July 8, 2020

How to plan your next trip using Project Management software — a short primer

Isn’t it weird that after you learn about something, you start to see it everywhere? Like if you were in the market for a car and you wanted to buy an Audi SUV, you start seeing Audi SUVs everywhere you go. You didn’t notice them before but for some reason, you notice them now because it’s at the top of your mind.

This is something I’ve noticed with books as well – I’ll sometimes have a book in mind at a used book sale and lo and behold, it will magically show up for me to purchase. In a way, I think this speaks to how your desires can translate into real things if you put your mind to it.

As I was planning my next trip, I had heard a lot about using project management software to organize the trip. I thought, why the hell not, and as I started looking into it, I saw a number of articles pop up in my feeds talking about how to manage your trip like a project. Specifically, I have heard a lot about how Trello is a great tool for organizing trips.

For those of you that have never used Trello before, it’s a web app that acts like a big whiteboard where you can organize ‘post-it’ notes in whichever fashion you want. The post-it notes are organized into lists. And each post-it note can have additional information like attachments, comments, due dates, responsible individuals, etc.

What I decided to do then is to start by conducting a significant amount of research into the place that I am planning on traveling to (Japan). I looked up restaurants and things to eat and put up a ‘post-it’ for each place I wanted to go. I looked up things to see and do (sightseeing activities, museums, other unusual things) and again, wrote up a post-it for each place. I then created similar lists for cultural considerations, outside spas, shopping and more. The idea is that in this research phase, I organize the lists into the different kinds of activities that I could do. Next, I invite my friends to add to the lists as they see fit. Finally, once I set the dates for travel, I then create a list for each day that we are there (e.g., Nov. 13, Nov. 14, Nov. 15). For each of the days, I then move the post-it from one list to the day and in doing so, I can start to see what activities I will be doing that day, what I will be eating, where I will be traveling to, and what I need to do ahead of time, if anything (like pre-purchase museum tickets or make reservations at a restaurant).

It’s an interesting way of organizing a trip and my first time using Trello as a trip planning tool. How do you like to organize your trips? Do you have any recommended places to go in Japan (restaurants, museums, sight seeing, ryokans, etc.)?

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