Five Things I Learned By Missing Some Awesome Travel Deals Today

I was up late last night, catching up on Homeland and sifting through my cluttered twitter feed in between episodes when one tweet in particular caught my interest:

Surely this was too good to be true! The Points Guy had found some outrageous roundtrip flight deals leaving NYC - $275 to Johannesburg, $178 to Abu Dhabi, and around $300 to Mumbai and Hong Kong. I went to Google Flights, and verified his findings, and was pondering how I could squeeze each one of these trips in over the next few months. But after being completely overwhelmed with a million reasons why I couldn’t book these trips right there and then, I just decided to succum to my tiredness and go bed. By the time I woke up, some of these deals were still there but I was waiting on my friends to get back to me to see if they'd be up to go on a trip with me. By dinner time today, the deals were all pretty much gone. This has left me a bit frustrated, since I could have booked a handful of really cheap trips, but didn’t because I just couldn't get my act together in time. Here is how I will try and rectify this in the future:

1. Always Buy First And Confirm Later

Usually you are allowed to cancel any flight you purchase within 24 hours without paying any fees. This is exactly what I should have done this time. I should have bought tickets for myself the second I found out about these days, and just cancelled them a few hours later if I wasn't really feeling good about the trip. There's really no excuse here, and I guarantee I won't make this mistake again.

2. Have A Group Of Friends Ready To Pounce

Probably the biggest impediment to booking a trip was that I couldn't get anyone to commit to join me on a few hours notice. This isn't to say that I must travel with other people - I've traveled solo in the past, and really enjoyed myself. However, a lot of these trips would be more fun with friends, and I want to have that option. One of my friends from college was very excited about the idea of a 5 day getaway to Abu Dhabi, but told me that he couldn't go because it was too short of notice to plan a trip outside of the country. He suggested that we get a few of us to commit to pouncing on future deals like this. This would entail each of us being mentally and logistically prepared to say yes right away the next time a deal like this comes along. I hope to get together a few groups like this over the next few weeks.

3. Have A Conversation With My Boss About Vacation

I have a fairly loose vacation policy at work, but my boss likes to know in advance when I'll be out. This is to make sure that we always have enough engineers on staff to deal with any issues that could crop up with our web application, and also to make sure we have other people in the office to pair program with. Despite the need for giving notice in advance, there’s no reason I couldn’t have a conversation with my boss where I explain my desire to pounce on flight deals like this (after all, the trip would be weeks to months away) and see where the cards fall. Maybe this won’t work, and I really do need to get permission to take time off before I make my plans. But maybe it will fly, and by asking if this kind of trip planning is okay, so can I - and on the cheap!

4. Create A System For Getting Travel Alerts

While I am very grateful for the serendipity that occurs on twitter, for things like travel deals I'd rather systematize the process so that I can be guaranteed to find out about these deals on a regular basis. I'm aware of a few sites like The Points Guy and FlyerTalk, but that's not really enough. Getting a daily email is too slow, and having to constantly browse a forum is too time consuming. Perhaps this is an area where I could put my web application building skills to work, and create an alert system for me. I have a few ideas about web scraping, and perhaps using ITA data - but nothing more concrete yet. Maybe this could be my next side project!

5. Get Comfortable Committing To Travel Plans In Advance

I hate pinning myself down to travel plans far out in the future, especially many months away. This is primarily because I haven't historically had stability in my job situation, and was thus worried that I'd either be wasting my savings if I was out of a job, or would have moved far away and would need to travel out of a different city than I booked the trip for. However, looking back over my working 'career', although there has been lots of change and uncertainty with my jobs, I always end up fine life-wise in the long run. Furthermore, I've also been hovering around the NYC area for a while now, and unless I’m in a remote working situation probably will in the future as well. All this is to say that I need to separate how stable my job is with how stable my life is. My job may change, but my life will be stable enough for me to book a flight flight a few months out without worrying.