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Is Your 5-Year Career Plan Missing a Sabbatical? Here’s What Might Be Holding You Back

Have you thought about your 5-year career plan? Does it feature a big promotion, a career pivot, a coveted job title, an invitation to a renowned conference, or finally working for your dream company? Most of us focus on climbing the career ladder, but what about carving out time for yourself—for your family, your passions, or even just for dreaming and exploring?

What about a year-long sabbatical?

Wouldn’t a career that includes both ambition and personal dreams be the real definition of success? We invite you to consider adding a sabbatical year to your 5-year career plan.

Can a sabbatical prevent burnout? Click here to find out

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Is Your 5-Year Career Plan Missing a Sabbatical?

Not everyone with the means and desire to take a sabbatical will actually take one in their lifetime!
How come?

“Over the years, we’ve realized that people may have the money to take a break but they lack confidence in being able to step away from a steady paycheck. It feels like they want permission, someone telling them “yes you are allowed to take a break”. Financial planning helps them get that confidence, to show them they are still being smart about their future and their money. It helps them see that things are still under control and that they can take the break they’ve worked hard for.”

Even if you have the resources, internal and external barriers can hold you back from fully embracing a sabbatical. In this blog, we’ll explore some of the common obstacles, helping you address them so that you can carve out the break you deserve.

So, what’s really stopping people from taking a sabbatical?

What's holding you back from your sabbatical?

Three Common Concerns Keeping Professionals from Taking a Sabbatical - And How to Tackle Them

Money can be planned for—financial planning is essential, and that’s where we come in! But the truth is, money isn’t the only barrier holding people back from taking a break. While finances are often cited as the reason, they’re sometimes used as a convenient excuse to avoid addressing deeper concerns. Before diving into the financial side, it’s essential to tackle other key obstacles that prevent professionals from making their sabbatical dreams a reality.

Here are three significant concerns we’ve found that often keep people from moving forward with their plans. These lingering questions and doubts can stall the steps needed to bring your sabbatical vision to life.

1. What Will I Do for Work When I Return?

The uncertainty around job security and career progression is a common fear. Questions like, “Will my skills still be relevant?” “How will employers view a gap on my resume?” and “Will I still fit into the industry?” often surface, creating doubt about what lies on the other side of a break.

💡 Action Step: Integrate your sabbatical into your career plan. 

Plan your sabbatical strategically. Set aside time at the end of your break for a smooth reentry, and ensure that your financial plan includes a few months of expenses so you’re not rushed to find work.

Consider best- and worst-case scenarios. Really go into detail about what these scenarios may look like. Is your best case scenario worth taking the leap for? What actions can you take now to set yourself up for success? For example, if your best-case scenario is returning to your current company, learn how to pitch your sabbatical to your boss. Or if it’s to work for your dream company, start networking and consider using part of your sabbatical to gain skills that will make you an ideal candidate.

How to talk about your sabbatical to your manager: learn more

Use LinkedIn’s “Career Break” feature to highlight the skills and experiences you gained during your sabbatical, demonstrating personal growth and adaptability to potential employers. Instead of hiding your sabbatical, showcase it proudly.

2. How Will I Find Time to Plan a Sabbatical? I’m Already Too Busy.

With packed schedules and family responsibilities, carving out time to plan a sabbatical can feel daunting. Months and years slip by, and the dream of taking a break lingers on the back burner, never quite reaching the top of the priority list.

💡 Action Step: Use your project management skills

Think of your sabbatical as one of the “big rocks” in your life—something worth prioritizing. Instead of tackling everything at once, break down planning into smaller, manageable steps. Use a project management approach to gradually work toward your goal, or even use vacation time as a “mini practice sabbatical” to get a feel for what will work best. If planning feels overwhelming, don’t hesitate to consult a professional to help you map out the process. You can outsource this!

Is Your 5-Year Career Plan Missing a Sabbatical?

3. What About the Kids, the House, and All Our Stuff If We Go Abroad?

The logistics of a sabbatical—especially if it involves travel—can feel impossible. Questions like, “Where will the kids go to school?” “What happens to the house and car?” and “Who will care for the dog?” can make a sabbatical feel unattainable.

💡 Action Step: Start by imagining the positive possibilities

Establish your non-negotiables early—consider school schedules, healthcare access, or experiences that are a priority for your family. Visualize the unique experiences your sabbatical might offer. For example, do you want your kids to attend school in a different language? Would you like them to experience one location or multiple locations? What would you like to be doing while they’re in school? Start to tick off the questions one by one to get a picture of what life on sabbatical might look like.

Then for your home, car, and other possessions, evaluate what’s essential and what can be sold, donated, or rented out. Consider options like hiring a housekeeper or using a service like TrustedHousesitters for pet care, so you return to a well-maintained space. Or, if it aligns with your goals, explore the idea of selling your home, car, or stuff to alleviate financial burdens. 

On the flip side, you can store your stuff or bring some of your things (even big things) with you! Be creative and don’t limit your options before fully exploring what it would take for you to have things play out exactly as you would like.

If you’re reading this, it’s likely because the idea of a sabbatical is calling to you. Don’t let doubts stand in your way. Before deciding that time away isn’t possible—whether due to finances, career opportunities, or personal commitments—give yourself the chance to imagine what it could look like if you went for it. Often, these concerns remain in our minds, making it hard to step back and find practical, realistic solutions.

Plan Confidently for Your Sabbatical—and Beyond

When considering a sabbatical, knowing you have a sound financial plan can make all the difference. At Middleton & Company, we empower you with clarity and confidence to pursue your dreams while staying on track with long-term financial goals. From assessing your current finances and budgeting for your sabbatical, to optimizing tax and investment strategies, our financial planning process covers every aspect of your sabbatical—before, during, and after—addressing both the practical and personal elements of taking a meaningful break.

financial planning for sabbatical planning

We’ll work with you to identify what’s essential for your time away and ensure you have the financial stability to come back to a life that makes sense to you! 

It’s never too early to start planning for a future sabbatical. Whether you’re looking to take a break in the next five years or ready to step away in just a few months, we can guide you through strategies that leverage low-income years to your advantage. Our goal is to help you fully embrace this journey without compromising your financial future.

Ready to Explore Your Sabbatical Possibilities?

If a sabbatical is calling you, let us help you make it a reality. Schedule a free consultation with Kailie and Taylor to explore a financial plan tailored to your goals—so you can confidently step away from the everyday and into an adventure that’s truly your own.

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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.