Entrepreneurs, Here’s When to Take a Vacation

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For small-business owners and bootstrapping startup founders, it's tough to completely retreat from work. If you’re an entrepreneur, you may feel there’s too much on your plate, no one to take over, and that any downtime will lead to lost business. It's not easy to decide when to take a vacation.

When to take a vacation

However, even a tiny vacation is critical, both for your personal health and sanity, as well as for your business. Studies show that as leisure time decreases, we experience more negative emotions, more stress, more health problems and lower life satisfaction. Even if you love what you do, you can’t live on work alone. Taking time off is essential to recharging your batteries and avoiding entrepreneurial burnout.

[quote align=”left”]When a leader takes vacation, it gives everyone else a chance to step up his or her game.[/quote]

Think of it this way: How strong can your business be if everything crumbles without you? If you can’t take a few days off, you’re not building a business; you’re building a job.

When a leader takes vacation, it gives everyone else a chance to step up his or her game. It gives employees and assistants the opportunity to navigate day-to-day duties and challenges. As a result, the team gets stronger, more independent, more confident. In this way, a vacation is an excellent practice run in preparation for periods when time off is absolutely necessary (e.g., medical leave or an extended fundraising tour).

The question to ask is not "Should I take a vacation?," but "When’s the best time to take a break, and how can I make my getaway as smooth as possible for all involved?" To that end, here are five things to consider.


[toggle_item title=”1. Leave when you’ll be missed the least.”]

Most businesses involve some kind of seasonality. Maybe your major clients or customers take off in August. Maybe you foresee downtime between major software releases. Identify a week or two when your services won’t be in high demand — that's a great starting point for planning your vacation.

[toggle_item title=”2. Start with smaller breaks.”]

If getting away for an extended period of time doesn’t seem realistic right now, start slow with smaller chunks of time — a few long weekends, for example. It gets the team used to working without you, and ideally, you'll discover that everything won’t fall apart the moment you disentangle yourself from the office.

[toggle_item title=”3. Make sure there’s enough prep time.”]

No one wants to be caught off guard, including employees and clients. Enjoying a smooth vacation requires thoughtful collaboration and advance planning. Detail how matters should be handled in your absence, for example, customer and client management, priority tasks and non-urgent side projects. Keep in mind that the more freedom you give your team, the more opportunities they’ll have to grow and thrive.

[toggle_item title=”4. Set clear expectations for communications.”]

Let everyone know what he or she can and can’t expect from you while you’re away. Will you schedule a daily/weekly call to check in? Will you have access to email, and can people expect a response each morning/every week until you return? Who should contact you, and under what circumstances? When setting expectations, remember it’s always better to underestimate your availability and be more available than originally planned.

[toggle_item title=”5. Prioritize your break.”]

In most cases, there's never a perfect time to break away. And if you’re a solo-preneur or running a very small business, any time off may lead to lost business opportunities. But sometimes, that’s okay. Consider it just another cost of doing business. Recharging, avoiding burnout and being your best are more important than remaining available 365 days a year. If you want to head to the beach with the family in August or see Yellowstone in the fall, make it a top priority.


How do you unplug for a vacation? Which planning approach works for you and your work team? Share your tips in the comments below.

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