3 Reason Entrepreneurs Need Family Vacations

“I don’t know.”

This is what my ten year old daughter said to me when I asked her to consider our yearly extended family vacations and what they have meant to her. I poked around some more with what I thought were better questions only to be met with mild irritation and the growing scowl of an adolescent.

On the surface, this is not very encouraging, especially when considering the fact that these are not easy endeavors for a family of four to take, nor is it easy to take that much time off from our community and a business we run. A lot has to happen in order to unplug and detach from the world around us. The very business of detaching can be as appealing as spending three weeks with two children in a small car for six hours fording and hauling wet bodies in and out of a cold river.

True story. 

And consider the cost—destinations that take twice as long to reach as was promised, endless amounts of dirty clothes, ripe bananas eaten in warm cars, mud under fingernails, unteachable moments, the very threat of revolt, lack of appreciation or understanding of the present circumstances, flicking, sweaty backs on vinyl seats-all the disasters familiar to fans of the Vacation movies.

So why do we do this?

Over twenty years ago my wife and I dreamed of sharing our love of travel with our future children. Our dream became reality when both of our kids reached five years old and were about to enter kindergarten. We set out on a 5 1/2 week vacation that began with a flight to California, and ending with a drive from Los Angeles to Vancouver BC, then from the northern U.S. to Toronto, and down the east coast. We have since done trips to the southwest, New England, and England. The trip we took last summer, included eight days in a 1972 Volkswagen campervan driving across southern England from the Cliffs of Dover to Land’s End.

What we believed twenty years ago and what we have come to know now through these experiences has been an affirmation of a core belief about our deepest desires as humans—that we all long to be known. One way in which we are working this out practically is through profound, shared experiences connecting us to each other outside of our normal, everyday lives—trips that seek to do more than entertain, but that complement and affirm that we are made for more.

Living intentionally in this way—choosing to take from the “material possessions” pot and pour into the “experience” pot is where a great part of our family life is experienced. Of course, we have learned a few things about ourselves and our children through this—

“choosing to take from the material possessions pot and pour into the experience pot is where a great part of our family life is experienced.”


Children don’t care about money.

Children are a barometer for life. They don’t get nuance. They don’t live in the neutrality of experience as an adult can. Their black and white is honest, but it also taps into deep truths about what we all long for. Another moment together. To be loved and adored. As best as I can remember, my children have never asked how much money we’ve got saved away for retirement. What they do care about is having time with us, that we come home from work when we say we will, that we don’t check our email at home,  and that we don’t make conference calls when we are on vacations.

Sacred time is invaluable.

Sacred means to be set apart. Not ordinary. When you intentionally set aside sacred time for your family—apart from the noise of the world—you are inviting your family to move into a deeper place. You are acknowledging that your family is worth the investment. By going into the wilderness you are saying that the business of your everyday life is not as important as the health of your soul. When that happens, beautiful things start to occur. That ten year old who has been trying to act like his 14 year old neighbor starts behaving like a ten year old again. The cynical outer shell starts falling away leaving tenderness and a softness of spirit in its place. You hold hands again. Wonder and awe penetrate your soul again and you let yourself become remade in front of your children. You make room for change to happen, to listen to one another, to speak into each other’s lives in more meaningful ways.

Community is not the same as mission.

In our day to day, we can believe that our family is all on the same team. That we’re building fidelity and trust in driving from lacrosse to swimming, attending school plays, or watching a movie together. These are all good things. But what we’ve found is that until you are on uncertain ground as a family, you aren’t facing life together as a team. Spending time in uncertain surroundings forces you to rely on one another in the subtlest of ways, and in some way it puts children and parents on a level playing field. How you move through the uncertaintly as a family helps unite and transform you.

 ”Until you are on uncertain ground as a family, you aren’t facing life together as a team.”

Our children can’t describe what our trips mean to them. We have to trust that what we are doing is worth the effort. As we journey together over the next ten years, we hope to create more little islands of memories so that one day, when they are much older, they will be able to hopscotch back to an essential truth about who they are—that they were loved and enjoyed. That we cared for their hearts and prized our time with them more than our stuff or our work.


  1. Plan up to a year in advance (seriously), particularly if you are using frequent flier miles, going overseas, or visiting/camping in National and State Parks.

  2. Let your team know as soon as your plans are made so they can start thinking about what your time away will mean for them, and so they don’t plan vacations at the same time you will be away.

  3. Avoid scheduling anything that requires your attention when you are away. Plan to have big projects wrapped up a couple of weeks before your departure, and not to kick off anything new for a couple of weeks after your return.

  4. Advise key people (clients and vendors) a couple of months in advance, assuring them that your team is prepared to serve them in your absence.

  5. Leave several days open before your departure to wrap things up so that you don’t come back to them. Empty your email and assign tasks to others.

  6. When you leave, set your email to out of office, directing everyone to contact the appropriate person on your team for each specific question or need they may have (HR, Accounting, Project Management, etc.). Additionally, let the sender know that you will not receive the message, and they should call the office or resend the email when you return. Then set your email to auto delete. Your children don’t want you to work on vacation, and you don’t want to come back to thousands of unread messages.

  7. Make each member of your family responsible for his/her own bag (assuming they are old enough), only one bag per person. You will never use everything you take with you. One stuffed animal each, a small bag of toys each (think of the quart-sized bags used by TSA), and one iPad for the many things you may want to look up on the way, a place to keep notes about all your grand creative thinking that will take place, and a way to watch an occasional movie on a particularly long driving day. No other technology! If you want to play video games and watch movies all day, stay home. Do take Uno and a book each.

  8. Don’t move around every day. Stay three or four nights in some places, or stay several weeks in one place. Your kids don’t want to travel every day of their vacation, and really, neither do you. The time allows for decompression and to get into a rhythm. If you’re worried that you or your kids will get bored, try to let that go. As you settle in and have time, everyone unwinds and finds things to do. This is where the magic happens.

  9. If your kids are like most, plan to stay in a place with a swimming pool every second or third night, and a place with laundry service/facilities once a week.

  10. Make reservations for where you will sleep each night, and get tickets in advance to specific shows/sights that may require them. Otherwise, leave your daily schedule flexible.

—José and Nikolle live in Atlanta, GA. and run a design firm called Metaleap Creative. Some people think they make metal, but they would be wrong. Their two children Ella and Alex live outside and seldom take baths because they are children and all children hate to take baths. They also enjoy raising an assortment of animals; their dog, Roxy and their two rats, Bianca and Suzanne. And a pet fish. But she died. See our latest journey on Tumblr: tumblr blog: http://roadkings.tumblr.com/archive