There's one quality that virtually all entrepreneurs share: the desire to become their best selves. They aren't interested in seeing how much downtime they can steal away. Instead, they want to discover just how high their smarts and inner drive can take them.
When aspiring entrepreneurs are working full-time jobs while building new businesses, they typically use their "free time" working, learning, and making connections that can bring their ideas to life. And established business owners usually spend any down time trying to make their current projects better, or concocting the next big plans.
But this attribute can also lead to some, well, (to be blunt) stupid behavior. They'll work to the point of burnout. They'll see their groggy minds and dark circles under their eyes as badges of pride. It's proof of their dedication, rather than something that needs to be fixed.
You might be able to maintain that nonstop pace for a while. Months, even. But it's just not sustainable.
Occasionally, you're going to need to step away and take some time off.
But since you're an entrepreneur, you need to do it strategically. Here's how you can take a vacation, never allow your business to miss a beat, actually enjoy yourself, and come back with the energy and insight you need to crush it.
1) Prepare For A Business Without You
Here's the funny thing about taking a vacation as an entrepreneur. If you're a workaholic, you might fear that taking a little R&R makes you weak or lazy. But in reality, it's one of the best tests of your entrepreneurial skills.
Being a business owner who needs to constantly be there for their business is like being a clockmaker who needs to turn a crank to make their clocks work. The point isn't to create something that requires your constant input. The point is to make something that functions independently of you. After all, the more you can let go, the more your business can scale.
There are two ways to make a you-free business run well.
Delegate
Flex those managerial muscles. Think about everything you're responsible for in your day-to-day work. Who is responsible for what in your absence? Weeks in advance of your vacation, get crystal clear about what your business without your presence looks like.
Schedule Your Vacation Time Strategically
Startups tend to ebb and flow. Your operation might be hopelessly crazy for a few weeks and then relatively relaxed for a few weeks afterward. Schedule your vacation for a time when there are few meetings, no conferences, and little risk of encountering problems.
2) Only Respond To Emails At A Certain Time Each Day
You'll find plenty of entrepreneur vacation advice that says "unplug, throw your phone in the ocean, and just get away from it all!"
I'm not going to patronize you like that. If you're the kind of person who's able to completely disconnect from your business operations, more power to you. I say, go for it.
But if you're like most early-stage entrepreneurs I know, then you get queasy at the thought of being 100% disconnected from how your business is running. You're not going to cut off all lines of communication just because some guy on the Internet said it was a good idea.
What I am going tell you is this: turn off email push notifications on your phone. You don't need to react to every single email the second it hits your inbox. Instead, commit to a certain time each day when you'll glance at your emails. For example, commit to taking a peek at 6 p.m. every evening. And set up an away notification alerting people that you're not going to be instantly responsive. After you see your messages and you are satisfied, close your email app and don't look at it again until the next day.
You'll feel comfortable knowing how things are running, so it will be easier to just let go and indulge in your time off.
3) Set Emergency Triggers
"What if something happens while I'm gone?"
Most business owners are paranoid that a minor issue will snowball into a major problem, simply because they are away and out of touch. Even while hiking, enjoying an exotic meal, or taking in art at a museum, their thoughts drift to "What if my business is imploding right now, and I'm here doing this."
For those incidents that require your immediate attention, you can establish emergency triggers. When disaster strikes, you can make it so that you're notified.
Here are a few common emergencies you can plan for.
Your Website Goes Down
Every online business owner's worst nightmare is for a database problem, DDoS attack, or other snafu to knock their site out of commission. But you can get updated when this happens immediately through the help of Uptime Robot. This is a free service that monitors your site every five minutes. If it notices that your site is down, it will immediately send you an SMS message or other alert.
A VIP Needs To Get In Touch With You
There are some people you just can't ignore. And don't want to ignore. But unfortunately, important, powerful people tend to set the schedule, contacting you whenever they feel it's best. And if they email you, you don't want to make them wait half a day or more until you get back them. You want to know immediately.
You can easily be alerted by using IFTTT. This is an app that sets up triggers to certain events.
Let's pretend you're waiting on an email from a big shot investor, who may or may not email you this week with exciting news. You want him or her to pierce through your email blackout if they decide to get in touch with you. So you use IFTTT to send you a text message that says "KA CHING" when you receive an email.
![2015-10-17-1445106288-7437345-IFTTT.png]()
Easy. Now only the most crucial emails can get through, and the rest can wait until you're done unwinding for the day.
A Partner Or Manager Needs Your Immediate Attention
You should, of course, also discuss with your colleagues the situations that would warrant an interrupted vacation.
What you deem to warrant an emergency contact is specific to your business. But for the sake of your vacation, and your health, please only limit these to genuine emergencies, the kind that can't be ignored. Or the kind that would make you kick yourself if you ignored them.
When you have these triggers in place, you can finally relax and stop feeling guilty about your time off. If you aren't getting the notifications you set up, you'll know that everything is running as intended.
No news is good news.
4) Know That You Are Preparing For Your Best Work
This is perhaps the most important, and the most difficult to grasp, piece of advice.
Don't see your vacation as a distraction from your work. See it as part of your work. You need occasional, significant breaks from the challenges of running a business if you want to be your best self. Going full throttle all the time, and never allowing yourself a few days to just relax and reflect on your life is like driving a race car every day without ever changing the oil. Eventually, something is going to break down on you.
If you're the type who always gives your best, then give your best to your time off. Enjoy leisurely, meandering days, just like you used to do when you were a kid. You won't just be de-stressing, you'll also allow the lessons you've learned as an entrepreneur sink in.
A strategic holiday might be the savviest business decision you make. When you do so much nothing that you get sick of it, you'll come charging back to your business with more creativity and inner drive than ever before.
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When aspiring entrepreneurs are working full-time jobs while building new businesses, they typically use their "free time" working, learning, and making connections that can bring their ideas to life. And established business owners usually spend any down time trying to make their current projects better, or concocting the next big plans.
But this attribute can also lead to some, well, (to be blunt) stupid behavior. They'll work to the point of burnout. They'll see their groggy minds and dark circles under their eyes as badges of pride. It's proof of their dedication, rather than something that needs to be fixed.
You might be able to maintain that nonstop pace for a while. Months, even. But it's just not sustainable.
Occasionally, you're going to need to step away and take some time off.
But since you're an entrepreneur, you need to do it strategically. Here's how you can take a vacation, never allow your business to miss a beat, actually enjoy yourself, and come back with the energy and insight you need to crush it.
1) Prepare For A Business Without You
Here's the funny thing about taking a vacation as an entrepreneur. If you're a workaholic, you might fear that taking a little R&R makes you weak or lazy. But in reality, it's one of the best tests of your entrepreneurial skills.
Being a business owner who needs to constantly be there for their business is like being a clockmaker who needs to turn a crank to make their clocks work. The point isn't to create something that requires your constant input. The point is to make something that functions independently of you. After all, the more you can let go, the more your business can scale.
There are two ways to make a you-free business run well.
Delegate
Flex those managerial muscles. Think about everything you're responsible for in your day-to-day work. Who is responsible for what in your absence? Weeks in advance of your vacation, get crystal clear about what your business without your presence looks like.
Schedule Your Vacation Time Strategically
Startups tend to ebb and flow. Your operation might be hopelessly crazy for a few weeks and then relatively relaxed for a few weeks afterward. Schedule your vacation for a time when there are few meetings, no conferences, and little risk of encountering problems.
2) Only Respond To Emails At A Certain Time Each Day
You'll find plenty of entrepreneur vacation advice that says "unplug, throw your phone in the ocean, and just get away from it all!"
I'm not going to patronize you like that. If you're the kind of person who's able to completely disconnect from your business operations, more power to you. I say, go for it.
But if you're like most early-stage entrepreneurs I know, then you get queasy at the thought of being 100% disconnected from how your business is running. You're not going to cut off all lines of communication just because some guy on the Internet said it was a good idea.
What I am going tell you is this: turn off email push notifications on your phone. You don't need to react to every single email the second it hits your inbox. Instead, commit to a certain time each day when you'll glance at your emails. For example, commit to taking a peek at 6 p.m. every evening. And set up an away notification alerting people that you're not going to be instantly responsive. After you see your messages and you are satisfied, close your email app and don't look at it again until the next day.
You'll feel comfortable knowing how things are running, so it will be easier to just let go and indulge in your time off.
3) Set Emergency Triggers
"What if something happens while I'm gone?"
Most business owners are paranoid that a minor issue will snowball into a major problem, simply because they are away and out of touch. Even while hiking, enjoying an exotic meal, or taking in art at a museum, their thoughts drift to "What if my business is imploding right now, and I'm here doing this."
For those incidents that require your immediate attention, you can establish emergency triggers. When disaster strikes, you can make it so that you're notified.
Here are a few common emergencies you can plan for.
Your Website Goes Down
Every online business owner's worst nightmare is for a database problem, DDoS attack, or other snafu to knock their site out of commission. But you can get updated when this happens immediately through the help of Uptime Robot. This is a free service that monitors your site every five minutes. If it notices that your site is down, it will immediately send you an SMS message or other alert.
A VIP Needs To Get In Touch With You
There are some people you just can't ignore. And don't want to ignore. But unfortunately, important, powerful people tend to set the schedule, contacting you whenever they feel it's best. And if they email you, you don't want to make them wait half a day or more until you get back them. You want to know immediately.
You can easily be alerted by using IFTTT. This is an app that sets up triggers to certain events.
Let's pretend you're waiting on an email from a big shot investor, who may or may not email you this week with exciting news. You want him or her to pierce through your email blackout if they decide to get in touch with you. So you use IFTTT to send you a text message that says "KA CHING" when you receive an email.
Easy. Now only the most crucial emails can get through, and the rest can wait until you're done unwinding for the day.
A Partner Or Manager Needs Your Immediate Attention
You should, of course, also discuss with your colleagues the situations that would warrant an interrupted vacation.
What you deem to warrant an emergency contact is specific to your business. But for the sake of your vacation, and your health, please only limit these to genuine emergencies, the kind that can't be ignored. Or the kind that would make you kick yourself if you ignored them.
When you have these triggers in place, you can finally relax and stop feeling guilty about your time off. If you aren't getting the notifications you set up, you'll know that everything is running as intended.
No news is good news.
4) Know That You Are Preparing For Your Best Work
This is perhaps the most important, and the most difficult to grasp, piece of advice.
Don't see your vacation as a distraction from your work. See it as part of your work. You need occasional, significant breaks from the challenges of running a business if you want to be your best self. Going full throttle all the time, and never allowing yourself a few days to just relax and reflect on your life is like driving a race car every day without ever changing the oil. Eventually, something is going to break down on you.
If you're the type who always gives your best, then give your best to your time off. Enjoy leisurely, meandering days, just like you used to do when you were a kid. You won't just be de-stressing, you'll also allow the lessons you've learned as an entrepreneur sink in.
A strategic holiday might be the savviest business decision you make. When you do so much nothing that you get sick of it, you'll come charging back to your business with more creativity and inner drive than ever before.
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