When you realize you need a vacation, it is already too late to plan the vacation you need. If you hit the wall and imminently need a vacation, it is probably too late to get the time off of work because someone else has already requested the time off in your team’s calendar. The rates for your favorite relaxing getaway are too high because you are trying to book it for two weeks from now instead of six months from now. It would cause more stress to plan to leave your daily life for a week because you have not planned for a vacation gradually.
Planning a vacation before you need it is important to remain balanced. Particularly if you are an entrepreneur with a busy season, manage multiple streams of active income, or participate in hobbies and community activities beyond your job and family, planning how you will maintain this balance is important. However, the folks who need to prioritize vacation for their own recovery tend to be the individuals who also find it most difficult to commit to a vacation, due to time and energy constraints.
Take Care of Yourself First
The financially savvy know to pay themselves first. They commit to funding their retirement investments before spending any money to fund their current lives. Through automatic transfers, they typically remove the money they pay themselves first before they even see it, so they never miss the money in the first place.
You can do this with vacations or even required relaxation times. The beginning of January was busy for me, and I knew this would be the case. It culminated with a busier than normal five days in my day job followed by a Friday-Sunday rugby conference, after which I knew I would crash. The Monday following that conference was Martin Luther King Jr. Day, a federal holiday observed by my employer. I often schedule some Phippen Tax tasks on these federal holidays because I typically have some time for relaxation earlier in the weekend, but I knew that would not be the case here. I assigned myself an off day on that Monday.
What do I mean by assigned? Back in December, I looked at the month of January. First, I put the vacation we are currently enjoying on the calendar, and I put the big meetings and priorities from my day job in the calendar. Then, I scheduled the events I already knew in advance (my monthly massage, a birthday party, that rugby conference I mentioned, the day I am hiking with friends, etc.), and my routine workouts. Finally, I started entering all my side hustle tasks for the first couple weeks. While filling out my calendar back in December, I could easily see, “Yup, I am going to crash on January 15, so I can’t plan anything for that day.” I plugged in “DAY OFF” into my calendar to make sure I would remember this planned crash day.
There are two important aspects to this planning that are how I take care of myself first:
I put my next vacation in the calendar first.
I analyzed my schedule to identify any points where I would crash before that next vacation and allocated the time I would need to regain my energy.
Actually putting any “me time” events in your calendar, even if you just need a Friday evening to yourself to unwind, commits you to taking care of yourself. By allocating this time well in advance, you prevent that time from getting taken for the last-minute favor for a friend or request by a client. You also cannot just forget that you planned to have a recovery day, if you are someone prone to forgetting obligations.
The same goes for vacation, even if you do not have your precise vacation booked yet. We keep a Sports & Travel Schedule so we can identify time periods throughout the year when we would like to travel and when we anticipate needing a vacation. Once you have a general idea of a time window, you can block those dates in your calendar. For example, I know I have a time window between June 6, 2024 and July 2, 2024 that would be ideal for me to travel because that window is after my regular rugby season and there are no local sporting events I feel strongly about attending. It is also before a probable work obligation that should become more important in July and after tax season.
For now, those general dates just have a marker on my Sports & Travel Schedule. This marker will make me hesitate before making other commitments. But it also recently allowed me to discuss going to the 2024 London Series with a friend who is a Mets fan, and I immediately knew that the dates could work if they end up going because the dates fall in my potential vacation window. Giving yourself these time windows where you are permitted to prioritize vacation first allows you to avoid local commitments and more easily say yes to fun experiences.
Determine Your Best Vacation Times
In order to take care of yourself first, you have to learn to determine when you will need a vacation or just some downtime. This is often the trickiest part, particularly if you are the kind of hardworking individual who throws themself into their commitments until they nearly crash.
If you are struggling to pinpoint a good vacation frequency for your lifestyle, a starting point may be to identify your busiest times of the year. This may be your peak times at work, but it also may mean your busiest times of the year personally—particularly if you put your life first, which you should!
For example, my annual vacation calendar generally looks something like this, where “short” means about one week and “long” means about two weeks:
Late January/early February: Short vacation
May/June: Long vacation
Early August: Short vacation
November/December: Long vacation
Under this construct, my short vacations both fall immediately before busy seasons. In February, I start coaching and playing rugby and tax season is in full swing in our household. In late August, I again start coaching and playing rugby, the end of the fiscal year in September and analysis of the previous year in October make the two months my day job’s busiest time of year, and the tax extension deadline hits.
My long vacations are similar, but they both fall after the busy seasons of life and work to decompress. I find that I need a bit more time to decompress and get into relaxation mode after being extremely busy, so a two-week vacation makes sense. However, prior to a busy time, I just need a getaway to get excited for the upcoming busy phase so I can give it my full energy.
Your own busy times of year will be different from mine, and you may have additional considerations, like when your kids are in school. Additionally, I acknowledge that I enjoy a privileged vacation schedule thanks to a job with unlimited leave and know some folks may not yet have this freedom. That said, identifying your busy seasons and thinking about how you feel immediately before and after those times is a great starting point to identify your ideal vacation time. Are you always exhausted after a busy season? A vacation immediately after may be ideal. Do you find yourself lethargic at the beginning of a busy season, dreading the long weeks ahead? A vacation right before your busy time may be better. Even if you can only take half the time I do, there are ways to maximize your recovery for your health and energy.
After experimenting, you also may find that your crash times have nothing to do with busy season. Particularly if you have many things going on outside of work or your main commitments, like a busy family life or unexpected illnesses, a different schedule may be better for you. Maybe you can get through an entire year just fine but need to take the entire month of December off for yourself! We are all different in terms of how we can commit our best energy to all parts of our lives, but it is worth figuring out how you recover so you can show up to daily life as your best self.
Pay Attention to Your Needed Recovery Time
If you only have ten days of leave each year, you will probably find yourself simply taking them right before or after your busy season or using a combination of one recovery week and one holiday/family-visiting week. There is not a lot of flexibility to add additional recovery time if you are limited to ten days each year, and I would recommend negotiating for a few more since having more than ten days of leave is a reasonable work demand.
However, once you get up to 15 days, you start having a bit more freedom. Fifteen days of leave is the marker where you can decide if you would rather have a two-week vacation or two one-week vacations in addition to some holiday time off spent with family and friends. Assuming you have 15 or more days of leave, it is worth gauging how much time you need to recover or energize yourself and planning your vacations accordingly.
As I previously mentioned, I need more time to recover after busy times than I need to energize before busy times. Patrick always says that all his favorite vacations are the ones where we get to go to one place for two entire weeks. Yes, there also is a different feel to two weeks spent in three different locations where you need to change lodging as opposed to settling in to one place for two weeks. Our vacation to the Philippines where we took planes between Manila, El Nido, and Coron was much different than our vacation to Crete where we stayed in an AirBnB overlooking the Mediterranean Sea near Chania. Both were terrific, but the Philippines allowed for more adventure while Crete made space for more relaxation. (If you have the freedom of five or more weeks like I do, try one of each this year to see if you have a preference or just prefer one of each in perpetuity like me!)
(If you want to enjoy this relaxing view at dinner, I would recommend our AirBnB in Chania to anyone!)
Pinpoint Your Ideal Downtime Frequency
Particularly if you do not have as much leave as you would like, the next step is to also identify how to give yourself a day, or even an evening, off when you absolutely need to recover and are not close enough to your next vacation. This is part of taking care of yourself first, and it is why I scheduled the Martin Luther King Jr. holiday as a day without plans for myself. Sometimes, we all just need a day.
I am considered relentlessly energetic when it comes to getting things done and pursuing more streams of income and activities. But I also take six weeks of vacation and take additional crash days. And I added all those streams of incomes and obligations one at a time so I could test my energy levels in the new environment each time. My only superpower is knowing when I am going to crash so that I can make sure it happens when nothing important is happening and I do not have to talk to anyone.
The more you pay attention to your energy as a variable that you can predict and control with advanced planning, the more you can anticipate when your energy will hit zero. Being able to predict when hitting zero will happen allows you to make sure it does not happen in the middle of your work presentation, the final week of tax season, or minute 60 of an 80-minute rugby match. It takes time to perfect your own energy maintenance because all of us are different, but it is worth figuring out your own needs to feel better and show up to the most important parts of life with your full self.
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