I recently went on a very unique vacation.  I went with some friends, the Bowers.  More specifically, I went with my friend Don and his daughter Ginny, although we just refer to her by her nickname Gin.  Initially it was just supposed to be a fishing trip with me and Don, but as time went on, it morphed into a quasi family trip.  Gin often vacations with her dad, and since Gin is a single mom she has to bring her kid pretty much everywhere she goes as his dad is completely out of the picture. Since she brought her kid, I brought mine as they are fast friends as it’s always better for kids to have a friend while on vacation.    Since there were three of them, two of which had birthdays that week, and they picked up the room, we mostly vacationed by their schedule and followed their family traditions.  That was the first important point, I was exposed to a type of vacation that was out of my comfort zone.   The second point, one I already alluded to, was that it was just me and my kid, something I hadn’t done before.   These two experiences in conjunction with something else going on in my life brought about some serious reflection on vacationing.  Ultimately, I had what I thought of as a bit of a vacation oriented existential crisis.   

When I was single, before children, vacations really meant going to see family.  This made sense as I wasn’t very self confident about exploring the world on my own and the ties to my youthful network of friends were still strong.  Things didn’t change that much after I got into a relationship, and ultimately got married. My vacations mostly stayed the same.  We just had two families to visit instead of one.  Also, even in the first years of marriage, I was in the early part of my career, so spending money on big vacations seemed exorbitant.  As a bit of time went on, we would start to go on trips just by ourselves, usually to see or experience something new, but that was mostly limited to long weekends and destinations you could reach by car, with the only exception being cruises.   We went on a bunch of those because we owned Piedmont Cruises, a small home based travel agency, as our side hustle. The cruises were especially valuable in helping me form theories on what you should and, more importantly, should not do on vacations.     Between the family trips, the couples weekends away, and the cruises, we developed our vacation template. 

We attempted to continue this structure when the kids arrived, but that turned out to be challenging.   When you have kids and your visiting someone else’s home, it brings a measure of chaos that in my opinion, doesn’t quite work for you, or for the family you are visiting.  As a parent, at least if your a halfway decent parent with consideration for others, you are worried about your kids behavior and trying to minimize the impact of rambunctious behavior and related child rearing. The vacation can be as much or more parenting work as it is relaxation.  It becomes harder to achieve the traditional ‘unwinding and refreshing’ which is traditionally the point of a vacation.  If you’re the grandparents or other family members who are the one hosting the visitors, it’s just a lot of extra work and change to a comfortable routine.  

Ultimately we’ve found it best to just go rent a house, usually near a beach, and spend a week there.  Considering that virtually 100% of the beach houses today are little rental businesses, I’m not alone in my thinking.  If our family or friends want to come out to the beach for a bit, it can be a nice way to get in the family time and still keep from turning their day to day life upside down for a week.   Since most of the homes near the beach are for-profit businesses, the costs can be very high, especially in season.  To help mitigate that, we happened upon the idea of splitting the house with another family we get along with who has kids the same age as ours.  As long as you are compatible with your value system, it mostly works out, at least mechanically.  The way we do it, we have breakfast at the house in the morning.  The mom’s and kids enjoy the beach or the pool during the day.  I rarely enjoy the beach or a pool, so I’ll keep myself busy with writing or doing something related to work,.  Sometimes I’ll do some things I enjoy with the other dad and sometimes by myself.  I will go pier fishing, hit a local bar for a beer, and often I’ll do a daily grocery trip to Walmart just to get out. Once or twice during the week we will go out for a meal at a restaurant. The benefit of going with another couple is that one of those nights can be a date night with just me and my wife.  We do a quid pro quo with the other couple so they can have a date night too.

I’ve enjoyed vacationing with our friends to the extent that I can enjoy vacationing with anyone, and have done it for so many years I almost forgot what it’s like to not vacation with family.   That brings me back around to Don and Gin.  Don and Gin’s philosophy on vacationing is that you go on vacation to specifically do the things that you don’t do at home. This means they go out to eat twice a day, they have many activities lined up during the sunshine hours, and party at night wherever possible.  I’m sure there’s a strong commentary that could be developed around my experience of watching  a mid to late 30’s mom and a 60 something grandpa drinking and behaving like they are 21 year old spring breakers but that is not the point of this article.  What I realized is that they do some things that I enjoy, and they do some things I don’t.  What made these points so important to reflect upon was something else I was planning, it was my big cross country trip for the summer of ‘22.

As I’ve mentioned before on this blog and on my podcast, I’ve recently transitioned from a job that’s more heavily focused on the work world, to one that’s more aligned with life.  More specifically I went from interfacing with businesses as a grant program manager to interfacing with youth as a college instructor. There is a serious perk to being a teacher in a traditional school system, and that is time. For the most part, even if I’m teaching a part-time class, I’m off during the summer.   Initially, my thoughts were about living at the beach full time during the summer.  In effect, taking my week-long vacation during the summer and making it extend out to three months similar to what my family did  years ago on Keuka lake. Unfortunately, the housing market bubble, aggravated by a massive exodus of information professionals from the cities to remote leisure destinations made the purchase of a piece of property near the ocean unfeasible.  

What was feasible, as I’ve written about, was the cross country road trip dream that I had and tabled decades ago.  The trip was an inspiration for my article about expectation inflation.  Specifically, the vehicle needed and my wife’s expectation of what constitutes a minimum requirement, versus my own expectations.  But what about when I’m on the trip by myself or with my child?  I questioned if there were things I planned to do because I feel like I have to do it?  What would I actually enjoy doing now that the trip was a real possibility?  My time with Don and Gin really brought those questions into focus.  I spent a good deal of time reflecting on the whole thing.  It may seem trivial, but when you are face to face with something that has been in your mind space for the majority of your life, it takes on new meaning.  I realized the answers to these questions may inform how I treat my leisure time in the future.  In effect it was a vacation existential crisis.  

For me, what was needed was an assessment of what I actually enjoy. Ironically, because it’s been so many years since I’ve really enjoyed the majority of a vacation, I couldn’t immediately form a list.   Even now, as I write this, I’m almost stuck.   I figured I’d do an assessment of what I enjoyed most about my recent vacations as well as others I’ve taken in the past.  This is where my son comes into the picture.   This was the first vacation I spent with just him and I, and surprisingly I enjoyed that aspect of it a great deal.  I’m not going to lie no matter how politically correct it is. I hate traveling with the kids, I mean I really hate it. You spend all your time parenting and seeing to their needs.  

I know I’m not alone because I’ve spoken with many other parents who agree with me including my own father.  I remember my dad chuckling at a car parked on the side of the road of the Florida Turnpike, or the Disney highway as we thought about it as kids.  Inside the car were a couple of parents in the front seat and the kids in the back.   The father in the parked car was clearly reading the kids the riot act for what was most likely misbehavior brought about by road trip induced boredom.    As Dad snickered he told me how much he remembered doing the same thing with us at that age. Clearly it’s fun after the fact but only because it was so bad during the experience.  

When it’s just you and one other child, it’s much more enjoyable. You spend a lot less time stopping bad behavior and a lot more time interacting.   When I told him about the experience, a buddy of mine said “Yeah man, Dude trips are way easier”.  He was right.  This confirmed that when I go out with one other person, I enjoy the trip way more than when I’m with the family.  This sort of speaks to Don and Gin’s philosophy that you should go on vacation, you do it to get away from what you do at home. At home I parent and I don’t really want to do that when I’m on vacation because parenting is stressful. 

The next thought is about activities.  All of my friends who vacation tend to fall into the trap of spending a ton of cash while on vacation. I do as well, but my splurges are much more reasonable. As an example, one of the splurges that I do on vacation is to buy new shoes. I would have to do that at home, but by saving my shoe spending for vacation time it gives me something to do and I feel like I’m spending money freely, even if it is a standard cost of living.  My point is, I enjoy spending a little, but not insane amounts of money on vacation. I don’t want a spending hangover when I’m done.  This gets really tricky when you’re with other people and they want to do things like go out to expensive restaurants or do high cost activities.  

I realized there are other things I like to do, like go to bars and people watch and explore interesting but hopefully not overly expensive experiences.  Yet a soliloquy on my vacation preferences isn’t the point of the article.   I think for everyone else reading or listening to this, the big lesson is an analytical assessment of vacation preferences.  Normally we feel our way through vacations.   We listen to sales pitches, we go with our gut.  Maybe we go with what we think we should be doing.  Often we don’t get into the nitty gritty of asking ourselves what do we enjoy, and what do we not enjoy?  What is the purpose of going on a vacation?   This changes your thought process. 

As an example, if you are the type of parent who wants to enrich your kid’s life, why on earth would you take them to Disney World?  It’s usually uncomfortably hot.  When you get there your day is filled with mostly waiting in very long lines, and when you do get into the attraction they are not nearly as entertaining as most people think it will be.  I recall the conversation I had with a friend who, as a child, was surprised with a trip to Disney.  She didn’t recall anything but the surprise.   What does that tell you about the quality of the experiences inside a $116 to $230 per person per day theme park?  

I think the only caveat to this is marriage and family.  When a close family member’s value system is not your own, it can have challenging consequences.   Consider the well meaning grandparent who wants to pay for everyone to go to Disney even though it’s going to be a miserable experience for most of the parents.  Or the parent who wants all of her adult kids to come on a beach trip even when there is serious personality conflicts between the siblings.  Sadly, there is always a longer term fallout to not taking part in the family group think.  

Going back to Don and Gin, I got a subtle sense that they weren’t really enjoying themselves completely.  It could have been my presence cramping their style or it could have been that the activities didn’t turn out the way they expected.  I wonder if either of them ever really asked themselves what they enjoy on vacation or if they are just following a preconceived notion of what a vacation is supposed to be.    

For my own part I’m going to rethink my family vacations and my planning for my cross country trip.  I’m going to continually ask the questions: What is the purpose of this trip?  Will I really enjoy this, or am I doing it because it’s there to be done?  Who do I want to share this with vs. who am I expected to share this experience with?   I suspect my change of thought will have big implications for my trip, and possibly for future trips.  It’s going to be interesting in the years ahead as I use the summers to try and explore new and different experiences and vacation structures.  
Right now, there is only one thing I’m sure of.   If I’m able to pull off this cross country trek, I’m definitely going to bring along the Grateful Dead’s “What a long strange trip it’s been” album.  I’ll use that as my vacation soundtrack.   I can’t think of a more fitting album when you consider how I’m going to handle my vacation decision making from now on.  

Posted by Mike Peluso

Mike Peluso writes about the collision between between the business / professional world and life. He also writes about the journey involved with the Peluso Presents efforts including the Blog, Books, and Podcast so that others may benefit from his efforts. From Mike: I spend hundreds of hours working on these articles every year with no compensation other than support I get through donations. You can support with a tip and by Subscribing to the Podcast (and writing a review on iTunes would be really appreciated as well!) One time tips: www.paypal.me/pelusopresents https://venmo.com/pelusopresents

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