chapter 3: if you fail to plan, you plan to fail (part 2)
my gift to you: my color-coded annual travel calendar template for turning your bucket list into an organized visual journey around the world
tactics and tools for being the man (or woman!) with a plan 📝
Last week, I shared my firm opinion on the value of planning travel in advance due to the financial and psychological benefits of booking early and having things to look forward to well ahead of your travels. This week and next week, I’ll share some key tools and templates for turning those plans into reality.
If you haven’t read my last post which is Part 1 to today’s newsletter, check it out below:
On my Instagram story poll last week, I asked if y’all like to plan trips and got the following responses:
Yes 100% (37% of responses)
Sometimes, if I have time to plan (47% of responses)
Nope, prefer to go with the flow (16% of responses)
I’m so happy to see that my audience is mainly fellow planner-types, or aspiring planner people! Fully agreed that having enough time amidst a busy social and professional life is often the deciding factor for whether to plan or not to plan… which is why I often utilize my network of well-traveled people to solicit their recommendations or previous itineraries when I might not have time to start from scratch with my trip-planning research.
A lot of you – readers, strangers, and friends alike – have hit me up over the years when you are in the process of planning out a trip to a place that I have visited, and I’m always happy to share my tips, recommendations, and past itineraries as resources if I have them handy!
Later this year, I’ll be formalizing more of my previous trip itineraries (especially the most highly-requested ones for Southeast Asia 1-2 week backpacking routes, a week on the big island of Hawaii, and a 2-week tour of Argentina through the world’s largest waterfalls and Patagonian mountains) as widely distributable and downloadable travel resources that you all and any citizens of the internet can use to plan trips of your own.
And in the next newsletter, I’ll share my per-trip itinerary building process and the template I designed that I personally follow for every trip I’ve planned in recent years. It’s a simple way to keep all your travel information organized and makes it clear what still needs to be booked as you piece together your trip little by little in the months leading up to your departure date.
But for now, before getting into the nitty-gritty of planning individual trips, a great place to start off in the beginning of each new year is mapping out your own personal annual travel calendar.
the holy grail of trip planning for the ambitious traveler… the color-coded annual travel calendar
For all you “go with the flow” people… be warned, the following color-coded annual travel calendar template may stress you out (so I’ve been told by my very Type B friends). Meanwhile, shoutout to my Type A girlies who have praised me for this peak organizational flow.
Most people use a normal calendar app like Google Calendar or Apple Calendar to map out their travels, but I have discovered that neither of those exactly fit my needs. I want a bird’s eye view of my entire year at once, where according to color coding, I can tell where I’m traveling that day / week / weekend and can easily know when I am at home.
This is especially useful if you have very frequent or nonstop travel, like I did in the summer of 2021 when I was fully nomadic without a lease, ping-ponging from coast to coast and between the US and Europe full time traveling (more info and reflections on this experience in future newsletters…)
No existing calendar template worked for me, so I created my own. I have used this color-coded annual travel calendar every year since 2021, and will likely use it for the rest of my life. I’ve shared it with friends over the years and many said they copied the template for their own personal planning schedules, so now I’m opening up and sharing with you all!
I personally prefer having this template in Google Docs since it’s easily sharable via a link, for any friends and family who want to keep tabs on where in the world is Caitlyn. I am also providing a template in Google Sheets, because for most people that is more than sufficient – I simply prefer a table within Docs instead of a full spreadsheet because to me it is more easily customizable with colors and highlights within separate rows, which Sheets is not as flexible about. But choose what works best for you!
**These are available totally free to download - but pay-what-you-wish option is available if you find these valuable and want to monetarily support my work in creating and sharing these :) Each link separately includes:
A blank template in either Google Docs or Google Sheets for you to make a copy of and use yourself
A filled-in example of my personal color-coded annual travel calendar to inspire you how you can fill in your own
A video walkthrough of me talking through how I use these templates
At the end of 2022, I also used this template to tally up how many days I had spent in different locations, and used this to calculate my overall summary of where I spent my year. A “where in the world is caitlyn” 2022 Wrapped, if you will.
I am honestly OBSESSED with doing “life analytics” like this (can you tell I work in tech? 🤪) and find it helpful and interesting to have all this information easily documented for reflection at the end of the year and in the future.
Even if you don’t travel as often as I do, my friends have also used my color-coded annual travel calendar template to just visually see which of their upcoming months have weeks-long trips or weekend getaways, to plan out necessary decompression time in between travels (something I have yet to prioritize for myself 😅).
Stay tuned next week when I’ll share the template I use to plan individual trips!
xoxo your *thrives on organization* Type A travel-planning bestie,
Caitlyn
🚨 If you enjoyed this newsletter and think any of your friends might find this template useful, forward it to your friends! I am doing this all completely free and out of the kindness of my heart because I want to share my knowledge to help as many people as possible travel more economically, more sustainably, and more intentionally…
so forward this email, share the link, post it on your IG story… share it far and wide, please, if you find this valuable :)
📝 travel hack of the week
Last week I mentioned how I was planning to call and complain about my 4-hour delayed Alaska flight to their customer service phone line - I did, and they rewarded me $200 worth of free travel credits for future flights to make it up to me.
All it took was waiting an hour on hold while doing my work — all you have to do is ask! You can also complain if your bags arrive to baggage claim later than 25 minutes after arrival, and usually airlines will give you $25 off a future flight as an apology for the inconvenience of holding you up at the airport.
These rules aren’t necessarily published but every airline customer support team has a budget for making customers happy… they know that only a small portion of customers will actually take the time to reach out and complain, so be that customer and get those future discounts you deserve!
💙 a few faves…
Thanks to everyone who replied to the last two newsletters with your favorite place you’ve traveled – here’s a visual summary of your favorite travel destinations! The biggest ones were the most popular recurring responses – makes me happy to see that so many people loved Florence, Italy as it’s one of my former study abroad homes :’) Adding some of these like Fiji, Greenland, Banff, Cape Town, the Maldives, and the Himalayas to my personal bucket list!
If you’ve ever listened to my podcast interviews these are answers I refer to often, but among my favorite places I’ve personally visited are: Antarctica, Argentina, Tanzania, Laos, Australia, Slovenia, and Malta!
🌎 where in the world is caitlyn?
I’m currently writing to you from New Orleans with a cup of chicory coffee in hand, a bite of sweet King Cake in my mouth, and the sound of live jazz music in my ears. ☕️⚜️🎷🎶
I’m here leading a group trip to experience Mardi Gras – a combination of friends from Los Angeles, San Diego, New York, and (as of a last-minute addition yesterday!) San Francisco all joined together for this trip to experience the lively parades through the streets of The Big Easy (which indeed is quite the laid-back juxtaposition to the frenetic energy of The Big Apple, my former home).
Last weekend while I was in Lake Tahoe during a snowstorm that dropped 19 inches of snow on us while snowboarding (my first pow day out of my short-lived 5-nonconsecutive-day winter sports career), I got to play the introspective-question-prompt card game We’re Not Really Strangers with a group of actual strangers I had never met before who share a ski lease with my old roommate.
I thoroughly enjoy delving into deep questions with people I have never met before and maybe will never meet again, which is a reason I love staying in hostels and meeting as many random new people as possible while traveling. I’m always an open book when it comes to answering questions about myself and my life, but it’s lovely to have question cards prompt vulnerable and honest conversations with brand new people.
Through deep conversations with strangers, we all can relish in the fact that we are all humans, with deep emotions and reactions and ability to ascribe stereotypes, whether true or false, to others based on the way we perceive them. Highly recommend this game and will be incorporating it on all my future group trips to help everyone bond and have meaningful conversations!
👯♀️ group trip opportunities
After this current group trip in New Orleans, I’ll be spending next weekend in Death Valley with a group of 9 girls who were all down for an adventure with new friends, and the following weekend in Mexico City with a group visiting the monarch butterfly sanctuaries at the peak time of year to see the monarch butterfly migration. I love bonding with new friends and old friends alike by experiencing bucket list memories together and saying '“yes” to things outside of our comfort zones.
My next group trip you can join is a ski/snowboard weekend trip to Mammoth Mountain, CA from March 24-26! ⛷🎿🏂🏔
It’s half full already, so reply to this email or shoot me a message on Instagram @caitlynlubas if you are interested in joining us on the mountain!
I snagged a beautiful Airbnb with a balcony, fireplace, and hot tub that is mere steps from the mountain for easy access to the slopes. With 8 people capacity, it works out to $156 per person for the 2 nights there (a steal!). I’ve only been to Mammoth during the spring, but it’s a quaint little town tucked away in the Sierra Nevadas and is known to have less crowds then Tahoe and Big Bear, which are closer to the major California population centers.
Since this is a road trip just for a weekend, it probably only makes sense to join if you’re already located in California during March… but reply to this email if you’re interested and want more details!
🪣 bucket list inspo
Three years ago today, my best friend Maddy and I had landed in Nairobi, Kenya to start a 7 week-long camping safari. We were about to travel through Kenya, Tanzania, Malawi, Zambia, Zimbabwe, Botswana, and South Africa via the big yellow truck pictured below.
We were ready to set up camp every night and pack it all down every morning to go on game drives through the Serengeti, Masai Mara, and other East African safari lands for 7 weeks straight in February and March of 2020— or so we thought, until the coronavirus pandemic spread and all the country borders started closing, leaving us no choice but to last-minute flee the continent.
There’s an entire chapter about this in my book, You Are Where You Go: A Traveler’s Coming of Age Journey Through 70 Countries and 7 Continents During College, if you want to read all the details of this truly wild adventure! 🦁🐘🦛🐆🦏
📖 read with me
BOOK CLUB UPDATE: 10 people have joined my Wanderlust Reads book club so far, and more are welcome to join!
You have the next 3 weeks of February to read the female traveler-narrated memoir called What I Was Doing While You Were Breeding. Then, we will have a zoom call on or around Feb 28 (depending on group availability) to share our thoughts, reactions, and favorite moments from the book.
Let’s get back into reading more, together!
Click here to join my virtual book club on a social reading app called Fable that I’m trying out – if you choose to read the ebook in the app, you can write comments on specific chapters or paragraphs that the rest of the book club members can also see!
But if you’re old school like me and want to buy and read the physical copy of the book, you can do that too – just reply and let me know that you’ll be participating so I can include you in a book club group chat :)
💭 self reflection prompt of the week
I’ll be visiting the San Francisco Bay Area more often this year as a result of both old friends living there and my remote job being headquartered there. Originally, I was supposed to move to SF post-grad for my first full time job working at Instagram, and spent years mentally preparing for that cross-country move after having spent all of my prior years growing up in New Jersey and going to school in New York City at NYU.
Although I ended up never fully moving to SF, I lived there in a short-term lease in 2021 for 3 months until I decided that I would quit my job at Instagram before return-to-office took effect and I would effectively be rooted down there for a while. I quit that job, took a few months to be fully job-free and lease-free, and lived out my nomadic full-time travel dreams while finishing up writing my travel memoir and working on a travel startup idea. But more on that journey another day…
Spending last weekend in a place I used to think I would call home longterm made me feel quite nostalgic for my past temporary life there, and also made me curious about the ~alternate universe Caitlyns~ who are currently living out that potential life path.
If you’ve seen the stellar movie Everything Everywhere All at Once that came out last year, perhaps you’re already familiar with this concept of alternate life paths that I’m talking about here. Even in my book published in late 2021, I wrote about how I always think about alternate universe versions of myself that got to continue traveling for 7 months after graduation in a world where the coronavirus pandemic never happened. The parallel realities of who I could have been if I lived in SF instead of LA really got me pondering this past weekend…
What is alternate universe you doing today? What are the main choice(s) you’ve made that diverged those life paths of the alternate version of yourself from your current self?
Hit that reply button and let me know your answer if you care to share!
📱let’s connect
If you’ve got feedback on the format of this newsletter, or suggestions for travel topics you want to hear more about, don’t be shy! Reply to this email or DM me:
Instagram: @caitlynlubas / @you.are.where.you.go
Twitter: @caitlynlubas
TikTok: @you.are.where.you.go
LinkedIn: Caitlyn Lubas (feel free to reach out if you want to talk about working remotely, transitioning careers, etc!)
That’s all for now…
Remember, you are where you go – never stop exploring the world and yourself! 🌎 🌍 🌏
If you enjoy my writing in this newsletter, you’d love my book called You Are Where You Go: A Traveler’s Coming of Age Journey Through 70 Countries and 7 Continents During College. Feel free to pick up a copy on Amazon, Barnes & Noble, or reply if you’re interested in me sending you a signed hardcover or paperback copy :)
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