Lessons Learned on a Two Month Family Road Trip

We spent more time planning for this trip than we’ll be experiencing it, so it’s a great test of the value of planning vs agility, at least for specific use cases. We decided to build out a van (in partnership with Outside Van) for driving, camping, and depreciating, which means we had high capital costs, long lead times, and painful change costs. We even doubled up the planning: Because we’re traveling through the summer (a necessity given our children are school-age), our destinations are in high contention, so we needed reservations nearly every night.

Like a software project from the 80s, we had specifics for hardware (the van), software (everything inside the van), and workloads (the itinerary, built around each night’s lodging and day’s activities). We were free to spend as much money, time, and stress on it right up until the morning we left, then we had to make it all work. We could tune in production, by visiting REI, Cabella’s, etc, on the way, as long as we’re willing to sacrifice other activities. Some days we could shift plans with little effort (camp sites were low contention at Cumberland Falls), but others were locked in (no chance of shifting your night at Old Faithful on short notice). For extra points, our network access for at least the first two weeks was just enough to be a joke.

Technically, we didn’t quite ship on time. Unlike all those software projects from the 80s, we were only a few hours late — we left in the afternoon. I’m not sure lateness in software can even be measured in units as small as hours, so I felt pretty good, but when it comes to figuring out where your kids are sleeping that night, it involves a bit more stress.

We made a lot of bets when planning for this visit, and it’s been interesting seeing which ones worked, which ones were ok, and which fell down.

So far, one of the big bets — having a complete plan, with reservations for every night — has been a pretty big relief. It has its downsides, but given no work we still have a place to stay, and with our limited internet access and all the full campgrounds, it’s obvious we couldn’t often have rocked up and gotten a space at the last minute. We’re now reaching into a long stretch of camping, in areas where there’s less contention for spaces, so we might find we can be a bit more agile in the plan, but even then it’s nice to make small shifts to a schedule rather than having to invent as we go.

When it comes to the software in our trip — that is, everything inside the van, rather than the van itself — organization has been a major theme, both in planning and in execution. We’ve generally gone with bags of bags or boxes of boxes. We have collected all of our personal stuff into small bags, mostly quite different and thus easily identifiable. When in the van, we keep these accessible in a cabinet, and when heading into a hotel, we throw all of them into a large duffel. The bags include toiletries for each person (with the twins sharing a set), shaving kits, shower kits, charging cables, camera gear, and anything else. Our kitchen stuff is arranged in different bins (cutely called our pantry, or our kitchen, depending not he bin).

We’ve organized our clothing so that it is permanently installed in cabinets in the van, so it’s easy to reach when we’re living out of the van. When we check into the hotel, we’re mobile enough that we pull an outfit or two out of the van and, again, stuff them into little bags, organized so each person can easily find them. We started out by stuffing them loose in the big duffel, but this was a mess. We also have a couple of mesh bags we use for dirty laundry — one tends to stay in the van, one travels with us into hotels, etc. I also started rolling my clothes, instead of folding them, because they’re really stuffed in, and rolls are much easier to slide in and out than folds, because they’re stiffer. They also pack more easily into other bags.

One interesting aspect of this was how to color coordinate our bags. We initially picked one color per person, but then we realized that most of the bags stay in the van, which means each person is picking among apparently identical bags. It made more sense to rely on variety to enable easy separation, rather than matching in some way. Just more evidence that Tim Harford is a genius.

Our kitchen works is another big organizational challenge. We started with three bins under the bench, holding food, tools, and miscellaneous, but found too many things were in the hardest to reach bin. We haven’t rearranged these yet, but I expect we’ll rebuild them by frequency of use rather than by function, as we have many other parts of the van. We also started with a folding kitchen (really, a folding table and cabinet) by Trailkitchens. It’s a really great device, but the setup and tear down times are relatively high. Given that all but one of our camping nights is in bear country, this meant the kitchen was just too much work (because it has to be taken down and stowed after every single meal). We happened to meet up with some friends who were moving to Portland a couple weeks later, so they’re bringing the kitchen back with them. instead we bought a couple more bins, and have moved our stove and all of our dishes and pans into them. They have the added benefit of being far more portable — the kitchen weighed about fifty pounds, and its door couldn’t be opened without removing it from the van. Now our transition times are faster and we use everything more because it’s more accessible.

The big problem area right now is the section under the bed. The bikes define the space, but actually leave a lot of emptiness between them, which we then stuff things into. We don’t have a lot of choice, because that stuff has to go somewhere, but it ends up being really hard to get to anything — the bikes are hard to remove because of all the stuff, and the stuff is hard to get to because the bikes are in the way. We seem to go through waves of being very tidy for a while and then periodically just panicking and shoving it all in there when we’re in a hurry to leave.

Above the bed, we have a bunch of random stuff, but it’s all light (sleeping bags, pillows, etc.), and we have a mesh net in front of the bed to keep it from flying into our heads. It’s annoying to move all of this back and forth as we set up and tear down the interior sleeping arrangements, but it’s all self-contained and generally soft, so it’s not really been much of a problem.

A mixed success for us has been all the bags and hooks we bought to hang off the back of the front seats. We couldn’t live without them right now, but they’re all pretty cheap, and they result in a lot of stuff just sitting in space. We end up having to move a lot of these around, such as when accessing the fridge. It’s brilliant having easy access to tissues, bear spray, and all of the other critical stuff, but it would be much more brilliant if these hooks were designed for long trips in the van we have, instead of infrequent trips in a small sedan.

I keep messing with camera storage. It’s hard because the use cases can be so different. Driving around Yellowstone I mostly would jump out of the van and shoot, or even shoot from inside when there were bears in the road, but other times I carry the camera with me. I started out storing it all above the visor, but now I’m mostly keeping it in my backpack, which I hang behind my seat. This means I can’t easily get to it, but it’s always right there, and when I leave the van I know I can grab my bag and I’ll have everything.

In the west, we were only camping in the van, but once we reached the land of heat, humidity, and thunder storms, we started staying in the tent more. This meant we needed easier access to the huge 6 person tent, which added another usage pattern. It was simple, but not easy, especially when we need to dry the tent. We ended up with an REI tent rated highly by the Wirecutter, because we knew we needed wind and rain protection on the Oregon coast. It’s easy to set up and take down, it just involves what seem like hundreds of yards of fabric, between the tent, the footprint, and the rain fly. Oh, and it weights 30 pounds and takes up a lot of space. We started out with all of this stashed in the back between the bikes, but now we have to access it frequently, so our system that worked well early on fell apart and never reached a new equilibrium. It was all so hard to set up, take down, and dry, that we’ve decided to do everything we can to sleep in the van from now on, just to simplify our lives.

I’ll close on an unquestionable success. We bought a ton of different hanging pockets — shoe pockets that hang on closet doors, random pockets that I assume are also meant to hang on doors, sets of pockets that have no discernible purpose. We installed grommets in most of these to make them easier to hang, and then strung them up around the van wherever we had free space. It was a huge success. The back doors of the van are now covered in little pockets where we have all of the little stuff we need easy access to. The bigger pockets are inside and are stash spots for iPads, toiletry bags, and anything else we use constantly but need out of the way.

It’s been fun, and deeply interesting, seeing our plans tested by reality. While I’m committed to real-time decision making and I decry unneeded up-front design, most of this couldn’t have been planned in the moment. I would have spent more time at the Container Store getting “one more thing” than camping. There was no way to avoid a large amount of untested work, but we reduced that overhang by taking two shorter trips before the big one, and Cindy and I have such different organizational strategies that we’ve ended up with a high quality result.

We could not have done all of this without great resources online that helped us design a good solution. Some sites, like Traipsing About and Sprinter Van Diaries, had complete build stories, while others had small tips about how to manage toiletries for families. Each of them improved our thinking, and it was great being able to build on so many other ideas and experiences. We used Pinterest, Trello, and many other tools to organize and discuss what we were thinking.

The real key, though, was partnership. Successful partnership with Kenny at Outside Van, who came through on a tight timeline and really listened to us was critical. Most importantly, Cindy and I were able to partner on what we wanted, how we wanted it to work, and how we expected to adapt and evolve our solution over time. I owned the hardware, she owned the itinerary, and we both worked on the software. It’s not surprising that a relationship of twenty years can do this, but it’s still pleasing when it works.

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