Your Questions, Vaguely Answered

You know that face someone makes when you hand them a gift certificate to Cheesecake Factory? That rewarding expression of unbridled, childlike joy? Well, suffice it to say that’s not the kind of admiration you’ll garner when first revealing to them your plan to circumnavigate America. The reaction is more of a “what’s that smell?” look followed by a slew of questions about how we’re going to handle something like a life-threatening injury at the Grand Canyon, because that happens all the time when you’re waiting in line at an observation deck.

Actually, our families have been extremely nurturing and generous. But, since this blog is partially meant to help guide future travelers whose support systems may not be so robust, we’ll answer some of the most frequent questions we’ve received here — and know there will be more detail around each of these answers provided in future blog posts.

Q. What will you do for money?

A. The same thing we do every day. One of the core philosophies of this trip revolves around remote employment. Both Hailey and I are technically capable of working from anywhere, so that allows us to stay employed in some form or another. If it sounds like an expensive venture, I assure you we did the math from several angles and will be writing a post about that soon.

Q. Are you getting an RV/Camper?

A. Nope! Hailey wanted one, but she was kind enough to let me convince her otherwise, using some statistics and a lot of whining. We’re getting an SUV of some sort — something we can sleep in if we need to, but doesn’t become our mobile home. What’s the fun in seeing America if you spend every night in the same place? We plan to stay with friends and take advantage of unique Airbnbs wherever we can. More to come on that front as well.

Q. When are you going and how long will you be gone?

A. The plan is to embark from Florida in late January / early February. We both have work obligations in January that take priority, and the later we leave, the fewer the weeks of winter we’ll be dealing with in the Southwest. No strict plan on when we’ll finish; there are a few routes we can take once we’ve conquered the Midwest. But, we do plan to be around for the 2017 family holidays.

Q. What about health insurance?

A. Interestingly, this is a question that pretty much everyone over 40 has asked and no one under 40 has asked. To allay any concerns: we will indeed have health insurance through our jobs. But, if for some reason we lost our jobs, we would just buy health insurance. It’s merely an expense at the end of the day, even if you are employed. Both Hailey and I have purchased health insurance as contractors before.

Q. Are you going to “X” place?

A. This is usually more of an exclamation than a question, as in, “you should go to X!” That’s great — please keep it coming. This is a big country and we’ve already made some route adjustments based on the experiences of friends and family. We do have a general route planned, which we’ll soon share with you.

Q. What are you packing?

A. Both Hailey and I have moved around and cut enough fat that we don’t have much in the way of material things to argue over. Beyond packing clothes, it’s mostly electronics and hardware for work, recreational gear, and peanut butter.

Q. What will you do once you finish the trip?

A. Man, tough crowd! We’ve only planned a year in advance. We’ll let you know once we get back to Florida.

Q. What was the inspiration for this?

A. Hailey, without a doubt. She’s wanted to do this for a while, and until I met her, I had only begun to appreciate the idea of travel as an investment in oneself. Hailey is an awesome travel partner and most of our fondest memories stem from the trips we’ve taken, so all it took for this to make sense was a good look at the financials.