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Confessions of An Over Thinker Planning for a Vacation

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vacation planning over thinker

Summer is wrapping up and kids are either back in school or getting ready to go back to school. Randomly I thought it would be fun to share what an over thinker goes through when planning for a vacation.

What areas do you over think or over research whether personally or professionally? Do you think this has held you back in some way?

One personal example of over thinking is vacation planning. I think I actually enjoy the planning piece as much as I like the actual vacation.

However, when I am on the trip, I am exhausted and ALWAYS feel like I need another vacation to get away from the intensive itinerary I put together.

I am not a world traveler although I did visit South Korea for several weeks for the 2018 Winter Olympics. I do not even travel domestically. Try not to hate, but the only times I visited New York were to visit Syracuse University and when I fly into JFK or LaGuardia. As a big baseball fan, I did ooh-and-ahh over driving by Yankee Stadium.

What I absolutely love is to hike…solo hiking to be specific. Not the hiking that involves heavy backpacking gear and camping, but more of the mid-tier strenuous level of hiking.

I always spent a minimum of 2 nights to take advantage of the hiking experience, but my itinerary was packed and by the time I was home, I had to take the day off the next day just to recover. Mentally and physically I was drained because I had to stick to the schedule I put together for myself. Clearly you can tell by now that I am not that spontaneous. Perhaps I need to be spontaneous once in a while?

I have not had any desire to travel to Europe or other parts of Asia or any other specific place in the world. My favorite vacation spots have been hiking trips conveniently available to me in the states.

Here is how I generally planned my solo hiking trips, which were and continue to be my best vacation plans.

  • Research, research, research – I spend countless hours researching. I read hotel reviews on several sites beginning with TripAdvisor and Yelp. I read hiking trail reviews including researching hiking destinations and reading countless reviews on specific hiking trails. I mean I want to know the best hiking trails because of my limited time in that area. This also includes researching spots to eat in that area. The list goes on. I research a lot. I want to make the most of my time and get the most bang for the buck.
  • Itinerary is time based – I plan to the hour. My itineraries are meticulously created. This includes what time I wake up, sleep, eat, and drive. This includes how long each of my hikes are expected to last. The research I do on the hiking trails I select always gives the length of the trail and the approximate time it takes to hike. Based on my hiking experience, I have a good sense of how long it will take for me to hike based on how strenuous the hike is.
  • My day has to be filled – because of the way I create my itinerary, many will view this as excessive and actually stressful. I will not disagree there because many have said that to me. That is probably why I solo hike because I do not need to please others. That is also probably why I am single…I am selfish in that respect. My itineraries rarely have a chance to be spontaneous. However I do put in time to enjoy the scenery. Some of the hikes I have been on were absolutely breathtaking and I knew to expect this because of all the research I did looking at pictures and reviews.
  • Budgeting is always included – this comes naturally as I review hotels and restaurants. I have never gone over budget on any of my solo hiking trips, but I am also more conservative similar to the planned trip I made in August as part of my side hustle.
  • Accept that I will never have enough time – this one continues to be a difficult one to accept. I have a slight case of FOMO (fear of missing out) and part of the big reason for having an itinerary. At National Parks you cannot possibly enjoy each piece of a National Park within a few nights. I quickly learned to accept this fact, which goes back to why I research so much and am strict when creating my itinerary.

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