Stress Free Travel: How to Avoid Travel Mistakes

By Sean Ogle •  Updated: 09/29/21 •  9 min read

Stress Free Travel How to Avoid Travel MistakesIt’s 1:23 pm on a cloudy Monday afternoon in New York City.

You’ve just hopped off the NJ Transit train to Newark Liberty International and you’re excited to get back home after 10 days of networking, socializing and business meetings.

As you’re on the AirTrain you pull up Tripit to figure out which terminal you’re supposed to be getting off at.

“2:45 – JFK Gate 23 Terminal 3”

You know that moment where you realize you’re at the wrong airport less than 90 minutes before your flight? Yep, that’s me as of about 20 minutes ago.

I’ve been relatively lucky with my travels, as this is the first full on, all out, stupid mistake I’ve ever made.

2021 Update: This mistake paled in comparison to that one time in Tokyo. I’m gonna just leave this right here:

Sure I’ve had some close calls and other stressful situations, but this is the first time I’ve ever had to slump back in my seat, look out the window, and finish out my train ride to not only the wrong terminal, or even the wrong airport – but to an entirely different state than where I was supposed to be.

So what do you do in a situation like this?

Do you frantically call up a desk agent and plead your case? Do you fall to the ground screaming “noooooo!” while cursing the world and raising your fists in the air?

Do you just give up and go back into NYC for an indefinite period of time?

I did none of those things.

I walked up to the desk, told them what happened and told the agent I’d gladly pay the $50 change fee for a flight that gets me in only two hours later.

Now I just have an extra few hours to kill in Newark and a slightly bruised ego.

90 Minutes Later…

My secret to stress free travel is coming in just a minute.

But for those of you who were thinking “for your worst travel story of all time, this isn’t that bad….’

Don’t worry. I got you.

In an absolutely shocking twist of events (sense the sarcasm?), when I returned to the counter an hour later to finalize the flight change, the new guy working the desk informed me in not-so-polite terms that I was an idiot for thinking the change was only going to be $50.

It was actually $143.

We went back and forth and brought in the original agent, as well as the manager.  At the time, Delta had a same-day change policy that essentially allows you to show up at the airport and make any same-day changes for $50.

ONLY, however, if you’re at the same airport – I was not, hence the higher price.

The lady told me that in normal circumstances they’d honor her word, give me the ticket at $50 and be done with it.

But an hour had passed since then (as I was told needed to happen), and when they went to finalize the booking, the price of the flight change had jumped to $459.43.


I mean I get that I’m the idiot in this situation, but this was getting ridiculous.

They told me I could head to JFK and they can put me on another flight for $50 there.  There was a direct flight to Portland leaving in just under two hours.

“You might want to take a cab” the agent said.

Gee, thanks. Asshole.

$143 in fares, tolls, credit card fees, and tip I arrived at JFK 61 minutes before the flight.

I gave the new agent the 30-second rundown and she got to work.

“You barely made it, 3 minutes later and I wouldn’t be able to get you on this flight. But we can get you on the direct flight for $50.”

“I love you.”

The whole time all of this is happening all I could think about is the first half of the post I’d written 90 minutes prior:

“Sure it might be inconvenient, frustrating, or even expensive, but it’s all part of the fun.”

This afternoon proved to be all of those things.  But it makes for a good story and is a solid reminder that sometimes you just need to be able to have a laugh at your own expense and enjoy the adventure.

Ready to make your travel stress-free?

The Adventure of it All

In the last ten years I’ve been to a lot of places and had a lot of incredible (both good and bad) travel experiences.

Just last night I was telling the story of my motorbike fiasco in Bali.

I was meeting the General Manager of the Como Shambhala Estate in Ubud and had a 45 minute or so ride from Seminyak to get there.  Everyone told me it was pretty easy, so I didn’t think much about it, and gave myself plenty of extra time just in case.

Ubud is in the middle of the island, and about 90 minutes into my trip I come around a corner and see something extremely unexpected:

The ocean.

That’s not good.

It took me another hour plus to wind my way through the jungles of Bali, stopping and asking for directions every few kilometers before I finally found myself in Ubud.

It also didn’t hurt another dude on a motorbike was polite enough to let me follow as he was going the same direction.

In this situation, similar to the one I’m currently facing, I could have panicked and freaked out at the fact I could miss my meeting, or at the fact, I had to practically use sign language to get my point across to the locals I was talking to.

But once again for whatever reason I stayed calm and did what I needed to do to get to the right spot.

Stress-Free Travel: The Ultimate Secret

In this post, I could throw down bullet points and common sense checklists that you’d skim, maybe nod your head to a couple times and move on from.

But the fact is, most of that would have nothing to do with why I’m successful at traveling stress free 98% of the time.

No, the real secret is that I treat my life as an adventure.

Just the fact that over a decade later I’m still telling the story of my Balinese motorbike incident means it was totally worth it. I did something memorable, something that made for a good story.

I originally wrote this post as I was experiencing my JFK debacle.

Again, as I update this post nearly a decade later, it’s still a story I tell again and again.

When was the last time you told the story about your routine cross country flight where you arrived on time and slept the whole way through? Yeah, that’s what I thought.

The beauty of this lifestyle is that if you wish to, you can make every day an adventure.

One of my first days living in Thailand I saw an elephant walking down the street.

A year later in LA I’m getting life and business advice in an incredible mansion from Orlando Jones.

Or how about that time I hung out with Steph Curry at Pebble Beach?

You have to take the bad with the good and recognize that almost always a bad situation will make for a great story later on.  Sure it might be inconvenient, frustrating, or even expensive, but it’s all part of the fun.

How much would life suck if you didn’t have stuff like this happening to keep you on your toes?

Most of the time travel goes off without a hitch.  Sometimes things happen beyond your control. Other times you’re just a complete idiot and get off at the wrong airport, or decide to hop on a “Cambodian Death Bus*.

*Note: This was the not-so-affectionate nickname we gave to our overnight sleeper bus to Siem Reap from Pnomh Penh. We learned the hard way that not only are those buses disgusting and beyond old, but there are no paved highways through the countryside.

Was that night miserable? Of course, it was! But it was an adventure and a great story.

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How are You Framing Your Experiences and the World Around You?

Most people go through their daily routines with insane monotony.  Doing the same thing over and over with no change can drive you insane.

However regardless of whether you have a stable life with a good job, or you’re a global entrepreneur, making the mindset switch from living a life on repeat to living a life of adventure can make all of the day to day stuff not only more bearable, but more fun and memorable as well.

I like to think of my life as one giant version of The Amazing Race.

Just yesterday I was walking through New York trying to find my way from Grand Central to Columbus Circle.  I passed by Spiderman in Times Square and had one of the cities finest $.99 slices of pizza.

Grand Central Station in NYC

Inside Grand Central Station in NYC

Each stop was another aspect of the race and getting to each one became part of the experience.

I still have a ways to go today before I land safely in Portland, and technically I don’t even have a confirmed ticket yet.

But you know what? From now on, whenever someone asks me what my best travel tip is, I can say without hesitation:

“Make sure you show up at the right airport.”

From another New York Adventure:

Other Stress Free Travel Tips:

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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13 comments on "Stress Free Travel: How to Avoid Travel Mistakes"

  1. I have a similar story to share.

    I had a flight with Vietnamese Airlines from Sydney to Korea to visit my girlfriend. But I was told at the airport that I needed visa to pass trough Vietnam. Since I had a local flight in Vietnam from Saigon to Hanoi, I needed the visa I didnt have. My agency didnt tell me that.
    Lucky for me, there was a storm that morning and some flights, including mine, were delayed by an hour. Only because of that, I had enough time to take a taxi back to the city centre to get my visa and got back on time.
    100 bucks lighter, but I could make it and meet my girl in Korea 🙂

    1. Sean says:

      Glad the story had a happy ending! I almost had some visa issues in Vietnam in January, but it all worked out 🙂

  2. Happened to us in China (Beijing) so, I can totally understand your plight. The most important thing is to TRY to stay calm and think of it as a learning experience and not get pissed off. Our problem was we missed our flight due to non-English speaking nor understanding workers at China Airways….. But, we finally made it home after a 2 day delay! :/

    1. Sean says:

      At least you have a good story to tell! Mine would have been MUCH worse if they hadnt spoke English or if there was a line at the ticketing counter at JFK. For all the bad luck yesterday, definitely had a few breaks as well.

    2. Daniel says:

      “Our problem was we missed our flight due to non-English speaking nor understanding workers at China Airways….. ”

      The Chinese workers for China Airways in China didn’t speak English? That definitely sounds like it was their fault.

  3. Randy says:

    And on an even brighter note, it brought you some entertaining site content! lol nice!

  4. Emily says:

    Happened to me in Tokyo. Having a midnight flight I firstly mixed up my dates, thinking I wasn’t flying out for another 24 hours. A thought struck me with only a few hours until boarding to check my flight details while I was in the middle of shopping. Shock horror! I had to fly out in a few hours and had to get back to my homestay family’s house, pack my stuff, explain the mix up, say my goodbyes and get out of there. In the hustle, I forgot to double check WHICH airport I was flying out of. I only made the airport train with a second to spare. 15 minutes or so into the journey, I look at my itinery. Shock horror again! I was heading to Haneda airport when I needed to be heading in the other directino to Narita! I took a deep breath made an intuitive decision to just jump off at the stop we had just pulled up at. I had no idea where I was. I look up at the train timetable. God was looking down on me favorably tonight because I had gotten off at the last stop to transfer to the connecting train that would take me straight to Narita airport. I made it the to airport just in time to board and was on my way to London. It was a flight I couldn’t afford to miss as it was only the start of my 6 month travels and was non-refundable. PHEW!!

  5. Chas says:

    Not exactly the same type of story, but when leaving Kauai I hopped on a puddle-jumper with OK Airlines (Oahu-Kauai Airlines) 🙂 . As we were taxi-ing down the runway, the flight steward couldn’t get the door closed and was yelling up to the pilot telling him the situation- the pilot was concentrating on one goal- the end of the runway and lift-off and would have none of it. Fortunately, the steward got the door latched just seconds before we left the ground. I asked if he had more of those tiny bottles of rum.

  6. For me, I always get stressed at border crossings. It’s something that I never can truly relax at. I’m always assuming that I’m an easy target for some sort of scam.

    I need to chillax a bit I think 😉

  7. Darlene says:

    Two stories come to mind.

    #1 leaving Las Vegas we get to the airport to find an empty check-in counter, no line up. Not good! Only to find out our flight left 2 hours earlier. It had changed and we didn’t bother to confirm it, nor did our travel agent give a call (booked that one with an agent long time ago) or email to say it was changed and she had new tickets for us. Short story is of the 4 of us in our party, two got on a flight home that night and two of us overnighted and were on the phone with our agent at 5am to fix it and get us home. We were outta money (it IS Vegas) so took our free buffet and stuff my purse full of fruit and muffins in case we had to kill all day! LOL. We got home and ended up splitting cost of two new tickets with the agent. It was partly her fault, but learned a big lesson to confirm flights. Have an app for that now!

    #2 – landed in KL (Kuala Lumpur Malaysia) and looked at options to get into the city. Ended up with a taxi for about $40. When we were leaving a couple days later, I “found” some paperwork that I had actually booked us on round trip shuttle busses and prepaid for them both ways. OOPS!

  8. Terrin says:

    Two similar stories happened to my amidst my world travels….

    1) When my sister and I were backpacking though Europe, we had taken a train to London to the Luton airport and were sleeping in the airport as we had a 6am flight the next morning to Barcelona (we were backpacking and trying to save money after all). So after a long, uncomfortable sleep in the Starbucks chairs, our gate finally opened at 4am. Unfortunately for us, we were flying with Ryan Air, and didn’t have our boarding passes printed because we didn’t have access to a printer at our hostel (even though we were checked in online). The CSA at the gate said we had to go get our boarding passes printed at Customer Service and it would cost 40 £ each (almost $80 each Canadian). We tried to explain our story to the Customer Service agent, hoping she could give us a break as we were both booked on the same booking number. But sadly no, she was extremely unhelpful and charged us the full 80 £. We were tired, grouchy from no sleep and my sister started to comment on how rude she was being for a “customer service” agent. I just pinched her leg and told her to keep quiet and just gave the agent my biggest fakest smile and said “thank you very much, have a wonderful day, we’re going to Barcelona now.” All I could think to myself was “we’re off to Barcelona now and she’s stuck behind a desk so screw her!!” That positivity just got me through!

    2) Similar to your Terminal situation. My sister and I were recently traveling Australia, and had just flown into Brisbane from Whitsundays. We had prior booked a bus shuttle to pick us up at the airport and drive us to Byron Bay. However, after waiting for the bus and it still not showing up I had called the Bus Shuttle company to make sure we were being picked up at the right spot. After talking back and forth on the phone we discovered that we were at the wrong terminal!! We had somehow scheduled the Bus shuttle to pick us up from the International Terminal as opposed to the Domestic Terminal. However in this instance, the Bus driver was kind enough to drive to the Domestic Terminal and pick us up!! He was a little grouchy that he was behind schedule now, but he warmed up. We were just thankful that he wasn’t leaving us stranded in Brisbane!!

    Side note: I have just recently stumbled upon your website, and am loving everything on it! Thank you for all of your insights and you have been inspiring me to figure out my American (well Canadian) Dream!

  9. Sean says:

    Thanks everyone for sharing your stories as well! It’s good to know that I

    1) Am not the only person to make a stupid travel mistake every once in awhile
    2) Am also not the only person to catch a lucky break or two!


  10. Leigh says:

    I think anyone who’s traveled has their fair share of stories. Usually when I’m in the midst of something that’s not particularly nice I do try to remember that it will be a good story or perhaps even a blog post. Most recently I had a 14 hour bus ride into the mountains of Colombia – not fun but interesting in hindsight and something I don’t regret doing.
    I have never gone to the wrong airport – in the wrong state – YET. But we have shown up for flights that have departed with no others scheduled for 24 hours.

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