I try to visit my family on the other side of the country a couple times a year. Most of my family has migrated to the west coast from the east. The migration, at least in my immediate family, began over ten years ago, and more of the clan join the California contingent each year. Having family gives me a nice excuse to travel, though, and I’m trying to visit more often.

Over the last few years I’ve tended to not have real vacations while I travel, and I’m now considering that to be a problem. While away from home, rather than also separating myself from work, I’ve mostly remained connected and involved. As a business owner, I felt I had that responsibility. I hope to change that aspect of my travel this year, and have some thoughts on doing so, but first I wanted to write about my latest flight search experience.

Since beginning regular travel to the west coast several years ago, I’ve noticed my location and destinations generally led to Continental Airlines for the lowest fares — often lower than the recommended JetBlue and Virgin America (whose flights out of New York City tend to be less convenient, anyway.) Southwest is the most popular recommendation I receive, but they don’t fly the routes I travel most often. For a few years, I’ve noticed the good pricing pattern with Continental, and that led to my decision to give into marketing pressure and focus on the Continental frequent flyer program.

Having accrued a good number of miles, the airline has succeeded in converting me to a loyal customer, price-checking my flights but usually selecting Continental and United. In just a few days, the merging airlines’ frequent flyer programs will be consolidated, making it theoretically easier to use the miles I’ve accumulated in both programs. My favorite benefit comes from holding the co-branded credit card. Most of the time, I’m able to bypass the long security lines, even when I don’t have a first class ticket. (I’ve only flown first class twice, which I was only able to do by cashing in miles I earned mostly through credit card usage for an upgrade. Paying for a first class ticket is not something I would consider at this point in my life with my finances.)

I could have saved some money by choosing inconvenient flight times. Had I chosen to depart at 7:00 am or fly overnight, I might have spent $50 less on the airfare. For me, traveling is not always about choosing the least expensive options, it’s about convenience and compromises. I’m willing to pay a little extra (in this case about 10% more) for convenience. In fact, if I were able to choose a different week to travel, I could have found flights for a little more than half the cost of the dates I chose. I’m bound to what happens to be a popular week for travel, and prices are higher when flights are in demand.

A few days after my flight was ticketed, I decided to compare prices. I was able to find availability on the same flights on the same days in the same fare class for $10 less than what I paid. That’s a $5 savings per passenger. Obviously, this was not significant enough of a price decrease to warrant changing bookings for a ridiculous $150 fee per ticket (the fee does make sense if you consider it as a disincentive to change flights frequently, but there’s no justification for the fee in a “cost of processing” sense). It did make me consider that the day you book a flight might have an impact on the final price. Saturdays may be expensive while the middle of the week could offer slight discounts.

Checking for the same availability today, I see the fare class I originally booked on the return flight is no longer available, and the total price increased by $300 for two passengers.

Unlike every so-called vacation I’ve taken for the past five years, I’d like to prevent myself from working. I usually fall into the habit of mostly continuing to do business while traveling, and I hope that this year I can begin finding time truly for myself. That’s the plan; I’ll see how it works out.

How to take a real vacation from work

If you run a business or are responsible for a major project, it’s difficult to leave your work behind and trust that any plans you put in place for the work to continue while you’re away.

• Start planning as soon as you know you’re going to travel to have any necessary responsibilities or tasks handled by someone you trust. This might take some training, so thesooner you can start, the better.
• Proactively notify your most important contacts, internal and external, particularly anyone who relies on you.
• If you intend to refrain from answering or reading work-related email, make sure your system sends an automated response to outside contacts informing them of your unavailability and offering options for alternative people to contact.
• Remove the temptation to check your email or voicemail. If you don’t have your mobile phone or laptop with you, you might find it easier to relax. It won’t be as easy to check in with your coworkers or clients.
• Realize that the world will not end if you’re not immediately available.

What are your tips for taking a real vacation?

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