How To Take a Vacation as an Entrepreneur

Most people take time off from work, especially around the holidays. But what can you do when you're the only employee, or when stepping away from your business feels impossible?

Don't worry, you can take time off as a business owner—and beyond that, you should.

We know you love your business; you wouldn't be hustling so hard if you didn't. But occasionally stepping away from work is an important part of building a sustainable company. And with a bit of planning, your business will still be there when you get back (promise).

Think about it this way. If you never take time off, how will you feel about your business in three months? A year? Three years?

There’s nothing worse than investing all of the time and energy needed to build a business from scratch, just to burn out because you couldn’t create space for rest. Sure, your business depends on your time, but your enthusiasm for it depends on your time off.

We rounded up some strategies you can use to step away from your business to get the time off you need (and deserve!) this holiday season.

Before you can plan for a vacation, you need to decide what time off looks like to you.

Maybe you want to fully unplug for a week or two, or maybe you just need a weekend away from your business to recharge. Maybe vacation just means a break from most tasks, but you’re happy to spend an hour or two every day handling shipping and email replies.

The duration and structure of your vacation are entirely yours to decide, and based on those two choices, you’ll know how much you need to prepare.

To prep for your time off, you’ll be trying to find a balance between the two main ways to carve out time away from your business: hiring short-term help, and automating as much as you can.

Image credit: Burst

Hire (or find) short-term help

Whether this is your first time hiring help, or you already have trusted pinch-hitters on call, there are a few steps that can make introducing someone to your business easier.

Outline and document your processes

Depending on what you want handled by your new hire, you’ll need to get your knowledge about those tasks out of your head and into theirs.

Consider each task you’re going to hand off, and map out what needs to be documented ahead of time. That might include:

Customer service. Do you have any policies that live in your head, like always offering a hassle-free return for new customers, no matter what?
Social media. Do you have any standard guidelines for figuring out whether something is on brand for you to share? Do you swear on social media? Do you handle customer issues there, or direct them to email?
Shipping. What gets included in every order? How quickly do orders make it out the door? Are there any tricky issues they should watch out for?

Save time for training

Documenting your processes is great, but if you’re bringing in someone new to hold down the fort while you’re gone, nothing replaces one-on-one time walking through each task with the expert (that’s you).

Book a few hours with your new hire to walk through everything IRL before you take off. You don’t need to take a crash course in teaching to get them ramped up. Instead, you can steal a quick-and-easy one-liner that’s been commonly used in surgical teaching for a long time: “see one, do one, teach one.”

Training shortcut: see one, do one, teach one.

For each key task, show your trainee how you’d do it, have them do one themselves, and then have them “teach” it back to you to explain the process. Multiple studies have shown that people learn best when they’re actively involved, and this framework helps you get them involved in the tasks they need to know.

It might be the difference between panicked calls about how to handle customer service issues and uninterrupted time off.

Get major tasks off your list ahead of time

There’s only so much you can expect someone to manage when they’re new to your business. You should aim to finish up anything major ahead of time, and do everything you can to make sure your time off will be business-as-usual. Restock popular items, make sure your shipping supplies are fully prepped, and don’t plan any major announcements, campaigns, or events right before you leave.

Can’t hire help? Try a swap instead.

No money to hire help? That doesn’t automatically mean you can’t find (exceptionally qualified) help to handle things while you’re away.

Turn to your community of other business owners and see if anyone would be up for a swap. If they can handle your shipments and customer service while you’re off, you’ll do the same when they need a break later in the month.

It’s not quite at the same level, but that’s how the merchants on Almonte’s main street manage the unexpected, like when events mean they might not be able to open up their storefront on time.

Merchant to merchant support extends to neighbourly favours, like helping each other open shop when someone’s kid is home sick. In Almonte, the shops communicate frequently via Facebook.

“We have a Mill Street Merchants private group,” Emily tells me, “It’s where someone will say ‘Okay guys, it's a snow storm. What are we doing?’ or over Easter weekend, ‘Who's open, what hours?’ When you go a mall, everybody's open. We're a destination like that. If people are going to come here, we want everybody to be open.”

FURTHER READING: Here are four other ways small business owners have collaborated to build their businesses together.

Streamline your processes to create time off

Maybe help just isn’t in the cards, either hired or bartered. That doesn’t mean every day has to be a 12-hour day, or that you can’t work some downtime into your routine, especially around the holidays.

Image credit: Burst.

Automate your routine tasks

Automation can take care of routine tasks for you, or take them off your plate entirely for a set amount of time.

Each task you automate is one more thing you don’t need to handle while you’re trying to carve out downtime this holiday season, and while there are some tasks that will still need your attention (we haven’t found a good shipping robot yet) you’ll be able to scale down your work hours if you need a break.

FURTHER READING: Looking for more ways to automate your business? Here are some great tools you can use, and ways to implement automation across your business ahead of the holidays.

Update your customer-facing information

Your customers are reasonable people, and they understand everyone needs a vacation. Telling them (with advance notice, and clear communication) that you’ll be taking a break goes a long way when it comes to creating time off for yourself.

Once you’ve decided what your vacation is going to look like, and how it’ll impact your customers, you can set the right expectations before you jet off for some R&R.

Make sure any communications include:

How long you’ll be away
How it’ll affect their orders and interactions with you
What they should do now

For example, let’s say you’ll be away for two weeks, and all orders will ship out the day after you get back. Your communication plan to customers might look like:

A fixed banner on your store announcing that all shipments will go out on the day you get back
An email to your newsletter or customer list filling them in on the details
A short sentence on the cart
Updates to your social media profiles

You won’t need to put all the info in every update, but it might make sense to set up a blog post or FAQ. That way, you can easily link to one place for complete information. You could switch up your Instagram bio to link to your “I’m on vacay” blog post, which shares all the important details, or link to it from your store’s banner.

Offer incentives for “vacation” orders

Not being able to pack up and ship out orders ASAP is, understandably, one of the most nerve-wracking things about stepping away from your store for even a day. After all “Buy now, and it’ll ship later!” isn’t the most conversion-friendly call-to-action.

That said, it is possible to keep the orders rolling in, even if they won’t ship out for a week or two while you’re gone—that’s what promotions, discounts, and bonus offers are for.

It is possible to keep the orders rolling in, even if they won’t ship out for a week or two while you’re gone.

As you’re updating your customers to let them know you’ll be off for a few days or weeks, explain that while orders won’t ship out until you’re back, they’ll score a discount or a free gift by ordering while you’re out of the office.

Make sure you’re clear on when orders are eligible for the offer, and what specifically they’ll receive. If it’s a discount, you can make it even easier on them by setting up a shareable discount link ahead of time—it’ll apply the discount to their cart automatically.

Plan for the financial implications

Whether you’re hiring help, planning for a slow-down in orders, or offering discounts to keep the orders coming in while you’re away, there’s one constant: all of those things will impact your business’ finances.

Which isn’t a reason to skip your vacation! But just like you’d plan for the financial implications of a vacation in your personal budget, you should think about how it’ll impact your business’ budget, too.

If you’re spending money to hire short-term help, ask them for a quote ahead of time. They may bill by the hour, or quote a price for full service during the time you’re away, both of which can work—but if it is hourly, make sure to plan for contingencies in case they find it’s taking more time than estimated.

For example, if someone quoted you 10 hours to handle your shipping, you should make sure you have a bit of wiggle room in the budget in case they need to go over. You can also set a hard limit, and reply to their quote with the go-ahead for up to 15 hours. Beyond that, you’d prefer they leave the work until you get back.

And if you’re offering a discount, bonus, or a free gift to encourage orders during a shipping shut-down, make sure you understand the margins before making any decisions. You’ll still need those orders to be profitable when they’re placed, after all.

Image credit: Burst.

You need (and deserve) a vacation

Whether you’re gearing up for a few days off over the holidays, or planning a two-week travel extravaganza, with a bit of planning your business will still be there when you get back.

Beyond that, you’ll be in a much better frame of mind to take your business to the next level. You’ll also be on your way toward creating a sustainable company that can provide perks, like vacation time, to its first employee: you.

Entrepreneur vacation FAQ

Do entrepreneurs have vacations?

Yes, entrepreneurs can and do take vacations. It is important, however, to plan and manage the vacation time properly to ensure that the business is still running smoothly while the entrepreneur is away.

Can you travel as an entrepreneur?

Yes, entrepreneurs can travel. Many entrepreneurs use travel to attend conferences, meet potential partners, and explore new markets. Additionally, business travel can be a great opportunity for entrepreneurs to take time to reflect on their business strategies.

How often do entrepreneurs travel?

This depends on the type of business and the individual entrepreneur. Some entrepreneurs may travel frequently, while others may rarely travel.