TravelTravel Hacking

Travel Hacking for the Successful InfoSec Pro

By November 6, 2018 No Comments

So, you want to be a road warrior? Maybe your job has morphed into something where travel is now part of the fun. Or maybe travel is required to reach that InfoSec rock star status you’ve always desired. Either way I want to share some of the tips and tricks I have learned during my stints traveling for a living in the hope that some travel hacking will make things a little easier for you. First off, let me offer a sincere, “Welcome to the club”! In no time at all, you too will have the 1000-yard stare and be able to tell the difference between an Airbus A319 and an Airbus A319EOW by the number of life rafts and vests. This is an invaluable skill which you can use to impress family and friends at the next holiday gathering.

I’ve had a couple of different road warrior jobs. Both have involved flying often. In my first travel job, I was a field service engineer fixing cancer diagnostics equipment in hospitals and labs across the western United States. That job was pre-911 and involved flying to a different city every day, while usually only finding out my destination while driving to the airport. My second real road warrior job is the one I am in now as the Security Awareness Advocate for KnowBe4. In this role, I get to travel all over the United States to speak and work at cybersecurity conferences and similar events. While I typically only stay for a day or two at a time, this still involves a lot of travel especially at peak times of the year.

Now don’t get me wrong. I love what I do. The fact that I have numerous speaking engagements, have been repeatedly chosen to represent my employers and have done more articles and webinars than I can count, makes me proud. My successes in the InfoSec industry have allowed me to rise in my chosen career, given me a pretty decent personal brand and provides nicely for my family. However, getting there as well as staying there often comes with the unavoidable baggage (pun intended). And with multiple traveling jobs and years of experience, I’ve learned to spot certain patterns as well as where the ‘system’ is vulnerable. Here’s just a few items to get you through the airports, hotels and beyond.

Take Care of Yourself

I want to start by saying that it is very important to take care of yourself when you travel like this. Many people assume that traveling is exotic and exciting, and there are times that it can be, but it may also become tedious and tiring before you know it. I have found that the only way I can keep pace and be effective in my job is to make sure I take intentional steps to care for myself. What exactly does that mean? Well, major struggle comes from the fact that when I’m on the road, there is no real time to take care of the “honey do” sorts of things that add up around the house. Those little things that you can usually be handled in the evening when you are home, really start to pile up. Before you know it, they can become a mountain.

To counter this, I have started to outsource far more than I used to. I am an insufferable tinkerer and mechanically inclined person, so paying someone else to change my oil or mow my lawn was tough for me at first. It has, however, become a big relief. Having someone else do these tasks allows me to spend the limited time I have at home with my family and gives me a chance to recharge. Your situation is probably different than mine, but keep a mental note of the things that consume the most precious commodity, your time. So don’t feel bad. Hire someone else to do them, so you can recover some of that time you lose while traveling.

You also need to understand how you recharge, because travel will wear you down. Of the 16 personality types from the Myers-Briggs Type Indicator,  I am an INTP (introversion, intuition, thinking, perceiving). That means by nature I am an introvert. That doesn’t necessarily mean that I don’t like being around people (quite the contrary), but it does mean I recharge myself by spending time alone. Here’s an example of how this plays out in real life. Recently my schedule has had me speaking in a couple of cities each week. During that time, I think I turned on the TV in my hotel room once, only because the quiet allows me to recharge. In a formulaic expression, it means that my time watching TV in my hotel room is inversely proportional to the speaking engagements I have that week. Being aware of your personal recharging style and embracing it will play a huge role in combating burn-out.

Dealing with Airlines

In my experience, dealing with the airlines and airports is an exercise in frustration. It is however one of the best ways to test your faith and spiritual fortitude while shaping your very view on existence. I am fortunate that I am a military veteran. The military taught me 2 vital life skills that help me deal with the frustrations of air travel:

  • Patience – I can stand in any line, or stay on hold for hours on end, not even knowing why I’m in the line, or have been put on hold. I have a very particular set of skills. Skills I have acquired over a very long career. Skills that make me a nightmare for people like them.
  • Need to Know – It doesn’t have to make sense. Many times, what I experience makes no sense to anyone, even the airline representatives. I have learned to ignore the nonsensical nature of the issue and just roll with things in order to get them worked out. Uttering the phrase, “But that’s the dumbest thing I’ve ever heard” is not liable to get you more than a fake smile and bat of the eyelashes from the representative. If you let this bother you too much, insanity is only one delayed flight away.

Having said that, I have developed an airport routine that helps me deal with any issues that arise with the least amount of stress or angst. This will not stop silly things from happening but can reduce the level of stress it causes. This is how my routine goes:

Upon arriving at the airport, I get paper boarding passes printed at a kiosk, even if I don’t check luggage. I’ve had my phone lose service and fail to pull up the electronic boarding passes at the TSA checkpoint more than once, so I don’t risk it anymore. If you don’t want to get a printed copy, screenshot the electronic boarding pass so it’s always available as an image.

Before heading to the checkpoint, I empty my pockets completely and put everything except my ID card and boarding pass in my backpack or luggage. I have TSA pre-check (a must-have if you will be traveling often), so I get to keep my laptops in the bags and shoes on my feet. Far too often I see folks struggling to get everything in order while holding up the X-ray conveyor. Don’t be that guy or gal.

Next, at 20 minutes before boarding, I use the restroom. I do this even if I think I don’t need to in order to avoid having to use the one on the aircraft. Those are tiny places and are getting smaller with each refit cycle of the aircraft.

While waiting I get out the things I will need (earbuds, headphones, tablet, whatever) before boarding, so I don’t have to block the isle while I unpack. This lets me smoothly put my items in the overhead storage space and take my seat quickly, so we can get on with the flight.

When it comes to the actual flight, there are a couple of golden rules:

I personally like window seats, so I get to my seat, put on my headphones and try to tune out the rest of the boarding “experience”. In the window seat, I also don’t have to get up for anyone needing to use the restroom mid-flight or when boarding. Some like the isle as they feel less packed in. And then there are the emergency exit rows or bulkhead seats. Many may prefer them because of the extra leg room. For me, I actually don’t like them as they are more narrow to account for the food trays in the armrests. I’m a big guy and every millimeter of width I can get is appreciated. You will find your preference soon enough.

Some Travel Hacking Tips and Tricks

I fly American Airlines a lot. I have Platinum Pro status, and the loyalty does pay off in some cases. As a Platinum Pro flyer, I get free standby flight changes on the day of flying, a perk that has allowed me to get home early on more than one occasion. I also get earlier boarding and free upgrades to premium seats in coach as well as free bags. I might even get a 1st class upgrade, but, even at Platinum Pro, it’s not something that happens very often.

EH-Net - Kron - Travel Hacking for the Successful InfoSec Pro - T-Mobile

T-Mobile Perk with AA

Some airlines may offer things you don’t think about. For example with American Airlines, as a T-Mobile cellular customer (and nothing to do with status), I get 1 free hour of internet access plus the entire flight worth of texting and messaging for free. I just sign in to a special section on the captive portal and all is well. This is a little thing I miss dearly when I fly on other airlines, but it’s not very well advertised. Explore and look for little perks like this on whatever airline you fly.

Even without special status, you can get some perks pretty quickly. If your organization will allow you to use your own credit card to book flights, you can still get free bags, earlier boarding and even more miles for each dollar you spend.

If you are just getting started, or starting to travel on another airline and want status in hurry, consider doing a “challenge” or status match on another airline. For example on American Airlines, you can pay a $200 fee, and, if you travel 16 segments or 12,500 qualifying miles and spend $2000 in Elite Qualifying Dollars (EQDs) in 90 days, you can become Platinum almost immediately. In addition, if you have status on one airline and start to travel on another, many airlines will match status for a limited time while you complete a challenge on the new airline. I have done this twice, and it was well worth it both times. The Points Guy website has a great breakdown of current (as of 2018) programs at

Be kind to the flight crew. Smile when you come on board and say hello. Those folks work very hard and get little respect. Please follow their instructions, and, even if something is not going well, let them know you are frustrated with the situation not at them personally. This goes a very long way to easing situations. The flight crew can make your flight very enjoyable or downright miserable, if you motivate them to. I’ve had crew members grab a seat next to me and carry on great conversations (and perhaps even a free drink or 2), just because I treated them as humans. A little spot of trivia… Flight crews only get paid from he time the aircraft door is shut to the time it opens again. Yep! Boarding and deplaning, waiting in the airports, etc. is all off the clock. Have mercy on them please.

Don’t forget to look out the window. Some of the most magnificent views I have ever experienced were out the window at 30,000 feet. It’s easy to get tunnel vision on the plane, but don’t forget to enjoy the unique experiences that only commercial air travel can provide.

EH-Net - Kron - Travel Hacking for the Successful InfoSec Pro - Airplane View

Don’t forget to stop and take in the view.

Finally, If you can get the company to spring for it, join a “Club”. I’m a member of the American Airlines Admirals Club. This allows me to go hang out in a place with free drinks (soda, beer and even house liquor) and snacks. Many include showers, work cubbies, phone chargers, faster internet and the coup de gras, clean bathrooms. It’s not cheap at about $500 a year, but I have found that having access to the club allows me to get a lot more work done than when I’m out with the general population. It’s more magical than Disneyland for the frequent traveler.

Ground Transportation

Once you are at the destination, you will need to get around. I use Uber quite often, however I have found that sometimes Lyft is considerably less expensive for the same route. Taxis are everywhere but tend to be expensive. If you are renting a car, find out if your own insurance or the companies insurance covers damage to the rental car. And I can’t stress this enough: know this before you leave on the trip!, This can be a big extra charge, and there is no sense in insuring the vehicle against damage twice. Or even worse is having to pay for damage, because there is no insurance. Ouch!

The Perks

Ah yes, the perks. So far we have mentioned the challenges of travel. Let’s talk a bit about the perks now. Business travel, while often lonely, also comes with a great sense of independence and freedom. You get to see parts of the country you would not otherwise see, enjoy foods you may not otherwise ever enjoy, and meet wonderful people from all walks of life. Because of my work, I have had cheesesteaks in Philly, barbecue in Kansas City, explored Time Square in New York City and enjoyed the great musical offerings of Austin. I’ve seen the sun rise over the Atlantic Ocean and set over the Pacific, all in the same week.

The ability to get free recreational travel becomes easier as you gain status and get bonus miles on top of the miles you normally fly. For example, as Platinum Pro, I get an 80% miles bonus on top of those that I fly. That adds up quickly and allows me to send my family on trips back home without costing me a dime. On top of that, the hotel points rack up, allowing us to take quick, well-deserved stay-cations to help relax after all of that travel.

I have also stayed in some magnificent hotels, ones that I otherwise would never have been able to afford. This is thanks in part to being a part of the hotel rewards program and being kind to the folks at the front counter. Getting upgraded to a suite can make you feel like royalty, especially after some crazy days on the road.

EH-Net - Kron - Travel Hacking for the Successful InfoSec Pro - Vegas Suite Upgrade

A fantastic suite upgrade with a huge Jacuzzi tub in Las Vegas.

Travel Hacking Resources

Much like any other kind of hacking, having resources is very important. I have found that these websites are great resources when traveling. Each one provides information that I have found very useful in my travels.

  • Flight Aware ( Do you want to know where your incoming plane is or about delays at airports across the country? This site has you covered with extensive information about what’s happening in the air at all times.
  • Seat Guru ( Do you want to know if your next flight will have a power port, or if the seat reclines? Seat Guru can tell you which seats have obstructions that limit the legroom under seats and all sorts of other useful information.
  • The Points Guy ( This site has everything you ever wanted to know about maximizing points that you can use later for personal travel, as well as various program information and even fare sales. It also has an active user community full of other tips and tricks.
  • Trip Advisor ( If I’m staying at a new hotel chain or somewhere I have never been, this is my go-to site to see how the place will be, and what I need to know before I book. The reviews can be very brutal and honest, which is a good thing, as it’s not just watered-down reviews from the proprietors.
  • Yelp ( Find out where the good food is. This is more helpful than I ever considered before traveling and has helped me avoid some real dives in favor of much better, local establishments.

Obviously, living the jet set lifestyle isn’t always fun, but with a little preparation, some knowledge and patience, it can be incredibly rewarding. Even if this is your first foray into the road warrior lifestyle, if you use some of the resources above and take advantage of some of the tips, you will have the opportunity to see some incredible places, have some amazing experiences and meet some wonderful people. Embrace it, enjoy the freedom and always be looking for new ways to leverage the system to your advantage. In other words, keep hacking the system.

Be sure to leave your own travel hacking stories or feedback on what I’ve shared in the Comments Section below.


EH-Net - Kron - PicErich Kron, Security Awareness Advocate at KnowBe4, is a veteran information security professional with over 20 years’ experience in the medical, aerospace manufacturing and defense fields. He is the former security manager for the 2nd Regional Cyber Center-Western Hemisphere and holds CISSP, CISSP-ISSAP, MCITP and ITIL v3 certifications, among others. Erich has worked with information security professionals around the world to provide the tools, training and educational opportunities to succeed in InfoSec.

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