5 Things I’d do Differently if I Left the USA Today

Leaving on your first big trip? Congratulations.

I get a lot of emails from people who are gearing up for a big adventure, and the most common question is: how do you prepare for this?

While this isn’t the full checklist (I’ll post that at some point), here are a few big things I wish I’d done before I left in 2011.

If you’re only making a short trip this may not be worth the effort, but if you’re in this for the long-haul these 5 things are worth considering.

#1 Sell everything you can.


[Ahem. Ok, maybe not everything]

I did this in 2011: a massive Craigslist sale, re-gifting to friends, taking a few trips to Goodwill. But every time I visit the US I’m appalled by how much is still left. Thousands of dollars in vehicles, equipment, clothes–mostly useless, replaceable, and only losing more value or becoming completely worthless over time.

I’ve been back to California six or seven times since 2011, and each time I’ve rounded up what’s left and gifted, sold, or donated 25% of what’s left.

It’s hard to get rid of things, but it’s better to have a tight kit. That pile of stuff would be a lot more useful as dollars in my online bank account. Cash is king and it makes little sense to keep it tied up in stuff if you can help it.

This doesn’t necessarily apply for shorter trips, or to anything you know you’ll use in less than a year. But 90% of the time I’ve been wrong on how usefull something will be in the future. The hardest choice is the car: it’s nice to show up and have a vehicle. But sitting in a snowbank for half the year isn’t doing that Subaru any favors.

Time-constraints limit how much selling you can do before you leave, but spending a few days taking pictures, posting on Ebay and Craigslist, or taking bags of detritus to second-hand stores can really pay off.

#2 Get an international driver’s license.


This goes into the bucket of ‘nice to have’ and it’s total BS, but it would have saved me some grief on the road. Most tourists who ride around on motorbikes in SE Asia get shaken down for a) not wearing a helmet (including passenger) or b) not having an international driver’s license.

This happened to me in both Bali and Indonesia, and I completely avoided riding a motorbike in tourist spots in Vietnam based on what I heard.

From what I gathered at the California DMV, the ‘international driver’s license’ is literally a sticker they attach to your license for a fee. Yes–this is a total joke–but may give you more options for car rentals and other situations, and could give you the upper hand the next time the cops ask for a handout.

While I’m skeptical that this would actually have helped (the cops probably would have made up another violation had I actually presented an international license) I’d love to try it sometime.

#3 Get a second passport.


I didn’t learn about this until recently, but US citizens can get a second passport as long as he/she can demonstrate a need for it.

A second passport is useful if/when:

  • You travel to a politically sensitive area where a passport stamp my limit future options or land you a bunch of questions from officials (e.g. also traveling back into the USA).
  • You need to drop off or mail your passport to an embassy for a Visa, or leave it anywhere else. Nothing makes me more anxious than leaving my passport with a foreign entity, but with a spare it isn’t a big deal.

Hat tip to Chris Guillebeau on this one. Here is his short guide to getting a second US passport.

Again, goes into the bucket of nice to have, but useful if you can make it happen. It’s more important that your current passport has an expiration date years away from now and plenty of blank pages.

#4 Permanently move to another state, like WY, NV, TX, or FL.

What do these states have in common? No income tax.

I’ve been in California about 10 of the last 400 days. My only ties to CA now are:

  1. Pile of things and a car stored there.
  2. I will probably go back some day.
  3. The state likes to send me an income tax bill every year, regardless of where I live.

Now I have no problem paying taxes, as long as everyone else does. But at some point you start to wonder why you’re paying taxes if you don’t live there.

I’m not suggesting you should fake a move to another state because, well, that’s perjury. However, why not move to Austin and live there for a bit before leaving home? Or go explore the hinterlands of Wyoming?

If you’re already making some dough it’s also worth considering the details of the Foreign-Earned Income Exclusion, which is a legitimate way to reduce the Federal income tax you have to pay (assuming you qualify). I’m no tax advisor so I’ll leave it to the pros to explain.

Just keep in mind this is all irrelevant until you make some real money.

#5 Set up a virtual mailbox.


finally did this last month, but it would have saved some grief over the last few years.

Mostly, mail is easy to have handled by a parent or friend–assuming you’ve taken necessary steps to eliminate as much mail as possible (set up e-delivery of all credit card and bank statements, canceled all mail subscriptions, signed up for every do-not-mail list available.)

Every once in a while the relative-based mail delivery system fails though: parents are out of town, they neglected to tell you about the letter that came from the tax office, they only have a PO Box and you need a street address, or maybe you need to receive a new credit or (God forbid) ATM card.

This is where a virtual mailbox comes in. You simply:

  • Sign up for the service.
  • Change your mailing address to the company’s street address plus your unique identifier (eg #6667).
  • Receive mail at that address and is collected and scanned into your account.
  • Get an email with a picture of the mail and you can choose to open and scan/shred/forward etc.
  • You can even have checks deposited that come by post.

I avoided signing up for a virtual mailbox only in an effort to minimize monthly service fees, but this one is worth it.

Examples of how I use a virtual mailbox:

  1. Cashing personal and business checks sent to me.
  2. Keeping an eye out for DMV or tax notifications/bills.
  3. Getting images of new credit cards sent to me so I can activate and use them (virtually).
  4. Forwarding mail I physically need to my location or to home for future processing (yes international forwarding is an option).

There are a number of services to choose from, including:

I narrowed it down to TravelingMailbox based on pricing ($15 a month). Each of the services above charges fees for forwarding, cashing checks, and so forth, so read the fine print.

#6 Give a highly trusted relative power of attorney.

Nothing worse than needing a document signed when you’re 2,000 miles away on an island.

A power of attorney is simply legal authorization you give to someone todo things like sign documents in your name.

I never made this happen and it hasn’t been a trip-ender, but it could have been very helpful at times.

You’ll need to fill out some paperwork and get notarized signatures with your relative before you leave, and make sure the trust bridge is pretty strong there.

Check out the resources on getyourshittogether.com, which also includes free templates and information about things like living wills, etc.

If you’re just starting out, would I recommend any of this?


(With the exception of #1, selling everything).

Any impediment to getting on the road should be discarded. Just go, you can sort the rest out later.

What did I miss?

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