Vacation tips for planners traveling with non-planners

This year I took a group ski vacation to the Adirondack’s, and summer kayaking vacation to Pictured Rocks National Lakeshore in the Upper Peninsula of Michigan.

While I had a great time at each, it was also a bit challenging for me as a planner hanging around non-planners for a week.  It is good to get a personality assessment, such as Meyers Briggs, to understand your style of communicating and interacting with others so that you can adjust your style to others as needed.

I did learn a few things that will help me on future trips.

  • Go with the flow.

Accept the fact that if you’re a hard-core planner, you’ll probably be the most “planningest” person in the group, and reel yourself in to go with the least common denominator.

For the ski group, we planned where and when we were going to the destination, and who was cooking a meal. And that’s it. I really had a hard time not knowing which night I’d be cooking a meal, and what we were doing each day, but I had to let that go because no one else wanted that kind of structure on the trip.

With the kayaking vacation, we planned out which guided trips we were taking, but that was it.

Though it was difficult, having a more “unplanned” vacation allowed for more serendipity. We enjoyed being in the moment and had the flexibility to take advantage of new activities, new restaurants, and doing what we felt like “in the moment.”  And I found that to be kind of fun.

  • Make your own plans.

Even though each vacation was unstructured, I did have the opportunity to make my own plans. For the ski trip, I planned out a snowmobiling excursion and my own cross-country ski plans. I had to reserve the snowmobiles, but I didn’t have to plan out the cross-country skiing – and it was kind of freeing to relax in the morning and decide each day what time I wanted to head out.

For kayaking, I added on 1-2 days at the beginning and a few days at the end of the trip to build it into a week-long trip. If I was driving that far, I wanted it to be worth my while. Others decided just to head home.

  • Let the trip unfold on its own.

I’ve developed an appreciation for letting a trip unfold on its own and letting others take the helm. It’s relaxing as I don’t have to do anything. It’s fun as others will take me to explore new places and new things. And I’m learning self-control the more I tell my inner planner to sit back and relax.

  • It’s Ok if things don’t go as planned.

This summer I first had a camping trip in which it rained and rained (like 3 inches of rain, and rain every day), followed by a camping trip in which it did not rain at all.

I can’t expect everything to always go perfectly, and if I let go of my expectations, it’s easier to move forward and hope the next trip works out better.

  • Plan for a smooth transition back to the office.

The one thing I hate about vacation is that my weeks before and after a vacation are horrible in terms of trying to get work done. I’m an entrepreneur and do it all myself. This time, I closed up most projects before I left, and I came back on a Friday, which gave me the weekend to unwind, unpack, and do laundry. I also kept up on emails while on the trip so I did not have to come back to them.

I still have a hard time getting away, but these practices did make the week after slightly more bearable.

In summary, being aware of your personality style and adjusting it to others will help you interact better, especially on group trips and in communications.