10 Things Every Business Owner Should Organize Before Going on Vacation
Going on vacation should be exciting—not stressful. Yet for many business owners, taking even a few days away can feel impossible.
Will clients need you?
What happens if an invoice needs to be sent?
Who knows how to access your calendar?
Can someone answer urgent emails?
If you've ever found yourself checking emails from the beach (can you relate to the woman above?) or taking client calls while you're supposed to be relaxing, you're not alone.
The good news is that vacation planning is actually one of the best ways to improve your business preparedness.
If your business can function while you're away for a week or two, it's much better prepared if life ever throws you an unexpected curveball.
Key Takeaways
✔ Preparing for vacation helps identify gaps in your business before an emergency happens.
✔ Business preparedness isn't just about illness or death—it's about making your business less dependent on you every day.
✔ Organizing a few key pieces of information can make time away less stressful for you, your clients, and your family.
✔ Every vacation is an opportunity to strengthen your business.
Why Vacation Planning Is a Great Business Preparedness Exercise
One of the questions I often ask business owners is:
"If you had to leave tomorrow for two weeks, what would happen?"
You don't have to imagine the worst-case scenario.
Think about a planned vacation instead.
If preparing for a week away feels overwhelming, it's often a sign that your business relies heavily on information that's only in your head.
Vacation planning helps you identify those gaps before they become bigger problems. Here are 10 key steps to prepare and plan before going on vacation — short or long-term:
1. Update Your Calendar
Review your calendar(s) before you leave.
Reschedule meetings where possible and make sure clients know when you'll be unavailable.
If someone else will be monitoring your schedule, ensure they know how to access it.
2. Let Your Clients Know
Give clients plenty of notice.
A simple email a week or two before your vacation helps manage expectations and gives clients time to ask questions before you're away.
You may also want to prepare:
an out-of-office email
a voicemail message
an automated response
emergency contact instructions, if appropriate
Good communication builds trust.
3. Review Upcoming Deadlines
Ask yourself:
Are invoices due?
Is payroll coming up?
Are taxes due soon?
Are there important project deadlines?
Do you have contracts requiring action?
Taking care of these items before you leave helps prevent unnecessary stress while you're away.
4. Organize Important Passwords
If something unexpected happened while you were away, could someone access the information they genuinely need?
Consider where important login information is stored for:
email
accounting software
CRA
business banking
website hosting
domain registration
cloud storage
scheduling software
Use a secure password manager or another trusted method — never leave passwords written on sticky notes or in unsecured files.
5. Make Sure Someone Knows Your Key Contacts
Would someone know who to call if there was an urgent issue?
Keep an up-to-date list of:
accountant
lawyer
insurance advisor
IT support
website developer
bookkeeper
key suppliers
POAs (if applicable)
One phone call at the right time can prevent a small issue from becoming a major problem.
6. Know Your Minimum Viable Business
Not everything needs your attention while you're away.
Ask yourself:
What absolutely has to happen for my business to continue operating for two weeks?
This is what I call your Minimum Viable Business.
It might include:
responding to urgent client inquiries
processing payroll
paying critical bills
monitoring one shared email inbox
approving time-sensitive decisions
Everything else can probably wait until you return.
7. Check Automatic Payments and Subscriptions
Many business expenses continue whether you're working or not.
Review:
recurring software subscriptions
utilities
loan payments
insurance premiums
membership renewals
Knowing what's coming out of your account helps avoid surprises while you're away.
8. Organize Important Business Information
If you unexpectedly needed to stay away longer than planned, would someone know where to find:
business registration information
insurance policies
banking information
client records
important contracts
business licences
Having this information organized benefits you today—and your family if an emergency ever occurs.
9. Identify an Emergency Contact
Choose someone you trust who could be contacted if an urgent business issue arises.
This doesn't mean giving them access to everything.
It simply means someone knows:
how to reach you (if appropriate)
who your professional advisors are
where important information is stored
what should happen first during an emergency
10. Take the Vacation
This may be the hardest one.
Many entrepreneurs struggle to disconnect. (I know I do!)
If you've done the preparation, give yourself permission to step away.
Rest isn't a luxury.
It's an investment in your health, your decision-making, and ultimately your business.
Vacation Planning Is Business Preparedness
Preparing your business before a vacation isn't about expecting something to go wrong.
It's about creating a business that's less dependent on one person.
The more organized your business becomes, the easier it is to take a vacation, recover from an illness, manage family responsibilities, or respond to unexpected life events.
Business preparedness starts long before a crisis.
Sometimes, it starts with booking a vacation.
Frequently Asked Questions
How far in advance should I prepare my business before going on vacation?
Aim to start preparing at least two weeks before you leave. This gives you time to notify clients, complete outstanding work, organize important information, and address any last-minute issues.
Should I check my emails while I'm away?
That depends on your business and your comfort level. If possible, create systems that allow you to disconnect for at least part of your vacation. Preparing in advance often reduces the need to stay constantly connected.
What if I'm a solo entrepreneur with no employees?
Vacation planning is still important. Organizing your business information, communicating with clients, and identifying a trusted emergency contact can make your time away much less stressful. — Note: This is me! I am a sole owner and still actively prepare and plan my businesses before going away on vacation.
How does vacation planning relate to business preparedness?
A vacation is a planned absence. If your business can continue operating while you're away, it's often better prepared to handle unexpected situations such as illness, hospitalization, or family emergencies.
Related Resources
Business Preparedness Checklist & Organizer
Check out the full Business Preparedness Resource Directory
Blog Post: Preparing Your Business for an Unexpected Hospitalization
Learn More: The First 72 Hours After a Business Owner Becomes Incapacitated
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Disclaimer
This article is provided for educational purposes only and does not constitute legal, accounting, tax, financial, insurance, or other professional advice. Every business is different, and requirements may vary depending on your business structure, industry, and province or territory. Consult the appropriate qualified professionals for advice specific to your situation.
Your Business Executor helps Canadian entrepreneurs prepare their businesses for unexpected life events such as illness, incapacity, or death. Through business continuity planning and business preparedness consulting, business owners can document how their company operates and ensure their family, clients, and advisors know what steps to take if the owner is suddenly unable to run the business.