to Jackson, Wyoming. And we take everything. I know, it's hilarious. I was having the time of my life. I was a new me. No more advertising, no more phone ringing. I was the agency fireman.
Because I was very good with clients, and whenever there was a problem, I would go and solve it. And there was always a problem. And I was always in an airplane and doing this and doing that and blah, blah. And I grew to hate the telephone 'cause every time it rang, you know, it was bad news. So anyhow, we get to Jackson. The kids have a great time. Some of them take up mountaineering. Some take up kayaking. It's a great place in the summertime.
Note: The transcript above has been condensed from its original audio recording to improve the flow and readability of the story.