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Ideas On Dealing with “The Family CRAP”

The Area Where So Many Things Break Down

Anyone who has any experience dealing with families in business together will recognize that such situations are rife with challenges.

Many experts say that situations involving the family relationships are more often the cause of business failures than problems that are “strictly business”.

Regular readers of mine will not be surprised to hear that I agree.

Yet so many professionals and experts who support business families concentrate their services in the business and ownership areas, and prefer not to get involved with all that “Family Crap”.

So this week we’re going to look at how some successful families actually deal with their “Family Crap”, and I’ll share some ideas that help families move forward.

All Families Need to Convene

The initial angle I was going for as I conceived this week’s post was around the verb “to convene”.

My good friend Mr. Google can help us out here, if I just enter the word “convene”, he returns with:

      Come or Bring Together for a Meeting or Activity, Assemble

I think that definition is helpful, because it puts a bit more formality around the idea of having a family meeting.

It speaks to the idea that someone has to initiate the “bringing together” and the fact that there will be some “activity” going on.

I’m often in a position to suggest that families get together more often to discuss important matters, and I’m starting to like the word “convene”.

They Need to Convene Regularly

So once we’ve agreed that convening family members is a worthwhile exercise, there are still a few other key elements we need to consider.

Quite often family elders and leaders will clearly understand that sharing information about how family assets are owned and organized is something that needs to be shared more broadly within the family group.

See Inheriting Wealth, AND Structures

And those folks also typically just want to get it all over with in one fell swoop. I get it, it probably won’t be fun, so let’s just rip the band-aid off and be done with it.

The problem with that approach is that it almost never works well, even if it feels good in the short term.

See The Dimmer Switch Vs. the On/Off

I always suggest that families get into the habit of convening regularly.

Letting the Clarity Evolve Over Time

When families establish a process of having regular meetings (quarterly or annually are popular intervals), information can be shared gradually, and family members who are usually not in the loop can absorb the information, and learn as they go.

The biggest problem with the “one big meeting” to get it over with, is that many family members end up drinking in the information through the proverbial fire hose, which is not the ideal way to satisfy one’s thirst.

So you want to get in the routine of convening the family regularly, and that’s still not enough.

You also want to ensure that the meetings are productive.

The meetings need to be set up so that when a meeting ends, things are more clear to everyone than when the meeting started.

CRAP: Convening Regularly And Productively

Apologies for waiting so long to get to the punch line, but the best way to finally deal with the “family crap” that so many families and their advisors try so hard to avoid, is to counter that crap with CRAP.

          Convene Regularly And Productively, i.e. CRAP!

You won’t be surprised to learn that I believe the key to “productively” is to have a neutral third party run these meetings.

Families all have their set ways of dealing with each other in the family group, or “family system”.

See Diving into a Family System Without Making a Splash

What I’m proposing in this “convening” is something special enough to warrant hiring an outsider to handle the facilitation of these meetings.

Yes, at first it seems like a luxury. In the long run, it is the biggest difference maker.

No, This Is NOT Easy. Most Families Don’t Do This, Either.

I’ve tried to simplify things here because simple is easier to understand. But simple doesn’t mean easy, and I’m not saying this work is easy to do.

Most families don’t do this. 

Most families don’t have as much at stake as families who own a business or assets together, that they are hoping to transition to the next generation.

That work takes planning, and making sure everyone is clear on what’s happening.

Start taking care of the Family CRAP.

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Let’s All Stop “Should’ing On People”

Say It Out Loud, Really Fast, for Effect

Writing this weekly blog is the main way I communicate my thinking, and it’s a wonderful medium to share my thoughts, for the most part.

Sometimes, it’s not quite as good as the spoken word, because the attempt at humour that I’m going for depends on the ability of the reader to pronounce a word in the exact right way to get a joke to work.

So I hope you’ll all been able to get it, and maybe the accompanying visuals will help.

If not, it’s OK, because the joke isn’t germane to the point, which is that we might do better in our attempts to advise people if we didn’t simply always tell them what they “should” do.

Yet Another “Combo Post”

So this sound-based double-entendre between should and “poop” is the initial inspiration, but on its own, it didn’t have the heft to carry a whole post.

As often happens, an idea sits in my Blog Ideas folder for a while, and then something else will come up and I combine ideas.

A while back, I had yet another exchange with a regular reader in which they relayed something about “changing ‘shoulds’ into ‘coulds’” being healthier when advising families. (Thanks JG!)

The point is that having a family come up with their own solutions is almost always better than having them simply follow the instructions of any advisor.

Let’s Stir In Some Self-Righteousness

Thus far you may be thinking that I’m directing these thoughts to advisors who work with families, and of course I am, but this also applies equally to members of families when dealing with each other.

The final part of the inspiration for this post was a missive from a few weeks ago, On Vulnerability and Self-Righteousness in Families.

Therein, we looked at how those who are self-righteous come from a position of assumed moral superiority over others.

When you add in that element to someone who’s constantly “should’ing on you”, I think you can imagine why such messages are sometimes not well received (even when they are acted upon).

When I say “I think you can imagine”, I do realize that while most people get this, those to whom this message is being directed are unfortunately least likely to recognize themselves.

From Know-It-Alls to “Just Trying to Help”

There are always people who just think that they’re so smart and are also very certain of themselves, no matter the situation.

Many people who grow up in successful families are blessed (cursed?) with such parents.

Most of these “know-it-all” types also convince themselves that they’re coming from a good place and “just trying to help”.

It can be difficult to escape their force field, especially when there’s ample evidence of their success, making their ideas seem like they should be correct.

We can have such people around us at work or within friend or community groups of course, but they’re often most dangerous within a family.

Insidious Within a Family

I’ve had the privilege to work with many family groups, where several people who are related by blood need to work together, in order to make decisions around assets that their family owns for the benefit of the group.

The propensity to “should” on others most often happens between generations, but also sometimes occurs in sibling or cousin groups.

It can actually be even more fascinating to observe in such situations, because it’s rather rare.

And when I say “between generations” you probably default to parents should’ing on their “children”, but in some families the script gets flipped as parents age. 

See My Favourite Oxy-Moron: Adult Children.

The attitude of moral superiority and certainty, which combine to define self-righteousness, is sometimes difficult to watch; imagine living under it!

Mel Robbins – The Let Them Theory

I probably shouldn’t mention a book that I have not read myself, but I will make an exception, based on the reviews it has received and some personal endorsements for it that I’ve heard from people I trust.

I can’t put it better than this, directly from the Amazon listing: “a simple mindset shift, to break free from others’ opinions, drama, and control”.

The book’s title suggests that it’s aimed at the “should’ers”, but that phrase implies that it’s also for the “should’ees”, which makes me want to read it.

It’s hard to get the “should’ers” to stop, so maybe equipping the “should’ees” is the way to go.

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Improving a Family’s Situation Vs. Solving their Problem

The Two Approaches Are SO Different

Enterprising families preparing to transition responsibilities and asset ownership to their next generation typically rely on various experts along the way.

Regular readers of mine know that I specialize in accompanying families on such journeys, trying to help them get things right.

You’ll also recognize that I’m sometimes frustrated that this “human relationship” work often plays second fiddle to that of the experts who support families with easier to understand services, like investment management, tax strategies and trust structures.

Each week here I try to illuminate some of the challenges in this work and this post is no exception.

I’m also a life-long learner, always working on finding new and better ways to support those who choose to work with me.

Family Systems Theory as a Base

It’s been over a decade since I first immersed myself into learning about Family Systems Theory, specifically the Bowen variety.

I even wrote a book about this effort, Interdependent Wealth, published in 2019.

More recently, I stumbled upon a course on Systems Thinking (i.e. general, not simply family systems) and decided it was worth taking.

I knew I’d learn a lot from it and I did, and this week I want to share one specific learning for the benefit of others involved in family continuity work like me.

The title of this piece gives a strong hint, yet I know that I need to put this all into proper context to make it make sense.

Let’s just start with what I think is obvious, that those who serve families with products and services like those noted above are problem solvers.

And families do have problems to be solved, so those problem solvers are very much needed.

Please Don’t Stop There. More Work Lies Ahead!

What so often occurs, however, is that once one of those “problem solutions” is put into place, the family believes that their work is done and that everything else will automatically take care of itself.

So many of those who serve families come from the “solution provider” angle, and not enough of us come from the “how can we improve your family situation?” side of things.

The Systems Thinking course I took gave me a fresh way to think about and talk about this challenge, as I had hoped it would.

The “problem solving” versus “improving a situation”, comes from two different kinds of systems thinking, unfortunately named “hard” and “soft”.

Hard Systems Thinking and Soft Systems Thinking

When I use the word “unfortunate” above, it’s because it just repeats a term that gets misconstrued in this work, which so often has the area in which I specialize categorized as “soft skills”.

I’m not sure why, but soft skills are frequently denigrated as less important.

I’ve written plenty on this, notably in Liberal Arts vs. STEM Skills to Serve Families, and Circle Gets the Square, Non-Hollywood Version.

In short, hard systems thinking is about solving a specific problem, while soft systems thinking is about improving a situation.

Here’s what Google’s A.I. summary shared when I asked it:

        Hard systems thinking applies quantitative, structured methods to solve well-defined technical problems with single, optimal solutions, focusing on objective criteria and predictable outcomes. 

         Soft systems thinking uses qualitative, human-centered approaches to address complex, ambiguous problems involving multiple, subjective perspectives, aiming for achievable and desirable changes rather than a single perfect solution. 

(Emphasis added in bold and italics)

More Metaphors and Analogies

It struck me that because I deal with families, I should share some analogies or metaphors related to families.

So here goes.

Having just celebrated my 33rd wedding anniversary, let’s go there. We had a wedding, during which we signed some documents to officialise our union.

That was a one-day event, and the following 33 years of our marriage have been all about learning to live with each other.

The priest who married us took care of solving our problem of not yet being married, but the work of a marriage and living together is much deeper.

Along Came the Children

Years l later, my wife delivered two great children to the household, assisted by some doctors and nurses along the way.

They helped solve the problem of getting the babies out of her womb, but the work of raising them was an everyday undertaking.

The soft stuff is always there, and it’s a lot of work.

Helping some families with the tasks of figuring out complex transitions goes better with the right support, hard and soft.

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Challenges Re-Engaging Families for Yet Another Journey

How Did Their Previous Ventures Together Go?

Each week here I share some of the realities that surround the kind of work I do with families.

Recognizing that my work is part of a “niche within a niche”, I know full well that most people have difficulty grasping just what it is that I’m trying to accomplish with my family clients.

As I crafted the title for this post, I stumbled upon a pretty apt word, “journey”.

Just about every family I’ve worked with has come to a point on their journey where they recognize the need to broaden the base of family members involved.

The current leading generation eventually accepts that there will be a point where they are no longer in charge, and preparation for what comes next must begin.

Bringing In Outside Support

Wise family leaders also realize that in order for this next phase of the journey to go well, they’d best bring in some outside support, because things can get complex pretty quickly.

I always applaud them for coming to this conclusion, even though sometimes it takes them more than one attempt to find the proper resources to assist them.

This week’s post is inspired by the fact that it recently dawned on me that I have three current family clients who initially embarked on some version of an expanded family journey with the rising generation a few years back.

And now, those past experiences are creating additional challenges for me as I try to help them navigate this next leg of trying to progress to a better place together.

Journeys Evolve Along with their Participants

My writing about journeys here goes back several years, my first post on this being There Is No Destination.

That post looked at how too many people consider so many aspects of life as “somewhere to get” as a goal, whereas I think it’s much healthier to focus on enjoying the journey along the way there.

I followed that up a few years later with Guiding a Family’s Interdependent Journey, which detailed how family members’ lives are probably more intertwined than they may realize.

Supporting families as they prepare for an eventual wealth transition is a very long process.

Ideally the work is spread out over years, although sometimes it happens in fits and starts.

The life stage of the participants is always an important factor to consider when assessing how much engagement you can get from everyone whose input and participation you’re seeking.

You’re Not the Boss of Me

Professionals who work with businesses are often surprised at how difficult it can be to get a large number of family members into a room together, or even on a virtual call.

In a “normal” (i.e., non-family) business, the boss calls a meeting and everyone shows up. If not, there are consequences.

Such rules are subject to different interpretation in many family situations, where offspring cannot simply be ordered to attend meetings.

So imagine families who’ve been on some kind of journey together, but it got “stalled” for some reason.

Trying to energize everyone to re-enroll in something again will probably come with major skepticism.

What a Difference a Few Years Makes – 3 Versions

Sanders:

Back around 2020, the “Sanders” family was fresh off a liquidity event. 

They all lived close together, and ideas of keeping the family fortune together had them assembled together with advisors from their accounting firm.

In 2025, now geographically scattered, their needs were now much different, and re-engaging them into a family project is more difficult.

Perry:

Around 2016-2018, the “Perry” family still had a large operating company run by 3 “G2” siblings, and they began working on gathering together as a large tribe to sketch a way forward to bring in G3.

After selling the OpCo, the work on the journey forward with one of the branches around the dining room table looks much different, and patience with “re-doing” some of this again is in short supply.

Taylor:

In 2019, “Mike Taylor” was looking for support to bring his teenage G3’s into a discussion about their wealth.

Now that most are in their 20’s and working, those shifts demand a new approach.

Facilitating Things from Where They Are NOW

When guiding them on these journeys and facilitating their meetings, I’m constantly re-assessing where they all are, and how the journey is progressing for each of them.

I’m meeting them “where they are” and that’s a moving target!

And I’m hoping they’re up for it.

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Handling the “Family Office Question” from Clients: How Advisors Can Respond with Confidence

One of the most stress-inducing questions that many financial advisors receive from wealthier clients is, “Do I need a family office?” Any suggestion that a valuable client is even considering switching can create anxiety, even for the most seasoned professionals. Responding with a simple “yes” can make it seem like you don’t value them, or worse, that you’re ready to walk away. But saying “no” in the wrong way may not inspire much confidence either.

What if there were a way to do what’s best for your family clients while remaining an essential part of the team that helps them achieve everything they’re looking for?

Unpacking What Clients Really Mean

The truth is that most families don’t need a family office, although some may like the cachet of saying they have one. The real questions for advisors are

How can this family get what they need? 
and:
How can I help them get there?

When clients see that you’re genuinely focused on their interests and act on that, they usually see even more value in the relationship.

Someone holding up a chalkboard that says 'ask the right questions'

Ask the Right Questions.

At this point, curiosity is key. Asking questions like, “Can you help me understand what it is you’d like to accomplish for your family?” opens the door. Often, clients aren’t seeking a massive internal structure. Instead, they may feel overwhelmed by complexity, frustrated by disjointed advice, or uncertain about how to engage the next generation. They want their advisors to work together more effectively and want better ways to involve family members.

That desire for “something more” is valid and is an opportunity. The solution they imagine may not be the solution they actually need. 

Alternatives to a Traditional Family Office

A single-family office (SFO) is designed to serve one family, often spanning multiple branches and generations. In practice, the wealth threshold usually starts in the mid–nine figures (around $500 million), given the cost of employing a dedicated team of professionals.

Some families will have been approached by multi-family offices (MFOs), which aim to provide SFO-like services at a lower level of wealth. But the term “family office” has become loosely used, and offerings vary widely. Many families end up competing for attention or discovering that the promised support doesn’t quite match reality.

What most families are really looking for, when they raise the family office question, is not a large staff but relatively greater sophistication and coordination in how their wealth is managed, tailored to their specific situation and delivered when needed. They require a range of expertise: investment management, tax planning, estate planning, philanthropy, family governance, education, and more.
For many, the best answer is not to build an internal family office but to create a network of trusted, external specialists who can be brought in as required. This approach provides flexibility, scalability, and cost-effectiveness.
pegs with interconnected ties representing a network

Creating a trusted network is key.

Advisors who build trusted partnerships can deliver many of the same benefits while avoiding the pitfalls. By collaborating with complementary firms, they can cover much of that range, and, increasingly, even MFOs are seeking out such partnerships to expand what they can offer.

Your Role as Strategic Architect – Partnering for Scale, Sophistication, and Trust

At the core of every advisory relationship is trust, and if a client is asking you about a family office, it’s likely because they already trust you deeply. That’s a good sign. But it’s important to acknowledge that no single advisor can meet every need. Rather than trying to be everything, you can position yourself as the strategic architect of their wealth plan. You can be the advisor who ensures all the moving parts fit together.
For clients, this means access to the right expertise at the right time, without unnecessary cost or duplication. For advisors, it means being able to deliver more without overextending themselves.

Clients’ desire for more sophistication is not a threat. It’s a chance for you to step into an even more pivotal role.

Blackwood logo, with the last piece of a puzzle being fit in.

Key advisors know the pivotal role they play.

Building these partnerships allows you to deliver what families want without presuming to be everything they need. At Blackwood, we regularly collaborate with other professionals, especially in areas outside traditional financial expertise, such as family governance and intergenerational engagement. Because we don’t sell financial products, our work is entirely conflict-free, and our role is to enhance, not replace, the work of existing advisors.

Why This Approach Wins – For You and Your Clients

When you’ve already earned a family’s trust, expanding your role to help them access the right expertise is a powerful way to become indispensable. Families appreciate when their advisors recognize limits but also take the initiative to connect them with solutions. By guiding them to the right partners, you demonstrate leadership, foresight, and care.
The family office question isn’t a threat to your client relationships – it’s an invitation to elevate them. By building strategic relationships with complementary providers, you can position yourself as a trusted partner who orchestrates the right expertise at the right time. This approach strengthens client loyalty, enhances outcomes, and protects your role as a trusted advisor.
The next time a client asks, “Do I need a family office?” remember they’re not asking to leave you. They’re asking you to help them think bigger about how to manage their wealth. The only real question is, are you ready to meet them there?
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Family Wealth – a Safety Net for Taking Risk

Looking at Family Wealth from a Different Angle

A few weeks ago, in Soaking in the RendezVous Experience, Again, I noted that while that blog was all about the lived experience of that great annual happening, there would be future posts inspired by the conference’s content.

And once again, I’m being true to my word.

The final half-day, Thursday morning, began with a great panel that was titled “Fellow Forum on Well-Being”.

It featured a moderated discussion with 5 “PPI Fellows”, all sharing many tips, ideas, and secrets to their success over their decades of serving families.

While it was about well-being, their comments meandered over much broader territory.

Lots of Wisdom Shared, One Unexpected Nugget

I don’t normally take a lot of notes at conferences, preferring to pay close attention instead, on the assumption that anything worth remembering would surely stick.

I’m not sure if it’s because I’m getting older, or maybe it’s because they gave out cool pocket-size notebooks, but this time I came home with many pages of notes, including a bunch from that session alone.

One of the panelists mentioned that at a certain point in his life, he considered one of the key benefits of a family wealth cushion as “the ability to take a risk”.

As someone who regularly deals with families who’ve achieved a certain level of wealth, and who sometimes lament that that wealth can create certain disincentives in the lives of some family members, this resonated with me.

I’m always on the lookout for new and interesting ways to talk about wealth with families, to help them figure out the best way forward for their family.

Finding the Goldilocks Zone

So let’s think about this for a second.  Having a “safety net”, so to speak, sounds like a good thing, doesn’t it? 

Well yes, and….

If you have some family wealth to “fall back on”, you can try certain things that you otherwise could not.

That certainly provides one with more flexibility in life choices than not having such a cushion.

And, like any other seemingly good thing, it can be taken too far, in some cases.

Like so many concepts, many of which I try to explore in these weekly missives, it can become a negative, if taken too far.

As I considered this idea, I began to look at it from the viewpoint of many different families I’ve worked with or known, over the years, including my own.

As is so often the case, the trick it to find the “Goldilocks Zone”, i.e. just enough, but not too much.

Not Naming Names, As Usual

Without naming names, because I always need to be careful not to reveal too much here, let’s consider some real life versions of this phenomenon.

Consider a G2 family member who was gifted a certain percentage of the business started by their Dad that was soon after sold for nine figures.

That 8-figure cushion in the pocket of a thirty-something allowed them to move across the country with their spouse and a few grandchildren, much to the lament of the business founder.

Whether or not that ability to take a risk is a good thing or a bad thing depends very much on one’s perspective, doesn’t it?

Or the G3 twenty-something, who talks about the ability to “just be a school teacher and basketball coach”, if that’s what he wanted to do.

Judging by the look on his Mom’s face when he mentions this idea, I’m not sure she’s convinced that that would be a good use of the family’s wealth.  

See Challenges Transmitting the Value of Industry to the NextGen.

The Road Not Taken, But Could It Be?

Another client still has an operating business, so liquidity is not as plentiful, but he also struggles with questions of whether or not to even mention that some family wealth could be available to his offspring for them to consider career choices based on things other than the ability to generate sufficient wealth.

It can be difficult for me to even suggest such ideas to some clients for them to consider.

In my own family, my twenty-somethings have benefitted from educational opportunities many could not afford.

They’re now early in careers, and this question of opportunities to take risks is as salient as ever for us to discuss.

I think that it’s a great way to frame the discussion, and will encourage families I work with to have these intergenerational conversations going forward.

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On Vulnerability and Self-Righteousness in Families

Exploring the Relationship Between Two States of Being

As I write this week’s missive, I’m excited to see what I’ll come up with as we look at a couple of “states of being” that I’ve often seen in family client situations.

Regular readers can surely guess which one typically leads to more successful family relationships.

This post has its genesis in the opening keynote presentation at a recent conference I attended.

A couple of weeks back, in Soaking in the RendezVous Experience, Again, I promised that some of the content from that “conference” would soon be shared, and here we are.

All About Authenticity

Mike Robbins, author of Nothing Changes Until You Do, among other books, kicked off the day with a thought-provoking talk titled “We’re all in this together”.

He shared his “Authenticity Equation”, highlighting three components to authenticity: Honesty, Self-Righteousness, and Vulnerability, to wit:

 

  Authenticity   =   Honesty   –   Self-Righteousness   +   Vulnerability

 

I’m of the belief that any good equation is open to moving parts of it around, at least as a learning exercise, so I hope you’ll join me.

Let’s dispense with honesty first. 

Of course it’s important, but it’s really only table stakes, i.e., the price of admission.

If you’re anything less than honest with your family members, well, good luck.

So What About Self-Righteousness and Vulnerability?

Here’s where I think it gets interesting.

I thought about writing about these two separately, because Rogers suggests that you need to minimize the first one (i.e. subtract it) while maximizing the second (i.e. add it).

I fully accept that any amount of self-righteousness will lessen one’s authenticity, while any amount of vulnerability will add to it.

But as I considered this whole idea, I felt like there might be more to it.

Could the relationship between these two be one of mutual exclusivity?

In others words, can you even be both vulnerable and self-righteous at the same time, or does one preclude the other?

Could they be two ends of a continuum?

Compare: Being Curious vs. Being Judgmental

Let’s look at this by comparing it to another pair of states of being that some suggest are also mutually exclusive, curiosity and judgment.

I’ve heard (and come to believe) that you cannot be curious and judgmental at the same time.

Try it.

Getting curious precludes your ability to be judgmental, at least for a moment.

See No Room for Judgment when Working with Families

I hereby propose that the same is true of self-righteousness and vulnerability

Can you be both, simultaneously? I think not.

What Does Mr. Google Think?

When dealing with specific words that define a state of being, I always like to check with my friend Mr. Google to make sure I’m on somewhat solid ground.

For self-righteous, he came back with:

    • Having a certainty that one is totally correct or morally superior
  • A person who thinks their beliefs and morals are better than everyone else’s

For vulnerable, he returned:

  • Capable of being physically or emotionally wounded
  • Being in a situation where one is likely to meet with harm

Okay, I’ve got to admit, it’s not as clear as I would’ve liked it to be, so I’ve got a bit more work to do here.

Maybe if I put it into my preferred context, family relationship situations, I can make myself clear.

How This Affects Family Relationships

Let’s imagine a family meeting where there are members of at least two generations present.

I’ve been privileged to be in the room in many such situations with families other than my own.

I’ve seen my share of self-righteous parents lecturing their offspring.

I’ve witnessed them trying really hard to not sound self-righteous.

And yet, even unspoken, it is often right there, front and center, to the point where it’s all the others can see.

It’s the classic “one up, one down” scenario. 

I’m up here, you’re down there.

 

Leading with Vulnerability Instead

I’ve also been in the room when parents have shared real life stories from their past with their offspring where they were at less than their best.

Owning up to failures and missteps where the parent demonstrates their humanity (you know, humans make mistakes!) can be such a disarming gesture of vulnerability.

I always try to impress upon the family leaders I work with that what they should be aiming for is to have “adult-to-adult” relationships with their rising generation.

You are not always right, and they know that.

So please stop acting like you are.

 

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Responding Versus Reacting, Revisited

One Is Usually Better, But Not Always

This week we’ll be looking at an idea I’ve touched on in the past, but in a new light, thanks to an interesting exchange I had at a conference I recently attended.

When I crafted the title to this blog, I was convinced that I’d be able to link to a previous post that I’d written specifically on the “Responding Versus Reacting” concept I so often mention when speaking with people, but alas, that blog exists only in my imagination.

I will, however, still be revisiting the idea, because the conversation noted above forced me into a few different reflections: on the subject itself, how universally true I thought it was, and on how I share my thoughts on it.

So far this has been rather vague, I realize, so thanks for indulging my meandering style of setting up these weekly missives.

The Perfect Set-Up for Sharing a Favourite Idea

Allow me to set the context for you. 

It’s the evening before the first day of the conference, so I headed down to the hotel bar to see who else flew in early.

After chatting with some long-time friends and acquaintances at a table, I’m heading back up to my room to get some sleep when I happened to recognize a face from last year at the bar.

Next thing you know I’m offered a drink and I’m suddenly chatting with a small group of mostly strangers here for the same gathering.

One of the men begins relating a story about tension between a father and son, and we start talking about ways the son can learn to avoid similar situations with his own, teenage son.

Next thing I know I’m sharing one of many Zig Ziglar stories I have in my repertoire. 

(Curious readers are invited to type “Ziglar” in the search feature of my website).

Responding Versus Reacting

So I begin sharing the key differences between responding to a situation and reacting to it.

The simplest way to remember it, is to consider a medical situation and how we speak about the interventions that happen at the hospital.

“They gave him medication and he is responding” is always positive, whereas, “He had a reaction to the medicine” is negative.

When we take a step back and compose ourselves and respond to something that happens or what someone says, we have a better chance of things going well, versus immediately reacting without thought, which often escalates a situation.

When taken aback, I sometimes deliberately pause and even say, “I want to take a moment to think about this so I can respond, rather than simply reacting”.

I Thought It Was Clear, Until….

I felt like I’d made my point well and the conversation veered into a few different directions.

But imagine my dismay, when a while later one of the guys was relaying another story, where this time the problem was that someone had become way too complacent with a situation, and the protagonist was not responsive enough.

And as he concluded, he pointed to me and said, “Like you said, he should have reacted!”

Wait, what? 

I felt stumped and was thankful that the number of beverages consumed by all made this fade away as the subject once again got changed.

But I now had some reflecting to do, as my concept had been turned on its head.

Time to Revisit This

I think it was on the plane back home a few days later that it hit me that I needed to circle back and reconsider what happened and how I talk about this important subject.

Did I not explain myself well enough, was there a problem with my metaphor, or is it something else?

I believe I did explain it well enough, but there are limits to every metaphor, this one included.

It is still a good idea, in most cases, to pause and take a moment to provide a considered response to something, rather than simply quickly giving your gut reaction.

And, there are also times when pausing for way too long can be sub-optimal.

Flexibility Is an Asset

We need to recognize the limits of rigidity and the benefits of flexibility in many areas.

How long we take to reflect before we respond is probably one of those areas, but I will continue to err on the side of pausing.

/by
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Soaking In the RendezVous Experience, Again

My Tenth In-Person Gathering with My Tribe

This is an easy blog for me to write each year, but also a difficult one.

I attended my first RendezVous of the Purposeful Planning Institute in 2014, as I was just discovering the world in which I am now fully immersed.

I vowed then to never miss this annual experience and I’ve been true to my word.

If you add in the two RendeZooms we did in 2020 and 2021, I’m now on a twelve-year streak.

If you’re wondering why this is difficult to write, it’s simply the challenge of converting a lived and felt experience into words.

But I think I’m above average at that, so I’ll give it my best shot.

Setting My Intention Going In

As I was getting ready for Monday’s opening reception, I decided to set an intention for the next few days.

This year, I was just going to try to “soak it all in”.

Over the years, I’ve played a variety of roles for this organization in preparation for this annual extravaganza, but I only had one small part to worry about, so just soaking everything in seemed like a good idea.

There was, as usual, a whole heck of a lot to soak in, and my proverbial sponge got quite heavy.

By the time Thursday rolled around, I was ready for a respite, if only to try to digest everything I took in.

It’s Not Like Any Other Conference

One of my favourite things to do during RendezVous is to find first-time attendees and ask them what their experience has been like.

Almost all remark that they’ve never been part of such a welcoming group of people, which is usually when I then share that by the end of the first day of my initial attendance, I told myself that if I could only attend one conference a year, it would be this one.

Someone noted that it wasn’t really a conference, it’s more of an experience, and I guess that’s a nice way to phrase it.

All Working Toward the Same Goal

There’s something about finding one’s “tribe”, and just coming together to share how we’re working our way through the many challenges we face in our work with families.

What we all have in common is that we’ve dedicated our careers to helping families plan for the transition of their businesses or wealth from one generation to the next.

While many professionals do work in this space, the vast majority do so in very technical specialty fields like law, accounting, banking and wealth management.

What brings the PPI community together is the work in what I sometimes call the “family circle”.

There’s a certain amount of “a calling” or vocation to the way many of us approach our work.

Still Feels Like a Niche

Because it’s a calling, people have very strong feelings about it, and when like-minded and “like-called” people meet, there’s a special attraction.

Many of us feel a bit lonely over the other 51 weeks of the year, so it’s a wonderful change to just be with and interact with others who are going through a similar life and career experience.

We all also know that there is a huge need out there from families who could use support with their challenges.

And as I like to put it, even though there is a huge need, that doesn’t necessarily mean that there’s a corresponding huge demand for our services.

The result is that we can all use each other’s support in trying to translate that need into demand for our services.

Who We Are Versus What We Do

We’re getting to the end here and I still haven’t shared any of the great content I picked up; fear not, many upcoming posts will dig into that.

Likewise, the entire RendezVous is more about who we are together and how we are together, and who we are becoming together, than about what we do.

It was, once again, an enriching experience because of the great folks I’ve met there over the years.

The fact that I got to go up on stage wearing my Fred Flintstone shirt again (as MC of the FRED Talks session) was just a bonus.

The laughs I shared over Thursday’s “family dinner” with KH and AK were a wonderful way to cap off the week.

See you there again next year.

/by
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The Elusive One-Big-Happy-Family

All Happy Families Are the Same…

Most weeknights after having dinner and watching the news, my wife and I watch Jeopardy together.

A couple of months back while doing this, there was a clue that referred to a famous quote from Tolstoy’s Anna Karenina.

Because my wife was unfamiliar with it, I asked my friend Mr. Google to get me the exact line, which is actually the opening sentence of that classic book from the 1870’s.

It reads, “Happy families are all alike; every unhappy family is unhappy in its own way.”

Unfortunately, this highlights the fact that there are lots of ways for families to be unhappy.

99% Unhappy, 1% Happy?

The very next day we were driving somewhere together and for whatever reason, it came up again, and we talked about it.

She noted that there are way more unhappy families, suggesting the figure of 99%.

I chose not to argue with her, and we both agreed that I had the workings of a blog post about this, so here we are.

The title of this post is meant to highlight the fact that most families want to be perceived as “One Big Happy Family”, but that under the surface, very few of them actually are.

As someone who works with families on the important subjects relating to their future wealth transitions, helping move a family from “unhappy” to “happier” is part of what I’m usually going for.

Who Gets to Judge this Matter?

A constant challenge to this work is that the family is not one unit, it is a system of many interdependent human beings, who each have their own views, opinions, feelings, and behaviours.

Many of the professionals who handle the more technical aspects of this work can get away with thinking about the family as a unit, but those who work on the relationship angle between the family members are constantly confronted with individual differences in each person.

There are usually some people who think of their family as a happy one, where other members of that same family would disagree.

Who gets to decide if their family is happy? 

What if I think we’re happy but I’m the only one who thinks that?

Ideally, we can find a way for families to talk about this to find ways to make each person a bit happier, which should thereby make the family happier as a result.

Could it be that simple?

Looking Back at a Couple of Past Posts

Thinking about this subject conjured up a couple of posts I’ve written here that touch on this subject.

First, in On Wellness, Performance, and Relationships in Families, we looked at how those three subjects are a convenient way to consider how people are doing.

Are they feeling well? Can they do what they’re trying to get done? Do they get along with all the people they interact with?

I suggest that the more Yes’s you get to those questions, the happier you’ll be.

And if more members of a family can get 3 Yes’s, that family would likely be happier too.

Key Question: Are there ways for the family’s wealth to support and contribute to getting more Yes’s to those questions from more family members?

Should Happiness Be the Goal?

Unfortunately, many people put a bit too much focus on happiness as a goal, which can bring negative results.

Back in 2022, I shared Make Sure Happiness Is a By-Product, Not the Goal.

That post was inspired by a session at an FFI Conference where a person who specializes in addiction treatment and recovery was the one who stated the line I used as my title.

How many parents do we know who did everything to make their children happy, and then realized (and regretted) that their kids did not develop enough resilience and independence to launch into adulthood.

Maximizing Each Family Member’s Human Capital

As is so often the case, when I set out to write on this week’s topic, I didn’t know where it would lead.

Between you and me, that’s what keeps me coming back each week, but please keep that to yourself.

If you want a happy family, those “interdependent human beings” that compose the family should probably be your focus.

If you’re fortunate enough to have accumulated plenty of wealth, why not use a portion of it to try to enhance the “wellness, performance and relationships” of every family member?

Maybe that’ll help you have that One-Big-Happy-Family we all strive for.

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