Sometimes spending a little more on your comfort is really worth it.

I was brought up in a lower middle class family that, in my later teen years, was upgraded to middle class after my mom’s divorce and remarriage. I struggled financially to live on my own for a while after college, and then struggled a little less when I began living with my future wasband. It wasn’t until I was in my late-thirties that I began earning what I’d consider a very good living.

Living when money is tight — but not tight enough to actually cause you to miss meals, get evicted, or turn to payroll lending storefronts to meet financial obligations — teaches you frugality and comparison shopping skills. You quickly learn that if you need to buy something, you need to shop around a bit to get the best deal. You need your money to go further. This becomes a mindset, something you do naturally. Something you can’t imagine not doing.

Travel on the Cheap

Even when my personal financial situation started looking very rosy, I was stuck in that mindset. That was especially so when I traveled for business in my early years as a writer. I was a regular speaker at Macworld Expo in San Francisco, Boston, and later, New York. I even spoke twice at the event in Toronto.

Macworld did not cover my cost to travel to these events. Its only compensation was free unlimited entrance to the show, snacks and swag in the Speaker room, and a Speaker ribbon that often led to more swag at booths. (The Press ribbon, which I earned by writing for some tech magazines back then, actually worked better.) The cost of airfare and hotels was on me. This was a pretty big financial burden, especially when I traveled to expensive San Francisco from the New York Metro area.

So I shopped for airfare. And yes, I’d even stoop to taking a non-direct flight or redeye if it could save some money. And then I shopped for hotels, winding up with satisfactory lodging within walking distance from the venue.

The crazy thing about all this was that my travel related to the event was a business expense — no doubt about it — and I could write it all off on my taxes, which I did. (Contrary to what some people think, writing things off on your taxes doesn’t mean the government pays for it. It means that it reduces your taxable income. So if you spend $1000 on a trip and your tax rate is 28%, it’s like getting a 28% discount on that expense.) But I was still in that watch-every-penny mindset and even though I could afford better flights or lodging, I just couldn’t see spending more when I could spend less.

That all came to a head one year on a San Francisco trip.

Seeing the Light

Macworld Expo in San Francisco was held in January. While the weather in San Francisco in January isn’t nearly as frigid as it is where I lived in New Jersey, it could be cold. I’d booked a room at the Victorian Hotel — now the Mosser Hotel — on 4th Street, less than three blocks from Moscone. (I think the hotel was just beginning its name change process back in those days — maybe 1998? — because I remember the new name.) I’d stayed there at least once before, so I knew what to expect. (Or thought I did.) The hotel was popular with speakers because it was relatively inexpensive. But it was inexpensive for a reason: it was old and in sore need of renovation. (I hope it’s been fixed up since then.) It did have a good restaurant on the ground floor, though: Annabelle’s was the name. (Funny the things we remember.)

On that particular year, San Francisco was cold and so was my room. The heat — a radiator! — simply did not work. I called down to the desk to see if they could do anything and they sent up a bellman with five blankets. I slept under a pile of seven blankets for the next few nights and dreaded showering.

I remember thinking to myself: What the fuck is wrong with you? You can afford a better room that this! Isn’t your comfort worth it?

The answer, of course, was yes. The next few years, I stayed at the W across the street from Moscone, where I was introduced to modern rooms, feather beds, and other very nice treats.

Airline Travel

The airfare lesson took a bit longer to kick in.

I admit that I stopped doing flights with connections unless there was no other option early on. (My wasband, however, did not. I remember one year when he paid for his family to come to Arizona from New York for Christmas. He bought them tickets on an airline called ATA, which was really cheap, probably because it only had like four planes. The flights had a stopover in Chicago, but not at O’Hare like a normal airline. They stopped at Midway. As anyone could expect in December in Chicago, weather moved in and the plane got suck at Midway. Then there was a mechanical issue. The delay was long and when his mom and sister finally arrived in Phoenix, they were extremely travel worn and cranky — can you blame them? The punchline: he only saved $50 per ticket over a direct flight with another airline. And yes, he could afford the $50 per person.) I’d had enough experience with the problems that arise when you have connecting flights and unnecessary stopovers. Why make a trip more difficult than it needs to be?

Of course, I usually fly out of Wenatchee these days and Horizon only operates a turboprop to Seattle, so all of my flights to anywhere other than Seattle have at least two legs. That can actually work out to benefit me, as you’ll learn in a moment.

(The only trip I occasionally do that I can’t avoid three flights is to visit my sister in St. Augustine, FL. The closest airports are Jacksonville and Daytona and the last time I went there no direct flights from Seattle. That meant flying from Wenatchee to Seattle to Atlanta to Jacksonville and then doing all that in reverse on the way home. No matter how you slice it, you’re traveling for a whole day.)

A few years back, when I was still doing frost control work in California from January and into March, I had a contract where I could stay home until called out. The call would come at 3:30 PM, which is when the hyperlocal weather forecast the grower subscribed to would be released for the evening. As I talked to him, I packed. When I hung up, I booked a flight from Wenatchee to Sacramento. As I was driving to the airport, I booked boarding for my dog, Penny, and dropped her off. As I waited at Wenatchee airport for my flight out, I booked my hotel and rental car. I’d arrive in Sacramento before 9 PM, get my car, and go to my hotel. In the morning, when I was released from standby, I’d book my return flight, check out of the hotel, and go home, picking Penny up along the way.

Every time I did this trip, I earned four legs on Alaska Air’s frequent flyer program. I did it six times in one season. That put me into MVP status. Suddenly, when I started flying Alaska Air, I’d get automatic upgrades to First Class at least 75% of the time. I enjoyed that for a year and a half — and I was doing a lot of airline travel back then. It spoiled me.

First Class is the Way to Travel

You have to understand that First Class isn’t just sitting in a bigger seat at the front of the plane — although, admittedly, that’s a real bonus. It’s free luggage check in. It’s often (depending got how you got to First Class) entry into the Alaska Lounge at SeaTac and a handful of other airports. It’s boarding first. It’s having a flight attendant take your jacket and put it on a hangar (and return it to you later while taxiing to the gate). It’s not having to shuffle down the aisle, hoping there’s space in the overhead bin for your bag. It’s having a drink — whatever you want — as everyone else boards. It’s having a warm towel to clean your hands, more drinks, a hot meal, and often a warm-from-the-oven cookie. It’s not having to worry about someone’s brat kicking the seat behind you or the jackass in front of you reclining his seat so you can count his hair follicles. It’s civilized and comfortable. It makes airline travel bearable.

Honestly, if you spend enough time on long flights — which I consider any flight over two hours — in First Class, you’ll wonder how the hell you managed to fly coach all those years.

Well, that’s how it was for me.

Good things don’t last forever and eventually my status as an Alaska Air MVP lapsed. I was back in the world of regular travel and I can’t say I was happy about it.

But what I discovered is that if I buy my ticket far enough in advance and I’m flexible about travel dates and times, I can often buy a first class ticket for just $100 to $300 more than coach. Here’s a random example for Alaska Air; in this case, if I were going to visit my brother in New Jersey, I’d be buying that First Class ticket leaving Wenatchee at 6:25 AM (keeping in mind that I’m a very early riser):

Would you rather spend five hours and 20 minutes in First Class or stuck in coach, rubbing elbows with some guy with body odor while a kid kicks the back of your seat? Oh, and don’t forget the ability to wait in the Alaska Lounge in Seattle for the two hours between my flight from Wenatchee to my flight out to Newark. Yes, it’s worth an extra $272 to me.

While I realize that not everyone has a few extra hundred bucks sitting around to piss away on air travel, I usually do. I don’t travel by air that much anymore and I want my experience to be as comfortable as possible. I travel alone now, so I don’t have to buy a ticket for traveling companions or worry about what they might be able to afford. I’ve come to realize that my comfort is worth the extra money.

Travel in Comfort

As I get older, I’ve come to realize that my personal comfort is important to me. If I can afford going First Class, I will.

That’s why I’m flying First Class from Los Angeles to Seattle next week. (There is no First Class on Seattle to Wenatchee legs.)

If you’re in a similar situation — older, traveling alone, money in the bank — and you’re not treating yourself to First Class travel when it’s available, why the hell not?