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6 Things That Can Ruin Your Sabbatical

Taking a sabbatical is a big commitment for most people. And along with big commitment comes big questions and fears. So how can we make sure to not waste this amazing experience? We’ve noticed 6 things that can ruin your sabbatical.

Let’s find out what they are! 

6 things that can ruin your sabbatical

More and more people are opening up to the possibility of going on a sabbatical. It’s becoming more popular as a reason for people to either leave their jobs or switch up their career paths. 

“What if the new word for our generation wasn’t burnout, but sabbatical?” Read the full blog here

Before we continue, what exactly is a sabbatical?

A sabbatical from a traditional perspective is often an agreed upon period away from work, usually unpaid, where you still remain an employee of the company. However, the traditional rule books are being thrown out the window with newer sabbatical experiences taking place. Some people leave their jobs entirely, some work abroad for extended periods of time, and some take a few months off work to focus on their well-being.

So, what could ruin such an amazing experience?

6 things that can ruin your sabbatical

What we find here at Middleton & Company is that some people are afraid of going anywhere even before they begin the planning process. They focus more on what could go wrong, than what can go right! Here, we summarize some potential things that can ruin your sabbatical experience, and how to avoid them, to set you up for sabbatical success!

#1 Letting your sabbatical “stay as an idea” instead of actively creating the experience


How often have you had a dream or an idea and it’s stayed exactly that? Here at Middleton & Company, we work to proactively turn your ideas into goals, and your goals into a lived experience. It takes courage to say yes to your ideas; it can be the hardest part of the whole process. Once you’ve committed, though, everything can start falling into place with the right strategy and support.

We know that ‘ruin’ is a strong word, but take this real-life example from one of our past clients:

We had a couple who had a great sabbatical plan in place. The date was set, they were actively saving up, and everything was about to begin. The reason they had wanted to take a sabbatical was to gain more clarity on their future career path – a common reason we hear. That was until a new job opportunity came up and they chose to accept it, delaying the entire trip indefinitely”.

The sabbatical went sideways before it even began.

While it is great when new job opportunities, promotions, etc. come up, continually taking them can mean you maybe never get off the “carousel”. You still like the idea of a sabbatical, but you don’t get the time away that you originally wanted.

We’ve also seen people begin hesitating as they begin to get into the planning details. Doubt takes over. They ask themselves how they’re really going to do it – both financially and logistically – how will they get it all done? Allowing hesitation to trip you up can really impact the experience.

“There’s always going to be a reason why we can’t do something. Life is potentially always getting in the way of what we want.” – Kailie Abascal, Financial Planner

>> So, what can you do instead? Our advice is to get very clear on your ‘why’ for going on a sabbatical. This will help you when distractions arise! If you are offered a promotion or a new opportunity, does that align with your ‘why’ for going on a sabbatical? Or is it actually feeding into what you don’t want long term? Being honest with yourself is really important. Read point 2 below to learn more about your why!

>> If you find yourself hesitating a lot, changing your mind, and feeling guilty because you thought you would take your sabbatical 2 years ago and it still hasn’t happened, it might be time to ask for support. We help you set a date and plan your finances, your career, and your dream sabbatical around it! If you’re curious, you can book a free discovery call with us!

sabbatical planning resources

#2 Not knowing your personal ‘why’

We previously mentioned it, and we are mentioning it again: Your ‘WHY’ is the foundation from which you’ll create your sabbatical plan! Having the idea of taking a career break is one thing. Clearly understanding why you’re taking a break is something else!

Having a clear and personal ‘why’ can help you to stay on track in more difficult moments, both in the planning process and while on a sabbatical. And having an emotional relationship with your ‘why’ can make it that much stronger. It’s what helps you to recalibrate in times of change or when negative experiences occur.

Take this client experience as an example:

“One of our clients was this couple who had an amazing sabbatical planned, had quit their professional jobs, packed up their house, and moved abroad. And then the pandemic hit. They couldn’t stay in the country they had originally chosen. Instead of giving up on the experience, they reconnected to their ‘why’ and found a different country that met their needs. This kicked off a brand new journey that they never would have planned”.

While a lot of people would have been discouraged and maybe even given up, they were able to pivot and live the experience they were desiring. 

On the flip side, NOT knowing your ‘why’ can amplify unexpected or inconvenient occurrences. And in our experience, there’s always something unexpected that happens while traveling. In these moments, you can ask yourself:

  • what are you really hoping to get out of the experience.
  • Is there a way to appreciate that things aren’t going perfectly to plan?
  • Can you still accomplish your ‘why’?

>>> Our advice? Write your ‘why’ down and get very clear. Note how you want to feel each morning and the exact types of experiences you want to have. This is an exercise we give our clients, and we review their answers often. As financial planners, we can use this to help make better decisions in regard to their financial plans.


what can ruin your sabbatical

#3 Not having clear enough goals


“I wanted to drop the structure of my life. I knew that while I was enjoying climbing the career ladder, and I was successful at it, it wasn’t what I wanted to do forever. When my husband and I took our break, we looked for experiences that specifically led us to places that we wouldn’t necessarily have chosen ourselves.” Taylor Anderson, Financial Planner

Knowing ahead of time what you want and having goals can help you get the most out of your sabbatical experience. 

We advocate for having two different goals:

  1. One that is connected to your career growth
  2. One that is more connected to your desired experience – a more emotional goal that transcends outside of your career.

You can prioritize both goals.

 You can grow your career and broaden your life experience through your sabbatical. Both goals can support each other simultaneously.

Going on a sabbatical can open up opportunities that would only ever exist because you chose the sabbatical experience itself. For example, having that life experience on your resume can be beneficial to employers and open up new doors upon your return. And how you balance your work and personal lives may also be more in line with your values. Sound good? We think so. 

Here are three questions to consider:

  1. What can you do in your career that can help your sabbatical?
  2. What can you do on a sabbatical that will boost your career?
  3. How can taking a sabbatical offer you the clarity you need about what you want next in your life?

Your answers can help you develop goal statements that give purpose to your time away. They don’t have to be SMART goals, but it sure does help to have a general direction of where you want your life to go after your sabbatical.

Both types of goals can propel your career forwards or in a brand new direction.

>>> Spending time during the planning phase to set your sabbatical goals will make the whole process much more intentional, smooth and will help create THE experience you currently need and desire. Not sure what your sabbatical goals are? Let’s find out. Click here to define your sabbatical goals in 5 questions.


#4 Not being prepared for the ‘unplanned’ 


Your plans will change, or you will encounter things that are out of your control. Being flexible will allow you to simply bend when unexpected things occur, instead of breaking.  

“I spent the summer in Cuba before moving to Mexico to teach English. The airline that I had booked my ticket with went out of business and I was completely unaware until I arrived at the airport. I had to buy a new ticket on the day of travel.” Kailie Abascal, Financial Planner

Moments like this can happen multiple times on a trip, so it helps to be flexible with your expectations. And to have some buffer in your budget so you have options when the unexpected does come up (we specifically plan for these in our process). We also recommend getting insurance that covers you well for any occurrence that is out of your control. 

If you expect your plan to go exactly as, well, planned, you will likely be surprised at least once while you’re away. And you’ll likely be justified in feeling frustration or anger at some point(s). Some things are just irritating, unfair, inconvenient…a whole host of other-than-pleasant adjectives. And from our perspective, that’s just international travel for you. We think it’s character-building, and will actually help you on your return to work. Being able to navigate change and challenges with grace is a great skill set that employers actively seek out.


>>> You can’t control everything, but you can control your expectations, the amount of flexibility you build into your plan, and your reaction/response to any number of experiences that come your way. Thinking about this and planning for it ahead of time can be helpful. If you’re ready to go with the flow a little, you may just come back with some amazing, adventurous stories! 

Make sure to also have the funds to cover any unexpected experiences. 

“8 unexpected ways to fund your sabbatical”, read the full blog here

sabbatical mistakes

#5 Leaving no room to switch up your destinations


Last-minute changes can be one of the best parts of traveling abroad. When we can reframe experiences from negative to positive, it opens up so much more for us. 

 “While in Indonesia, we had booked our trip, unknowingly, over Ramadan, when a lot of things are closed and in-country travel is hectic. We chose to change our travel plans last minute. Over dinner, in Singapore, we met a couple who recommended the Philippines, and from this conversation and a chance meeting, we pivoted our plans and went somewhere that we weren’t planning on. It ended up being one of our favorite places and we hope to go back again with a budget that will allow scuba diving. When your plans change, it can sometimes be the best thing that happens!” Taylor Anderson, Financial Planner


This is an example of adding a whole new country to an itinerary, but there are often also smaller versions that come up. When staying in a place for a little longer than a typical vacation, without a packed agenda, there’s likely to be at least one opportunity to get guidance from a local or fellow traveler to go somewhere that wasn’t on your list but that might be amazing. Who says that you have to show up to every new place with a full list of things you want to do? Maybe it works to just go somewhere interesting or beautiful and ask around! 

Experiences such as an off-the-beaten-path hike to a waterfall, a hole-in-the-wall coffee shop that makes amazing pastries, a little-known viewpoint, and a temple that has a gatekeeper if you just know where to ask…These can be some of the most memorable moments of the trip, and they weren’t planned for. You have to be there to discover them.

>> So as much as we love planning, we love leaving flexibility for the unknown as well. That’s planning in and of itself if you ask us! 


#6 Not planning downtime

It’s tempting to try and take advantage of every single moment on a sabbatical (I mean, who knows if you’ll do this ever again, right?). But traveling and being away for a longer amount of time is different than a vacation. You’ll need to do laundry, buy replacement toiletries, and grocery shop, not to mention plan ahead for visa requirements if you’re traveling between countries, coordinate transportation logistics, and find places to stay as your travel itinerary adjusts. And wait, are you ever going to edit and post photos, journal, or call home? The sabbatical experience is awesome, but it’s also tiring. 

Even if you want to soak up as much as possible on sabbatical, not leaving time for the realities of life and the cumulative strain of travel can lead to burnout. Ironic, right? Burnout during a sabbatical, how can that be?  

Downtime means different things to different people, so what does it mean to you? Do you like it evenly mixed into your days, or do you like to run hard for a while and then take an extended breather to recharge? What kind of setting do you need to relax in? Have you built this into your plans? 

>>> Make sure to not overpack your schedule and remember things take usually longer than you ay imagine.

6 things that can ruin your sabbatical

As you can see, you have control over your sabbatical experience. ‘Ruin’ is a strong word. Just committing to going, and having some idea of what you want, all the while leaving flexibility to change, can help keep your sabbatical a positive experience. 

From the planning to the trip itself, to your return, we are with you every step of the way and we help you avoid these 6 things that can ruin your sabbatical. 

>> If you are unsure of what the first step could be, get in touch. With experience in both sabbaticals and financial planning, we’re here to support you in making your sabbatical dream a reality. Ready to get started? Click here to learn more.


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This blog post is provided for educational, general information, and illustration purposes only. Opinions expressed herein are solely those of Middleton & Company, unless otherwise specifically cited. Material presented is believed to be from reliable sources and no representations are made by our firm as to another parties’ informational accuracy or completeness.
Nothing contained in the material constitutes financial or tax advice, a recommendation for purchase or sale of any security, or investment advisory services. We encourage you to consult a financial planner, accountant, and/or legal counsel for advice specific to your situation. Reproduction of this material is prohibited without written permission from Middleton & Company, and all rights are reserved.