The holiday season is fast approaching, and for many entrepreneurs, the thought of taking time off may seem daunting—or even impossible. As female entrepreneurs, we juggle multiple roles, from running businesses to managing households and being there for family and friends. It’s easy to feel that stepping away, even briefly, could lead to missed opportunities or falling behind.

But let me share something with you: taking time off is not just a luxury—it’s a necessity.

Recently, I took a three-week trip to Portugal, which was a game-changer for me, personally and professionally. While I initially had hesitations about such an extended vacation and leaving my business behind, this break became an essential reminder of why I became an entrepreneur and why rest and recharge are critical for success. Here’s how I planned my time off, the lessons I learned, and how you can do the same this holiday season.


1. Plan Ahead: Protect Your Time and Business

Checklists are more than just a way to keep track of tasks—they provide mental clarity and peace of mind. Research shows that creating a checklist relieves cognitive load, allowing the brain to focus on higher-level tasks instead of holding onto minor details. By breaking down tasks into a series of small, manageable steps, checklists make complex processes (like packing for a trip) feel more organized and achievable.

Here’s why checklists are so effective:

Before heading to Portugal, I knew preparation would be key to fully enjoying my time away. Here’s how I approached it:

  • Set Boundaries: I informed my clients and team well in advance about my trip. Clear communication is vital, whether through email autoresponders, a note on your website, or a quick heads-up to key stakeholders.
  • Automate What You Can or Work Ahead: Automations saved me from worrying about daily tasks. For instance, Blogs and social media posts were scheduled, client communications were streamlined with email workflows, and systems were in place to handle inquiries.
  • Delegate: Don’t be afraid to ask for help. Whether it’s an assistant, a team member, or a trusted partner, delegation ensures that things run smoothly while you’re away.

Tip for the Holidays: The same strategies can apply to holiday breaks. Schedule communications and workflows ahead of time, and give yourself permission to let go of what isn’t urgent.

2. Let Go of the Fear of Falling Behind or Missing Out

One of the biggest hurdles for entrepreneurs is the fear that the world will fall apart without us. Or maybe there will be a missed opportunity. But the truth is, it won’t

During my Portugal trip, I learned the importance of trusting my systems, my team, and my worth to take this trip. I signed a new client right before I left. By being honest about the trip and my availability, we discovered that it was best for both of us to delay our start until I returned. It was then that  I realized that keeping those boundaries didn’t just benefit me—it also gave my team a chance to step up and shine. I was leading by example to my clients.

Ask Yourself:

  • What’s the worst that could happen if I’m not available?
  • Do I have systems in place to minimize risk?

Sometimes, the fear is just that—a fear, not a reality. 

Tip for the Holidays: Trust the systems you’ve built. And if you’re still in the process of building those systems, view this time off as an opportunity to identify gaps for improvement in the future. Don’t be afraid to communicate your needs to those you are working with or will work with; it could be a win-win for everyone. 

Bonus tip: When you have very limited time, anything that is not important will be dropped, postponed, or forgotten. Anything that falls into that category, it’s time to reconsider its importance. It might be time to get rid of those tasks. 

3. Create White Space in Your Schedule

Entrepreneurs often feel the urge to fill every moment with productivity, and that has often spilled into my vacations. But one of the most important lessons I’ve learned is to intentionally create white space—unplanned time in your schedule. I do this in my workday with breaks, and I’ve learned this is even more important when I’m on vacation. This space isn’t about being lazy; it’s about giving yourself room to rest, recharge, and adjust when life throws surprises your way.

Why White Space Matters:

  • It prevents burnout by giving you time to breathe.
  • It allows space for creative thinking and problem-solving.
  • It creates flexibility for unexpected changes or delays.

As mentioned, I build white space in my every day by leaving white space in my calendar and buffers between commitments. I have also learned to say “no” when “hi” gs don’t fit don’tign. 

With vacation, I plan for lots of free time. I don’t book a tour on the same day we travel, and I break up walking tours into small-sized pieces. It leaves lots of time to grab a coffee, ice cream or drink sprinkling wine and eat oysters while watching the boats. 

During my trip, the time spent sitting on a train or strolling through quiet streets gave me the chance to dream, think, and plan. White space isn’t wasteisn’te—it’s where it’sity and inspiration live.

Tip for the Holidays: As your calendar fills with obligations, be intentional about leaving gaps. Whether for a quiet walk, a cozy wine or tea break by the fireplace, or simply doing nothing, these moments will restore you and make the busy times feel less overwhelming.

4. Re-entry: Easing Back into Your Business

When I returned from Portugal, I didn’t dive headfirst into work. Instead, I eased back in intentionally.

  • I reviewed what worked (and didn’t) while I was gone.
  • I focused on high-priority tasks first, leaving less urgent ones for later.
  • I carried the lessons from my time away—especially the importance of being intentional about my time and setting boundaries around my day. 

Tip for the Holidays: Plan a buffer day or two before returning to full work mode after the holidays. This allows you to transition more smoothly and with less stress. 

5. The Holiday Season: A Chance to Practice Self-Care

The holidays are the perfect excuse to take time off and reset. As women, we often put everyone else’s needs before our own. But remember: you can’t pour from an empty cup.

Give yourself permission to:

  • Celebrate: You’ve worked hard all year; celebrate your wins, big or small.
  • Reflect: Use this time to evaluate what’s working in your business and life and set goals for the year ahead.
  • Rest: Step away from the hustle and enjoy being present with loved ones—or even just with yourself.

Final Thoughts: Rest Is Part of Success

Taking time off doesn’t mean you’re abandoning your business or losing momentum. On the contrary, it’s a sign of strength, self-awareness, and smart leadership.

Full transparency: I did work while I was away. But my day-to-day tasks were planned, automated, scheduled, and delegated. I only worked durning pre-scheduled days/hours, and I was focused and intentional because I had limited time. 

The rest of the time, I soaked up the culture, the people, and the beauty of the country I was in. 

As a female entrepreneur, you have the power to design a life and business that works for you. And part of that design includes rest. Whether it’s a trip abroad, a staycation, or simply unplugging for a few days over the holidays, remember: you deserve it.

So, this holiday season, I encourage you to take time off intentionally and wholeheartedly. You might be surprised at how much better you—and your business—will be for it.

I wish you a joyful, restful, and inspiring holiday season!

Are you ready to create a plan for stepping away and scaling up? Let’s work together to make it happen.

Almost everything will work again if you unplug it for a few minutes, including you.

Anne Lamott

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