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Too Much Vocation, Not Enough Vacation

It’s Important to Find the Right Balance

Welcome to another episode of word play, where I have fun juxtaposing similar words in new, useful and entertaining ways.

This blog style may feel familiar to regular readers, many of whom also live and/or work in the family wealth transition space like I do.

Helping families overcome some of the challenges with transitioning their business or wealth to the next generation is quite the little niche, but over the years I’ve come across lots of folks here, from all over the world.

Many of us are drawn to do this kind of work as a sort of “calling”, which is one of the words I often use to describe my own A-Ha moment when I finally figured out what I wanted to be when I grew up, which occurred when I was 48.

So that’s where I’ll start, with the idea that this kind of work is often a true vocation.

Vocation as a Strong Feeling

I just asked my friend Mr. Google for the meaning of “vocation”, and he says it’s a strong feeling of suitability for a particular career or occupation.

I’m not sure I could sum it up much better or in fewer words, so let’s go with that.

That strong feeling brings with it a lot of positives, of course. 

“It doesn’t feel like work when I’m doing this” is a common statement made by those who are lucky enough to have found theirs.

But naturally, I think, such positives usually have a corresponding negative, and that’s where we’ll go next.

It won’t surprise some of you that a recent peer group meeting is at the genesis of this blog post.

In fact, this is already the second post to emerge from that particular encounter, the first one being Circle Gets the Square – Non-Hollywood Version.

“I Really Need a Vacation”

This peer group runs on a “school year” calendar, from September to June.

So the wrap-up for the year just took place, and it was a full day, in person get-together.

As we were each doing our check-in with the group, I was struck by how many of us, myself included, mentioned how tired we were, and how much we were looking forward to some time off this summer.

That got me thinking that perhaps this wasn’t just some coincidence, but that maybe there’s something to this worth exploring further.

To do this work well, you need to put more than just your brain to work, because when you work with families, emotions are never far away.

While we also work hard not to become enmeshed with clients, that’s also another workload to consider.

Rodeo Clown and Court Jester

Things can get messy and scary at times when you’re playing a facilitation or mediation role among family members.

The ability to bring some levity to situations that are getting serious has us sometimes play the role of a “court jester”.

Other times, we need to jump in and be the rodeo clown, you know, those guys who jump in the ring with the wild bull after the rider gets bucked off, so everyone can escape without getting hurt.

Having said that, I just completed a wonderful family meeting recently with a family I’ve been working with for a few years, and I left feeling great, and on a high.

But, I was burnt out too, because the job of holding that space is exhausting, with much of the effort going into making it look easy.

We Are the Main Instrument in our Work

Sitting in a room with members of the same family when you are the only outsider (or one of a very small group of outsiders) is a special privilege that not many people get to experience.

We arrive with a proverbial toolbox and our experience, but we are there to take care of the process, while the family members supply the content.

That means that while we can (and do) plan these meetings, we don’t always know how things will play out. 

We need to bring our whole selves to such meetings; we are the main instrument of our work, the craftsman who brings the toolbox.

The tools themselves are not worth much in the wrong hands.

It’s hard work. And it’s rewarding. 

And you need to take time off to rest and recover before you burn yourself out.

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Challenges Transmitting the Value of Industry to the NextGen

Working Hard So They Won’t Have To

There are some challenges that people in my line of work see over and over again, but that usually lie somewhere beneath the surface.

We’re talking about transitioning family wealth from one generation to the next in a productive and meaningful way, which is so challenging because the creation of the wealth and its eventual transition typically occur in very different contexts.

Most wealth creators began from a place of scarcity and true need to do something to put food on their literal and figurative tables.

Decades later, when they get around to planning for the transition of that wealth to their heirs, those conditions are quite far in the rear view mirror for them, and possibly nowhere in the memories of those heirs.

Unfortunately, the value of “industry” does not always fall close to the tree.

A Confluence of Client Situations Creates a Spark

Some version of this challenge is percolating to the surface with a few clients with whom I’m currently working, which is what made it a salient subject for a blog post.

I wanted to find a phrase that captures it well, and settled on the “value of industry”.

It’s not perfect, but I like the fact that it leans towards a much less common use of the word “industry” than we usually come across.

I often share Google search results here, and now they arrive in the form of an AI summary, to wit:

   “When used to describe a person, “industry” signifies diligence, effort,                      and a persistent habit of working hard. 

    It implies a dedication to work and a strong commitment to                     achieving goals through sustained effort.”

Every hardworking wealth creator I’ve ever met hopes that this part of their DNA will live inside each of their offspring and all future generations.

Many end up disappointed.

Big Safety Net – Pros and Cons

Quite simply, most rising generation members of wealthy families become accustomed to living with a large safety net.

Many of those who don’t suffer from this are those whose parents worked extra hard to hide their true financial wealth exactly because of this fear.  But that method comes with its own set of drawbacks.

The word “entitlement” may be front and center as you read this. I’ll remind you that children become entitled in large part because of how they are raised. Entitlement Road is a two-way street.

Parents all say they don’t want their offspring to be entitled, and then many unwittingly parent them in ways that foster it.

The safety net is good, as most things with “safety” in their name are, but the other side of it is that it almost can’t help but erode the “industry gene’s influence” on how people choose to live their lives.

No Simple Solutions

I like to think that regular readers are used to the fact that I rarely provide simple solutions to the many challenges I share here weekly.

I sometimes talk about parents instilling a love of business to their rising generation, rather than a love of the specific family business they are currently involved in.

If everyone in the family has the “entrepreneur gene”, this can work well.

But societal norms are a huge headwind for many parents in their 60’s whose thirty- and forty-somethings do not value the 70-80 hour weeks of years gone by.

As I write this, I just received an email with the subject line, “Why younger clients want to retire early”; I could not make this up.

I know that the elders worry that their preteen and teen grandkids are getting a much different household vibe around the value of a job at which one toils for most of their adult life.

Sharing Stories and Co-Creating a Future

One thing I do know, though, is that parents lamenting this and keeping it to themselves isn’t usually helpful.

But regularly complaining about it in a judgemental way as a method to counteract it isn’t any better.

Perhaps the best antidote is regularly meeting as a family and talking about such matters, in and adult-to-adult fashion.

Sharing stories about hard work and its benefits and trying to help co-create a future in which this value of industry is a worthwhile pursuit for all family members can help normalize it as a laudable family trait.

It’s better that ignoring it or complaining about it.

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The Illusory Time/Money Trade-Off

Sounds Good, But Is It Real?

This week’s topic falls into the category of “I can’t believe I haven’t written about this yet”.

I’ve been sharing thoughts on the challenges in the family wealth space here every week for over a decade, and I don’t think I’ve ever dealt with this specific topic.

Not only that, but the catalyst for this post was a call I had recently with an old friend and former work colleague, who doesn’t fall into the wealth category that most of my clients inhabit.

Nevertheless, when we were catching up recently after far too long, he lamented the fact that he wasn’t wanting for more money, but was certainly being stretched for time.

That got me thinking that people who have plenty of money often believe they’ll be able to exchange some of that money for more time, but that that equation is not as straightforward as they’d like.

Wouldn’t It Be Nice

With a timely hat tip to the recently departed Brian Wilson, wouldn’t it be nice if you could actually buy more time?

Unfortunately, many people bust their hump for decades with the hope that some day, eventually, they can stop working so hard so that they’ll have more time for other things.

Of course there are some people for whom this does work out quite well, and maybe we should be asking them for their tips.

But if you take a look at my aforementioned friend, he’s dealing with an aging and ailing parent, and some very young grandkids who are clamouring for his time.

At the same time, his work life is now at a point where he’s busier than ever, and can’t see a short term solution to his being needed so much.

I happen to be a trustee of his family trust and we were talking about the fact that he needed me to sign some distribution cheques with big numbers on them.

“As you can see, money is not what I need more of, I need more time!” he said.

Do We Care Too Much?

Together we agreed that his biggest problem is that he cares too much about others, and if he were selfish, a lot of his problems would go away.

That’s almost a subject for a whole other blog post, but that may be too depressing to consider, because I think many people suffer from a similar condition!

But it does underscore the fact that simply taking some of one’s plentiful stock of money and believing that you can easily exchange it for more time is not as simple as you think.

And that’s true for a variety of reasons, most of which come down to the reality that dealing with human beings is rarely as simple as we’d like!

Where It Works Well

There are some straightforward areas where you can “buy” more time.

You can pay someone to mow your lawn or paint your house, thereby freeing yourself up for more enjoyable tasks.

But when you’re building a business that you’ve been dedicating your life to, it can be difficult to stop leaning forward and learn to lean back instead.

It can be done, and some people manage to accomplish it, but it doesn’t just happen

What Else Do We Need to Do?

There are a few things one needs to do to make this work.

I’m going to try to make them easier to remember by making them all start with the same letter.

Decide

Like so many other important steps we take in life, it starts with a decision. 

This might come as a result of a specific incident that sparks a lightbulb moment, or it might come as a result of an accumulation of exhausting days or weeks.

Either way, you need to make up your mind that you’re now going to change.

Delegate

Unless you don’t care about others and are ready to just drop everything, you’ll need to find others to step up and fill in.

This isn’t as easy as it sounds and can take time.

Even if you need to spend time training someone else, you’ll get that time back many times over later.

Don’t Back Up

Things will not go in a straight line or easily, but you need to continue to push forward, and never let up.

Whatever you do, don’t back up, or back down!

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“Circle Gets the Square” – Non-Hollywood Version

Throwing Another Analogy onto the Fire

If the quote in my title sounds familiar, you’re probably a boomer like me, who watched lots of American TV in the 70’s.

Peter Marshall, then host of the original Hollywood Squares TV show would utter that line several times an episode.

And that all has zero to do with my topic this week, i.e. circles and squares, and an analogy shared by a colleague recently, which I immediately embraced.

We’ll take a look at it together, as well as share an article I wrote a couple of years ago that deserves to be revived here too, because many readers probably haven’t seen it.

So we’re going to look at the Ten Domains of Wealth model from the UHNWI, bring in a piece I wrote a while back, and then layer in some circles and squares.

Let’s get started.

Ten Domains, and Ways to Look at Them

When the Ten Domains model came into being just a few short years ago, it resonated with me immediately.

It has evolved and been refined since then, and I like it even better now, because it clearly distinguishes between the four more technical domains across the top of the model and the five more relational domains along the bottom.

“Wealth Creation and Stewardship” is the label for the first four, while “Cultivation of Family Capital” is the moniker for the other five.

A couple of years ago I wrote a piece for CanadianFamilyOffices.com, which they titled “As Clients Demand More, Ten Domains Model Can Help Family Offices Deliver”.

That article was the first time I labeled the domains as “nine slices of a pie with a scoop of ice cream in the middle”.

The ice cream is the tenth domain, (or maybe it’s #1?) and it’s called “Family Advisory Relationships”.

So What About the Squares and Circles?

With that context now in place, we’ll move on to the squares and circles, and for that I need to thank a guy. That guy is actually named Guy, by the way.

As part of my participation in a local French-speaking group called Collectif Oria, I got to spend a whole day with my colleagues, discussing all matters relating to our work with families.

It’s a diverse group, and Guy noted that he considered himself and others who have a technical practice (he’s a financial planner) as “des carrés” (squares) while the relational experts (including me) are “des cercles” (circles).

He noted this early in the day, and as we progressed, I couldn’t help notice how many times it resurfaced in my head during a variety of discussions, and I shared those instances with the group at least a handful of times. 

Finding New Shapes, Squaring the Circle

Something that comes up in discussions with professionals who work with families who each arrive at this work from some “profession of origin”, is that many of us come in from one preferred “shape”, square or circle, in this instance.

But we quickly recognize that if we’re to be able to serve families well, we need to learn to appreciate the other shape, and understand them and their legitimate place at the table.

Many work very hard to learn to take on some hybrid shape, sort of a square with rounded corners, or perhaps a circle within a square or vice versa.

As a Canadian, the shape of a hockey rink comes to mind, which is not an ellipse but a “rectangle with rounded corners” as my friend Google just told me.

The article noted above talks about the fact that those who come from the professions who originate in the four domains of Wealth Creation and Stewardship typically know each other and are used to at least cooperating, and the same is true of those who work in the five Cultivation of Family Capital sections.

Can labeling them as squares and circles help make this more understandable?

Soft Versus Hard, Process Versus Content

There are many ways that I’ve written about this subject over the years, about soft skills versus hard, process or content specialists, and STEM versus liberal arts.

Getting back to Hollywood Squares, which is essentially Tic-Tac-Toe, at the end of every game there are both X’s and O’s all over the board, in different places.

In order to play a key role in Family Advisory Relationships, you need to be fluent and comfortable with all shapes.

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Enough – Assez – Basta – Genug

Lots of Ways to Say It, and to Think About It

There are words in every language that are used in a wide variety of ways, and as someone who bangs out over 700 of them every week here, I’ve developed a certain appreciation for many.

This week, we’re going to hone in on the word “enough”, especially as it relates to the kinds of family clients that I deal with regularly, i.e. those who’ve created a business or amassed a certain level of wealth, and who are now concerned with transitioning those to their rising generation.

I had jotted down the idea of “enough” as a blog idea, and was wondering how to turn it into a longer title, and decided to go with translations into the languages with which I have some familiarity.

But rather than focusing on the concept in various forms used in different places around the world, I instead want to break my thinking down into its use with a few different verbs, to wit: Having, Being, and Doing.

Having Enough – How Much Does It Take?

The initial impetus for the idea behind this post came from something I saw online, probably on LinkedIn, that I clipped and emailed to myself.

It was a snippet from The Psychology of Money, by Morgan Housel, a book that’s chock full of wonderful anecdotes.

It describes a scene in which two guests at a party being hosted by a very wealthy man are discussing how much money their host had recently made in a single day.

One of them states to his friend, “Yes, but I have something he will never have: enough!”

And therein lies the obvious question when discussing the ultra rich: how much is enough?

I recall an interesting response to this that I once heard, which was “About 25% more than I have now”.

The man quoted in the story did have enough, while his much wealthier host seemingly did not, and the assumption is that no matter what, he never would.

And which of them is happier, I wonder?

I Am Enough – Not Always Easy

While the idea of having enough or not will often be a question we consider when thinking of those who created lots of wealth, let’s move now to something that will more typically affect their offspring, being enough.

Friend and colleague Dr. Jamie Weiner refers to this dilemma faced by many rising gens as the “Quest for Legitimacy”, and he wrote a book about it a few years ago. 

You can listen to The Quest for Legitimacy podcast I recorded with him.

His premise is that those who grow up in the shadow of very prominent parents so often suffer silently from the feeling that they’ll never be able to live up to the standards that those extraordinary parents have set for them.

This boils down to feeling like no matter what they accomplish, they will still never be enough.

Another friend and colleague, Danielle Saputo, wrote a book titled “I Am Enough” about her own version of this challenge.

I’ve Done Enough

My guess is that for many readers, the first two concepts above are ideas they’ve considered at some point, especially if they live or work in the family wealth and legacy space.

Let’s see if that continues to be true as we now pivot to the question of doing enough, or actually better stated as “having done enough”.

We are now in the world of “over-functioning” that some parents have a hard time letting go of.

We’re also back to the idea of having enough, so that we can now slow down and begin to thrive without having to strive as much.

See Striving Before Thriving in a Family Enterprise

The stages of life through which we progress are full of twists and turns, and how we occupy the majority of our time is naturally one that offers lots of opportunities for reflection.

What have I done, or accomplished, feeds into what should I do next.

Is there some “unfinished business” that needs to be tended to?

More of the Same, Or a New Direction

I began a fresh new decade of my life last year, which has me now asking such questions of myself.

It strikes me, though, as someone who works with multiple generations in families, that the questions around having enough, being enough, and doing enough are constantly sitting there.

I hope this framework helps you with your reflections.

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Making It Safe to Share Your Feelings with Family

Some Recent FEC Symposium Takeaways

Much of the work I do these days comes down to helping families talk about important subjects together in a productive manner.

This involves coaching and facilitation skills, and sometimes a little bit of mediation too.

Most of the conversations that I assist with are around topics that every family knows they should be discussing, but without someone helping guide them, the conversations often feel a bit too risky to attempt, so having a neutral outsider along makes sense.

I’m always grateful for the opportunity to assist in such situations, because I understand why families are hesitant to attempt some of these discussions alone.

I’m just returning from the recent Family Enterprise Canada(FEC) Symposium in Halifax, and there were a couple of sessions on the first day that dealt specifically with helping to make it safe to share feelings among family members.

Allow me to relay some of my takeaways from them, because the question of safety is often at the root of the difficulty.

Fatherhood Unlocked

The first was a plenary session title Fatherhood Unlocked, featuring Dan Doty.

I had some idea of what to expect, because I’d recently hosted an episode of FEC’s podcast, Let’s Talk Family Enterprise (ep. 66), with Doty as my guest, as a tease before the conference.

It was one of the final messages during his talk that stayed with me, and I want to share his 3 keys to remember when you want to help someone open up and share their true feelings with you.

It’s OK to Feel your Feelings

The first step is to make sure to let the people know that it’s perfectly OK to feel the feelings that you’re feeling.

While this sounds pretty simple, it’s actually huge, because it runs counter to so much of the lifelong programming that many people, especially men, have been receiving for most of their lives.

You will feel feelings, I think we can all agree, but not everyone understands the importance of acknowledging them and trying to understand what they’re telling us.

Leaders Go First – Modelling the Behaviour

After reminding people that feelings are OK to have and acknowledge, there’s still a bit more work that needs to be done to get people to open up.

That’s where “modeling” comes in. Modeling is a fancy word for what we’re getting at, which comes done to this: Go first!

If I want you to do something that you might feel is risky, I’m much more likely to succeed in getting you to take that step if I jump to the front of the line and I go first, to show you not only how it’s done, but that it’s entirely survivable and even cathartic.

Be a Great Listener

Most people believe that they’re good listeners, and a lot of them are wrong.

But they aren’t usually wrong because of what they don’t do enough of, but because of the extra things they do that aren’t helpful.

Doty explained that it’s so hard to not jump in while listening to someone who’s sharing something difficult, because we want to be helpful.

We are prone to offer advice, and to try to “fix” the situation.

That doesn’t make one a great listener, and more often than not, simply listening so that the other person can feel heard is what is really needed. 

Avoid offering advice and trying to fix someone.

Moving Towards Safety, Or Away from It

After that plenary, it was time for a breakout session and I chose the one lead by friend and colleague Shauna Trainor.

It was about getting (and keeping) families aligned and accountable.

One of the exercises she had us do at our tables was to make two lists, while thinking about creating a safe space and environment for teams to share ideas with each other.

Her prompt was, “What do people do that moves people towards safety, and what do we do that moves people away from safety?”.

We all came up with long lists and you can too, but I’m sharing this because in the moment I felt like it dovetailed so nicely with what we had all just heard about in the previous session.

Groups, including families, work better when they can share openly and learn together.

The safety that we help create and the culture we build to make things go well are a constant work-in-progress.

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On Accepting Acceptance and Self-Awareness

It Is What It Is, And What It’s Going to Be

I’ve been known to say, somewhat cynically, that the secret to happiness is having low expectations.

The reactions that this statement elicits vary, of course, but rarely do people take me up on it for discussion.

So this week I feel like delving into the question of what we’re willing to accept, and how thinking about that can be helpful in managing oneself, especially in the context of working with family members.

This may get a bit hard to follow, so I apologize in advance, but I hope you’ll stick with me until the end to see how this will unfold.

Accepting That You Have to Accept Things

I can’t control anyone except myself. 

And neither can you, but of course we’re now talking about “yourself”, and not me anymore!

Far too often, we wish we could control others, and we even believe we’d be doing them a favour by doing so.

If you’re a parent, you probably have a certain perspective on this that others may not be able to relate to.

If you are a parent of young children, it’s actually a part of your responsibility to try to control your children, as you prepare them to become responsible adults.

But at some point, they do actually become adults, and then, controlling them is no longer their parents’ job.

Eventually, you need to accept that the child you raised into adulthood is now an adult, and they’re no longer your responsibility.

It Often Comes with Age

There is certainly a correlation between one’s age and one’s ability to accept that one can no longer control one’s offspring.

But age is only one component, as I know some people who’ve been alive for many decades who still haven’t arrived there yet, and I also know some younger people who already get it, despite their youth.

I only wish that those who have not yet arrived at this point would recognize how liberating it is to let go of this desire to ensure that others conform to their desires.

It really is a basic principle; I do me, and you do you.

Very simple, and yet not necessarily easy.

Once you do learn to accept that others are going to do what they want, and not what you want, a lot of pressure comes off.

An Unexpected Real World Example

When I first met “Lou” he was very high energy but also quite high strung.

He was a neighbour at my cottage, so I’d see him over the summer and then over the winter we’d lose touch.

One spring, he came over and seemed so much more calm, to the point where I mentioned it to him.

His recent divorce had caused him so much stress that his doctor had to have a serious discussion with him about the negative health consequences he was dealing with.

“So did he prescribe you some meds?”, I asked.

No. He told me to let it go.

There was more to it than that, of course, but that was the key. I’m glad that Lou was able to take the message to heart, because otherwise I fear he may no longer be with us.

Lou’s doctor helped him see that the stress he thought his ex-wife was causing him was actually something he could control, by letting it go.

Coming to Your Own Realisation

Each person either comes to this conclusion or doesn’t, but like I said earlier, anyone who has arrived here can tell you how liberating it is.

Are you aware that you are causing yourself harm by continuing to hang on to that desire to have others behave the way you wish they would?

That’s the self-awareness angle I hinted at in by title.

I’ve been over this ground in the past, in Rest in Peace, While You’re Still Alive, and in Equanimity, Yours for Only $250 Million.

If you devote only a small portion of the energy and emotion that you are dwelling on about how others are living their lives, and instead decide to focus on getting on with your life, you too can benefit.

The Greatest Irony of It All

One part of this that always strikes me is that those who are most guilty of this flaw are typically perfect case examples of those who themselves behaved very much counter to the desires of their own parents.

You raised them to be adults, now let them be adults.

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Knowing What Your Family’s Stuck With

The Latest Legal Documents Typically Rule

When it comes to the planning that families work on to transition their assets from one generation to the next, there are lots of moving parts.

It’s not unusual for discussions to drag out over months and years, when family leaders are trying to arrange things for the future. 

That isn’t necessarily a bad thing, because in my view it’s better to take your time to get it right than to rush into something that turns out to be sub-optimal.

But there’s also a danger in taking too long, or waiting too long to take care of overdue updates and revisions.

If someone important happens to die before everything is signed, you may very well be stuck with what was written the last time that agreements were actually fully executed.

The Illusion That All Is Good

Because the vast majority of people really don’t like to think about this stuff very often, there’s a tendency to delay taking action, even when you know that you really should be working on making your latest ideas and plans official.

Quite often a family will undergo weeks and months of discussions and drafting and revising and signing documents, and so when that’s finally all done, the last thing they want to do is open up that Pandora’s box again, even if several years have elapsed in the interim.

So more often than not, they continue to live under the false illusion that all is good.

Far too often, the sprint to wrap things up, and the fatigue that naturally occurs afterwards, means that few of those family members affected by these agreements actually know what’s really in them or have a good understanding of what’s to occur upon someone’s death.

The exhaustion feeling is a real thing.

“They’re Stuck with It!”

This subject came (back) onto my radar a while back during a peer call, when one experienced colleague was lamenting the fact that she often has to deal with such situations, where a family realizes that what they signed is not what they actually thought they’d agreed upon.

It’s also not what they want nor what they need.

This call was in French so I’ll give you the direct quote followed by my translation:

                           « Pis là, ils sont pognés avec ça! »

                           “And then, they’re stuck with it!”

I can’t convey her tone here, but let’s just say there was a certain amount of frustration in her voice, likely amplified by the number of times she’d experienced this (Merci AV).

So often this is the result of well-meaning professionals who were trying to do right by the family, but who, for a variety of reasons, ended up supplying “standard” documents that did not respond to the “custom” situation of the family in question.

All Good, We’ll Just Revise Them!

I noted above that this occurred a while back, and yet I’m only writing about it now, because I wasn’t sure there was enough there for a blog post until this past week.

I had the opportunity to be part of an annual forum over a couple of days with other professional who serve UHNW families in Canada.

While most of the peer groups and events I’m involved with are dominated by those who work the “family circle” around process, relationships and family dynamics, in this group I was a part of a small group of such specialists, surrounded by technical experts from the tax, trust and estates world.

The discussions we had brought this subject back into focus for me in a real way.

A Case Example Brings It Home

We were assigned into breakout groups to discuss a case loosely based on the Yellowstone TV series.

It was during my discussions with lawyers and tax specialists that it became very clear that it didn’t really matter what the family wanted, because if John died before they could get it all signed, sealed and delivered, they’d all be stuck with whatever his last will stated.

The Antithesis of “Plans Are Useless”

Back in 2019, in Plans Are Useless, Planning Is Indispensable, we looked at how important it is for families to come together to discuss and clarify what they want to happen in the future.

But unless EVERYONE agrees, they’ll be stuck with what’s written in the legal documents.

Best keep them current; but that takes work, time, and intention.

Let’s get going then.

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On Matching Families with Advisors and Teams

So Many Matches to Try to Get Right

When families are trying to get their continuity planning right, there’s never a single professional advisor who can handle all of the family’s needs.

That statement is becoming accepted today, more than ever, and that’s a good thing.

Of course that doesn’t mean that there aren’t still some who see themselves as able to cover off most of what a family might need, but we’re thankfully finally arriving at a place where most professionals openly acknowledge their limits.

They’re recognizing the importance of collaborating with others in service of their family clients.

Unfortunately, there remains a huge gulf between saying that you’re open to collaborating, and actually collaborating well on some regular basis.

If it were easy, more of us would be doing it, and doing it more often.

See Key Challenges to Serving Enterprising Families

The Initial Introductions Are Simple

Let’s get to back to the idea I broached in the title, on matching families with advisors.

A family leader will often know an advisor or have a friend in a similar situation who will introduce them to an advisor they know and like.

But after that, it gets difficult for that family leader to evaluate if that advisor they met is a good fit, and to what extent they can be a good resource for their family.

Most often, such relationships begin with technical advice around legal and tax questions, which regular readers will recognize that I find is a sub-optimal place to begin.

Eventually, some families get to the point where they recognize that they need support with getting the other family members to the table and involved in discussions and planning.

The family may realize that they need someone else to come in to deal with the dynamics and relationship issues, without which much of that technical work will be at risk or perhaps for naught.

Solopreneurs, Some Pros and Cons

Many of the specialists in the “family circle” space are independent, “solopreneurs” if you will, like me.

A major advantage we have is the flexibility to collaborate with others, regardless of the logo they have on their business card (remember those?).

Speaking from experience, this is an important asset.

But on the con side, I have spent over a decade waiting for most of the “institutional” players to understand and adopt this mentality.

Ten years ago, I was hopeful (perhaps naively so) that those who serve families on technical aspects of their planning would clearly see that they’re not necessarily well equipped to work with the family dynamics challenges and invite me in regularly.

Referral as a Handoff, Or an Integrated Team

Being referred into a family is wonderful, and it would be nice if it occurred more frequently.

Perhaps some of the hesitation to do so comes from the view that one is “handing off” a client to someone outside their firm.

Nothing could be further from the truth of course, as any good independent consultant recognizes that while serving the family comes first, a very close second lies in making the “referrer” look good (if only to hopefully encourage future referrals).

The idea of having an “integrated team” is beginning to see the light of day in some of the larger institutions, as they recognize the importance of offering a full range of services to families.

But the number of places where you can do “one stop shopping” is not large. See The Elusive Perfect “Cookie Cutter” Solution

Integrated teams are mostly aspirational, at least as far as finding the mix of technical skills and also the relational savvy to deal with an entire family.

Serving Every Member of a Family

Thus far I’ve only been speaking of the advisors, and I haven’t even touched on the fact that for anyone to be able to serve as a facilitator for their family meetings, you need to have very close to unanimous approval of all participants.

I always say that if one single person doesn’t want me there, it really makes my job nearly impossible.

They don’t all have to love me, but it’s better when they at least like the person who is running their meetings.

It’s also important that that person have what some call “multi-disciplinary fluency”, or an ability to understand what the other, more technical advisors, are talking about with the family.

Finding the right match for a family can take work, but is worth the efforts.

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On Peer Groups and Feelings of Infidelity

Sharing and Learning from Each Other

Working with enterprising families is naturally quite challenging and not for everyone. 

It can also often feel quite lonely when you are the only person who comes from outside the family system that you’re working with.

For those and many other reasons, I’ve always been on the lookout for any way possible for me to interact with peers who do this kind of work in one fashion or another.

Sharing and learning with other professionals who work with similar client bases in related ways, or even in almost exactly the same way, can be a very enriching experience.

Regular readers will recognize that many a weekly post here has its genesis in some sort of peer group experience, of which this is simply the latest.

Different Formats, Similar Results

I’m writing this piece on after having just completed two of my favourite group meetings, and they were very different yet equally enjoyable and stimulating.

One group convenes in person for one weekend annually, and fourteen of us gathered recently.

The other is a monthly hour-long Zoom call, where there were 10 of us this latest time.

The former group also added monthly Zoom calls in the past few years to great success.

Something that these groups have in common is that as members get used to being together, the conversations get easier, friendlier, and thus much deeper.

Each gathering feels more and more like a safe space to share, and that’s when the good stuff comes out.

The Meta View of Work with Families

What I also find incredible is how often the work we do together as a group mimics what we’re all trying to do with the families we get to work with.

Like how I just talked about the safe space and the comfort level that grows the more we gather together as a group.

Another such angle is around the leadership of each group, which can vary but is typically rather informal.

A related question surrounds the various roles that each participant plays and is expected to play, and whether or not such roles and leadership are fixed or will vary over time.

Sometimes It Feels Like I’m Cheating

As these peer groups mature, the closeness that members feel for each other can begin to feel pretty intimate, which is a feeling I enjoy developing with peers.

But my personal experiences are a bit different from most such members, I think, because I’m involved in a handful of such regular group gatherings with like-minded professionals, and it almost feels like I’m cheating on one group when I spend time in another!

I say that because in many of these meetings, someone will utter something like “I love these get-togethers with you all, because this is the ONLY place where I can talk about this stuff”.

Whenever I hear that, and it happens several times a year for me, I get a bit of a guilty feeling because I have a few other places where I get that warm and fuzzy glow.

But that guilt normally quickly morphs into gratitude for the fact that I have other such deep relationships, and even get to do this in more than one language.

Jealous of the Families We Serve

The concept of jealousy doesn’t only happen around the peer groups I’m part of.

Sometimes it can be the families themselves that can make me feel a pang of jealousy.

This doesn’t happen as often, but I have had (and still have) some client families where I admire what they have built as a family who regularly enjoy each others’ company.

What these situations have in common is that there are people who come together to talk with each other and spend time with special people in their lives.

It’s All About Affinity

One of the founders of this field is James E, (Jay) Hughes Jr., and he talks about creating a “Family of Affinity”.

For any peer group to have staying power (not all do) you need to create the type of culture around how you “are” together, even more than what you are going to “do” together.

Peer groups that begin to feel like an affinity group will do better than those where that culture doesn’t get developed.

Each group member bears some responsibility for its culture; I like to think I’m doing my part.

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