When you intentionally put your thoughts into writing every week, and you’ve been at it for over a decade, you end up recycling ideas that you’ve raised before.

Occasionally, you think you’ve come up with something novel, only to realize that you already covered it before, and you now have a dilemma.

Of course, there are always new ways to spin something and give it a new flavour, so I normally just press on because something compelled me to “go there”, even if “there” is some place I’ve already ventured.

So, we’re returning to the area of addition by subtraction, again.

See Addition by Subtraction in the Family Business from 2024.

Part of why I felt the need to write about this expression again stems from the fact that I really like to use the “addition by subtraction” phrase.

I’m not sure if it’s because it’s only three words or because of the ironic juxtaposition of the two main words, but it’s become something that rolls off my tongue any time a situation even bears a hint of making more with less.

But because my normal professional playground typically involves people who are related to one another, anytime such a situation even suggests itself, I actually hate the expression.

Whenever the idea of removing a family member is even a consideration for making things better arises, it feels like a failure of some sort.

As someone who is not part of the families that I serve, my perspective needs to be different, though.

For the members of the family, even a hint at the idea of getting a family member “out” feels like a no-go zone.

It’s so much easier to ignore the problem and just hope that it’ll resolve itself by some miracle.

Alas, hoping for a miracle is not a strategy, as you’ve surely already heard.

A while back, a longtime friend of mine who works in another field but also has some family business clients was telling me about a particular local FamBiz that he serves.

Not that I asked, but he shared that several siblings were in the process of taking over the business from their father.

He then added that one brother was not involved in this because

That line has stuck with me, and I’m not sure why. Perhaps it was said with a certain bluntness that makes it memorable.

I also don’t know if that phrasing is my friend’s interpretation or if that’s how the family members framed it when they told him.

When I think about families I know where members tried to stick together for the sake of sticking together, I have several examples where they hung on too long.

I even have one where the lawyers are about to be brought in and I may end up eventually being deposed.

Any family that manages to sustain some sort of enterprise over several generations must do some “pruning” along the way, otherwise things simply become too unwieldy.

See Pruning the FamBiz Ownership Tree.

I just unwittingly brought us back to the three circles by mentioning ownership.

See Three Circles + Seven Sectors = One A-Ha Moment (from 2013!).

Families need to decide who can and will own the business, as well as who can and will work in it.

But family remains family no matter what, right?

The threshold for being kicked out of the family is certainly higher than the other two.

At a recent FamBiz conference I attended a session addressing exactly, this subject, i.e. yes, you can fire a family member, from the business, but not from the family.

As I ponder situations I’ve been involved with, I realize that when we enter, we see things a certain way and conclude that someone may seem irredeemable.

I’m in one right now where ideas about how to extricate a family member from the business were top of mind when we started, but now things have changed.

The family, left to themselves, would probably have given up and fired them by now.

But with some intention and effort, we were able to find the right role where they could thrive and add value to the business, for a true win-win.

If you’ve been reading my missives each week recently, you’ll know that I recently attended my favourite annual event (see Coming Down from Yet Another Rocky Mountain High) and that the very engaging and profound sessions I attended have already sparked one recent post. See On Connection, Belonging and Learning in Families.

Now that I’ve processed everything a bit more, we’re returning to some of the thought-provoking wisdom I gathered from the various plenary sessions.

My thinking will surely continue to evolve as I compose these next paragraphs, which is secretly (or not!) why I force myself into this weekly ritual. I hope you stick around to see how I land it all.

One of the topics I so often return to here is how difficult it is to describe the work that my colleagues and I do, and so whenever I hear elders in our space share some of their thoughts on this, I jump into note-taking mode.

It bears mentioning that there are some definitions of “elder” that minimize the part about chronological age, and those are the ones I prefer.

For the second year in a row, one plenary session during Rendez Vous ’26 was a Fellows Panel, where three of our PPI Fellows were interviewed to share some of their wisdom, followed by a bit of audience Q & A.

Stacy Allred mentioned that her work involves “walking alongside families” and minutes later Matt Wesley shared that he “tries to stay one small step ahead of his families”.

Later, Wesley noted that a big part of this work is simply “being available” to rising generation family members, which I hadn’t necessarily heard anyone put that way, but which resonated with my work.

None of what I shared above is rocket science, but for those engaged in this work it’s important for us to have ways to describe our services in relatable ways.

I appreciated the simplicity of the wisdom they shared and felt better about the fact that I haven’t been missing that much in my own ways of talking about this family work.

Somewhere along the way, either during that panel or another session, I jotted down

and this is where we’ll now pivot.

Again, nothing revolutionary there, but when one works with families, which is complex work, we can sometimes get lost in the idea of finding the right next step “for the family”.

When we concentrate on serving the group, we can sometimes lose sight of the individual members along the way.

This work is centered around human capital, as opposed to the financial capital. We can’t ignore the money, but we need to focus on it less, because quite frankly, there’s already too many other specialists who are working on that part of the family’s wealth.

Working with the whole family requires facilitation, i.e. helping all the family members have productive conversations that they otherwise will not get around to having, despite knowing that they should.

A huge part of that is simply getting the family into a rhythm and a cadence of meeting together and then holding the space for them so they can speak and hear each other safely.

But facilitating the family space is not sufficient.

That’s where coaching comes into play, to work with each individual human on their own individual journey.

This gets back to the “being available” to the rising gen family members, but it is potentially much more than that.

As the father of a son and daughter in their mid-20’s, I know firsthand how difficult it is to resist trying to give them guidance on life that they are not asking for, even though they could surely benefit from it.

This is precisely the time where they are discovering things on their own, and that is as it should be.

They want to be the authors of their own lives, not the life that Mommy and Daddy envisioned for them.

At the same time, though, we’re there for the whole family, and the family has hired us to do what we can to keep them all together.

We serve families and their individual human members, and we want what’s best for all of them, as well as for each of them.

My Favourite Week of the Year

I’m starting this post at the Denver Airport on the Friday of another fulfilling week of connection with colleagues, including many who’ve become dear friends.

Regular readers will recognize that I’m referring to the annual Rendez-Vous of the Purposeful Planning Institute, which I’ve attended every summer in Colorado since my first time in 2014.

A Rocky Mountain High is the best way I can describe what I’m feeling in my heart and in my bones after four days of being with old friends and making new ones.

I enjoy most conferences I attend every year, but there’s nothing like the PPI crowd to warm my heart and refill my pitcher.

Section 01

Pouring Out for 51 Weeks a Year

Working in a niche of enterprising and wealthy families is really cool, but since I’m not an accountant, banker, or lawyer, the work I do isn’t easily explained.

So many of the other members of PPI are in the same boat, also working the “qualitative capitals” side of the street.

Because this work is so rarely understood by most of the people we interact with, we all spend an inordinate amount of time trying to explain what we do.

It can be exhausting, constantly pouring out such explanations.

Then we arrive in Colorado for a week of “adult summer camp”, as some have described Rendez-Vous, with our pitchers empty.

A few days later, they’re all invariably overflowing again.

Section 02

Like-Minded and Like-Called Fellow Pilgrims

Last year in Soaking in the Rendez-Vous Experience, Again, I mentioned that those who attend are mostly “like-minded and like-called”.

And this week in the closing panel/keynote, we heard from the venerable James E. (Jay) Hughes Jr., who referred to us all as fellow pilgrims.

I asked my good friend, Mr. Google, for his insights into the term “pilgrim” to see what I could learn from his vast wisdom.

Of his many responses, here’s my favourite:

Section 03

My Thoughts on this Pilgrimage

Let’s dissect that description a bit for its applicability to the situation that my fellow Rendez-Vous devotees and I are in.

It does feel like a journey, and a long one. There are no quick fixes or short-cuts.

The place we’re all going does seem sacred, although it isn’t really a destination. In fact, it’s not even really our “destination” either, but more of a desire to bring our client families to a better place.

There’s also a lot of devotion involved because many have become discouraged and abandoned the journey over the years.

The word “religious” doesn’t apply for me, but I do know some for whom it’s apt.

Section 04

Over-Functioning in Service of Others

In past years my post Rendez-Vous blogs have shared details on some of the content, but not this year.

You need to experience it to understand, and you can always come next year if you’re intrigued, but we sold out this year and had a waiting list, so don’t sleep on it too long.

I want to share my personal lived perspective.

I set an intention to be service-minded, and, as a long-time member, attendee, and pilgrim, to do everything I could to make first-time attendees and other newbies feel welcome.

I may have over-functioned in that respect, and at one point I was internally admonishing myself for this, especially regarding the two evening, self-directed, open-mike sing-along events.

Section 05

Not My Circus, Not My Monkey — Or Maybe It Is?

These informal, unstructured, evening outdoor gatherings were started years ago by someone who couldn’t make it this year.

Fearing that his absence would make it fall apart to some disappointment, I used my social capital to help make it succeed despite Doug’s absence.

This was not my circus, nor my monkey, but I cared too much to sit back and take the chance that it’d flop.

I’m glad we were able to find and welcome some new PPI rock stars.

(Thanks K.K. for the pic)

 

Section 06

Final Thoughts

Any organization that allows me up on stage with a microphone, in my favourite shirt, every year, is one I cherish.

The FRED Talks were once again a highlight; I worry that we set a high bar for coming years.

Finally, please recall PPI Fellow Matt Wesley’s statement during the Fellows panel:

If you want to discuss any of this, hit me up!

See you back in Boulder in 2027.

Not Something to Check Off a To-Do List

This week’s blog comes from the combined inspiration of a couple of posts I came across on my favourite social platform over the past few weeks.

As I consider their authors, it strikes me that one is from a man and the other from a woman, one is from the US, the other from overseas, and one is from a Gen-Xer and the other a Millennial (OK, I’m guessing ages here).

I believe diversity is a strength, as regular readers will recognize.

So, I saw an opportunity to combine these inspiring missives into one of my own, and now we’ll see if I’m up to the task. Wish me luck!

Section 01

Invitation or Interest? (Chicken or Egg?)

Taking the posts in the order in which I saw them, Andrew Pitcairn shared some thoughts on engaging the rising generation in a family enterprise context.

He nicely sums up a familiar refrain that so many of us in this field are familiar with:

Even if you haven’t seen this, you can certainly see the challenges this poses in any family enterprise situation.

He adds: “Two sides. Same longing. Zero conversation.”

As a fourth-generation family member who also serves as his eponymous multi-family office’s Ambassador and Governance Chair, Andrew has surely seen this dozens of times, right up close.

Section 02

The Problem with Purpose

Less than a week later, on LinkedIn once again, I stumbled upon a “slideshow” type post from Jessica McGawley of Dallington.

(Stay tuned for an upcoming podcast with her as my guest!)

The first slide caught my eye:

Hmmm, I wondered to myself, what’s wrong with purpose?

She continued, after grabbing my attention,

A-Ha, I quickly realized, that IS a problem I’m seeing…

Section 03

Go Find your Purpose, We’ll Wait

I replied to some comments to that post with:

Some of our major life occurrences occur within predictable age ranges, like puberty, menopause, and midlife crisis (?)

Finding one’s purpose is NOT one of those, so while encouraging young family members to go out and do that, with the expectation that it’ll come within a certain timeframe, isn’t helpful.

In fact, it’ll likely add even more pressure to them and is about as helpful as encouraging them to go out and find their soulmate/life partner. (Please don’t do that either).

Section 04

Back to the Invitation to Engagement

Let’s circle back to the first post’s idea of inviting the rising generation family members to engage with the family around the future of its enterprise.

Pitcairn’s lament is that there’s “Zero Conversation”, and that’s the clue we should be working with.

The idea is to create the conditions for conversations that show all family members all the possible ways that they can engage with the business(es) and ownership of the family’s assets.

Show them, ask them. Find opportunities, however small.

If family meetings seem like a no-brainer here, that’s because it is.

But thinking of an idea and implementing it are very different animals, with much different levels of commitment and effort!

Section 05

Talking Isn’t Enough — Action Is Needed

My comment on McGawley’s post about purpose continued, “something about ‘discover’ vs ‘find’ feels like it might be useful here”.

My friend Mr. Google came through again. To wit:

One’s purpose needs to be discovered, through action, and conversations including invitations to engage with the family, for support initially, and to support, eventually, are great ideas.

Section 06

Creating the Forum for Key Family Conversations

The work I do with families isn’t rocket science, yet most families have difficulty engaging and instituting regular forums during which to have these discussions.

But they are so worth it.

Reach out for support, we’re here waiting.