How To Manage Travel Days Gone Wrong

Recently, we had one of THOSE days – a travel day gone wrong.

If you have ever traveled, chances are YOU (unfortunately) know what I am talking about!

Here’s our experience flying from Grand Cayman to San Jose, California!  Hopefully, you will get a laugh out of our misfortunes.  Sometimes you just have to find humor in ALL that goes “wrong”, right???…and mind you, I do realize that these are definitely first world “problems”.  Last year my husband and I were nearly homeless, and couldn’t even buy an airplane ticket, so we do have much to be grateful for and I promise you, this post does not go without giving gratitude.  I saved the best for last!

So, anyways here it goes…

Our Expectation/Plan :) :

1.  Jack, Jack’s Grandma Eastman (my mother-in-law), and I are going to fly to San Jose, CA, so I can experience Brendon Burchard’s High Performance Academy.  Cool!

2.  Due to issues stemming from my accident, I paid the additional money for a first class experience, so this is going to be a great trip!

3.  We are going to have a smooth trip, loaded with travel mercies, good food, good memories, and lots of photos (of course) – I love taking photos!

R E A L I T Y:

1.  My husband, Tim, cannot accompany us this trip due to work obligations, but we were fortunate to have him accompany us to the airport to say “until next time”.  Until next times are so much easier than “good-byes”, right?

2.  WOOHOO, right up to the counter!  This priority check-in isn’t half bad!!  Or, is it?

3.  Grand Cayman Check-In Counter: We did everything right, we arrived plenty early, and it is a good thing we did.  With no known reason why, we stood at the counter for over an hour while several employees looked into the computer with blank stares, and phone calls were made with comments overheard including, “Well, then why were these seats released?”  At this point, Tim takes a moment from playing with Jack to ask what is going on.  Tim’s Mom, Elaine, and I tell him all is fine, but we too were wondering what the hold up was.  Then, FINALLY, the employees smile and one gestures in a way that relays that his heart was beating fast.  Should we have been concerned?  Hmmm…that wasn’t going to dampen our travels though, we are heading to Cali!

3.  Grand Cayman Security Check-Point:  I am not sure if there is a new company running security, or if a scorpion peed in all of the employees Cheerios this particular morning, but we definitely did not experience “Cayman Kind”.  I mean, it is great that security is on their game, but does it really matter what bin Grandma Elaine puts her scarf in?  Apparently to this narcissistic, power-hungry security personnel, “IT REALLY DOES”.  *Pick up head from ground and place it back where it belongs – ouch*  Then, we waited, because our carry-on bag was pulled aside for an additional check.  At this point, Jack is crying.  This is unusual for him, because he LOVES planes and traveling.  I think he sensed the negative energy that was filling the air.  Thank God for the kind man who came up and offered Jack a fist boom!  CAN YOU GIVE ME A BOOM?!!  This man earns the hero of the day award!

4.  We make it through security just in time to be told that WE are holding up the plane.  LAST CALL!  Oh, I am so sorry that it took YOU so long to check us in, and we still do not know why (not that it really matters at this point).  Oh, and thank you for finally saying sorry.  Saying sorry DOES go a long way.  WHATEVER, at this point I am telling myself that this is NO BIG DEAL.  Since we were the last ones on the plane, there of course was no room for our carry-on items, so our “priority bags” are getting checked too.

5.  Grand Cayman to Miami, Florida!  Nice flight and arrived safely!  However, I wouldn’t exactly consider the flight and flight service “first class experience”.  You’re welcome for the additional flight fare airline company and better luck next flight.

6.  Okay, so I know that many people despise connecting through Miami, however, this part of our trip went rather smoothly.  We actually made it through the customs station before the huge lines formed.  Jack fell asleep so we could not check in via the kiosks.  So to Jack, thank you for helping us bypass all of those people who nearly ran us down to get ahead!  Give me another boom, Jack! :)  Thankfully, we scored a funny and friendly customs agent who planned on winning the lottery jackpot by the time that we arrived in California.  I wonder if he has collected his $160 million yet?  After that, we reclaimed our bags, had one more pass through TSA (better personalities this time), and one more bag drop off area to pass through.  Now, we had a couple hours to kill.

7.  Miami Layover: I do have to say that we had a great time and great food at Clubhouse One!  Despite being busy, our waitress did a great job taking care of us and our food intolerance issues.  The manager was also a delight.  What a nice treat!  Off to our next stop – Dallas!

8.  Miami to Dallas: We made it over to our gate and noticed that they already boarded, but we were still on time.  Now, THIS PLANE was HUGE!  I do not know if I have ever flown on a plane as big as this one AND it had RECLINING CHAIRS!  Are you kidding, me?!  Yes, please, and THANK YOU!  This was definitely a first class experience and the 3 of us had a blast!  Lots of laughs, enjoyment, and more laughs!  Here are a few photos from this flight:


9.  We landed early in Dallas, however, we had to stay on the plane until a gate opened up.  During this time, Mom Elaine started chatting to a man who was originally from Colombia.  He told her how he traveled for work, and how watching Jack play and sleep during the trip made him think of how much he missed his family.  That would be tough.  It reminded me how grateful I am that my husband retired from his work in professional baseball as an umpire.  I do not miss those long distance days.

While Mom Eastman was getting acquainted with this man, Jack and I struck up conversation with the two men to our left.  It is amazing who you meet when you are on a plane!  These men were quite impressed by Jack’s abilities to identify his colors already and the one man took special interest in Jack’s fascination with planes.  The one man, Pierre, wore a orange hat and a green shirt per Jack.  He left his job in finance and now owns properties and a coffee company.  Mmmmmm coffee.  He was coming from Honduras, where he and his company use sustainability practices to help the people and get this, to minister to them.  Coffee and ministry about hope and faith – I’m sold!  If you are interested in learning more, then check out his company and mission at:  I look forward to building my own relationship with Pierre and his company.  Who knows where that journey will lead!

The other man, sitting to our left, told me that he worked for the airline company that we were flying on.  I asked for both of their business cards.  When I looked down at the one man’s card right before getting off of the plane, I noticed right away that it said “President”.  No way…the man who I was sitting to the entire time, the man who I commented to about Jack being a world traveler and having benefitted from free travel for those under age 2, and the man whose seat I accidentally stole…THAT man was the president of the airline that we were flying on.  Go figure!!

10.  Off of the plane in Dallas!  As we exited we were told that we did not have much time to get to the next gate for our flight to San Jose, CA.  Oh great.  WHY were we not surprised?  The woman directed us down the hall, up the elevator, and down to our gate.  We went down the hall to a broken, closed elevator and we are forced to go up the escalator.  We had no time to spare, a stroller, a few bags, a carry-on piece of luggage, and Jack.  I took Jack and his doggie backpack, and there was Mom Elaine going up the escalator with EVERYTHING ELSE.  I tell you, I was praying to God that she made it up.  She did thankfully and the next thing that we noticed is that our gate was pretty much on the other side of the airport.  After booking it with shoes, I realized that the wedge sandals were coming off and back pain or not, we were running!  YES, we were THOSE PEOPLE!

11.  Dallas to San Jose: We made it on the flight and were moved up to the first row seats, which gave us more leg room.  However, despite our excitement that we made it onto this plane, the people sitting behind us were less than pleased.  It was not long into the flight that the man behind us started stating how terrible the plane was, how this was not “first class”, and over and over again about how terrible the plane was.  He also started taking pictures.  His comments were contagious because before long the gentleman across the aisle from him started complaining too – no electronics, horrible food, blah, blah, blah.  I was just happy that we made it!  Then a man across the aisle from us shared what type of plane it was per his plane ticket.  The man who was displeased with the food, replied “(This airline) can go to Hell!”  Oh boy, next we experienced some turbulence and Mom Eastman and I just looked at one another.  Here I was, praying again!  I was thinking, “Please just get us there safely.”  Finally, after a long day of travel we made it to San Jose, California.  I vocalized how grateful I was to have made it there safely, and in one piece.  The gentlemen surrounding us heard me, and all of a sudden I think they were grateful too.

12.  Time to collect baggage and head to the rental car!  Getting close to being able to rest!!  P R O B L E M: Baggage does NOT arrive.  This same thing happened when I flew to California back in 2009 to meet the man who I met on – the man that became my husband.  I do not have good luck with California and baggage!  This time, no baggage, no diapers for Jack, and no carseat.  Are you kidding me?  As much as I wanted to cry and get angry at this point, I just couldn’t and after the day of travel that we had, neither could Mom Eastman.  It definitely was not the cute, older Asian woman’s fault who was delivering the bad news.  Heads hanging low, we say thank you and head over to find the shuttle to the rental cars.  We walked out of the airport with only our carry-on bags and a dirty old carseat.  We would receive the rest of our belongings in the morning.  At this point, I SO wanted to call the man we recently met.  I wanted to vent to that man who we sat next to, the one who was the president of this airline company; but, in my exhaustion and disbelief of the day’s events, I chose to let it go.

13.  Time to get the rental car.  Or, maybe not.  After I hand over my license to the attendant, he looks at me and says, “You know that your license is expired, right?”  I thought he was joking.  Unfortunately, he wasn’t and after repeating himself a few times, he showed me and he was right.  Who looks at their driver’s license expiration date on a regular basis?  Why didn’t I receive a renewal notice in the mail?  Living on an island means that our mail usually arrives about a month later, but…well, happy late 33rd birthday present to me! Sigh.  In my pit of exhaustion, I exclaim that the man behind the counter IS going to help us, because everything was going wrong, because our luggage did not arrive, because I didn’t have my son’s cloth diapers or his car seat, and because God is good.  As I finish my plea, the woman standing next to the man says, “All the time” and another woman standing next to me follows this up with “Amen”.  We must have looked pretty rough at this point, because the man did help us out, and he even gave us an upgrade.  Finally, off to the hotel.  We were so tired from our cross-country chaotic adventure.

14.  On the way to the hotel:  We joked that we would probably arrive to a room with one queen size bed, and well, the joke was on us.  We arrive to the hotel after 1 a.m., and they DOWNsized us due to someone else extending their stay.  We walk into a room with one queen size bed for the three of us, and wet carpet.  Apparently, they were in the process of cleaning the carpet in the rooms, but that left the ground soggy.  My mother-in-law was so exhausted that she chose to crash on the couch, and Jack and I made our way into the moist linens.  Having been given a room that faced the expressway, we were lulled to sleep by the sounds of buzzing traffic.

What a day!!!  

…but after the storm comes the rainbow, right?


We woke up in California to a better day.  We looked out and saw the mountains, which brought peace despite the noise.  By the afternoon, we had ate a nice breakfast provided by the hotel (their oatmeal was amazing), we received our luggage and tipped the man who usually gets scolded for something that he has no control over, we freshened up, and we were moved to the room that we had booked.  Thankfully, I believe we passed all of the tests placed in front of us during our travel day from ______ (you can fill in that blank).  Patience was tested, humor was revealed, and despite ALL of the trials (including me swallowing my dental crown during dinner one night), we arrived safely and gained a story to tell.  I attended the conference we flew out there for, Jack had quality time with Grandma Eastman, we enjoyed some tastefully delicious food, and we met some great people from all over the world.  Although I couldn’t make it through the entire conference due to pain and fatigue issues, and Jack couldn’t handle me leaving him for the last day because he simply missed his Mommy, I do believe that it was all worth the crazy day that we had getting out there.  The best part of our trip had to be the very last day when we decided to head out to the ocean.  I always find peace in water, and thankfully, Mom Elaine was up for a trip through the mountains and out to the coastline of Santa Cruz.  We had a great time!  Here are some of our memories from our walk along West Cliff Drive:  
DSC_3964-1024x682  DSC_3949-1024x682 DSC_3941-1024x682 DSC_3953-1024x682 DSC_3961-1024x682 DSC_3962-1024x682


Mom Eastman taking it all in, while we tried to figure out how these fishermen made it down there.


Looking straight out to pure beauty.


Loved the arch carved into the rock!



So fun to watch all of the dogs play!

So fun to watch all of the dogs play!


While those people were getting married, these people were singing to the whales...

While those people were getting married, these people were singing to the whales…

Although I felt like a total creeper, I just had to get a photo of this dog with a bowtie! We felt like wedding crashers, because this wedding was taking place amongst everything else that we were witnessing - keep scrolling down and you will see all of the excitement.

Although I felt like a total creeper, I just had to get a photo of this dog with a bowtie! We felt like wedding crashers, because this wedding was taking place amongst everything else that we were witnessing – keep scrolling down and you will see all of the excitement.

I was spotting seals

I was spotting seals

Jack was enjoying the California breeze

Jack was enjoying the California breeze

...and watching surfers surf amongst the whales and seals

…and watching surfers surf amongst the whales and seals

This guy was pretty good!

This guy was pretty good!

We also saw boats :)

We also saw boats :)

...and AIRPLANE kites - Jack is obsessed with airplanes!

…and AIRPLANE kites – Jack is obsessed with airplanes!

...and finally, on our way back we spotted a shark (in the sky)!

…and finally, on our way back we spotted a shark (in the sky)!

So, with all of that said, I think it is fair to say that one can successfully manage travel days gone wrong with these top 5 tips:

1. Being accepting of trials and the unexpected

2. Allowing for mistakes and expressing patience and grace in return

3. Learning from one’s own shortcomings, including expiration days

4. Finding a way to smile, embrace humor, and gratitude

(even in the most distressing situations)

5.  Trusting that in the end, good will come and beauty will prevail

Thank you for joining me here in this space.  I am grateful for your time and I would love to hear from you!  If you enjoyed this blog, then I would appreciate you sharing it with those you love.  Who knows who might need some added inspiration?    

Blessings, Love, and Appreciation