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Family Trip To Disney World; The Perfect Plan Wasn’t My Plan

Blog April 30, 2023By scott
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Recently, my wife and I decided to take the kids to Disney World, and while there was some deliberation on whether or not we should, we decided not to skip the memories and make the trip to see the mouse. 

Aligning your expectations with the type of trip you’re planning is essential; what do I mean by this? Any parent who has experienced a Disney trip can attest that there is nothing relaxing or rejuvenating about it, and it’s more of a trip and less of a vacation. However, as we had four kids and knew a tropical escape wasn’t feasible, we decided to go for it! 

While my first blog was about breaking down the financial costs of going on the trip vs. the familial costs of skipping the trip, this follow-up piece will cover some of the lessons I learned from the trip that are reflective of questions we’ve all got when plotting our financial journeys. 

Family Trip to Disney World: Everyone’s Got The “Perfect Plan”

Travel and vacationing have changed drastically over the last 20-30 years. Remember travel planners? If you’re in your mid-30s or older, there’s a chance you remember going to a brick-and-mortar office and sitting down with a travel planner to plot out your vacation, book plane tickets, and schedule everything. If they were sought-after travel planners, they had the “inside track” on the dos and don’ts to recommend regarding your vacation destination. In retrospect, having a one-stop resource to take care of all your vacation planning was nice; this is not the case today. 

If you Google “how to plan a trip to Disney World” or “best Disney vacation ideas,” you’ll find endless blogs and op-ed pieces on how to experience the competitive and ever-changing landscape that is Disney World theme parks. There’s endless commentary on how to experience the parks as best as possible. “Don’t miss this secret cafe!” or “Get in line at 7 am for this ride pass, and then hastily go to this other line,” I swear, I’ve never absorbed more information on how to wait in a line my life. 

Everyone has the “perfect plan” to make the most of your vacation. And, if it weren’t for a realization my wife and I had on day-2, it would have been easy to get caught chasing everyone else’s perfect plan. 

The Perfect Plan Wasn’t Our Plan

It was day-2 of scrambling and reading every piece of Disney park content, and my wife and I realized that this is not how vacation should go. We were sitting in our hotel room on the sofa, both on our phones, researching the best plan of attack for the next day, desperately trying to quell that feeling that we were going to “miss” something and regret it. We literally texted each other, “Is this vacation?” That was when I knew, and she knew, this was not the way to spend our vacation. 

Going with The Flow

The moment we realized that we didn’t have to “fit everything in” and battle every line and registration opportunity, the vacation became what we needed it to be, easy going and full of memories with our kids that we’ll cherish forever. By accepting that we wouldn’t be able to experience everything the parks had to offer and only prioritize what we cared about seeing, a massive weight was lifted off our shoulders. 

I had one personal experience/goal: to watch some NCAA Tournament at a sports bar near the parks with my two eldest boys and cheer on my alma mater. It quickly became evident that the effort needed to get to this destination to watch the game in my ideal atmosphere would be exhausting and unrealistic. I took a deep breath and decided that going with the flow and not paddling upstream was my best route. We ended up at a beautiful hotel pool with a swim-up bar, complete with NCAA basketball games on outdoor TVs mounted above the bar. I drank a pina colada (my sons had frozen virgin cocktails) and cheered on my favorite team with my boys and Isla; it was bliss.

family trip to disney world
My boys and I enjoying some cold beverages by the pool while watching the game!

Opportunity Costs With Every Decision

There are few decisions/transactions in life that don’t sacrifice one opportunity for another; it’s just how it goes. We (as a species) get caught up in trying to “complete” every checkbox because it’s how we can quantify experiences, but it’s important to keep this impulse in check. 

Now, you may be asking yourself, “Scott, these are some interesting philosophical notions, but what the heck does this all have to do with financial planning?”

In all my years as a family financial planner in Boston, Ipswich, Newburyport, Beverly, and beyond, I have seen similar patterns with clients that try to find the “perfect plan.” People ask me questions about strategies they’ve heard from others that will lead to financial success and satisfaction. I can’t stress this enough, everyone’s needs are different, and no two paths will be the same, so replicating others’ steps for success is a counterproductive effort. 

Regarding financial advice, relying on free resources like Google searches may seem cost-effective. However, the advice you receive may be generic and not tailored to your specific needs. And you’re allocating time/spending time to research and source the answers/information you need; it’s an opportunity cost because it’s occupying your time. It’s similar to planning a family trip to Disney World. While you could create an itinerary on your own for free, there’s a cost to the time and energy spent researching and organizing the trip. 

Imagine if Disney offered a “get organized” session where they got to know your family’s preferences and created an itinerary tailored to your unique circumstances – such as ages, favorite movies, and budget. The value of having a personalized plan in hand would likely outweigh any FOMO (fear of missing out) you may have had by not planning it all yourself. The same can be said for financial planning – a carefully tailored plan can curate a personal path to your specific needs and give you the financial confidence you need to enjoy your vacation or retirement.

Foundations and Flow

There are foundational pillars that should be in place, but we all must accept that while the destination (goals) will not change, the course we travel will have obstacles and surprises along the way. Pivoting to a new plan/strategy out of reactionary fear and desperation is never ideal; staying the course and adjusting to the current situation will historically yield the best results. 

But you can make course corrections; just like on the second day of our family vacation, there may be times when challenges arise, and you need to take a different route, at least momentarily. It’s essential to stay flexible and adjust to the current situation rather than continuing down the wrong path out of stubbornness.  

If you’re feeling overwhelmed or unsure, I’d happily discuss your financial and family goals. We can develop a flexible plan to handle unexpected obstacles while keeping you on track to work toward your long-term objectives.

Book a Call With Scott

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