2022 Recap & Maximizing PTO in 2023

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Merry Christmas (though I’m posting this from Japan where it’s already December 26th)!

By the time the ball drops on New Year’s Eve, I will have spent 92/365 days in 2022 outside of my home in Chicago (that doesn’t count days where we took a late-night flight after work). That’s a quarter of the year – all while holding a full-time job with limited PTO days! I am so grateful that Thomas and I both work for companies that allow us to work remotely, giving us the flexibility to see the world while still contributing to our respective organizations. Here’s a quick rundown of how I was able to pull this off:

January 1: flew home from Maui
January 15-17: long weekend at Copper Mountain for MLK Day
February 12-14: long weekend snowboarding outside Salt Lake City. Used 1 PTO day.
March 5-8: long weekend in Los Cabos. Used 2 PTO days.
March 9-11: working remotely from San Diego
March 24-27: bachelorette trip to Puerto Rico. My company happened to give us March 25^th off after I’d booked the trip, so I only had to use 1 PTO day.
April 23-24: weekend in Las Vegas (the topic of my very first blog post)
May 11-16: working remotely from Austin
May 27-30: long weekend in Catalina & Los Angeles for Memorial Day. My company gave us both Friday and Monday off so I didn’t use any PTO.
June 18-19: weekend in Saugatuck, MI
July 1-6: Munich trip – my company gave us 7/1 and 7/4 off, so I used 2 additional PTO days
July 30-August 7: Alaska cruise – used 5 PTO days
August 17-20: working remotely from New Buffalo, MI
September 3-5: long weekend in Vancouver, BC for Labor Day
October 1-2: weekend in Portland, ME
October 15-16: weekend in Portland, OR
October 17-25: working remotely from San Diego
November 10-13: NYC – we worked remotely from out hotel room for 2 days and enjoyed evenings + the weekend in the city
November 20-27: Iceland – this was the week of Thanksgiving and my company gave us Wednesday-Friday off, so I only had to use 2 PTO days
December 10-11: weekend trip to Orlando
December 21-January 1: worked remotely for 2 days, then took advantage of my company giving me 4 days off around Christmas and only took 3 days of PTO for a 12-day trip to Japan

As you can see, weekend trips made up the majority of our travels because they didn’t impact our jobs. We like to use these weekend trips to visit cities in the US that are easy to get to from Chicago (which lucky for us is most places since Chicago is centrally located and has 2 major airports). Given the short time-frame of these trips, they are not “relaxing” since we are very go-go-go for 48 hours, but they are so much fun and allow us to see so much more of the country than we’d be able to otherwise. I have a goal of visiting all 50 states and these weekend trips are a big way we’ve been able to tick off so many on the list (the ones I’ve been to are in pink below). With the travel time it takes to get to other countries, we try to save our weeklong trips for international trips to make the time we spend on the plane worthwhile.

The states I've been to as of December 2022

The other main factor that drives our trip planning are our company calendars. If they give us even 1 day off, we’re making a long weekend out of it, if not extending the trip the entire week. The biggest tradeoff here is that traveling during holiday weekends tends to be a bit more expensive since everyone and their grandma are traveling, but this is a sacrifice we choose to make to be able to see more of the world – for me, my time is priceless. One way to get around this is traveling to places that don’t celebrate that holiday. For example, Iceland doesn’t celebrate Thanksgiving, so prices weren’t really inflated for that week and everything was pretty business-as-usual there (the one exception to this may be flight prices). While we love our families and enjoy spending time with them, we usually travel instead of visiting them for the holidays, though it’s great when we all go on a trip together!

Pro tip: we always bring our work laptops with us (since we can’t use our personal laptops for work) even if we don’t plan on working remotely. This protects us in the case that our return flights get messed up so we can work remotely while trying to get home (which is what happened the first time we went to Seattle in 2021 where we unexpectedly had to spend a day working from an airport hotel in Denver on our way home). When we do choose to work remotely, we always try to keep Chicago business hours, which can mean working strange hours wherever we are. When we work from California, we are online from 7AM-3PM, which gives us the afternoons and evenings to enjoy our surroundings. Next year, we’ll be working remotely from Europe on 3 different trips, working either from 2PM-10PM or 3PM-11PM and getting the mornings to explore.

Looking to the not-so-distant future of 2023 (how is New Year’s less than a week away?!), I already have all my PTO planned out for the year, but if you’re not insane like me and work a job that gives you typical holidays off, here’s an outline of how to stretch your PTO further:

New Years – January 1 is on a Sunday this year, so most companies are giving the 2^nd off in observance. This could mean you take the entire first week of January off (bonus: since it’s after the holiday travel rush prices are likely to be lower).
MLK Day – extend your 3-day weekend to the entire week to get 9 days off for 4 days of PTO
President’s Day – use the 3-day weekend to go somewhere nearby
Memorial Day – take a day of PTO to get a 4-day weekend
Juneteenth – take a long weekend with no PTO
4^th of July – it falls on a Tuesday in 2023, so some companies may give both Monday and Tuesday off. Anytime you have 2 days off in the same M-F span, it’s a great opportunity to take the whole week off for only 3 PTO days.
Labor Day – use the 3-day weekend to go somewhere nearby
Columbus/Indigenous People’s Day – not every company gives this off, but take advantage if yours does!
Thanksgiving – take 2-3 days of PTO (depending on your company) and enjoy 9 days off
Christmas and New Years – New Year’s Eve will be observed Friday, December 22 and New Year’s Day is a Monday, so you can use 4 PTO days for an 11- day trip

Really what it boils down to is looking at your company’s list of corporate holidays and building your travel schedule around it. If you have destinations in mind, research when the best time of year to visit is and try to build a trip around the nearest holiday – also be open to traveling during shoulder season when prices are often lower!

Where you can fly direct internationally from Chicago

If you don’t have destinations in mind, start by looking at what direct flights you can take out of your home airport. Living in Chicago and having access to both Midway and O’Hare airports, the latter of which alone offers nonstop flights to 214 cities worldwide, I am grateful I’m able to get so many places without a layover eating into my precious travel time. I take flight schedules into consideration when booking trips and the feasibility of accessing one destination over another usually plays a large role in my decisions. If you can work remotely, be open to taking a positioning flight to get where you want to go – for example, we’re going to Paris next year but found great flight prices out of JFK, so we’re flying from Chicago to JFK, working remotely the next day, and then taking a red-eye to Paris that evening. It adds more logistical complexity to the trip, but can save you money or open up otherwise inaccessible destinations.

For more suggestions on how to maximize your PTO, check out the blog’s namesake post here.