For many entrepreneurs and business leaders, the idea of taking an actual vacation feels impossible. Your business is your baby, and stepping away can trigger anxiety about lost revenue, missed opportunities, or things simply going off the rails. It’s no wonder we come back feeling like we need a vacation from the vacation!
But here’s the truth: taking time off isn’t a luxury. It’s a leadership skill. When done right, it can boost your creativity, recharge your energy, and improve long-term decision-making. Trust me, it’s a lesson I had to learn, too. There have been times in my life when I neglected vacation—neglected real rest—and paid the price.
But I also recognize that getting away can be easier said than done. But it’s doable. Here’s how entrepreneurs and business owners can take a restful vacation without sacrificing momentum or peace of mind.
6 Essential Vacation Prep Steps for Business Owners
Step #1 – Plan Ahead…Way Ahead!
If you wait until the week before your trip to start planning your absence, trust me…you’re in trouble. I start preparing at least 4–6 weeks in advance:
Block your vacation on your calendar and treat it like a high-priority meeting.
Let your clients, team, and key partners know early.
Send a reminder a week before you go.
Avoid launching new products, campaigns, or high-stakes initiatives right before you leave.
Step #2 – Delegate, Don’t Just Assign
Delegation is more than offloading tasks. It’s about transferring trust and decision-making power.
Identify your go-to person (or team) who can make routine decisions and handle minor crises. You’re looking for folks with initiative and a sense of ownership over the work.
Create a clear “If This, Then That” guide for potential workflow hiccups.
Make sure they have access to everything they need: passwords, contacts, and tools.
Empowering your team shows you trust them — and helps them grow.
Step #3 – Automate What You Can
I know automation isn’t always a good thing. Few platforms execute automation flawlessly. A human touch is always needed! That said, business automation is every entrepreneur’s best friend when planning a vacation.
Schedule emails and social media posts using tools like Buffer.
Set up automated replies for your email and DMs to let people know when you’ll return.
If you run an e-commerce or service business, ensure order fulfillment and customer support are covered by a team member or virtual assistant.
What automation does is reduce the number of fires to be put out when you’re a man down. It takes time to set up, but you’ll be grateful when you come back to a relatively peaceful workplace with less to catch up on.
Step #4 – Set Clear Communication Boundaries
The biggest trap for entrepreneurs on vacation? Constantly checking in “just in case.” And I get that urge. I truly do. However, that constant stress and worry about how things are going will prevent you from relaxing.
Decide how connected you truly want to be:
Fully offline? Set up firm boundaries and communicate them clearly to everyone.
Light availability? Schedule a single, brief check-in (10–15 minutes) every few days, if absolutely necessary, such as for major project deliverables or other key milestones.
Boundaries create peace of mind. Your team can’t follow them if you don’t set them.
Step #5 – Prepare for Re-Entry
Many business owners dread coming back from vacation because of the mountain of emails, updates, and meetings waiting for them. Trust me, it doesn’t have to be that way!
Block your first day back to handle catch-up. No meetings, no commitments.
Ask your team to create a digest-style update with major developments and decisions. Like Cliff Notes from your time out.
Use that first day to prioritize and recalibrate before diving in.
Step #6 – Change Your Mindset: Rest is a Business Strategy
Entrepreneurs often equate hustle with success, but burnout is the enemy of growth.
Taking time off isn’t just good for your mental health. It proves that your systems work, your team is capable, and you don’t have to micromanage everything for your company to succeed. And that, friends, is a freeing feeling!
And when you come back, you’ll be more focused, more creative, and better equipped to make decisions that matter.
What rules do you set for yourself to ensure your vacations are truly relaxing? Share in the comments.