Guest Post: Taking the Fear Out of Trips

While I’m more of a stay at home kind of guy, I do enjoy listening to the travel adventures of my friend Keri from Heels First Travel. So much so, in fact, that I’ve even considered traveling myself at some point (for those who know me, this comes as a truly amazing revelation). When I asked Keri for her top suggestions to take the edge off my travel concerns, she offered the following excellent advice.

I’m an avid traveler. And by avid, I mean crazy. Like spending 25 hours in Alaska because a cheap fare came up and I really wanted to see it but couldn’t take time off work. So at this point I’ve made almost every mistake with my flights, hotels, and tours you can make. And far from ruining my trips I’ve actually found it freeing. Because now “the worst” has happened and I no longer have to worry about what I might have forgotten and can dare to be impulsive, spontaneous, and last minute.

But it took quite a while for me to initially get into travel because I was afraid of messing up and not knowing what I didn’t know. So I’m here to spare you my paralysis. If you want to travel, start booking! Are you going to get things wrong? Yes! And is it the end of the world or will it totally ruin your trip? Probably not.

Things I’ve learned:

  • Eventually you will oversleep and miss your flight. You will be able to rebook and/or afford a different last minute ticket.
  • You will not hear your flight announcement and miss your flight even when you’re in the airport. You might do it twice. Or more. This is why they have airport hotels.
  • No matter how much research you do, the place you most want to see, in my case the Louvre, will be closed, in my case on strike, the whole time you’re there. Think of it as a great opportunity to see the lesser known, hopefully just as awesome but less crowded, sites in the area.
  • You will show up at the hotel only to discover you had one more page to go before your reservation was confirmed, you booked for the wrong dates, or the hurricane that swept through New Orleans over Labor Day left your hotel without power. This is what Hotwire and Priceline are for.
  • Or you show up to discover the pictures on the website had caught that hotel at its absolute best, never more to be seen again. That just makes for a better travel story. J
  • Public transportation is unreliable (2 hours wasted on a 36 hour stay in Sydney Australia) and cabs are far more expensive than you think ($200 to the airport). Just roll with the punches and think about it as investing in colorful memories.
  • Sometimes the $5 mini bar snacks are better than wandering an unknown city at night for 45 minutes looking for a 7-Eleven.
  • You will repeatedly forget and re-buy phone chargers, laptop chargers, deodorant, and toothbrushes. If you’re averaging forgetting one thing or less every trip you’re doing great!

Some consider me an expert at travel, but I’m not afraid (although maybe a little embarrassed) to admit I’ve already re-experienced 4 of the things on the list above since the year started. So if a so-called travel expert can make these mistakes, you’re totally off the hook.

For more on Keri’s adventures and travel tips visit

Special Bonus Post!

Many thanks to the ladies over at Heels First Travel for having me do a guest post! Check it out now, and be sure to check out all of their great travel advice!


Go ahead, I’ll still be here when you get back.