At the risk of sounding like my parents and grandparents, life was a lot simpler when I was growing up!  As a parent, I often ask myself this question.  How do I ensure that my children and (someday) grandchildren thrive in the very complicated, fast-paced and connected world that we live in today?  Families that I work with share the same concern.  They often ask: how do we preserve and pass on family values for generations?  

While there are formal approaches to addressing this issue, such as defining family constitutions, family boards and formal family meetings, sometimes simply disconnecting and taking a family vacation is the best way to reconnect.  When families spend quality time together, they create memories and bonds that last.  They also reinforce and shape family values.  Here are five reasons I recommend taking time out for a family vacation. 



As children return to school, they are sometimes asked to write an essay about what they did and what they learned over the summer break. Here’s my back-to-school essay about my family vacation to Southern California.    

This summer marked a huge milestone for our family. We have two children, one entering her freshman year in college and one entering his freshman year in high school. I went into this vacation thinking of it as sort of the last time for us to be together as a family unit, parents and children, before things change a lot. I know that soon our children will become much more preoccupied with their own lives.  

Over the last 18 years, my wife and I have invested a great deal in our children. We’ve certainly spent money on extracurricular activities and traveling sports teams and the like. But beyond the money, we’ve also invested as much time and energy as possible into our children, by being present in their lives, attending events and spending time with them. I know that the amount of precious time I can spend with them is about to change a lot.    

I wanted our time together in Southern California to be something we would look back on many years from now with the fondest of memories.  But I also wanted it to be a time of mental preparation for the changes that are coming for all of us. Our daughter will no longer live under our roof. She will be making her own decisions. Our son will be exposed to all kinds of new people and pressures in high school.   

The next few years will be something of a proving ground for how effectively my wife and I have instilled values into our children. Our voices, our influence and our guidance will begin to take a back seat to other voices and influences. Our children are about to experience things that they’ve never experienced before, and this will change them. I acknowledge that.  

If we have done our jobs well as parents, and I believe we have, our children will be strong, resilient and judicious in the choices they make. The values we’ve instilled in them—values like love of family, self-discipline, education, respect for others, being people of faith and being open to new opportunities—these values will guide them even when we are not present. But in family life, like in business and investing, there are no guarantees. 

This is why I wanted our time together in Southern California to be more than just a vacation.  Don’t get me wrong.  I wanted us to have fun and see the sights.  But Southern California has so many things to see that we could have been running from sunrise to sunset. That would have left us no time to just be together and to let conversations flow naturally from what was on our minds.  

I believe this is the key to having family vacations become an opportunity to shape family values.  You need downtime and togetherness. You need a relaxed environment in which to reflect on the past and talk about the future. This is why we chose not to go on the five-hour tour of Hollywood’s must-see sights. We didn’t want someone else controlling the agenda of how we spent time together.  

So if I were to write an essay about what I learned this summer, it would include this key statement:  Time is precious and we have so little of it. When we have the time to spend with family, we have to make it count.  

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"I enjoy serving multi-generational families because I value trust and discretion. They often have very complex financial lives and multi-generational stakeholders who see things in different ways. I find satisfaction in leading a team of advisors in a united effort to serve these families exceptionally well."


It might sound strange to hear me talk about vacations as a means of protecting family wealth. But think about it this way for a moment. There are many things you do not control when it comes to your financial wealth. You don’t control whether a recession will take place or how the markets will perform. You can’t control trade wars, politics or changes to tax laws. These issues all could have an impact on your financial assets

But you do control how much time you spend with your family and what you do with that time. I would argue that a family’s greatest assets are their family relationships and the values they pass along to the generations to come.  You get to control these (at least in theory).  

Here are five reasons that I’ve come to believe family vacations really matter:

  1. They create bonds that unite a family and prepare them to face uncertain or difficult times down the road. 
  2. They allow you to have conversations naturally that might otherwise be difficult.
  3. They allow you to tell family stories that communicate values and create sympathy and respect for the generations that came before.
  4. They help you expose your young ones to new experiences that might really help them.
  5. They help family members from different generations come to understand and respect each other, improving communication and unity. 



Family photo albums are rarely filled with pictures of people at work. I know that photo albums have become somewhat passé as people take more and more digital photos on their phones. But the point is that family vacations seem to be THE time when people take pictures. Why? Because we want to remember them and enjoy, even years later, the time we had together.  

No matter how healthy your family might be, it is impossible to predict the future and how certain events might impact your family. I’ve seen families encounter all sorts of issues, some of which have been beyond their ability to control, even with the best of plans.  

The unexpected passing of a loved one, divorce, business failures: all of these difficult times put pressure on family bonds and reveal just how strong the connections are between people. These events can tear families apart.

Family vacations give you quality time with loved ones. If you consistently take these vacations, you create a defense against hard times, hopefully before you face them. The memories of being together, in one place, being happy and sharing food and laughter—those memories are powerful. They can sustain families in challenging times and create hope for better days ahead. While you may share these memories on Instagram instead of a photo album, the positive effects will be just as strong.  



Children and grandchildren do not enjoy being preached to. It can be quite a tricky thing to know how and when to insert our wisdom into their lives. If they don’t want it, they’ll probably just ignore what we have to say as mature people.  

One of my other articles suggests that instead of focusing on money, families should focus on developing their sense of purpose. A family purpose is comprised of a mission (who we are and what we’re about), a vision (where we want to go and how we’ll get there) and values (that have guided us in the past and that will shape our future).  

In my experience, it takes time, effort and a guide to develop the family purpose. This is why one of my top recommendations is that families spend quality time together. Quality time on family vacations allows people to talk about things that they might not talk about during their busy daily life and this can help lead to the formulation of a family purpose.    

For example, on our recent vacation to Southern California, my daughter (who just graduated from high school) started providing advice to my son (who is just entering high school). I can’t remember how the conversation got started. But it didn’t start out by my daughter saying something preachy like “let me tell you the five most important things I learned about how to navigate high school.”

Instead, my son and my daughter were just talking and the next thing you know—she was guiding him and providing counsel.  Better still—he was listening. Education is one of our core values as a family.  But I didn’t even have to enter that conversation because the two of them were already discussing our mission, even if they didn’t realize it.  



Family stories create unity and provide a sense of identity. They are like parables, a story with a meaning attached. Vacations are one of the best times to tell these stories.  In the hustle and bustle of daily life, it’s hard to find a time to sit down and listen to stories from mature people in the family.  

But on vacations, if you leave the space for them, there will come moments when there is a lull in the conversation, maybe while sitting around a fire or after a meal. This is the perfect opportunity to interject something like, “Did I ever tell you about the time…”

I’ve had the good fortune to listen to numerous stories from patriarchs and matriarchs from successful families. These stories are powerful. And here’s the thing—you don’t need to be a great storyteller to tell a great story that impacts the generations who follow you.  The most important thing is that the story is true: true to your memory, true to what you learned, true to how you feel.  



Family vacations are often based on travel. This provides an opportunity to expose members of younger generations to new experiences and new places, as well as different languages and cultures. This broadens their horizons and may even open their minds to new opportunities they had not considered.

For example, my daughter is quite interested in computer science. Before we traveled to California, I asked her a while back if she would ever consider living and working in the Silicon Valley, in Northern California. She said, “Dad, I love Chicago so why would I want to leave?”  

But after we spent a week together in Southern California, seeing the sights, spending time on the coast and soaking up the sun, I asked her—“So what do you think of California?” She said, “It’s beautiful and I could see myself spending more time here.” I chuckled to myself and thought back to what she had said the year before. But what pleased me most came a week or so later. She posted a photo on Instagram from our vacation and said she loved California and could see herself working and living there in the future.  



If you structure your family vacations with enough downtime to just be together, this might help you better understand where your children and grandchildren are coming from. This might help you see what the world looks like from their point of view. A moment ago, I described the importance of telling family stories. But it’s equally important to listen.  

I didn’t grow up in a world where I posted things on the internet, like to an Instagram account. I didn’t carry a mobile phone until I was a working professional. I didn’t have a constant barrage of online posts coming at me 24 hours a day. There was no such thing as cyberbullying when I was in high school.  Mass shootings in schools and public places were virtually unheard of.  

But all of that is here now and our children and grandchildren contend with it every day, whether consciously or unconsciously. It is a different world for them than the world we grew up in. I believe we would be wise to listen to them. This can help us communicate better with them.  

So often real communication is not just about what we say, it’s about how we listen. I believe that at least half of real communication takes place when the other person feels heard. This requires active listening, looking people in the eye and asking clarifying questions. I know it sounds cheesy, but the old standby—“So what I’m hearing you say is…”—really works.  

People who feel heard also feel connected. That connection might just protect your wealth down the road when a young person is making a decision. None of us want to disappoint the people we care about and feel most deeply connected to.  



I believe in the power of family vacations because I’ve seen what they do for my family. Our trip to Southern California was a reminder to me that time is precious, and I need to be wise in how I spend it with my family. If I can be of assistance to your family in helping create unity and protecting your wealth for the generations to come, please reach out to me.


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