The Best Use of Money I’ve Ever Spent

Recently we as a family did something relatively crazy. At least for us.

We spent 4 weeks in Florida. Leaving a snow-covered Pennsylvania terrain in pursuit of sunshine and 80-some degree temperatures.

And one of the reasons I wanted to write about it publicly is because we probably wouldn’t have done it if not for a pretty direct challenge issued to us. Last summer I had a mentor threaten to cut off all future communications unless I sent him a screenshot of our booking confirmation of such a trip within 48 hours.

While I’m not going to make any similar threats to you, I do want to at least plant a seed.

Quick word on semantics: I don’t call it a vacation for two reasons.

1- anytime you travel with small kids, “vacation” sets an unfair expectation of actually being able to perpetually relax. Reframing these ventures as “family trips” helps reset adult expectations, and honestly has increased our enjoyment of these times since we started using that phrase a few years ago.

2- we didn’t entirely vacate our responsibilities. Since I made the decision not to grow my firm, one of the tradeoffs of that was not having a staff to keep things running. In these crazy Covid times, school also looks different for our 3 school-aged kids. So they had to keep up with schoolwork on a daily basis.

It wasn’t as much vacation as it was living life in a different place.

But it was by far the best use of time and best use of money I can ever recall personally allocating.

I’ll say that again: those four weeks were the best time and money I’ve ever spent.

For those wondering already the dollars involved, I’ll get to that in full transparency at the end. It’s (probably) more affordable than you’re thinking.

What I really want to do is plant the seed for people (you) to try and make an extended trip like this happen – maybe especially those of us with younger kids. We as a family have memories that we’ll forever remember (if not, then we have approximately 1,000 photos to give reminders).

One of the results of the Covid lockdowns the past 12 months and counting is that many more people have seen that a lot of jobs can be performed remotely, at least for a portion of the time. And so the idea of getting away for an extended period is perhaps more attainable than it was, say, 13 months ago.

While the benefits of such a trip are probably too numerous to realistically list – and certainly would vary for each family and their specific situation and unique values – below are some of the biggest ones for us.

No urgency

When you’re staying in some place for 4 weeks, you don’t have to rush. Typically when we take our beach vacation each year, there’s an underlying sense of urgency to get to the beach each day, because you only have so many days. If it’s a little overcast or rainy, or a kid’s sleep schedule is all jacked up, or someone (ahem) got fried by the sun, or the kids are just generally miserable – you feel a sense to force yourself to go get stuff done every day.

Additionally – and I don’t think I’m alone in this – it also takes a few days to actually unwind when on vacation. Maybe even 2-3 days. So on a 7 day trip, that’s almost half the time adjusting. Depending on traveling, that might only leave 2-3 days of actually enjoying the time.

When you’re gone for more than 7 days, you also can afford to take some chill days – not do anything extra. Relax, read, take a nap. On shorter trips I always have this sense I have to make the most of each moment – that wasn’t the case here. And I was infinitely more relaxed because of it.

Paradoxically, we did an insane amount of activities (more on that below) over our time there.

Change of scenery

Look – I get we didn’t travel to another country or even to a different time zone, but it was healthy for the kids to see a different part of the world and really experience it. It was also good for us as adults to talk with different people, to see a different pace of life, and to get out of the daily monotone activities that come with being in your home and your community all the time.

Simplicity

We took a ridiculous amount of stuff with us – I think pretty much the full extent of what you can pack into and onto a family sized minivan.

But the house we stayed in was less than 1/2 of the square footage of our house, and the kids probably had 1/30th of their typical stuff to play with. And we realized that maybe we don’t need as much back home. Granted, we were in Florida, minutes from beaches and seconds from our own private pool – but it was noticeable how little things we really “needed”.

Realizing that, we’re currently in the midst of purging/donating/selling a goal of 1,000 items from our home as a way of not letting this lesson go completely to waste. I could probably write a whole post on this benefit alone.

Reminder that I’m not as Important as I think I Am

A big fear of mine was how my clients would perceive this, and I made sure to communicate to them that I’ll be away, will still be accessible, but might not quite be as quick in my responses. I want to think that I play a really important role in my clients lives – and I believe I do in a broader sense – however, the likely reality is that I think of them more frequently than they think of me.

As I communicated this trip ahead of time to clients, not a single one replied anything less than “Good for you – we’re happy you’re doing it” or some similar variety.

Certain items came up business wise that I did need to take care of – trades, money in or out, rebalancing, what to do with stimulus funds, etc. – but it was all easily handled. I think we deceive ourselves into thinking we’re more important and vital than we are in reality.

Harsh – but probably true.

And healthy to be reminded of from time to time.

Deepening relationships

I think I have a pretty healthy relationship with each individual member of our crew – my wife and all four kiddos. But doing life together away from home seemed to enhance each one in a different way.

My wife and I had to parent together in a different context, which led to healthy conversations and expectations.

Our daughter and I bonded over offshore seashell treasure seeking.

Our 8 year old son and I created all sorts of new athletic games to compete at.

Our 6 year old son and I spent hours snorkeling – first practicing in the pool, and later in the Gulf.

And our youngest and I bonded in new ways paddle boarding together.

The kids themselves interacted differently as well with each other. At home they usually pair off and do the same, somewhat predictable things – but down there they were all mixed up and creating these amazing games and activities altogether.

New realizations

Perhaps it is just the kids’ ages, or maybe it’s a new revelation entirely – but my wife and I realized we actually enjoy traveling. We haven’t done a lot of it together. We were married young, had our first kiddo very soon after, and so never had a ton of discretionary money or time to do much of it. And the times we did do it, it wasn’t all that enjoyable. During the trip we realized that maybe traveling really is something we’d like to plan to do more of in the future.

New experiences

Anytime you’re in a different context you have different opportunities for new experiences. We had a lot of family firsts down there. First time all kayaking. First time driving a boat. First deep puncture wound. First time paddle boarding. First 20+ mile bike ride with a kid. First time going out to eat as a family of 6 without meltdowns. First hermit crab find. First shark teeth find. First marina exploration. First family aquarium trip. First (and gigantic) conch shell find. First time picking fresh oranges.

All of these would have been fun in and of themselves, but taken together it made for so many memories for all of us.

The cost

I actually had a really large hesitancy in writing this – even though I want to encourage people to consider doing something similar. I didn’t want it to come across as someone financially independent (which I’m not – and whatever that term even means) who drops this insane amount of money and who can’t fathom a family not being able to do the same.

In fact, I even informally asked a few friends what they thought the trip cost. Some said $25k, some said $30k, some said $10k. Another knew I was self-conscious about the topic, figured it was cheaper than what he thought, and actually guessed it on the nose.

So I thought I’ll just be straight forward and disclose it all.

The trip cost us right around $8,500 all in. About $6,000 of that was for the Airbnb home we stayed in, and the rest was anything above average of what we’d normally spend on life in the course of a month (i.e. dining out, groceries, kids activities, fuel, etc.). Further, a good chunk of that extra went to an inflatable standup paddleboard that we’ll use for years.

That’s no small amount of change I’d throw around without serious consideration.

But it’s also not that large of an amount that is insurmountable for most people who read this site to afford. Shoot, I’ve heard of people spending that amount for 5 days at Disney. (Not a knock – just a comparison!)

A few parting tips of advice

If this is something you’re considering doing, a few tips of advice.

  1. Get a full home – not a condo or hotel. You’ll want the relatively-speaking extra space. If you go through Airbnb (or I’d imagine VRBO), ask for a discount for the extended stay. The site automatically gave me one, but I emailed the host and told her our budget and asked her what she could do. It was worth asking. Related…

  2. Have a separate place to work. Probably one of the smarter things we did was finding a home that had a designated home office. It ended up being more of an extended utility closet off the garage – but it was separated from the main home and the sometimes craziness of the kiddos.

  3. Find your cadence. It took us 3-4 days to find a cadence. In fact, after only a few days there and in not my proudest moment, I told my wife that “this was a ******* waste of $6,000” and was ready to pack up. We weren’t relaxed, I wasn’t getting anything done, and the lack of consistency and expectations were hard on the kids. Soon afterward that we found our rhythm – which was for me to spend the time I needed first thing in the morning doing whatever work I needed to get done, and my wife to do any schoolwork with the kids. This left from late-morning onward open.

  4. Keep up your habits. I slouched off on a few daily habits while down there (getting up early, drinking 90 ounces of water, exercising, daily reading, etc.). And while I didn’t notice it at first, these eventually started wearing away at me – mentally and physically. So after establishing the previously mentioned cadence, I made sure to reup on my habits commitment. That said…

  5. Don’t overschedule. Spontaneity – we found – was one of the greatest treasures down there. We ended up doing a lot, but we had a running list of things we wanted to do, and would decide sometimes at a whim which day to do it. And sometimes we didn’t do anything.

  6. Coordinate with another family. Another thing that made this trip unique was that we intentionally overlapped our time down there with another family set who had their own place about 10 minutes from ours. This was nice in that we could choose to meet up together (for the beach, a special outing, dinner, etc.) but also had the ability to choose to do our own things when we needed the space. So if there’s another family you’d consider doing life together with, it could add an interesting extra dynamic.

  7. Set a budget. As I talked transparently about the cost – you should set a budget that you can afford and doesn’t wreck you financially. We could have easily spent 2 or even 10 times the amount of money that we did. Maybe what we spent is monthly discretionary excess for you – or maybe it’ll take a few years to save up – but either way, be responsible.

Lastly – I’m not saying that this type of trip is right for every family. In a similar way of being able to personally define and implement Enough, I recognize the privilege I have of owning my own business and being in a profession where I can work remotely for periods of time.

But I also recognize that we can make excuses for why we don’t do things. And I don’t personally want to hide behind those excuses.

Maybe your boss is more open to the idea of a few consecutive weeks off than you thought. Maybe if you held off on some other purchases you could afford a trip like that sooner than you thought. Maybe the kids’ school is more flexible with remote work as long as you communicate well enough with the teacher and administration. Maybe the obstacles aren’t as immoveable as we imagine they are.

Further, I recognize that Tomorrow isn’t promised, and so I want to find that balance of living in Today. And I also recognize that quality family time is one of my chief personal values.

All of these realizations combined are what made this trip the best time and money I’ve personally spent.

(It’s not even a close competition between it and anything else.)

And maybe if you are – or were at some point in the past few minutes – nodding your head in some fashion, maybe it could be the best use of time and money for you as well.