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On the road in South Park, Colorado

What is the best questions to ask on a road trip? The art of a good question is something I have thought a lot about over the last few years, especially since that’s how I make my living.

I realized when looking at the data that other people must be interested in questions too because this has become one of my most popular blog posts. The original was written four years ago and still seems to be relevant, so I wanted to expand and provide these thoughts in a audio format as well.

I recently took a trip with my girlfriend and my parents through the Redwoods of Northern California – a pilgrimage of sorts. They were meeting each other for the first time – what better way to get to know each other than a road trip?

First of all, you might know that California is huge, which means spending large amounts of time in the car to get where we are going. Which means a captive audience that I can grill with my questioning

In podcasting, some of my favorite questions are those that cut to the core of someone’s experience such as:

• What didn’t you expect about that? What was a time you failed and what did you learn from it? How did that make you feel?

Some people find this style of question challenging, but I really like to create top 5 lists like they do on late night shows or in the movie High Fidelity. That might look something like:

• What are you top 5 bands? Top 5 cities you want to live in? What are your top 5 possessions that you make sure to take with you when you travel?

Another fun thing to do is something I call instant trivia. It goes like this: one person is the question master and comes up with questions relating to a specific topic like geography, music, or sports.  The first person to get three questions right becomes the new question master, and the old question master gives them a new topic category.  I like this game because it allows everyone to be the expert when they are the question master and gives a lot of variety of trivia.

Back when I was running Cross Country at Macalester College, we used to interview each team member at the begging of the season.  We would sit in a circle stretching before our daily run and ask all kinds of questions, some that I am still using:

• If you had to lose one of your five sense, which one would it be and why? If your life was made into a movie, what genre would it be and who would play you? What is the best book you read recently? Where is your favorite place in the world?

If you want even more good questions, my friend David Wood (from Art of Adventure Episodes 48 and 49) has a great app called Get Real/Go Deeper. Some of my favorites from the app are:

• What don’t you want me to know about you? If you traveled back in time to speak to your younger self, what would you tell yourself?

A great questions I learned from Lewis Howes and the School Of Greatness

• Describe your perfect day minute by minute?

My end of episode questions:

• If you could change or add one thing to the world, what would you want the world to have?
• What is your definition of Adventure (or other such word)?

Here is the text of the original post (an example of what an early blog attempt looks like):

Road tripping is to Americans as going on the Oregon trail is to earlier Americans.  And by that I mean we all do it – sometimes you start at midnight and drive across Nebraska in the middle of winter with your best friend so you can see the Grand Tetons the next day.

When I take road trips, or even long rides I like to have something to do (Hyperactive?).  My parents dealt with this on family road trips by giving me a new game every time I started to get bored (awesome!)

The way I get entertainment these days is by asking questions – its a game of finding just the right topic to fit the answerer’s mood and mindset.

Ever since I was a kid I have been perfecting my technique of asking questions that both satisfy my curiosity and engage the other person.  A good question will mean 10 minutes of talking, a follow-up question by me, and then 10 more minutes of talking. A bad question results in a brief one word or one sentence answer.

I have used this to great success with my fiance on our trips to Jackson, WY and Alaska recently to dig down and learn more about her hopes, dreams, inner monologue, and worldview.

Here are some of the questions I asked (with my favorite answers):

-If you had $400 million net worth and $40 million annual income, and assuming you had already bought all the fancy stuff you wanted, what are the three most important things you would do with your money? (Answer: Start an early education foundation)

-Who are the top 5 best rappers and why? (Answer: Outkast)

-What are the next three countries you want to visit and why? (Answer: Iceland)

-What is on your bucket list? (Answer: SCUBA dive the blue holes in the Caribbean)

-What are the three most delicious foods in the world? (Answer: Hawaiian Poke)

-What cities have the most interesting architecture? (Answer: Barcelona)

-If you had to lose one of your five sense, which one would it be and why? (Answer: Hearing)

-What is the best book you have read recently (Answer: The Last Child by John Hart)

-If your life was made into a movie, what genre would it be and who would play you? (Answer: Romantic comedy and Gwenneth Paltrow)

And finally: what is the best question you could ask on a road trip? Sooooo meta. (Answer: I don’t know, I’m tired of answering all these questions!)

Leave me a comment with your favorite road trip question or topic!