Balancing Entrepreneurial Life and Travel

It can be dangerous to own a business.  That’s right, I said it.  Those of you who know me may be confused.  Indeed, I love owning a business, including its ups and downs.  But it takes a lot of time and effort to keep things rolling, and distractions like travel or big hobbies often have larger consequences than when working for someone else.  Many of us started our businesses with freedom in mind.  The question is, how to balance it all?

Start Planning

The most important thing is to plan.  Plan plan plan.  If you can’t plan, you’re going to have a hard time running a business, no?  Start small — plan your daily life.  When do you start work?  When do you end?  I’ve discussed the importance of balancing the work / life divide before, and I stand by every word.  Knowing where your line is drawn in the day-to-day is the first step to knowing when you can ‘get away’.

Once you have a rhythm, start adding and taking away from it.  This will give you a better idea of what you can manage.  If things get overwhelming or out of hand, pull back or hire someone.  Make some changes.  And don’t stop experimenting while maintaining your foundation.


The most important important part of untethering yourself from the day-to-day is finding a system.  That system may be a person — either a manager, assistant, or trusted employee.

Virtual Assistants

Many small businesses, startups, and entrepreneurs take advantage of a Virtual Assistant to manage the day-to-day.  It is worth finding this person long before a trip so you trust them completely during your absence.  My personal favorite VA program is Fancy Hands, but a lot of entrepreneurs I know found theirs on Fiverr.


Simply working ahead once you have a trip / event in view may be all your business needs.  This includes alerting your clients that you’ll be less responsive for a period of time.  By telling them in advance how their accounts will be managed before you leave, they don’t worry.  Nearly everything in your day-to-day can be automated, including social media posts through the likes of Hootsuite.  For example, this post went live without me using WordPress’ post automation, as I am currently in Croatia.

Update Your Followers

My clients really appreciate knowing where I am so they can feel a part of the journey.  When I tell them I’ll be gone, I also offer to send a few photos of the trip.  That way they know they were considered the entire way.


Networking while on vacation is probably a bad idea unless you can compartmentalize and spend only one day per week away doing work / networking.  But if you’re like me and prefer to take long trips and work away from home, this is a wonderful opportunity to experience CoWorking Spaces and meet colleagues abroad.  Start asking your local network for connections where you’ll be at least three months ahead of time.  Reach out to those people or locations to introduce yourself and explain your intent.  Why do you want to network abroad?  Why do you want to work at a coworking space for a day?  Not only will you get valuable experience, you also may build connections that will grow your international referral network — and it makes your trip a tax write off!

Traveling takes your body away, but what about your mind?

I once heard a story about an entrepreneur who was checking his email in the lobby of a Caribbean Hotel while on vacation.  A couple walked by, and the woman said to her husband, “What a shame that he can’t let go of work while on vacation.”  Yes, it would be a shame if the entrepreneur was working for someone else and was forced to work during his vacation.  Luckily, the foundation of being an entrepreneur is passion for what you do.  The entrepreneur in this story felt very differently about his situation than the couple.  He was proud to be checking his email while away, to see how things were going, and maintain contact with clients and employees in spite of his travels.  Most importantly, he had a choice in doing so.  Likely, his level of commitment is indicative of a successful venture.

There is no harm in thinking about your business when you’re not there.  In fact, vacation can be the most generative time for ideas and growth.  As Inc. Magazine put it, some of the best places to come up with next steps for your business are way outside of your normal environment.  The most important thing is to make sure you document these ideas in a way that allows you to save them for when you get back, so you can relax while you’re away.  Draw a mind map, throw down some bullet points in a notebook, or record your voice on your phone.  Then set everything down and soak up some rays (or ski that alpine slope, if that’s more your style).

How do you manage work while you’re away?