Doing a retrospective after a trip is a great way to up-level your travel-savviness. In this article, I'll explain how to do one and why they're the key to unlocking stress-free travel.
I haven't worn a pair of denim shorts since I was in my twenties. While many pieces of adolescent fashion survived into my thirties, cut-off jean shorts are not one of them. I have, however, purchased many many MANY pairs of denim shorts since my twenties. Why? Because after living in Seattle and San Francisco for the past decade, every time I go on vacation somewhere hot, I realize I have no suitable tropical clothing and a pair of jean shorts manifests in my luggage. While on said vacation, I then routinely pass them over in favor of sundresses, rompers, or really anything else I've packed because I remember "oh right, jean shorts are not my style."
And then the cycle would continue.
Until one day, while on my honeymoon in Tuscany, I wrote a note on my phone that said "Don't bring jean shorts on vacation. You never wear them."
Six months later, I was packing for a trip to Tahiti and I found the note filed under "Vacation Retrospectives." Denim shorts were thus excluded from my suitcase and they were not missed.
Thus began yet another beautiful marriage of travel and project management, which I dubbed "The Travel Retrospective."
It's obvious by now that project management bleeds into every aspect of my life (see also How to Project Management Your Newborn) Sometimes it's practical, like when planning a move overseas. Sometimes it's a little neurotic, like my husband and I do weekly standups to check in on our relationship. Travel Retrospectives fall somewhere in the middle.
A retrospective is time you set aside to reflect on past events in order to iterate and improve on them for next time. At work, it's usually a meeting done at the end of a sprint or a project where teams talk how about what went well and what didn't.
A Travel Retrospective uses the same ideas but tweaks the timing and format to optimize for a broader experience. Most of us don't travel often enough to remember the little details that made a trip particularly enjoyable or challenging. We might remember an awful hotel room with a broken AC unit or an amazing dive bar with a Gin 'n Chronic cocktail (Rome, you really are the best city in the world) but we forget that the first 2 days of the trip were miserable because we bought new shoes that gave us blisters or that taking the red-eye actually didn't save us any time or money because we slept through most of the first day.
There are mistakes we make over and over because we simply forget. And we don't learn from experience, we learn from reflecting on that experience. Thus a Travel Retrospective is an easy hack to quit making those mistakes and start to really up-level your experience when traveling.
How to Do A Travel Retrospective
A Retrospective has three basic parts: Set The Stage, Brainstorm and Decide Next Steps.
Step 1: Set The Stage
tl;dr- Prime your brain for some healthy reflection.
Once you're settled back in at home, dedicate time to brainstorm by yourself or make it a group exercise with your travel buddies. Solo retrospectives are great, but it can be even more beneficial if you include the people you just traveled with. Not only is it fun to grab drinks and relive the memories, it almost always ends up being cathartic to make the space for therapeutic debriefing. I went on so many group trips in my twenties and wish I'd thought to do this sooner. So many of those tiny "group trip dramas" never get discussed in a healthy setting and can build up resentment over time.
To set the stage, it's put some stakes in the ground to keep things productive. If there's potential for tension, I like this grounder:
We believe everyone did the best job they could given what was known at the time, their skills and abilities, the resources available and the situation at hand.
Next, remind yourself, partner, or group of the goal of the trip. Some trips are aimed at exploring, others are meant to treat yo'self. Clarify the goal of your trip before brainstorming and create good guardrails. Some of my past trip goals have been:
Puerto Rico March 2020: To learn how to live and work comfortably with minimal possessions and figure out our set of requirements for long term nomadic life.
Italy April 2019: To treat my parents and in-laws to a stress-free family vacation in Italy with have lots of wine, good food, and ample time for bonding.
Tahiti December 2018: To spend Christmas on the beach vacation while enjoying as much diving and sunshine as possible.
Step 2: Brainstorm
tl;dr- Now it's time to talk about what went well and what didn't.
During The Trip
For me, the retrospective process actually begins the moment the trip starts. During the trip, I keep a running list on my phone of two things:
Working Great
Not Working
As things come up during the trip, I jot them down. You'll be surprised how many things come up the moment you leave the house and how much it puts your mind at ease to write it down and know you'll fix it later. Most of the things gathered during the trip will center around packing and it ends up serving as a great shopping list for your next trip. Here's an example of mine after 2 days in Puerto Rico:
Once you've gathered your crew and/or opened a bottle of wine, proceed through the following topics. Spent 3-5 minutes on each and write down everything that comes to mind. Go through the entire list before moving on to step 3.
For each topic, go through the trigger questions and ask what worked well and what didn't work well? It might be helpful to have info at the ready to jog your memory; for example, names of restaurants you ate at, airlines you flew. It can also be helpful/fun to go through pictures.
Step 3: Decide What To Do Next
tl;dr- Create a list of Action Items from all those insightful reflections.
If you're doing this with a partner or group, have everyone share their feedback one topic at a time and consolidate the insights in a master list. After everyone has shared on a topic, ask the group if there are any action items or things you want to remember to do differently next time. For example, if everyone agrees that the small kitchen in the house made it challenging to cook for the group, make a note next to the "Lodging" category to "choose a house with a large kitchen next time."
Some of the action items will be things you can do before your next trip (for example, buying a new sleep mask). These should go wherever you keep your regular todo list. Some things, however, will only be actionable when you plan your next trip (for example, make sure to pack extra Melatonin when going overseas or don't bring leather bag on tropical vacations, opt for canvas instead). For things like these, I maintain a Travel Retrospective doc and categorize it by trip type (Europe Winter, Tropical, Warm California Coast Weekends etc.) Then before I start prepping for another trip, I revisit the list.
And that's the whole hack. As an operations enthusiast, I've described my personal process which is naturally quite thorough, but it can be as simple as jotting down a few notes on your phone while you're waiting for your plane to taxi. Really, the goal is to capture insights while they're fresh in your mind and have everything run slightly smoother next time. And now, for your inspo pleasure, I'll leave you with an example retro from our last trip.
Puerto Rico Retrospective April 2020
Goal: To learn how to live and work comfortably with minimal possessions and figure out our set of requirements for long term nomadic life.
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