Traveling: Random but Important Details

Planning. Organization. Obsessive compulsive need to have every. Single. Detail. Outlined. Call it what you want. We’re not good at it. As you may remember from this blog entry. But that’s okay, because when you don’t know how to do something, you learn, right?

When you turn 18 and take a spontaneous trip to Canada without planning or foresight, what happens? For Jenn B-Owens, a couple things. She was not given permission to enter the country and the customs folks called her parents. Apparently they thought she was a runaway.

The more long term effect of the trip is that Jenn learned pretty quickly the art of planning. She doesn’t take a trip without oodles of planning these days.

When I got to thinking about how I don’t do much planning (read: almost none), I knew I had to find out more about how she does this. After all, as you know from my posts about traveling mishaps, well…a little planning couldn’t hurt, right?

So, if you’re a planner, sit back and enjoy the interview of a like-minded person. And if you’re a do-er, sit back and learn something. I know I did.

Question: Have you always planned your trips like this?

Answer: Yes, I can’t really think of a time when I didn’t. Well, except for that trip to Canada.

Question: How much time does it take you to plan a trip?

Answer: Everything I do is in bursts. So, after we get an idea of where we’re going to go, I’ll spend a full day on it. Or a couple hours a day over several days. From start to finish, it probably takes a total of 12 hours.

*For the record, I was shocked by the amount of time she spends on this. I think I spend a total of 3 hours max when it comes to reserving a vacation house. Isn’t that enough? I mean, it only takes a second to throw a dart at the map to decide on a destination, right?


Question: What does all that planning look like?

Answer: Well, I have an idea of what my wife likes to do or places she might like to visit. I take that information, add it to what I want to do or see and start researching. Then I start to compile the information I gather into a binder. ‘

Question: Do you have any special or favorite websites you like to use when researching trips?

Answer: The only websites that I visit for most of our trips (other than the airlines) are the CityPass/Go Card sites. These make getting from place to place so much easier.

Question: So is the binder “it”? The total plan for the vacation?

Answer: Well, it’s not final yet. When I’m done with gathering information and doing the research, I share it with my wife and she looks through it. This is the part of the process where things change a bit. After we look at the binder together, we might take something out or add something in depending on cost, location, and interests.

*At this point in our conversation, we were knee deep into a delicious dinner at a local restaurant with Jenn’s wife. She joined in our conversation and put an interesting spin on it. Oh, and the coconut shrimp and tiramisu was a*m*a*z*i*n*g.

Xio: You know, in this planning process, there are a lot of things I may never know about, simply because I’m so hands off in the whole thing.

*This is interesting if you think about it. She may never know about some great restaurant or activity if Jenn isn’t interested or knowledgeable about it.  The only things that go in the binder are things that Jenn researches.

Question: Using all of your organizational skills, where have you traveled to?

Answer: I tend to couple vacations and sight-seeing with trips that are work or education related. If one of us has to attend a conference or a workshop or a meeting for work, I’ll put together a binder and add in some fun things to make a vacation out of the trip.

Some of the places we’ve gone to include: California/Washington (a combination wedding & road trip), New Orleans, San Francisco, and Vancouver BC.

Question: So is vacation planning something you’ve always done since that interesting Canada trip you took?

Answer: It’s kind of funny actually. I visited my mom the other day. We’re all taking a trip together next week and she showed me her binder full of plans.


*My guess is Jenn’s ability to plan a trip down to specific details is part learning from her Canada trip & part genetic. When she sent me pictures for this blog post, I was shocked. I mean, I knew she was organized, but I didn’t know she was like, professionally organized. Her response to me:

“Lol! It makes it easier to enjoy the trip (and function in other areas of my life) knowing all the random but important details are accounted for & dealt with.”

Jenn’s philosophy on travel:





My philosophy on travel:



And you? What’s your philosophy on traveling? Are you a planner or a do-er? Do you have more fun when you’re organized or do you live in organized chaos?

P.S. We did finally make it to the Crescent City! I’ll tell you all about it next week!


One thought on “Traveling: Random but Important Details

  1. Pingback: Kiss Me in Kissimmee | the traveler's journey

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