Workcation Tips for CEOs: How to Stay Connected While Taking a Break

As a business owner, I often find myself juggling between taking time off and keeping the business running smoothly. Enter the workcation—a blend of relaxation and work that lets me unplug without feeling totally disconnected from my clients' businesses.

Now, before you think, Wait, don’t you preach about boundaries and real time off? Yes, I do! But as much as I love winding down, I’ve realized that I feel much more at ease when I have regular check-ins. It’s not about diving into major projects or running full steam ahead. Instead, it’s a way to keep my finger on the pulse and ensure that everything is flowing as it should—without overwhelming myself.

Here’s how I manage my workcations:

1. No Client Meetings, Just Check-Ins

I don’t take client meetings during my workcation. I want to truly enjoy the time away from the day-to-day hustle. But I also know that my clients’ businesses feel like my own. So, I do quick check-ins to ensure things are moving along smoothly. This gives me peace of mind, and my clients appreciate knowing I’m still in the loop.

2. Streamlined Communication

I use email, Slack, WhatsApp, and project management tools like Asana and Notion for communication during my workcation. These platforms make it easy to send updates and stay on top of important tasks without having to engage in long conversations or meetings. It’s all about efficiency!

3. Heavy Lifting Happens Before I Leave

In the weeks leading up to my workcation, I tackle the big projects and get all the heavy lifting out of the way. This is key! I give my clients 2-3 months' notice so we can plan and prioritize any major tasks before I go. I make sure everything is on track so that during my workcation, it’s just about maintaining momentum.

4. Clear Expectations & Friendly Reminders

I send out reminders as my workcation approaches, so there are no last-minute surprises. My clients know exactly when I’m leaving, how they can reach me, and what to expect while I’m away. It’s all about keeping the lines of communication open so everyone feels confident.

5. No Major Projects—Just Maintenance

During my workcation, I don't take on any large developmental projects. It’s strictly about maintenance—testing, tweaks, and minor adjustments that I can easily manage on the go. This keeps things light and manageable while still allowing me to feel connected.

By structuring my workcations this way, I’m able to enjoy my downtime without feeling like I’m neglecting my business or my clients' needs. It’s the balance I’ve found that works for me, and I know it could work for other business owners too!

Download My Vacation Guide for Business Owners

Want to know how you can plan your own vacation or workcation without feeling guilty? I’ve put together a guide that outlines exactly how I roll out time off for myself and how I communicate it to my clients. It’s filled with tips on how to balance being a human who needs breaks and a CEO who wants to keep things running smoothly.

👉 Download the guide here and start prepping for your next getaway!


About Crystal Eva

Crystal Eva is a Fractional Chief Operating Officer. She empowers and supports women entrepreneurs by streamlining their technology, enhancing client retention, and elevating the client journey and onboarding process with seamless efficiency.

P.S. Are you ready to streamline, elevate, and turbocharge your business growth so you can live a more balanced life?  

Here are all the ways I can help you

  1. Looking to impress clients from Day 1? Grab the New Client Onboarding Workbook that’s been tested and proven to be effective and for a limited time, Crystal is sharing this valuable step-by-step guide and templates with you for FREE!

  2. Feeling overwhelmed by the day-to-day tasks that are holding you back from scaling your business? Crystal’s Monthly Support Retainer Service might be the game-changer you've been searching for. Schedule a complimentary discovery call with Crystal today!


P.S. Got an upcoming vacay and not sure how to get your business ready? Snag my CEO's Vacation Guide now!

Enjoy your time off stress-free by planning ahead with this free guide—perfect for prepping your team and keeping your clients in the loop!




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