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3 Tips to Staying Stress Free When Taking Time Off

Updated on January 17th, 2022
vacationing budget

One of the greatest things about being an entrepreneur is the ability to dictate your own schedule. After all, your business is yours to run, which means you don’t have to answer to anyone else when you make decisions around how you spend your time.

That all said, there are always two sides to everything. While the flexibility is great, it also comes with a huge responsibility. As the owner, you owe it to the business and your team to devote the entirety of yourself to the company. That all said, is it even possible for entrepreneurs to take time off?  The short answer is yes, and in fact I highly recommend it.

Here are three tips to staying stress free when taking time off.

Find Your Second In Command

The absolute best way to confidently take a vacation is to find your second in command. This is why many entrepreneurs like to start their business with a co-founder.

If you don’t have a co-founder then you need to find another team member to take on this role. This should be someone who works directly under you and understands the business inside and out. In addition, they also need to be highly respected by the rest of the team. You need to choose someone who’s proven themselves to you and the company.

Before you head off on your trip, you should step back from daily operations a few times to see if this person can handle the job. This way you can test their abilities before taking off.

Choose Your “Tech” Hours Then Fully Disconnect

In a perfect world you should be able to fully disconnect from technology when you’re taking time off. That said, we all know this world is far from perfect. We also know it’s impossible to ditch your phone or laptop for the entire trip.

To stay disciplined you should choose certain hours during the day that you will make yourself available to the team. For example, I always make myself available in the mornings and late afternoon when taking time off.

Make sure you coordinate with time zones and share your calendar with your team well before you leave. If you’re well prepared, you can use the rest of your day to fully disconnect from your devices and relax.

Don’t Plan Your Trip During the Holidays

This one may seem strange. Since the majority of businesses shut down during the holidays, people would normally think this is the ideal time to take off. While this is very true, it also means you can expect the majority of your team to take their vacations as well.

That said, someone needs to be able to hold down the fort. Not only that, but the holidays are the busiest (and most expensive) time to travel. Assuming you’ve found your second in command, you should try to plan your trip at another time. This way, your team will be fully present and you can enjoy a low-cost, stress-free vacation.

Everyone needs to take time off. Yes, even us entrepreneurs. Taking breaks from work is imperative for your overall productivity and happiness. That said, it’s important to stay stress free while you’re away. If you want to accomplish exactly that, make sure you follow the three tips listed above.

Chalmers Brown - Former CTO of Due

Chalmers Brown - Former CTO of Due

I'm Chalmers Brown and former CTO of Due. I'm a big fan of technology and building financial products that help people better their lives. I have a passion for financial products that help people. I build complex financial infrastructure protocols that help scale financial companies. They are secure and support millions of customers worldwide.

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