Jet setting and remote work can go hand in hand. Here's how to maximize it.

Travel hacking

June 27, 2016

In addition to work flexibility, we may also have the opportunity for increased travel flexibility. And rather than travel with a status quo mindset, why too wouldn’t we approach things a little differently?

Here are a few key takeaways to get you jet setting with a travel hack mindset.

Plan Your Hack

Before diving into any travel plan it’s important to know what you’re aiming for. Ask yourself a few questions from the start:

  1. What are my travel goals?
  2. Where am I traveling most frequently?
  3. Do I always fly with the same partner?
  4. What airlines depart from my city?

Identify, then explore options. Depending on your location, you may have multiple airline options; hopefully more than one. The example I use quite often relates to domestic travel on Southwest Airlines. The Southwest Airlines credit card offerings are currently at the top of my list for maximum flexibility when it comes to traveling around North America (up to 50k points per card!).

Not only can you earn big point bonuses with manageable minimum spends, you can also double up those points with a business card. For extra credit, spend a few more thousand dollars over a few more months and attain a total of 110k points to earn Companion Pass status. Free flights for your travel partner on each leg of your booked journey for the remainder of that year, and the entire calendar year after that.

For international travelers, similar “plays” are possible under different carrier offerings. Check out the popular Cards for Travel website to get a high level overview on multiple options at once.

Bonus Tip - Start with one travel hack and don’t spread yourself thin. Be smart about planning bigger purchases for when you open an account so you’re only spending money you would have already planned to spend in the first place.

Create Boundaries

In the past I’ve written about traveling with family and friends and the potential pitfalls. Many of the same themes are true when traveling while working remotely; even on our own.

Know before you arrive what your schedule looks like, being aware of possible drawbacks or a plan b that might need to be drawn up depending on your destination. Here are the most important things to keep in mind:

  • Make your team aware of your schedule for the day(s) you’ll be at a new location. From where you’re staying to what time you’ll be situated each day, be transparent.
  • Be sure accommodations are fit for what you would define as comfortable. Stay away from budget motels or loud hostels (unless that’s your jam).
  • It still has to be said that in 2016 high speed internet can be hard to find. Triple check you’ll be able to conduct business as usual.
  • If you’re visiting others, or simply want to explore a new area, carve out that time after your remote work responsibilities are completed. Make dedicated time for both.

When we’re traveling, boundaries create expectations, which in turn establish trust and comfort around your remote work travel plans. Keep your team in the loop.

Bonus Tip - Ask your hotel or Airbnb host to run a speedtest on the wireless network, and have them send you the screenshot. Anything less than a few Mbps “down” will make it challenging to conduct business beyond email and chat programs.

Travel Wisely

I don’t travel every week like some, but I’ve picked up on quite a few tips that make traveling—something that can be inherently stressful—a little bit easier.

  • Invest in a simple, durable carry-on. Find one with USB chargers for your electronics so you’re never fighting for a wall outlet.
  • Get organized with a few cases or carriers for cords, personal items, and etc. The tidier the unit, the easier it is to travel with. Check Amazon for a variety of options.
  • Consider if TSA Precheck and/or Global Entry are right for you. Avoid hairy lines at the busiest of airports for the next five years with a little extra time upfront, and a small onetime fee.

Don’t be that person dragging around multiple bags, holding food while you dig around for a boarding pass lost in the abyss. Think ahead and make travel that much easier on yourself.

Bonus Tip - Standby can work in your favor if you think on your toes. Let’s say a conference ends early and you arrive at the airport hours before a flight. If you see another flight that departs sooner, it never hurts to sit on standby; there just may be a seat with your name on it.

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Hack Away

This is only the beginning, but now you have a sleuth of thoughts to consider as you plan for your own travel hacking endeavor. Remember to plan for the best travel hack for your goals, stay present with your team, and travel wisely. The rest will take care of itself.

See you in the sky!

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