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Why I Sometimes Struggle To Enjoy Vacations

Welcome to this post, “Why I Sometimes Struggle To Enjoy Vacations”!

I’m writing this post as I come back from a quick road trip to visit family this weekend. I also recently just got back from a 10 day international trip. 

Both of these trips were awesome. I got to spend a lot of time with family which is something I’m really trying to prioritize before heading off to college in a few weeks.

However, I would be lying if I said that I don’t sometimes struggle to enjoy vacations. In this post, I want to explain why. 

*Note: I don’t want this post to come across in the wrong way. I’m incredibly blessed and grateful that I’ve been able to go on so many vacations in my lifetime. My family is incredibly fortunate and I understand that not everyone is in the same boat. Some people never get to take a vacation in their lifetime, and they would do anything to be able to. 

But, going on vacation does come with a few struggles which I believe most people can somewhat relate to. I’m writing this post to share my thoughts and hopefully help someone out there understand perhaps why they haven’t enjoyed some of their vacations in the past.

Benefits of Vacations

Why I Sometimes Struggle To Enjoy Vacations

Before I bash vacations too hard, I want to start by sharing a lot of the awesome benefits of vacations. 

One of the most obvious benefits is time to slow down, rest, and relax. So often we go through our lives incredibly fast that we forget to take no time to slow down. 

Another benefit is that vacations can be a lot of fun. I know I have a really good time every vacation I go on. It’s a perfect excuse to spend time with family and make memories together. I know that I’m almost in a good mood on vacation.

This last one isn’t as obvious, but it’s one of my favorite things about vacations…you have time to think! In my regular life, I often go so fast that I forget to think. There’s something about vacation that brings new thoughts, fresh perspective, and big picture thinking. I love a long flight, a road trip, or just time relaxing to allow my mind to think.

Separation From Work

Why I Sometimes Struggle To Enjoy Vacations

While there’s some great benefits to vacations, there are a few downsides in my opinion. One of the things that I struggle with is separating from my work. Let me explain. 

For those that don’t know, I work as a freelancer and entrepreneur. I don’t have a traditional job. I basically work on my businesses non-stop. There’s no start and end of the work day for me. Sure, I take time to relax, but I just don’t follow a traditional work schedule. 

A lot of the work I do is done on an ongoing basis of needing to communicate with clients and team members. I can’t just go off-grid for a week without having repercussions in my businesses.

This makes it especially difficult to separate myself from my work on vacations. I need to check my phone for important messages at least a few times a day. As a result, it’s hard to completely stop thinking about my work and turn my mind off.

The positive side of that is that my businesses can continue to grow and produce income for me while I’m not even working! It’s definitely a benefit of entrepreneurship, but the downside is not really ever separating yourself from your work.

Read more about why I will be an entrepreneur for the rest of my life.

In addition, I’m a natural home-body which means I enjoy being home and in my regular routines. When I’m away from that I sometimes feel like I’m not functioning the best I can be.

Some people really don’t enjoy their routines and start to fantasize about their upcoming vacations. I think this is sort of a negative mindset because you hate your work so much and just live for vacations. 

I enjoy getting into my routines and really do enjoy the work I do. This makes it hard for me to take vacations, but I understand this is different for everyone.

Transition Time

Why I Sometimes Struggle To Enjoy Vacations

Another thing I struggle with on vacations is the transition time before and after the trip. I feel like it takes me several days before a vacation to get in “vacation mode”. Afterwards, it takes me several days to get back into the groove of my work and routines.

I really don’t like packing. I’m a pretty motivated person, but I often struggle to motivate myself to pack my clothes before a trip. I also don’t enjoy the process of wrapping up my work for several days before a vacation.

Once I’m there, things are great and I’m in a good space. But I really don’t like the prep-work of vacations. I know it’s kind of necessary, but that doesn’t mean I have to enjoy it, haha.

Coming back, it’s a similar struggle. It’s hard to get everything organized again and to gather the motivation to start working again after several days of a relaxing vacation.

Keys to a Good Vacation

Now that we talked about the benefits of vacation and why I sometimes struggle to enjoy vacations, I want to share a few keys to a good vacation:

  1. Leave your work in an organized state. If possible, try to wrap up as many projects as you can and leave as little as possible on your to-do list. The less you are coming back to, the better.
  2. Make use of the time you’re on vacation. Once you’re on vacation, utilize some of those benefits we talked about in the first section. Rest, relax, have fun, and take some time to think!
  3. Stay for the right number of days. You may not have much of a say in how long you’re on vacation, but if you do, think about how long you truly want to stay. I know any less than 3 days and things feel too rushed for me. Any more than 7 days and I kind of get sick of it and am ready to go home. I prefer vacations that are 5 days long where I have a day or two on either end for transition time.
  4. Coming back, try to get back into things as quickly as possible. I know it doesn’t sound enjoyable to jump straight into work. But, the faster you do, the faster you get out of that transition time. In my opinion, the transition time is the worst time to be in. You’re not relaxing and you’re also not productive during transition time. So, once your vacation is over, get back to work as soon as you can. I’m a firm believer that you should try to get through negative cycles as fast as possible. 
  5. Work on the right things when you return. The first thing I like to prioritize when getting back is a good weekly reset. Once I feel organized again, I start working on my obligations to other people (the things that I promised other people I would do upon my return). It’s easy to motivate yourself to do these items since other people have been waiting on you to do them. Lastly, I like to start with easy tasks or tasks that I am passionate about to get the motivation ball rolling. 

The Takeaway

That’s it! That’s why I sometimes struggle to enjoy vacations. I hope you learned something in this post and maybe have some better insight of why you haven’t enjoyed some of your vacations in the past. Please feel free to leave any comments, questions, or concerns down below. Otherwise, best of luck enjoying your vacations in the future!

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Hi, my name is Jacob and I am an 18-year-old located in Colorado. I love the outdoors, particularly, skiing and hiking in the mountains. And of course, I enjoy spending time with family and friends. I'm a freelancer working on Fiverr and an entrepreneur with many businesses. I’ve been an active member of my local FBLA chapter, participating and placing among the top positions at state for my business plans. I have a passion for business and finance and I love to share it with others! That's why I created this blog, to help other teens achieve financial freedom now and for the rest of their lives!

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