A Life of Travel

Jamaica, the gem of the tropics. Beautiful, he...
Jamaica, the gem of the tropics. (Photo credit: Wikipedia)

This is for my friend, Jenny, like many other friends that want to know how I travel so much. I write this while on vacation in Jamaica. Sounds cushy, right? Flying everywhere, vacations in foreign lands. It has it’s ups and downs.

First, yes, I fly a ton. Mostly for work though. Conferences meant new connections and the chance to teach others. Working for Distilled, I have less time to spend at conferences than when I owned my own business. Now I travel the most to see clients. That means at least three trips a year to see them, if not more.

So traveling ends up in two buckets: for work and for fun. For this post I’ll break down how to do the two kinds of travel more often (if you so desire).

Traveling for Work
To get the honor (promise it won’t always feel like that) of traveling for work, you need a few things. One is a desire to travel. Not everyone does. Traveling is time consuming and tiring if you do it too much. If you are bored of your routine, I promise you traveling will make you want that routine back. It makes you see what is great about your “boring” life.

You also have to have the availability to travel. My clients come first right now, so I can’t do as much conference attending as I might have done otherwise. You might have a dog, cats, kids, family, or other obligations. You have to take those into account when talking to your company about how much you would like to travel. If you have such a desire and availability, make it known. They might actually be looking for someone.

Third is the opportunity to travel.

  • Do you like speaking? (no really it can be fun)
  • Are there conferences in your industry?
  • Are you willing to put the work behind the presentations (for at least a month up to the conference, right until the day of, PowerPoint will be your best friend and hated enemy) and networking before, during and after a trip?
  • If you don’t want to speak, or it’s not possible, do you have clients?
  • Is there a need to go see them?

You have to have somewhere to go that will be an asset to the company if you expect them to pay for it.

One final thing here is be aware that not all work trips are as glamorous as they sound. I went to Hawaii for a conference earlier this year. All I heard was “oh man, I wish my company would send me to Hawaii.” There is a ton of work involved (see above) and you are usually at the location for a short time. Why didn’t I stay longer?

You could combine your yearly vacation with a work trip. It saves you a few nights hotel and (your) airfare. Just remember, going to a top destination like Hawaii or New York will set you back about $300-500 a night. Your company might pay for the required days, but the rest is on you. It’s never really worked out for me to take a vacation around conferences (I’m usually so stressed before and so tired after), but I have done it around client trips.  You have to consider if the savings on flight and a few nights hotel is worth it. Sometimes it is.

Traveling for Pleasure
Alright, I know, it’s the Jamaica trips people want to hear about.

Vacation Time

It looks like I travel a ton because of one main thing besides speaking and clients: my awesome company. I get 4 weeks paid vacation a year. Yeah, that’s what you get for working for a British company. And we have to take it.

Now do I take all 4 weeks to go to Jamaica and Hawaii? Nope. I spend a week of it going home for Christmas, probably another week going home to Texas for other things. There is a week for actual vacation with Dallas and then the other week maybe skiing with my best friend and the random thing here and there. So I actually only take 2 weeks vacation a year.

So … if you want to travel to exotic places personally, the first thing you need is an awesome company that gives and makes you take vacation. I’m a big fan. The other thing is money. Yes, money. You have to get good at saving and be okay spending that savings. We don’t keep money after we die, so don’t horde all of it. Life is meant to be lived, vacation is part of living it.

Frequent Flyer Club

Alaska Air 737 Combi landing at ANC
Alaska Air 737 (Photo credit: Alaskan Dude)

One other piece of advice is to pick an airline. One that goes everywhere like American/Delta/Alaska (Alaska is who I fly, and I get the benefits on the other two), or United/Continental. I know there are more, but that’s all I can think of right now. But the point is, pick one. Join their frequent flyer program, and just use them and their partners.

With my trip to Jamaica, I will have reached Alaska MVP Gold next year. I don’t want to list all the perks, you can look them up, but it’s nice. I’ve been an MVP for 2 years now and it’s so nice. No baggage fees, early boarding, and more.

Oh and be a deal hound. We are staying in Jamaica on a Groupon deal. We stayed in Hawaii at a Homeaway condo. Be on the lookout for non traditional ways to travel and you’ll save.

I think that’s it for now. If you have questions, do ask and I’ll update!

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