Strategies for Hassle Free Business Travel

People often complain about how difficult flying can be these days. I recently spoke with certified speaking professional and author Garrison Wynn to learn what can make it easier to travel and navigate the airlines. Wynn, who categorizes himself as a professional traveler, “commutes” nationwide to about 100 speaking engagements each year. Here, in a series of interviews, he provides tips for ironing the kinks out of air travel for speakers and others who often find themselves flying on business.

Linda Singerle: As a seasoned international keynote speaker, you travel almost continuously. What’s your strategy for eliminating some of the hassles that come with that kind of life?

Garrison Wynn: My advice is to travel light and travel easy. First off, your luggage is key. You want to have sturdy luggage with really good wheels that allow the bag to glide easily so you don’t have to pull it too much. You have to make travel as easy on yourself as you possibly can. In every airport, I see miserable people dragging squeaky-wheeled clunkers and wearing that “Someone please kill me” expression on their faces. My theme for traveling? Make it easy. If you make it difficult, you can’t do a lot of it and you show up at your destination with a new, self-induced priority of simply recovering from travel! You and your clothing have to show up in top condition to do the best you can.

LS: Whathave you learned about how much to take with you on business and how best to pack it?

GW: One thing is to realize the goal. The goal of packing is to arrive at your destination with the things that you need and to have those things arrive in good condition. But if you arrive with the distinctive look of a police mug shot… Well, it’s hard to be influential when you show up at the meeting looking like you’ve slept in the bar. I saw a guy one time who showed up to a conference fresh-faced, bright-eyed and bushy-tailed. However, his suit looked like it had a hangover. He made it to the meeting but his suit didn’t really.

LS: So how does one prevent that? I’ve seen you take the stage to deliver your keynote. You look like your suit just came off the tailor’s hanger. How do you not look wrinkled and travel weary?

GW: There are a lot of ways you can pack your clothing so that when it gets there, you almost need to have it pressed. If you don’t do certain things, you’ve got problems.

No. 1: The type of luggage is important. For suits or dresses, you want a tri-fold bag – the kind that your suit lays flat in when you’ve opened up or unfolded the three sections. But before you lay your clothes inside, put each suit or dress in a dry cleaner’s thin plastic bag. Then put one thicker plastic bag around the whole bunch. I often use a garbage bag, but you could also use the thicker bags dry cleaners use on wedding dresses. Just make sure the dry cleaner’s bag has the staples removed and the garbage bag never actually held any garbage (unless you’re looking to make a unique impression).

So the suits are covered in plastic and they’re put into a tri-fold bag. Your next step is to roll up a pillow case and place it at one of the folding points of the bag. Do the same at the other folding point. Now when you fold up the bag, there’s a rolled-up pillow case at the two pinch points. When you do this, you dramatically minimize the wrinkling of your clothing. You’re getting a light fold that’s not so severe that it can’t be steamed out or shaken out.

LS: So do you hang your suit in the hotel bathroom and let the shower steam it?

GW: Many people do hang their clothes in the bathroom and steam the shower up. What I think works a lot better – or even in conjunction with that – is to travel with a handheld steamer. The one I use, E-Steam, is available online for $50-$199. That’s quite a range, I know; it depends on where you get it online. This handheld steamer is a quality item made of hard polymer, and it takes up less space than a pair of shoes. This thing is a miracle item for me, allowing me to steam suits very quickly and effectively. Don’t be fooled by the claims made about other steamers. I’ve tried them all and they produce very weak steam but somehow manage to shoot water on your clothes from 10 feet away.

The first thing you do when you get your suit out of the bag is take it off the wire hanger you travel with (because wire is less clunky) and put it on the hotel’s hanger. Shake the suit out really well and hang it up. After you shake the jacket out, hang it on the hook in the bathroom, plug your steamer in, and hold the steamer about 4 or 5 inches away from the fabric. It works really well! Now, if you think this is something you just can’t do for whatever reason, you can use the shower to steam your suit; just make sure your pants and jacket are well away from the shower head and close the curtain. You want to avoid the appearance of being so nervous about your meeting that you have managed the seemingly impossible feat of sweating through a suit.

You’d be surprised how many businesspeople who are amateur travelers get to a destination and are unable to get their clothing in the condition in which they normally would wear it at home. Women’s business clothes are a little different – they’re made of rayon and polyester and all kinds of different fabric that might travel better or be easier to care for. But men, if you’re wearing a suit, then it’s worsted wool. If your suit’s not made out of wool, then you’ve got problems I can’t help you with. I’ll put it this way: If you’re traveling with a polyester suit, then when you get to where you’re going, whatever you do will not be good enough. If you’re wearing a suit you could strike a match on… If your suit is quite literally a fire hazard… If you start to feel a little hot before realizing your suit is melting… OK, sorry, let’s move on.

LS: Maybe this is a distinctly female question… I think I’m exercising restraint when I travel with four pairs of shoes, which is inevitably two too many. Are there things that people typically pack that we simply just shouldn’t take?

GW: Sure.First off, for women: take only the makeup you will actually wear. Do not take the stuff you’ll just carry in a bag and won’t wear.

And then, yes, there’s the shoe-for-every-outfit quandary. Sometimes I think a woman’s attachment to the “ensemble” overrides any logic. How are you determining how many shoes you need? It’s an odd process that maybe as a male I am destined to never understand. But for some women, it seems that having “shoe options” is more important than having room for anything else.

Basically, if you’re attending one event, one meeting, you would need one pair of shoes. If you’re going out somewhere that night, maybe you’ll need some dressy, strappy shoes. So I guess we’re talking two pairs of shoes. I always recommend you travel in some comfortable shoes and that those would also be the same shoes you wear the day of the event. However, some women may say, “No, no, no. I’m going to have my special travel shoes and then I’ll have my shoes that I wear the day of the event… and then the shoes I wear to dinner at night.” So we’re up to three pairs for one event. Please try to be as practical as possible; I have noticed that women who wear very high heels through airports have been known to check into hotels barefooted with a look of defeat on their faces.

What if you’re going to be multiple days in the city? Are you talking about a different pair of shoes every day? That’s the question you’ve got to ask yourself. If you’re going to wear a different pair of shoes every day, you now have a piece of luggage that primarily contains shoes. Do you travel with a second shoe bag? You’ve now just doubled your luggage. Is it more important to have the exact pair of shoes you want, or do you want to try to travel with a single bag? You could choose to be convenient and practical, or you could choose the flexibility of having a whole bunch of shoes in a separate shoe container. At that point, I think you’re one step away from hatboxes, steamer trunks and an entourage that travels with you.

You can find luggage with all kinds of compartments, with shoe pockets all over. But what condition do you want your shoes to show up in? When you start smashing shoes all together, even the best leather will rub and the contact will scuff your shoes. We will normally only tolerate scratched-up shoes on kids and strippers (although I’m not sure we will tolerate pairing the words “kids” and “strippers” in the same sentence). You have to individually wrap your shoes in a felt bag or something to separate them.

The women I see who travel professionally all the time have their travel shoes, their day shoes, and their night shoes. And they can work with that in a single bag, even if they have to leave some other things behind (like a husband). Women’s shoes, very complicated.

LS: Men don’t have this problem?

GW: Men’s shoes – very different. I recommend literally one pair of shoes. I recommend slip-ons, because you don’t want to be untying your shoes to go through airport security. I recommend that they be black. I’ll even recommend a brand: Ecco. These shoes are extraordinarily comfortable and very fashionable. They’re not cheap but not terribly expensive – a couple hundred bucks.

The whole idea of “I’ve got my black shoes, my brown shoes, my cordovan shoes” (whatevercordovan means) and then you’ve got to figure out which shoes you wear with which suit… I’m sorry. Too much unnecessary hassle. The average man doesn’t really know what goes with anything until he sees it on the mannequin in the store and thinks “Oh yeah… I knew that,” when really he didn’t! I still remember my dad in a white ’70s jumpsuit with gold trim, looking like he escaped from a dance team, telling me about the basics of men’s business fashion.

Thanks, Dad. But I prefer to keep it simple. To that end, let me restate that black shoes will look good with everything you wear. Black shoes, black socks, black belt – you’re done. That shoe I recommended is comfortable enough for traveling in the airport, easy enough to slip off at the security checkpoints, dressy enough to look good with a suit and versatile enough to go with jeans too.

LS: Do you have to have a backup suit? And can you recycle a suit for a second event? I guess what I’m getting at is this: How many suits are too many?

GW: Most suit carriers can hold two suits, or a suit and a blazer and a second pair of pants. If you have three days of meetings where you have to wear a suit, that can be an issue. There’s some good luggage out there that allows you to carry three suits, but beyond three, it can get a little more difficult. You’re talking about bigger luggage.

As a speaker I’m often going to different cities on consecutive days. I’ll wear the same suit in three cities, three different companies. I’m brand new every day. The suit I wore in Montreal is a brand-new suit to Cleveland. Speaking in three different locations? One suit’s fine as long as you are not seeing the same people. You don’t want to be a one-suit wonder. However, if you have three days of business and two suits, you can bring three very different shirts and ties (pinstripes and/or distinct solid colors) and repeat the first suit on the third day. No one will notice it’s the same if your suits are solid (no pattern) and you take a dark gray suit and a navy or black suit.

OK, ladies, you might now be thinking that men’s suits are more complicated than your shoes. But remember, we are trying to stay within the confines of our luggage, whereas you are trying to decide if you need to take “after-dinner shoes.”

The thing is to be practical. What do you really need? Remember that when you’re traveling somewhere, you will have a finite size of luggage, so the decisions you make are important. It’s really easy to say, “I’ll just take a lot of stuff, and when I get there I’ll decide what to wear.” That might work on a weeklong vacation with a giant piece of luggage that you could carry a spare air conditioner in, but it’s just not practical for business travel.

If I’m going to be in one city for four to five days, I’ll take a bigger piece of luggage called a European traveler. I could actually put a small person and a little piano in that thing if I wanted to, that’s how big it is. That type of luggage is an option if you’ll be gone for a longer period. How much you pack and what size luggage you take is truly a matter of how long you are going to be somewhere.

So, to reiterate what’s most important when you’re packing: good luggage, a tri-fold bag, and some realism regarding how much you really need.

My next segment with professional speaker and seasoned traveler Garrison Wynn focuses on streamlining your TSA experience.

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