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"blogger, InfoSec specialist, super hero ... and all round good guy" 



Travel Like a Boss - Road Warrior Tips

Many people who know me know that I have accumulated quite a few frequent flyer miles. Before COVID, I had many years where I would clock in 200k+ air miles in a single year.

It was pretty easy to rack up miles when you have a job that requires travel Sunday through Friday. I can’t say I don’t enjoy it. Some of that has to do with the fact that I have learned a few tips to make my travel life easier.

Before we get started I have a disclaimer or two. First off, none of these links are affiliates. Many of these items have alternate brands. Look around to see what makes the most sense for you.

Tip 1: Travel Underwear

Yea, I know I am talking about underwear, but this is a must for people who spend 100+ days on the road. These babies are soft as silk, durable as iron, and light as a feather. For you fellow travelers who know what it is like to need them when you need them, they dry incredibly fast. This is nice because if you need to, you can do a sink basin washing and they are ready to wear in a short period of time. Oh – and they are odor resistant. Yay!

Tip 2: Apple Airtags

Apple AirTags - can go a long way to help you track and find missing items.

I must admit, I have personally experienced enormous angst while waiting…hoping…that the baggage carousel would deliver my bags. Even though pro travelers should never check in a bag, there are those trips where it is a matter of necessity. The AirTags give me a sense of calm when I see my bags make it to my destination city.

Tip 3: Wear Comfy Clothes, but Carry Reserves

Sometimes my bags don't make it. I know, because my AirTag said so. Thus, on a few occasions, I have had to spend a night or even a workday wearing my baggy, comfortable, travel jeans to a client meeting because my bags did not arrive with me on my plane.

Not lately, folks.

The best way to avoid this frustration is to plan on making sure it never happens. As a traveler, I take control of this potential situation. An extra shirt, boxers, socks, and some items to make it thru the day or a meeting and look presentable should be doable in almost any carry-on option or even a laptop bag. As far as the shirt - fold it like when you bought it, slip it in flat, it will be fine. Wrapped in a thin plastic bag, such as the dry cleaner bags, will keep it clean and fresh (

Tip 4: Air Boss

This is controversial because many people prefer a roller bag, but please hear me out. This bag can carry about six days of clothing in it. It is especially helpful on longer business trips, (


Alternate Tip 4-A: Briggs & Riley Cabin Bag

Many people prefer this version because it will fit into the overhead bin of ALL the tiny regional jets, including the CRJ200s. I can put my Air Boss or a Tom Bihn (see below) on top of this bag, allowing me to roll them both on board. I get the best of both choices.

But when I really need to pack a lot of stuff, I’m always amazed at how much fits into the Briggs & Riley Rolling Cabin Bag.

The Briggs and Riley is an expensive luggage line. But with lifetime guarantees and no hassle returns/repairs, this is a favorite. It is a tough product, and if you are a road warrior it is well worth the price.


Alternate Tip 4-B: Briggs & Riley Carry-On Commuter Expandable Suitcase

Sometimes I prefer regular carry-on commuter spinner suitcases. B&R has a great 22-inch model, perfect for most domestic travel. Or if you are worried about the more restrictive international standards the 19-inch is surprisingly roomy. I settled for the 20-inch bag which seems to be a compromise, and haven't had any issues with any flights around the globe.


Tip 4-C: Other carry-on bag options

I usually opt for the Tom Bihn, as I like its looks and I happen to prefer having several pockets to help organize my belongings. And it can fit a lot of packing into it…more, in fact, than my back is usually willing to hoist. I have to be a little frugal.

As an added bonus you can wear the Tom Bihn as a backpack and roll on the Briggs & Riley cabin bag.

I personally like the Tristar model (above), as I like the look of it and I prefer the wider range of options for organizing my stuff. There are lots of pockets, plus it can fit a lot inside as well. For those who want to go a little more aggressive on size, there is the SkyTrain.

Tip 5: Roller Blade Wheels (Pro Inline)

This will probably be the most eyebrow-raising item on my list, but the first thing I do when I get new wheeled luggage is to change the wheels out for rollerblade wheels. They are far more durable, and the rubbery composition provides some shock absorption, which makes your bag feel like it’s gliding along rather than banging around.

Best of all, they are silent when rolling. I’ve included an Amazon link here just to give you a starting point, but I usually pick them up at my local sporting goods store. The trick here is to make sure you get the proper size to match the wheels for your bag. Measure the outside and inside diameters or better yet – take one off the bag and take it with you to the store.

I usually take that option so I can do a side-by-side comparison. I also sometimes need to make a trip to the local hardware store to get a couple of plastic washers to put on either side of the wheel, to keep it centered on the axle properly. It completely depends on the type of luggage wheel I’m replacing.

Tip 6: 20 ft extension cable

I am on the fence about this one, but pack it when I can. I usually prefer the mini “travel” versions of extension cords. But with just a minimal increase in bulk, I get not only the ability to multiply 1 outlet into 3, but I can also extend it to fit my power-reaching needs. It is truly valuable when everyone is huddled around the lone power outlet column at the airport. It is even more useful when you end up in a hotel room that only has one outlet on the other side of the room. Behind a desk. Guarded by a room troll.

Tip 7: Velcro Straps

I used to buy these a couple at a time, in various colors. Then one day as I wandered down the aisle at Home Depot, I discovered I could buy them in bulk.

Less than 10 bucks give me a roll of dozens and dozens of these. These attach to any cord or cable, and allow you to wind up your cord and secure it with this Velcro strap. No more tangled mess in your carry-on bags! But the more I use them, the more uses for them I find.

For example, when I set my Tom Bihn on top of my Briggs and Riley rolling bag, I use one of these Velcro straps to secure the handle on my Tristar to the telescoping handle of my B&R.

Tip 8: Plex Media Server (for the Techie)

I don’t normally like to leave my computer turned on at home. If you do, look at the Plex Media App. It takes a little effort to get it installed on your home computer. But once you do, you can stream ANY video you have saved on your home computer to virtually any mobile device or laptop that can run the Plex Media Player app. The iPad version will let you play videos from your computer at home onto your TV screen in your hotel in hi-def thru the Apple TV! No more extortion fees to the hotel for watching a movie. Now you’re all set with this NoPay-Per-View option!

If you are more technically skilled and understand the security risks you might want to consider a Plex hosting server or a Seedbox.

Tip 9: Media stick, AppleTV

OK, this one actually IS a luxury item. If you travel with an iPad you can justify it somewhat. Why mess around trying to connect your laptop to your hotel tv when you can use the Apple TV or another media stick with a remote?

The AppleTV and many other media devices let you stream media, share presentations, and even share your desktop as well.

Tip 10: The World’s Thinnest HDMI cable.

OK, if you’ve managed to read this far, then you’ve earned a bonus pick! This cable makes packing my Apple TV much simpler.

If you’ve ever dealt with the high-end ‘monster’ brand HDMI cables, you know how thick and bulky (and hard to pack) they are, almost daring you to fit them into the bag. These are easy to stow and come in a variety of lengths,

Tip 11: Compression Bags

Review from Amazon: Essential bags- lightweight, extremely durable, great buy.

I’m about to order the small version of this as I’ve used the large size large since 2005. My bag is still kicking strong, but I have grown so dependent upon it, that I want one or two more. This will help me organize my clothes more efficiently for a month-long backpacking trip through varied climates.

I travel extensively for work but have (oddly enough) never used this particular product for my formal travel. To me, it’s an absolute necessity for any kind of extended (to include adventure-related) travel. They are also tough - the large bag I own has survived some hardcore trips!

In the large size, I have fit more or less my entire travel wardrobe: 2 t-shirts, 3 tank tops, 1 pair of jeans, 1 pair of shorts, sundress. Just kidding about the shorts. Anyway, I plan to bundle my warmer clothes into the large ones, then tops and laundry into small ones.

Not only does it compress your clothing, but it also keeps everything smelling fresh and dry. I’ve read some of the other reviews of folks mentioning the zips can pull off. I was very careful with this bag the first few months of use, but this past year was the first time the zip pulled off. I think that was likely because it has loosened over the years (if that’s possible). I actually found the bag just as effective without the zip. It didn’t really matter to me and was more annoying to clip the zip back on than just zip it shut with my fingers while compressing it.

Tip 12: international Cell Phones

If you have an international cell phone, local prepaid SIMs are usually a good way to stay connected. Check with your carrier to make sure it is unlocked and compatible with your travel destinations. I try to buy local prepaid SIMs at my arrival airport or when I get into the city. If you want to order an international SIM card before you leave for your destination, check out One SIMCard (

BUT… I am a real fan of GoogleFi (

GoogleFi can replace your cell phone service and has no roaming fees for voice, text, data, and hotspot service on your mobile device. I found this the best and most ideal solution for heavy international travel.

GoogleFi is my primary cell phone carrier, and it is competitive in pricing and has fast data speeds. It uses the T-Mobile network in the United States when you are not traveling.

Bonus Tip: Have fun!

The last tip I have about business travel is to make sure you really have fun. If you are going to go through the pain of traveling for work, you might as well take advantage of it. I collect shot glasses; specifically, I make it a point to try and collect a Hard Rock Café shot glass if I can. It forces me to go into the city, do some exploring, and hopefully come back with a shot glass. It’s just the little bit of motivation I need to get out of my hotel.

What About You?

Do you have any travel tips? Please share them in the comments section below. When I do a follow-up article you might get published here!

1 comment

1 Comment

leslie donato
leslie donato
Apr 03, 2023

Traveling like a boss as a road warrior can be both rewarding and challenging. Thank you so much for this article its really helpful. By following these tips, you can travel like a boss and make the most out of your road warrior adventures.



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