I love solving complex problems.  Clients often come to me with situations that require a close analysis of several different options to identify the best solution.  It’s fun for me to dig in and do the research.  But there are some problems that no amount of data or financial analysis can quite address.  The most vexing challenges my clients seem to face are those relating to their loved ones, particularly their adult children.  

When I approach these conversations, I often feel the need to slow down.  I end up listening to stories about my client’s children—events that shaped their lives as they were growing up and continue to define how they think and behave today.  After hearing many stories, I’ve come to identify a set of questions that can help families find the best path forward. If you or someone you care about is trying to solve complex problems, here are some guiding principles that might very well help you. 



Most complex problems seem to coalesce to a decision-point with a set of possible options.  Should we choose option A, B or C?  Sometimes each option can have potentially attractive or unattractive outcomes.,  What makes these problems really challenging is that it can be nearly impossible to predict the outcomes of each option.  Sorting through each option can be time consuming, emotionally draining and physically exhausting.  

Here are just some of the types of complex situations I’ve seen my clients’ adult children struggle with over the years.

  • How do we handle a child or sibling who is behaving in destructive ways?
  • Should we have more (or any) children? 
  • Should we get a divorce
  • Should I take this important but challenging new job?
  • Should we start a business?
  • Should one of us quit work and stay home with the children?
  • How do we handle a loved one passing away?

You’ll notice that most of these questions have to do with family members and potential changes to family dynamics and lifestyles. But the biggest challenge seems to be that once decisions are made, once the events unfold, there’s no going back. The changes will be mostly permanent.  This is why I recommend that you slow down and really think through your options. This can be very draining. 

If you’re not sure why I say this, let me give you an example from the world of competitive chess. When chess grandmasters enter tournaments, they endure great stress. While simply sitting in a chair, they can burn up to 6,000 calories a day and lose from 10-15 pounds in short order. In fact, the 1994 World Chess Championship was suspended when it became too dangerous for the defending champion to continue—because he had lost 22 pounds and was too unhealthy to keep going.  

So if you wonder why you seem worn out after spending just a short amount of time thinking about the complex problems you or a loved one might be facing—there’s your answer.  It is exhausting to do this kind of complicated mental work. But it’s important.

My colleague David Peckenpaugh recently wrote an article entitled “How To Make Decisions You Won’t Regret.”  His valuable framework is about addressing specific questions in which the options might be somewhat limited. 

Fortunately, not every situation we face in life has more than a couple of options or outcomes that we cannot reasonably predict. But the really complex problems do. This is where I find a framework such as the one below can be quite helpful.  Even if you can’t predict the outcomes for each option, you can make a best-guess and then use these five questions to compare the outcomes to what matters to you:

  1. How will this impact our family?
  2. How closely does this align with our values?
  3. How does this advance us toward our goals?
  4. How much time is required?  
  5. How will this impact our wealth?

As we explore each of these questions, I’d like to tell you some stories from my own family. We have faced many challenging times and yet have remained a strong and loving family who support each other.  This has not always been easy. This framework has empowered us to navigate through difficult times and come out on the other side relatively intact. I share these stories not because my family is perfect—far from it. But they do illustrate how these questions can be a good guide.  

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"There are many investment options today for affluent families. I enjoy digging in, doing the research and bringing solutions to the table."


I believe this is the most important question. I’ve watched my father practice a family-first mentality since I was a child. One of the most trying times we have ever faced was the loss of my mother to disease many years ago. This was a dark time and the impact to our family was nothing less than devastating.  My father lost his loving wife of many decades and the mother to his children. She was also his best friend.

It might seem, at first glance, like this is really not a decision point. After all, we didn’t choose for my mother to succumb to disease. But we did choose, each of us in our own way, how to respond. My father led the way. I think he knew, in some sense, that he was setting an example for the rest of us about how to bear up in a time of trial. He forged ahead and got on with life, even though it was hard.

His wisdom and strength could very well have come from his experience of watching many affluent families face their own difficult times.  He has seen parent-child and sibling dynamics, forged many years before an event, suddenly resurge. Things said decades ago, positive or negative, can be replayed in difficult moments and shape how people feel and respond.  

I believe families would be wise, when facing complex situations, to ask themselves how the options in front of them will impact their family long-term. Here is a simple guiding principle that I believe can really help: The more permanent the outcome of a decision, the more time you should take exploring options and the more careful you should be in speaking to one another during this exploratory process. It is easy to unintentionally stir up old dynamics that might hinder productive conversations.  

For parents of adult children who are facing complex situations, here are some simple recommendations:

  • Ask questions far more than making statements. You might be surprised at how much thought your adult child has already put into the situations they’re facing.
  • Do the hard work of thinking through options in short increments,  no more than a couple of hours at a time. It can be exhausting to do this work and tired people can grow impatient and say things they’ll regret later.
  • Don’t rush it. Recognize that the bigger the problem and the more permanent the choice and the outcome, the more time is needed. It might also be a good idea to bring in a trusted third-party to help facilitate these conversations.  



I was raised in a family in which honesty, integrity and character were highly prized.  We don’t do things that are dishonest or even that might have the appearance of impropriety.  We seek to be fair and decent in all of our dealings.  These values were instilled into me and my siblings by the way our parents lived their lives far more than the things they said.  

Over the years of working with affluent families, I’ve discovered that each family has a set of values that guide how they live and the decisions they make.  I’ve also found that the values can be somewhat different between the generations. This is usually a matter of emphasis or priority, not a complete switch of values from one generation to the next. But these differences matter.  This is why I advise families to talk about their values and prioritize them before they face a complex situation.  

For example, my brother went through a divorce and children were involved. It would have been easy for my family to circle the wagons around my brother, to isolate his wife and to lay all blame on her. We sincerely tried not to do that because we knew that his children were watching us and they are the next generation. Our challenge was to balance a family-first core value with the fairness and decency value. In almost any divorce, there is more than enough blame to go around.  

Here are some recommendations for parents of adult children facing complex situations:

  • Make a list of the core values that have guided you and why they are important to you.
  • Share this list with your adult children, preferably before they face complex situations.
  • Ask them to develop a list of their core values and share it with you. 
  • As your adult child faces their own challenges, pull out the list and gently ask them how each outcome is most likely to line up with their core values. Tread carefully on this point because it’s easy to be seen as preachy and judgmental, not as someone trying to help.  



Nearly every successful family I’ve worked with is goal oriented. This is why they achieve great things. But sometimes, advancing toward one goal can actually prevent you from advancing toward other goals.  and it can be tough to make these tradeoffs.  Psychologists call this an approach-approach conflict, where two appealing goals are mutually exclusive of each other. 

Some of the situations I described above are negative in nature: passing of a loved one, destructive behavior and divorce. But many complex situations that people encounter are potentially positive—like moving up into a better job, starting a business, having children or leaving work to spend more time with them. However, even these positive circumstances can potentially produce negative outcomes in some areas of our lives.  

For example, when I was a child, my dad made a big career move. He was employed by a large accounting firm and was doing well at work. But at home, we all felt ignored. He had little time for his children and my mother counseled him that this situation was not tenable long-term. He listened to her.  

He moved over to a different company and this gave him quality time with us. At first, our family income dropped for a while. But this was a sacrifice my parents were willing to make even though it delayed our family from achieving certain financial goals. I honestly don’t know how connected I would feel to my dad today if he had not made that move back then.  

Sometimes it can be difficult to identify which goals are most important to advance toward right now. If your adult child is struggling with this, here are some questions to help them think about their goals:

  • Have they defined a five-year plan for where they want to be in their careers, their finances and their family life? If not, this is a good place to start.
  • What goals are most important for them to achieve right now, next year, five years or even ten years from now? Are any of those goals mutually exclusive or can they all be advanced toward, some at a slower pace than others?   
  • Are there goals that might be delayed until later, like the way my father chose to delay making the highest income possible so he could be a better father and husband? 



When solving problems, time is nearly always a major driver of decision-making. I think there are three crucial questions to consider:

  • How much time do we need to discover options, predict outcomes and develop the plan?
  • How much time do we need to give ourselves to execute the plan?
  • How long will it take for us to figure out if our plan is working the way that we want?

Most of the complex problems I’ve seen my clients’ adult children struggle with will require time to fully address. Let’s take a fairly simple (and hopefully happy) example: starting a family. This has a built-in time component—nine months of pregnancy. But long before that biological process begins, there are all sorts of other factors to consider:

  • Where will we raise the child if our current home is not ideal?
  • Where will the child go to school and should we buy a home in an area where we like the public school system?
  • What do we need to do to prepare our home for a child?  
  • If you’re the mother,  will you go back to work after the child is born?
  • Do we have enough life insurance to provide for the child through college should the unthinkable occur?

Here is my experience. Complex decisions in life seem to require a lot of time to figure out what you want and then more time to make these decisions become reality. Being realistic about time helps relieve pressure in what can be rather tense periods.  

If you are helping an adult child discover the best path forward for them, here are some questions relating to time that I think can help:

  • When do we need to make a decision?
  • If multiple steps need to be taken, in what order and timeframe do we take those steps?
  • How hard do we push toward the horizon versus allowing time for things to unfold on their own?
  • How long will it be before we finally realize the goal and how will we know we’ve realized it? 



You’ll notice that I placed this last in the order. It’s not that wealth is the least important consideration.  But for most of the successful families I’ve served, the money is there to support the family and to help them live the lives they dream of.  Being smart with money is important.  But sometimes, spending money—even a lot of money—is the right thing to do for the family.  Knowing when to do so and how this will impact the family in the long run is what most of my clients seem to care about. 

For example, when I was a child, my parents emphasized being wise with money. We all had jobs and incentives to achieve certain goals. I worked at a fast-food company. My brother mowed lawns. We had to earn our allowance—10 cents for dishwashing and 10 dollars to mow the lawn. As you might imagine, we fought to mow the lawn.  

My brother had to work to buy a keyboard he wanted. That ended up becoming his career—a career he loves in music. My parents used these disciplines to try to instill in us a sense that money doesn’t grow on trees and we needed to work for what we wanted. This also taught us to value the things we did acquire; we appreciated them more than if our parents had simply handed them to us. 

Even though our parents instilled these disciplines in us, I do not doubt even for a second that my father would spend a great deal of money to help his children today. He has proven that over and over by helping his children in difficult moments. He has a strong sense of what money should do to help our family. While I believe he would prefer to pass along, by way of inheritance, most of the wealth my sibling and I will see one day, I know he would help us now if we absolutely needed it and couldn’t provide it ourselves.  

If your adult child is struggling with problems that involve money, here are some questions for both of you to consider:

  • How much money is involved here and is this our money, our child’s money or inheritance money that we intended to leave to our child?
  • As a percentage of our overall wealth, how much money will it take to address this issue? Is this an acceptable level of risk for us to take? Do we even have the money to do this? 
  • If spending money does not solve the problem, will we look back with regret on this decision five or ten years from now? 
  • Based on what we know today, would we look back on this moment, five to ten years from now, and wish we had spent the money to help our child resolve this problem?



The five questions that I’ve recommended have served as a good guide for my family when we face complex situations.  I am confident they can help your family too.  If you would prefer to have a conversation about a problem you or a loved one are facing, I’d welcome the opportunity to speak with you.  


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