10 Reasons Why Planning Your Own Vacation Is Annoying AF

Believe it or not, 80% of the time I wind up coordinating my personal vacations off the cuff. I am simply too busy planning other people's trips! DIY travel planning involves a lot of things to consider and execute in a timely manner. It can be an unglamorous aspect of traveling but it must be done. In an ideal world, it would be so much easier and enjoyable to have my own travels coordinated by another like-minded expert. After reading this post, I guarantee that you will get where I am coming from.

1. Winning the war against perfectionism and procrastination is a constant struggle.

Trip planning can become super addictive for some people! It’s hard not to go overboard by obsessively searching for flight deals, hotels, tours, restaurants, etc. 24/7. After all, there is an endless amount of online content available at your fingertips. Many travelers, including myself, are guilty of falling down the rabbit hole by trying to read every travel website and blog out there in an attempt to find the perfect arrangements. This oftentimes results in action where nothing is booked at all. While waiting till last-minute and winging it is tempting, it rarely works out the way you fantasize. If you plan ahead of time, you're guaranteed to have the same, if not better trip, than playing by ear. The key is finding the balance between being overplanning and spontaneity. Just remember, when you are mentally stuck on greenlighting future travel is that any vacation you take is better than no vacation at all.

2. Figuring out where to go is no picnic.

Sure you have your own travel bucket list but when you are faced with the actual challenge of deciding where to go, it can be overwhelming. Once again, many people fall into the trap of endlessly scrolling and browsing online which is fine if you can afford to waste a good 5-10 hours of your time. Likewise, entrusted recommendations from friends and family who have been to a specific destination play a large factor in the decision making process. When people you know are posting insane Instagram shots of their vacation in Greece or the Bahamas – those places immediately jump on your radar. #FOMO is real. When push comes to shove, it’s Instagram that has helped inspire the Millennial generation to become wanderlust addicts. Bookmarking your favorite travel photos while browsing this app is a surefire way to jumpstart the booking process. All of these avenues are amazing, but do you really want to copy someone else’s exact photo, itinerary, or advice line for line? The Chinese saying “Don’t listen to what they say. Go see” is on point. Any and all advice should be taken with a grain a salt; and always try to keep your expectations in check (i.e. as low as possible). This way you can let your first-hand impressions and experiences formulate mind-blowing memories that only you will have.

3. Coughing up thousands of dollars for a trip stings and requires a level of accountability.


One indispensable element in being able to travel the world is money. While you may not need a lot per se, you must be able to splash some cash to finance your trip. Having your financials in order is essential and being real with how much money you can actually afford to spend without breaking the bank comes before anything. There’s no need to compare and complete with others. In theory, as long as you can afford the basics of getting there, having somewhere safe and clean to sleep, and have spending money to feed yourself, etc. – you are bound to make good memories. When planning a trip abroad with GlobalNomad, we offer and ask you to seriously consider travel protection in case something unexpected should happen. If you were on your trip and happened to have a medical emergency, could you afford to fly home last-minute? If not, travel insurance is a must; and believe it or not it won’t break the bank. The secret to winning at the trip planning game is getting the most value for your money. In order to achieve this, you need to become familiar with how much things realistically cost in your destination of interest which can be a real eye-opener. That, and by booking up to 6-12 months in advance!

4. Getting the days off from work is stressful.

Another annoying element to planning you own dream vacation is getting the time off from work or finding back up for any commitments you’d have while away. It goes without saying that you should handle this matter months in advance if possible. We all can agree that waiting till last minute to ask for PTO is not foolproof. Securing your well-deserved vacation days should be a priority every single year. It’s crazy that 1) 1 in 4 workers in US don't get any paid vacation time or holidays and 2) Only 28% of Americans plan to max out their vacation days this year. Even if you use them for staycations or shorter trips. When you have a travel agent, in all likelihood, the time needed off from work is going to be transparent, objective and calculated well in advance. GlobalNomad outlines the most convenient and cheapest dates. You mark your calendar and make the appropriate arrangements. No second guessing!

5. Those crazy cheap flight deals sell out like that.

Airfare can be both a motivator and deterrent when it comes to your dreams of seeing the world. I can’t stress this enough but it's true when they say that the early bird gets the best flight deal. When you find an amazingly cheap flight from NYC to Zagreb for $290 roundtrip – it’s a no brainer to explore Croatia for a week or two. The flight deals sells itself (true story… I actually secured an airline mistake fare and traveled to Croatia this April). On the other hand, when mid-summer flights to Greece are nearing in the $1000s and you still haven’t booked, the incentive to travel dwindles significantly. It can be extremely tempting to just keep monitoring fares – thinking prices will drop lower or at least stay the same. Not knowing when to pull the trigger and ultimately missing out means that someone else out there is living the vacation of your dreams. This is not OK! Instead of stressing out and spending countless hours checking a bunch of apps and emails every day, why not leave it up to GlobalNomad who is a cheap flight finding expert. Everyday we are researching and tracking the best deals published online by a multitude of our favorite sources. Jaw-dropping airline sales to an array of dream bucket list destinations are popping up every day. Which means that African safari or cruise around the Mediterranean might be closer to reality than you imagine.

6. There is a ton of pressure to secure the best accommodations possible.

The to-list and things to obsess over goes on and on including the eternal accommodations debate: Airbnb vs. hotel? Today’s traveler is usually open to both which means countless options to choose from. While Airbnb bookings are direct, figuring out whether to book a specific hotel through its own website or an online travel agent booking site like Expedia can trip some people up. The choice is easy – unless prices are significantly lower – always book directly (or with a travel agent) to make things easier in case you need to cancel or change your reservation. The bottom line is that no one wants to stay at a subpar place. There is a ton of pressure to show off where you are staying on the ‘Gram. Plus, the inner perfectionist within almost always comes out when searching for the lodging of your dreams. A travel agent eliminates this problem. GlobalNomad does all research, crunches the numbers, and pinpoints the best options out there matching your budget and needs. Usually 3 to 5 choices are enough to get the gist of what is out there and to compare and contrast. Did we mention we all make all requested bookings on your behalf?!

7. If you are traveling with at least 1 other person, consensus decision making and coordination need to happen every step of the way.

The people that you travel with can make or break a vacation. If you are going with at least one other person, you’ll have to coordinate everything to ensure all parties plans' are in synch and that everyone is on the same page. When in charge of planning a 10-person family vacation in Hawaii, the stress is on you to sweat the details and read the fine print. You also have to be the mediator of the group by getting everyone’s vote/opinion and leading the way towards compromise. Arranging group travel can be a lot less tedious when you have a travel agent to dot the i's and cross the t’s. GlobalNomad will glad spend hours checking pricing and availability on your behalf, as well as offer value added perks or discounts that can’t be found elsewhere. To make things easier, GlobalNomad prefers to work with 1-2 main points of contact who then relay information to the rest of the party. Too many chefs in the kitchen can turn into a cycle of nothing!

8. Figuring out what to do is confusing af.

Deciding on what to do and see in a place you’ve never been before is overwhelming to say the least. Common dilemmas include choosing between independent sightseeing and guided tours, and what tour company to book with. Once again, you'll have to pretty much become an expert by reading up anything and everything. Obsessively calculating what you are going to do and when takes all the fun out of actually visiting the place. If you are prone to sticking to the same routine, you would never discover cool places and step outside your comfort zone. The solution to this problem is booking 1-2 tour experiences that are likely to sell out in advance and have a flexible gameplan for the rest. There are a ton of mobile apps that help with activity recommendations worth utilizing.

9. Passport & visa matters are no joke.

No matter what you can't forget about passports and visas. I know of countless stories where dream trips had to be canceled because a person's passport is about to expire in 3-6 months. You don't want to be waiting for an expedited passport days before you leave. Same goes for visas. You need to do your homework beforehand by double checking State Department’s website for up to date information on entry and exit requirements (if any) and safety. You are also going to want to check the Centers for Disease Control and Prevention’s website regarding vaccinations or medications that might be needed. When it comes to these matters, We strongly urge you to create and complete a checklist especially if you are traveling to multiple countries; and make copies of all your travel documents. Otherwise, you could spend a few thousand dollars or more for nothing. When it doubt, it never hurts to have someone else like your travel agent cross-checking your documents to make sure everything is in order.

10. … Did we mention all the phone calls & emails?

While planning a good trip may only involve one or two booking sites, an epic bucket trip trip involves many moving pieces that need to be dealt with over email and phone. After all, it’s the little things like calling in advance to pre-order a vegan airline meal or emailing back and forth with a tour operator to arrange a private boat excursion that turn an okay trip into an epic one.

Final Thoughts

In the end, it’s a matter of whether you can dedicate the time and energy needed to appropriately plan a vacation. It can’t done with little effort or care. Arranging a trip to places like Machu Picchu, the Galapagos, Antarctica, and Italy's Cinque Terre which have yearly tourist limits means starting the process a year out or more especially if you are going during peak tourist season. It’s hard not to feel overwhelmed and stressed out during the period before your dream travel adventure. After all, it’s probably your one and only shot to fully experience a destination right not to mention all the money invested. In the end, it’s all about actually realizing the trip and making the best of it. And, in order to make that happen, you need to stop overthinking things. Remember, planning a trip doesn’t mean scheduling every hour of every day (too much pressure) nor completely winging it (results in disappointment if things are sold out and unneeded stress to reshuffle plans). It’s all about balance which is what a travel agent orchestrates best. Instead of thinking about the long check list of things that need to be handled, take some time to enjoy the pre-trip boost of happiness. Now you have something to look forward to. Let the daydreaming about the good times ahead begin… along with setting trip planning goals and crushing them!

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