Vacation Indecision

Fed up with the cold and in need of some time away from the daily grind, I decided that I was going to take a break. At first I felt relieved, since I had assumed that once I decided when to go, everything else would fall into place. However, just having a set of dates to leave and return was just the first of many other decisions that I’ve been uncharacteristically indecisive about.

I’m using airline miles to book my flight. One of the perks is that you can reserve a trip, and they will hold it for a few days before you actually have to book it. I’ve taken this generous policy, and frankly abused it. I’ve now canceled and re-booked my flights 3 times! This has enabled me to keep pushing off the decision of where to go, and what to do.

Because I work I only really get a few weeks a year to do whatever I want. While this makes me financially ‘rich’, the flip side is that I’ve become time ‘poor’. I have too many desires of what to do in my free time to realistically do it all in just these 2 weeks.

First, I know I want to go somewhere warm, but haven’t locked down where exactly that is! I could go somewhere warm but still in the US like Honolulu or San Juan, Puerto Rico. These places would be easier to get to, since I wouldn’t be leaving the US. However I’d rather try and work remotely for a week or two from these places than use my vacation days there. Central America would be great as well - but again cities here would be perfect places to try and work remotely from while I also perfect my spanish on the side. This is something I want to do soon, but am just not there yet. Then there are places like Indonesia and The Philippines that seem super cool but are far away, less safe, and I’ve already been to Asia a few times. Obviously I want to go to all of these places (and everywhere else in fact), but in the end, I need to pick one.

Second, I’m in need of an adventure. I’d love to do something challenging like Climb Mt. Kilimanjaro, but I’m a bit out of shape and would have had to train for something like this. However there are a bunch of less challenging treks and hikes that I can do. I can easily fit in one of these small outdoor adventures each week that I’m gone regardless of my other plans.

Third, I also have some learning objectives that I’d like to accomplish specifically around Ruby, JavaScript and Swift. I’ve have gotten really into video tutorials lately, and have half a mind of spending all day every day making a big dent into my ever growing video tutorial collection. However, do I really want to spend my free time learning how to code? I do that almost every other day of the year, so maybe for these two weeks I take a break from this.

Fourth, I have started a few side projects, and keep churning out new business ideas every day. I could spend these whole 2 weeks finishing up one of my side projects, or even hack together a prototype of one of my new ideas. Maybe I can also meet with some people in the local tech scene wherever I go, and collaborate with them! Although I would be coding if I did this, with the right level of discipline I could accomplish a lot, which would make me feel great.

Fortunately I can eliminate one big thing from the list - which is bouncing around from country to country. My passport is down to it’s last page or two, and I won’t have room for too many more stamps. It’s also expiring this year, and not worth adding pages to at this point, and it’s too late to get a new passport before my trip starts. Bottom line, I’ll be going to one country instead of a handful.

Anyway, I have another day to finalize my destination, and another week to figure out what to do when I get there. I think having such little time to myself per year has put me in super FOMO (fear of missing out) mode. However, even though I can’t see the whole picture, and concoct the ultimate plan on how to use of my time off, I’m still pretty sure I’m going to have a good time, and things will work out. In the end I’ll do at least some things I want, get some much needed sunshine, and if I’m lucky, experience the magic of serendipity that inevitably happens when you travel.