Why to Start Traveling as an Entrepreneur

Posted by Behere | December 11, 2019 | Article
traveling entrepreneur

You did it, you took the plunge to go full-time freelance or become an entrepreneur. After countless late nights, questioning whether you were ready and dealing with challenging clients, you took the leap. At first, it was amazing! You had all this free time, could work from home in your PJs, and do your laundry during the day. Over time though, this wears on you and you realize you’re working all the time and not taking advantage of the flexibility you created for yourself.

Sound familiar? For many freelancers and entrepreneurs, this is the case. When getting started you often need to just buckle down in one place and dedicate your time to landing clients. But overtime you settle into a routine and hopefully have recurring clients. Once you feel settled in your business, it’s the perfect time to start planning to work while traveling.

When we say that we don’t mean that you’ll be sitting on the beach typing or living out of a suitcase always in transit. No, the most productive way to work and travel is to spend time in a new place. To get to know that place and develop a routine but most importantly be inspired by the new environment you’re in. Ideally a month or more, so you feel settled, comfortable and productive. That’s why we’re sharing how to start traveling as an entrepreneur and why you should get out of your house.

  1. Choose your travel dates

    The first step is choosing a date that you want to start traveling on. Ideally, don’t plan it at the same time as you’re onboarding a new client as you want a day or two to travel and settle in. It’s important you choose a realistic date you can commit to and it’s okay if it feels a bit nerve-racking. We always recommend giving yourself at least a month in a new place to get settled and feel connected to a place. This also helps you feel more comfortable and productive. It also gives you the opportunity to build new connections in that place.

  2. Do the prep work

    Some freelancers like to tell their clients if they’re going out of the country or timezone. This is entirely up to you but make sure you outline what this process will look like for you. Ensure you download all necessary tools, like these tools for freelancers to make sure you are set up for success.

  3. Remember why you started

    When you first started freelancing what was your #1 goal? Was it to be your own boss? Work from anywhere? Travel more? Spend more time with friends or family? Whatever it is, you need to do those things. Life is too short to get stuck in a hamster wheel, especially once you started for different reasons. So if you want to travel, then make it happen and stop making excuses.

  4. Schedule in downtime

    You might want to explore and see everything when you get to a new place but pace yourself. If you try to cram every touristy thing in you’ll likely end up feeling burnt out and unable to work. Take your time exploring and schedule in downtime, for relaxation. While traveling as an entrepreneur it’s easy to get caught up in still working nonstop then filling your free time with exploring your new city. To stay balanced and not burnout, give yourself breaks and make ‘me-time’.

  5. Meeting new people can change your life

    If that isn’t reason enough to get out of the house, we don’t know what is. By traveling, or even just joining a coworking space, you can meet people that impact your life. Whether its a new business partner, connection, sale or friend, connecting with new people is essential. It doesn’t have to feel like stuffy networking.

  6. New environments create new inspiration

    It’s true, new places help you find new inspiration. They help your brain expand, and help you feel more creative and inspired. When visiting a new city or area, you’re often flooded with new and exciting sights and colors. These help you tap into new inspiration and ideas that you otherwise wouldn’t have had sitting at home. So if you’re feeling like you’re lacking inspiration, traveling may be just the fix.

  7. International cities give you a global perspective

    If you’re looking to take your business to the next level, going international might just help. By visiting other cities and seeing how business is done there, you might find new opportunities for your own business. Often gaining that new perspective is essential to helping you come up with new ideas for your business. Plus, you’ll get exposure to businesses and ideas that you wouldn’t have gotten while sitting at home or in your local coffee shop. By traveling as an entrepreneur you’ll gain so much new knowledge.

  8. Travel is FUN!

    Let’s think back to the reason you started your business in the first place. Hopefully, more flexibility and time for fun were part of those reasons. And travel is fun! It is an adventure and can be hectic but it’s an amazing learning experience. You have put so much work, time and effort into your business. You need to enjoy the fruits of your labor, explore and have some fun.

  9. Solo travel helps you gain more independence

    Maybe you are feeling just a bit too comfortable in your life and business. Perhaps a bit stale or unfulfilled? In search of something more? Traveling somewhere new can help you find that. Instead of waiting for someone to finally go traveling with you and making excuses, go solo! Solo travel is amazing, we shared all the benefits of it here. It also requires you to make all your decisions, become more independent and push yourself out of your comfort zone. It’s a perfect way to help you grow. This growth can translate into your business too.

As you can see, there are so many reasons to take your business on the road. That’s why we shared these tips for how to start traveling as an entrepreneur. If you really want to grow, learn, have fun and take advantage of the flexibility you’ve created then travel. After all, we know you didn’t start your business to sit in your house working for 16 hours a day ;).

Please note: We know not everyone has the flexibility to do this, and it is intended for those whose businesses do not have a physical presence nor have dependents to take care of at home. 


Ready to finally take your work on the road? We can help with everything from where to stay, to where to work, to where to eat. Learn more here.

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