Why I Stopped Booking Airline Tickets in Advance

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Or how I nearly blew $1500 booking tickets I didn’t need last year.

Back in the day, airline tickets were really expensive and inflexible. Not anymore.

Welcome to the world of low-cost, flexible world travel.

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While visiting family in February I decided not to get on my flight home. I wanted to spend some additional quality time there so I just didn’t show up for my flight.

Mom was flabbergasted: “You can do that?!”

Yep. You’d be amazed by what airlines let me get away with last year.

This conversation led me to the realization that in the last 19 months, every single flight I pre-booked more than a few weeks in advance I either didn’t get on or had to change for a lot of $$$.

If I no longer have pre-defined location constraints, and if pre-booking flights is both “a major turnoff” and expensive, why would I still do it?

Growing up, ‘flexible’ travel plans involved flying standby and frequently sleeping at the airport.

It never occurred to me until the last year that you could just not get on a flight you’d pre-booked because ‘you didn’t feel like it’.

The mentality of concrete travel planning is pervasive in a society with inflexible work schedules: if you get a week off to go to Cabo you sure as hell better use it, whatever the ticket price at that time.

But this is no longer a concern in the true location-independent working model, and another reason why you should bag your office job if you haven’t already.

Traveling flexibly isn’t just about goofing off or staying somewhere because the weather is good. Sometimes a business opportunity comes up, or you meet people who are doing something incredible, or you get into flow and you don’t want to interrupt momentum.

For this very reason I don’t like planning too far into the future, and pre-booking a actual flight is not only a major commitment but based on a few deep-seated nagging myths I’m trying to obliterate:

Myth #1: Pre-booking airfare saves money.

Not in my experience. Here are a few examples from the last year of travel:

EXAMPLE #1: My $800 Round-trip flight to Honduras

This was my initial ‘get out of Dodge’ trip after I quit my job and had no idea what was next. Buying this ticket (and getting on the flight) was the best decision I ever made.

Only problem: the $400 return flight I never got on (I ended up in Uruguay 6 months later).

EXAMPLE #2: Ticket prices don’t always go up

In December I booked a $650 one-way ticket from San Francisco to Bangkok (for February 2013). That flight hasn’t changed in price from December 2012 to today.

In fact, the cost of the flight went down by $100. I could literally book the flight to Bangkok for this afternoon and I would have spent less and avoided the hassle and fees of changing my booking TWICE.

I know you’re thinking “yeah but sometimes the price really does go up”.

EXAMPLE #3: The $800 flight from Eastern Europe to SE Asia

The thing about this one is that I expected a flight from Europe to Asia to be expensive, especially during the Euro-vacation high-season (July-Aug). So when I saw an $800 ticket a few months out I jumped on it.

But when I decided to stop and work for a month in Budapest I found the same flight a month later for $400, right smack in the middle of the busiest part of the year (August).

Luckily there was more flexibility here than I thought possible…

Myth #2: Airline Tickets are not flexible.

EXAMPLE #1: The $650 Flight from San Francisco to Bangkok

I was supposed to get on this flight on February 10th. Turns out a) I can change the ticket to any date I want for $20 (thank you Singapore Airlines, best company on earth) or b) if I don’t feel like going for a while I can use that credit for any time in the next year for the same route.

At this point I’ve paid $40 to change the ticket twice, and I probably just won’t show up for it when the next departure date comes around.

EXAMPLE #2: The $800 free refund from Malaysia Airlines

When I found the $400 ticket from Budapest to Bali I called Malaysian Airlines to find out (WTF) that for me previously booked flight the entire fare was refundable with no fees whatsoever. Thanks Malaysian Air!

This was my first real indication that yes, things are often a lot more flexible than you could have imagined.

The new, better way to book airfare for digital-nomads and flexible travelers.

At this point in my life I have no idea what I’ll be doing in 3 weeks let alone 3 months.

Here are a few tips & strategies to travel cheaply while never actually committing (yes, we fear this) to any single plan of action:

If you need to book early, book tickets along major airline routes, to major hubs: For example, my SFO=>BKK ticket gets me from the US to SE Asia any time I want in the next year, and once I’m there I have access to all of Asia on regional discount airlines. What this means is you can wait for the best possible airfare deal as long as you have a general idea about where you want to go in the next year.
If you screw up, most airlines give you travel credit and have (relatively) minimal change fees. Don’t be afraid to pay $150 to change your ticket. I’m in Hawaii right now, and spending $150 for another month was a no-brainer. I wasn’t actually sure I’d even get on the flight here (talk about one indecisive dude). No big deal: If I didn’t show up I would have had automatic credit for a pre-booked flight to Hawaii any time in the next year.
If at all possible, book airfare last minute, no more than a couple weeks out: I’ve gotten much more comfortable with this in the last year. The hardest part is not worrying about being in a specific place at a specific time, eg adhering to some arbitrary pre-determined travel plan that you came up with. Examples of last minute bookings: one-way Montevideo to San Francisco one week out ($129 + 20,000 miles), one-way San Diego to Las Vegas day of travel ($80), round-trip San Francisco to Hawaii 3 weeks out ($400).

I almost exclusively use a combination of Kayak.com’s flexible date search (+/- 3 days, start on Wednesday and move from there) and American Airlines reward search. For more read about how I flew around the world for $220.

When you own your time, things like airfare become much cheaper.

Sure, there will be times when you need to get from point A to point B by a certain date. But having a flexible lifestyle allows you to take advantage of huge discounts based on things like seasonality or even day of the week.

But the best part about this kind of flexibility is being able to seize previously unavailable opportunities. I mean, that’s why I’m doing this.

Good luck out there!

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