How to Live Life on Vacation: Your Guide to Living Well Every Day
A 4-Part Series — Part 3
In Part 1, we explored why living your real life as if you are on vacation is such a big deal. In Part 2, we covered how to do it. And in Part 3, we will outline the six steps it takes to make it happen right now.
Step 1—Meticulously research your desired destination and know where you are headed in real life too
For the purposes of this exercise, let’s imagine that you are planning to spend a month in the Mediterranean. For a trip of that length and distance, you likely wouldn’t just show up and hope for the best, adjusting as you go. You’d probably consider possible stops, choosing those that appealed to you and your travel partner.
You might make a list, think through the highlights of that particular locale and estimate how long it would take to see and do what you most want to experience. You’d probably figure out how to get from point a to point b, considering timing, cost, convenience and the mobility of your traveling companions.
You might consult several sources, the internet, guidebooks, travel experts, crowdsourcing your questions, or hiring it out. That’s because you’d want a return on your investment, you’d expect to spend a significant chunk of money, and you would want to make the most of your trip and maximize your time and budget while you’re there.
Let’s apply the lesson to real life. After all, real life is undoubtedly your most important journey. Be honest without yourself, how much of your life is just showing up, hoping for the best, adjusting on the fly? How often do you consider your destination? The stops you’d like to make along the way? Have you made a list of what you want, what appeals to you, the preferences of your life partner? Do you know the highlights you want to share together?
Do you know how long you want to be where you are, either physically or referring to your life stage? Do you know how to get what you want next? How much will it cost? How long will it take? What will you have to give up? Do you have resources to call on? A coach? A mentor? Friends? Family? A network that includes those who have gone first, who have lived the life you want to live, who inspire you, motivate you, and know how to achieve your dreams?
A lot of times it feels like work, all that planning, all that self-analysis. But what if I told you that if you look at life planning with the same excitement of planning a vacation, it too can be filled with anticipation and excitement? Think about that for a minute.
Step 2 — Choose your itinerary and set the tone for your trip and your life
Returning to the Mediterranean example… let’s imagine you decided to fly from the US to Rome, where you will spend three days exploring the ancient city before boarding a cruise ship that will depart on a 28-night/25-port Mediterranean itinerary. You’ll enjoy the highlights of Italy, France, Spain, and Greece and even see a bit of Monaco, Croatia, and Malta before returning to Rome for two more days.
It will be the vacay of your dreams, and you are determined to know everything you need to know before you go, so you can be as present in the moment as possible while you’re there.
Imagine, you’ve put down the deposit on your cruise, you’ve set an alert for your desired flights and the price you want to pay, you’ve researched your ports, studied the excursions available at each, and discussed it all at length with your travel partner, and you have loosely outlined each day.
You know which days you’ll aggressively squeeze in as much as possible — the day you visit the Coliseum, the Spanish steps, the Pantheon, and the Forum; and which days you’ll take it easy — the day you booked a private tour of the Vatican; and which days you’ll do nothing at all — the day you plan to stroll the piazzas, follow your whims, and consume as much pasta, gelato, and wine as possible.
You know the dress code of the religious sites you’ll visit, you know the cost of admission of the museums and attractions that are must-sees, you know where you want to explore on your own vs. where you want to retain the services of a tour company. You know what pace you can sustain, you’ve prioritized your wishlist, you’ve accounted for logistics, and you have a backup plan.
Again, think about your life. What’s the overall tone? Prepared? Inspired? On a mission? Frenzied? Stressed? Overworked? Constrained? Where and when are you maximizing your time? Investing in your future? Have you outlined your vision and made goals that support your vision?
Do you have a healthy mixture of days in which you’ll aggressively squeeze in as much as possible — by focusing 100% on your career to move your business forward, or days you’ll learn new skills or participate in a conference to be exposed to new ideas that will enhance your quality of life?
Do you schedule days in which you’ll take it easy — savoring meals with your family, dog walks, time at the gym, playing with your kids, and loving on your hubby? And do you have days which you’ll do nothing at all — reading a good book, snuggling up by the fire, a mug of hot cocoa and a decadent dessert?
Do you know what pace you can sustain? Have you prioritized your wishlist? Have you accounted for logistics, and do you have a backup plan?
There are two things to keep in mind as you fill in the gaps. First, like planning a vacation, this shouldn’t feel like work. This is the most masterful envisioning of all — you are getting the opportunity, discovering the privilege of designing your own life. Take it in! Let yourself go and relish this moment.
Second, does that mean it’s all going to work out, if you are diligent and thorough and manage the details? It’s unlikely, but don’t let that discourage you. Be too busy enjoying the moments that have come to fruition, be too in love with your vision, anticipating what’s next, watching with joy as it all unfolds, enjoying the deep work and feeling the lightness of possibility to worry about exactly how it will happen or if it goes exactly to plan. Your subconscious is more influential than you think and the Universe conspires in your favor. (That’s not woo, that’s true.)
As long as you have an idea about the direction and the tone of your life, the rest has a way of taking care of itself. Plus, as good as it is, and the better it becomes, the more likely your wishes, dreams, and vision is to expand accordingly.
Step 3 — Select details that matter and let go of what doesn’t to free yourself to prioritize and focus more strategically
You can’t see everything at every destination. The places are real and real people live there; they don’t exist only for the tourists. That means there are traffic and expenses and logistics to sort out. You’ll have limitations and constraints not just on the number of things you see, but on how long you can stay at each attraction.
As you map out your itinerary, think about transportation. Are you more of a public transport person who likes to mix and mingle with locals? Or is it more of an efficiency play — do you like to have a car waiting ready to whisk you off to the next stop without delay? Do you prefer to navigate your route or leave it to someone else? There are pros and cons to every option.
When you see an attraction, do you like the behind-the-scenes vantage point or would you rather have a DIY approach? As you are on the go, do you find that you like to linger just a little longer, that you like to wander and stroll, and stumble on hidden treasures, or would you rather book your itinerary hour by hour, with meal reservations and scheduled tours punctuating your visit?
Do you like to be dressed to impress or throw something on for comfort? Do you document everything by taking photos or journaling, or do you prefer to rely on your memories? Do you want to spend more on food, entertainment, travel, or accommodations? Where do you derive value?
Now think about moving through your life. Is there fluidity from work to personal and back again? Do you have a sense of community at home and in business? Do you prefer to mix and mingle or have strategic engagements? Do you like to make plans or leave it to someone else?
When you think about your job, your family, your health, and your other top priorities, do you have a need to know what’s happening at every level, or do you want to let experts call the shots? Are you a wanderer, beholden to your favorite people, or would you rather lead, planning activities, orchestrating moments, executing your vision? Do you prefer to be casual or formal?
Think about your values. Where does spending feel like investing and where does it feel like exasperating? Consider family, career, travel, health, and pleasure. What matters to you? How much time and energy do you spend on what matters and why and how much are you spending on things that don’t hold value for you?
Step 4 — Make a budget and consider opportunity cost to invest in what matters
Vacations are expensive. You’re still paying for real life — that month’s mortgage, payments, bills and you’re adding on the cost of the vacation, plus eating and logistics on the road. Money, like time, is finite. You’ll have to decide what matters to you and spend accordingly. Is it staying in 4-star hotels, flying first class, skip-the-line VIP passes, and Michelin restaurants? Is it brand-new gear, high-tech luggage, or new sunglasses and swimsuits for every beach? Is it safety and comfort and expertise or off-the-beaten-path adventures and exclusive like-a-local access?
You’ll have to decide how much to spend, where to spend it, how and if to insure it, and then build in a cushion for the inevitable extras. These choices aren’t make-or-break choices, but the more tailored to you your vacation is, the more you’ll love it.
Real life is even more expensive. You have bills, plus cost-of-living expenses, plus all the extras, and vacations. Finite as they are, money and time are exaggerated when you’re on vacation. Time stretches out with responsibilities and work temporarily on hold, and money flows easier as every option seems too good to pass up.
But when you’re in the midst of day-to-day life, you have to make time to make money, and make time to spend money, and make time to enjoy money. It’s a funny thing, the relationship between time and money. So few people find the sweet spot between earning, sharing, enjoying, investing, and maximizing both.
Living life like on vacation means coming to terms with both. Deciding how to prioritize time and money, choosing how to maximize time and be secure about money. They are both rather significant undertakings — managing time and money effectively. But if you can figure them out, how would your life change? And what if neither had to be a struggle?
Step 5 — Get outside of your comfort zone to have new, improved experiences
This step reinforces the why we started with. Your comfort zone is fear made tangible. It’s the boundary you draw around yourself, your bubble, that shows you where the edge of fear starts. Getting beyond that line isn’t about struggling or hustling or taking risks. It’s about growing, experiencing, and risking real feelings.
On vacation, you’re likely to try new things — like local food or local customs, to be more adventurous, to feel freer, and let go. You might wear your hair differently or dress more boldly or let loose. You probably don’t have preconceived notions about what a place looks like or feels like, what you must do or how you must show up when you are there.
You probably did the research first, but when you’re there, it’s time to go with the flow. Be open to opportunity. Pay attention to signs and take in the sights and the world around you. Set your to-do-list aside, put your worries on hold, and you enjoy the ride.
That is exactly what it means to be outside your comfort zone, and it’s profound. It’s an approach that says, I’m here, I’m doing this, I’m bringing my best self to the equation, and we’ll see what unfolds. It’s not sitting on the sidelines, or letting others blaze the trail. It’s you, showing up for your destination, taking advantage of the opportunity to see something, do something, be a part of something that you actively chose. It’s potency.
Imagine for a moment if you did the same each day, if you lived your life outside or even on the fringe of your comfort zone. What would change? What would be accessible to you that is currently out of reach?
Step 6 — Give meaning to your memories and choose exclusively for your benefit
There’s a coaching strategy that widens your perspective. You take a defining moment from your life and think about what it means to you. Then you repeat the exercise, but this time, you examine the time just before the moment and just after and consider the moment with a broader context to shift your perspective.
Often the meaning changes. You might have thought something was painful or traumatic then, but now can see the lesson or the value. You might have thought someone wronged you but looking back realize that you only saw part of their story. It’s a way to let your mindset influence your perception.
For example, if on vacation, your overall takeaway is it was a great trip, awesome memories, quality time with family and friends, definitely some highlights, some fleeting pain points and some inconveniences, but on the whole amazing and worth it and you’d do it again in a heartbeat, each isolated moment will mean what it means, but all the moments collectively will have the undercurrent of that overall positive and valuable tone.
But if your overall takeaway is it was a cursed trip, strained time with family and friends, some lowlights that are burned into your memory, some fleeting highlights and a couple of pleasant surprises, but on the whole pretty awful, not worth the time or money, and it scared you off travel until you recover, that’s a very different conclusion. Same trip maybe, but different perspective. Different mindset.
Now think about your life. What’s the internal narrative you’re telling yourself? What’s your mindset, recurring theme, or key takeaways? Are you starring in a sitcom or a romcom or a tragic thriller? Do you have some emotional distance from your life, and do you observe it even as you live it? Or are you embroiled in your life and do you react in the moment without consideration or awareness of the broader perspective at play? Does your attitude enhance or undermine your memories? Are you writing your future or resigned to your story?
You’re almost there. There’s only one part, Part 4, left in this series, and in the final section, we will look at two ways to make living your life on vacation work for you long-term.