Taking time off should be something to look forward to, not something that creates additional stress. Yet many professionals spend the days leading up to a vacation rushing to finish projects, responding to last-minute requests, and worrying about what might happen while they’re away. A relaxing vacation doesn’t start when you leave the office. It starts with the preparation you do beforehand.
Why Vacation Planning Matters More Than You Think
Many people focus on where they’re going, what they’re doing, or how they’ll spend their time away. Far fewer think about how their preparation before leaving will affect their ability to actually enjoy the vacation once it begins.
When work responsibilities are left unresolved, it’s easy to spend your vacation thinking about unfinished projects, unanswered emails, or problems that may arise in your absence. On the other hand, when you’ve planned ahead, communicated clearly, and prepared your team for your time away, you’re far more likely to disconnect and enjoy the break you’ve earned.
Preparing your workload before you leave is only half of the equation. Once your vacation begins, you’ll also need to give yourself permission to disconnect. We’ll explore that in our companion article, The Art of Being on Vacation: How to Disconnect, Recharge, and Return Refreshed.
6 Ways to Prepare for a Stress-Free Vacation
1. Start Planning Earlier Than You Think You Need To
One of the biggest contributors to pre-vacation stress is waiting too long to prepare. When vacation dates are approaching, it’s easy to underestimate how much needs to be wrapped up before you leave.
As soon as your vacation is approved, take a look at your calendar, deadlines, projects, and recurring responsibilities. Identify any deliverables that will need to be completed before you leave and flag anything that may require additional support while you’re away.
Planning early gives you time to address potential issues before they become urgent. It also helps prevent the all-too-common scenario of working extra hours in the days leading up to your vacation just to get everything finished.
The goal isn’t to complete every task on your list. It’s to create a realistic plan that allows you to leave with confidence instead of exhaustion.
2. Prioritize What Must Be Done and Let Go of What Can Wait
Many professionals fall into the trap of believing they need to clear their entire workload before taking time off. In reality, that expectation is often unrealistic and can create unnecessary pressure.
Review your responsibilities and determine which tasks genuinely require attention before your departure. Some projects may have firm deadlines, while others can be paused until your return without causing significant disruption.
Focusing on priorities allows you to direct your energy where it matters most. It also helps prevent burnout from trying to accomplish weeks’ worth of work in a matter of days.
Vacation is intended to provide a break from work. If preparing for vacation leaves you overwhelmed and exhausted, it defeats much of the purpose. Give yourself permission to focus on what truly matters and accept that some work can wait.
3. Create Clear Handover Notes
One of the best ways to reduce interruptions while you’re away is to leave thorough handover notes for colleagues who may need to support your responsibilities.
A strong handover document should include project updates, key contacts, upcoming deadlines, recurring tasks, and any information someone would need to address routine questions in your absence. Think about the questions you are most likely to receive while away and answer them before they’re asked.
Good documentation benefits everyone involved. Your colleagues gain confidence in their ability to manage situations that arise, and you gain peace of mind knowing important information is readily available.
Effective handovers also demonstrate professionalism and teamwork. By setting others up for success, you’re contributing to a culture where employees can take time off without feeling indispensable.
4. Communicate Expectations Early
Surprises are rarely appreciated when it comes to vacation coverage. The earlier you communicate your plans, the easier it is for everyone to prepare.
Inform coworkers, clients, vendors, and other stakeholders about your upcoming absence well in advance. Clearly communicate your vacation dates and identify who should be contacted if assistance is needed while you’re away.
Early communication often reduces last-minute requests and allows others to adjust timelines or ask questions before you leave. It also demonstrates respect for the people who may be impacted by your absence.
Remember that communication isn’t only about informing others that you’ll be away. It’s about helping them understand how work will continue smoothly while you’re gone.
5. Set Up Your Out-of-Office Message Properly
Your out-of-office message is often the first thing people see when they need your assistance during your vacation. A thoughtful message can prevent confusion and help direct people to the resources they need.
At a minimum, your message should indicate that you’re away, provide your return date, and explain when the sender can expect a response. If appropriate, include contact information for a colleague who can assist with urgent matters.
Avoid creating unnecessary anxiety by suggesting you’ll be checking messages constantly. If you’ve taken the time to prepare properly, your out-of-office message should reinforce your boundaries rather than undermine them.
A clear, professional message helps manage expectations and reduces the likelihood of returning to frustrated emails or missed opportunities.
6. Prepare for Your Return Before You Leave
Many people focus entirely on preparing for their departure and forget to prepare for their return. Yet a smooth transition back to work can have a significant impact on how refreshed you feel after vacation.
Before you leave, consider blocking time on your calendar for catching up on emails, reviewing priorities, and reconnecting with colleagues. If possible, avoid scheduling important meetings immediately upon your return.
You may also find it helpful to create a short list of priorities for your first few days back. Having a plan in place can make the transition feel more manageable and reduce the temptation to spend your final vacation days worrying about work.
The more thoughtfully you prepare for your return, the easier it becomes to enjoy your time away knowing you have a plan for when you come back.
What Can You Do Today to Make Your Next Vacation More Enjoyable?
A little preparation can go a long way toward creating a more enjoyable vacation. By planning ahead, communicating clearly, and setting your team up for success, you can leave with greater confidence and return feeling more refreshed.
If vacation coverage remains a challenge for your organization, temporary staffing can provide additional support during peak vacation periods, helping teams maintain productivity while allowing employees to take the time off they’ve earned.
Planning a staycation this summer? If you’re staying close to home or looking for fun ways to enjoy your time off in Winnipeg, be sure to check out our Summer Bucket List, filled with ideas to help you relax, explore, and make the most of the season.
