A Tail of Two Trips

July 12, 2023

My Dad passed away back in May of this year at the age of 89. When I spoke at his memorial, I tried to share all the things that made him a great father and a wonderful person.  He was very intelligent, kind, and genuinely interested in the wellbeing of others. He also had an excellent sense of humor.  He was even good at laughing at himself.  In fact, at the service, I related a story about how many times he moved to a different house while living in Houston and how poorly he planned each of those moves.  He was comically bad at it, and we all got a good chuckle remembering. The same was true of his vacation planning.

My parents divorced when I was about 8 years old. One of the very few silver linings to this was that every year, I was able to go on not one, but two, family vacations. In terms of planning and itinerary, these were two entirely different kinds of trips.  Let me see if I can paint a picture of each.

When my mom planned a vacation, most often to the beach, she planned out every detail.  She shopped hotel rates and made reservations (which was no small task since Expedia, or even the internet, was not around).  She planned meals. Growing up, eating out was not a frequent occurrence, even on vacation.  She was excellent at sticking to a budget.

We were usually at least halfway packed several days before the trip. All the stuff that had been stored all year like beach towels, chairs, floats, ice chests, etc. were brought out, dusted off, and staged for loading into the car.  The car had been gassed up, had the oil changed, the fluid levels checked, and tires checked.  Mom made sure it was in the most optimal condition to get us where we wanted to go and she had mapped out the quickest route to get there.  Prior to the day we left, my sister and I knew exactly what time we were leaving, how long of a drive it was, and how many stops were planned along the way.  With all this planning, very seldom did we forget any essentials.  We did not have to buy much when we got there, we hardly ever got lost and had to backtrack wasting time on the road (and there was no GPS), or make unplanned stops. 

Once we arrived, we were able to maximize our time spent having fun rather than spending it eating out or shopping for food and beach gear. This is not to mention the peace of mind we, especially Mom, had knowing what was coming next and not weighing different options throughout our stay. It may sound like these vacations were may TOO regimented.   Not at all.  They were well-planned and this facilitated the relaxation that vacations are supposed to provide.

Then there were the trips with Dad.  Like Mom, Dad was smart. He had a Doctorate in Education from Columbia University and was well respected in his field of Clinical Psychology.  He believed in the power of education, and he loved to listen and learn. But he couldn’t plan a trip to save his life.  I never fully appreciated what went into planning a vacation until I went on a trip with Dad. 

One summer, we decided to go fishing in Colorado.  That was the extent of our planning.

He was an early riser, so on the day of our departure, Dad woke me up at about 5 am and told me to pack.  I was 12 years old.  Needless to say, I did not pack well.  Meanwhile, dad spent about an hour digging fishing rods and tackle out of his cluttered garage.  We grabbed everything we “thought” we might need and jumped in the car.  The car was on empty, so we had to stop for gas right away.  Dad checked the oil because “the oil light has been coming on lately.”  Now, there’s some good news.

Leaving from Houston, we were able to get most of the way through Texas before Dad fished through the glovebox for a map.  There were a few times along the way when he would stop, check the oil, and revisit the map.  When we drove into New Mexico and Colorado, we had to stop and get more maps. I’ll be honest, I don’t recall where all we went in Colorado, but I do recall we didn’t know where we were going before we got there.  We found lodging by driving around and we ate out just about every meal (I really didn’t mind this aspect of the trip, but I know it got expensive and time-consuming). 

We really didn’t know anything about fishing for trout, so we had to inquire and subsequently buy additional tackle and bait.  Bait shops near the water are not known for bargain prices.  We spent quite a bit of time learning and gearing up before we actually fished.  I guess it was a good thing we hadn’t “planned” how long we would stay. 

Don’t get me wrong, we were not miserable.  We enjoyed each other’s company and all in all, it was a good trip. We even spent one night in a huge army tent, in the mountains, with a gold prospector who we had met while fishing. It was a unique experience that we couldn’t possibly have planned.  I just know we could have done more and spent less if we had done a little more planning.  Making decisions along the way - decisions that could have been made ahead of time – made the trip more stressful than it needed to be, especially for Dad. One could argue that a well-planned trip would allow more freedom and opportunity for spontaneity, instead of just worrying about what needs to happen next.

Planning for retirement, or for the time when we would like to be less dependent on income from employment, can go like either one of these two vacation scenarios.  The thing is, vacations are only for a week or so. You can learn from a poorly planned vacation and make it better next time. When it comes to financial planning, there is seldom a second chance. The longer you put off planning, the more you may have to save, or spend later to get on the right path.  The peace of mind that comes with knowing where you are going and what lies ahead cannot only make life easier and flexible in the future, it can also make it more enjoyable in the present.