Working on Vacation: Should You Do It or Take a Total Break?

Taking a vacation when you’re an entrepreneur can feel like a tug-of-war: the pull between running a business and truly taking a break is real, and finding balance can be complicated. For women who are not only business owners but also caregivers, partners, and parents, the decision to work or unplug on vacation adds an extra layer of complexity.

As the boss (or as a solopreneur), it can be hard to step away when you know that the job is always there waiting. Plus, many of us find inspiration while traveling, which also makes it hard to disconnect from work completely.

But is it better to carve out a few hours for work on vacation or to take a complete break? Let’s explore what might work best for you, your business, and the people you love.

Why Women Often Feel Guilty About Taking Time Off (and Working on Vacation)

Before we explore whether women who own small businesses should completely disconnect from work during their vacation days, let’s chat about why women feel pressured to do so. Of course, not all women feel this way, but many do! So let’s get into it.

Cultural and Societal Pressures

Society often places women in the role of “always available” caregiver, whether it’s for children, partners, or co-workers. This can make it feel “wrong” to take vacation time or even a few hours for yourself, as the expectation is that you’re always there to support others. Women who also run businesses may find that this dual caregiving expectation creates added guilt and makes it all the more difficult to enjoy a break, even if they’ve worked hard to earn it.

Perfectionism and Responsibility

Many women in leadership positions feel a sense of responsibility for keeping things running smoothly, even when they’re away, and perfectionism can magnify this pressure. The idea that no one else could “do it quite right” often keeps women working on vacation, worrying about what might go wrong if they’re not constantly involved. Letting go of this need for control and trusting others can be challenging, but it’s essential for true relaxation and rest.

Guilt about Putting Themselves First

Many women find it hard to prioritize their own needs, especially when they have partners, kids, or a demanding job. The result is usually a strong sense of guilt around fully relaxing, as if taking a complete break or spending time on self-care is somehow selfish. Recognizing that your ability to support others increases when you’re well-rested is key to letting go of this guilt and giving yourself permission to recharge without feeling the need to justify it.

Pressure to Justify Vacation

Business ownership comes with its own unique set of pressures, especially for women. The need to stay connected 24/7, manage a team, respond to clients, and oversee operations can make remote work feel like an extension of life itself. The flexibility to work from anywhere can blur boundaries, turning vacations into “mini-offices” and keeping business owners in permanent “work mode.”

For women in high-powered roles, there’s often a subconscious need to “earn” their vacation by being available even while on it or by making up for it with more work afterward. This can lead to never feeling truly “off,” which only adds to the exhaustion that a vacation should relieve. Embracing that rest is as necessary as work itself is a mindset shift that can ease the pressure to justify or explain taking a break constantly. We promise, your future self will thank you for actually using your Airbnb’s Wi Fi to watch movies instead of writing reports or emailing clients on your laptop.

Fear of Falling Behind

Many business owners fear missing out on potential opportunities or letting clients down—yet another reason why they choose to work while on vacation. This “fear of missing out” (FOMO) can make you feel like a few days away will somehow set your company back, even if that’s not the case. Realizing that one week away will likely have no long-term impact on your business success can make it easier to take a full break.

The Case for Taking a Complete Break

No matter what your position, research consistently shows that our brains need regular breaks to avoid burnout, develop creative ideas, and process complex problems. Taking a complete break, especially during vacation days, gives the brain the downtime it needs to rejuvenate, allowing us to return to our work and personal lives with renewed focus and energy. It also keeps you engaged in and satisfied with your work.

According to Laura M. Giurge and Kaitlin Woolley in an article for HBR, “When they engage in work during time that they think of as leisure time, such as the weekend, they experience conflict between their expectations and reality, and as a result, they find their work less engaging and less meaningful.” Constantly working without pause can actually reduce productivity in the long term and impact overall well-being. True rest is essential for women with jobs that require high mental engagement.

The Benefit to Relationships

Completely unplugging on a holiday can be one of the greatest gifts for your relationships because it grants you the time needed to connect without the distractions of Slack messages or work email. By being fully present, you create lasting memories with loved ones. They’re more important than that one extra work call! This focused time together allows you to enjoy your family or friends without interruptions and enriches your relationships far beyond what any brief moment between calls or messages could offer.

Setting Expectations for Your Team

Remote work can be such a joy; it lets us work outside the office, after all! But it also means that more people than ever feel pressured to work for their company while on vacation. Referencing a study in her article for CNBC, Jennifer Liu writes that “Some 35% of Gen Z workers say they feel guilty not working when they’re on vacation.” The same study showed that 29% of others from earlier generations feel the same pressure.

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Working on vacation might feel manageable for you, but it can signal to co-workers and employees that they should be “always on,” too. As a boss, solopreneur, or small business owner, the example you set matters; when a co-worker or employee sees you responding to work emails from a coffee shop on a trip, they might assume that they, too, need to respond, even if they’re away. Don’t let this happen!

Letting yourself rest fully creates a culture where your team feels supported in taking their own breaks, ultimately benefiting the entire organization’s morale and productivity.

The Value of Being Present

Vacations offer a rare and beautiful chance to step out of the “doing” mode and be fully present with yourself, your family, and life. By resisting the pull to check your phone or “just answer one email,” you open yourself to a deeper connection with the world around you—whether that’s a leisurely morning coffee with your partner or exploring a new city with your kids.

This time away from work can clarify your priorities and help you feel more grounded. Who knows, you might leave with a fresh perspective that benefits your personal and professional life long term.

Finding a Middle Ground: Working in Moderation

If taking a full break feels impossible, finding a middle ground can help you stay engaged with your business while prioritizing your vacation. Moderation lets you define when and how you’ll work, making it easier to enjoy your time off without feeling completely disconnected. By setting boundaries, involving family in your plans, and focusing only on essential tasks, you can enjoy the best of both worlds—maintaining some work engagement without letting it consume your entire trip.

Establish Boundaries

Setting clear boundaries before you leave can be a game-changer, allowing you to plan specific times or days to check in without letting work consume your entire trip. Defining these hours in advance gives you the mental freedom to relax. Work has its set times and that’s enough.

Communicate with Loved Ones

Discussing with family or a partner what minimal work engagement looks like can ease tensions around working while on vacation. Let them know you might spend a few hours catching up on essential tasks at a coffee shop or answering quick work emails but that the majority of your time will be spent together.

Focus on Essential Tasks ONLY

Before leaving, decide which tasks are truly essential and which can wait until you’re back. Limiting yourself to only the high-priority items frees up more time for relaxation, allowing you to support your business without letting it take over your break entirely.

Preparing for a Real Break: Setting Up for Success

To truly enjoy a break, preparation is key. By setting up systems that allow your business to operate smoothly while you’re away, you can relax knowing everything is under control. Automating routine tasks, delegating key responsibilities, and planning how to handle inquiries and emergencies in advance can keep clients and colleagues reassured and your mind at ease.

These small but impactful steps make it possible to leave work behind and return refreshed. You’ll head out on vacation knowing that you set yourself—and your team—up for success.

Automate and Delegate

Using tools to automate repetitive tasks or delegating responsibilities to trusted team members can keep your business running smoothly while you’re away. This setup lets you relax, knowing that daily processes, like responding to simple messages or handling minor issues, are in capable hands.

Create an “Away” Plan

A well-thought-out OOO message and a plan for handling inquiries can reassure clients and customers that their needs will still be met in your absence. Letting others know you’ll be offline and giving clear directions for emergency contact shows professionalism and sets expectations, allowing you to relax knowing everything is prepared.

Establish Emergency Protocols

Decide in advance what constitutes a true emergency and how it will be communicated, whether through a specific platform or a phone call. By defining this, you eliminate the need to constantly check in “just in case,” allowing yourself the freedom to truly disconnect.

Reflection: What’s Best for You?

Think about whether you genuinely enjoy light work on vacation or need a full break to feel recharged. Some people thrive with a bit of structure, while others need a complete disconnection to truly reset, so it’s essential to find what works best for you personally and professionally.

Take time to consider what your family or partner hopes for during the vacation and how that aligns with your ideal experience. If the people in your life need your full attention, making space for this can deepen relationships, creating a shared experience without work distractions.

Reflect on recent stress levels and whether this vacation could be a chance to recharge fully. If you’re feeling stretched thin or exhausted, allowing yourself a complete break can be invaluable for long-term health and work satisfaction.

Actionable Tips for a Balanced Vacation

Test out a weekend without work to see how it feels, whether it brings clarity, or even if it’s challenging. This short-term experiment can show you what a full break could be like and help you fine-tune your approach to longer vacations.

Consider setting a quick check-in time each day or every other day to respond to messages without getting drawn into tasks. Having a set schedule can help you stay on top of critical things without letting them overshadow your vacation.

Practicing mindfulness, whether through breathing exercises or grounding yourself in the present, can help you resist the urge to check work and be more fully present. This can also enrich your time with loved ones, allowing you to enjoy your vacation for what it is—a well-deserved break.

Final Thoughts on Closing Your Laptop While on Vacation

In the end, there’s no one-size-fits-all answer to the question of whether working on vacation is healthy and acceptable—what works best depends on you, your family, and your business. It’s perfectly okay to make choices that feel right for where you are now and to give yourself the grace to change your approach as you and your needs evolve.

Whether you decide to work a little or fully unplug, remember that vacations are about recharging. Embrace what brings you rest and balance so that you can return with fresh energy and renewed inspiration.