This week we’re going to an unexpected place, because I hadn’t planned to write about this topic, but feedback from colleagues has forced me into it.
As regular readers will know, whenever I hear something that is even moderately “blogworthy”, I send myself an email to memorialize it, and then it sits there until I either write about it or discard it.
Occasionally, an idea will arise, and I’ll write about it immediately that week, and it never even makes the “Blog Ideas” folder in my Gmail account.
But this week, I was inspired by what I almost thought was a “throw away line” but that got legs when the feedback it elicited made me realize that I could no longer ignore it.
Section 01
The Nebulous Nature of Working with Families
Almost everyone I speak with about the work that I do with families becomes quite curious, and it feels like most of them never really understand what I tell them about it.
I used to blame myself for this, thinking that I wasn’t conveying it properly.
I’m now much more forgiving of myself, because most colleagues who do similar work also have the same challenge, and few have a simple way to overcome it.
The biggest issue we face is that while we want to bring each family we work with to a “better place” and help them make progress on their journey together, we don’t know exactly where they want or need to go.
But we somehow convince them that we’re the right person to help them make the journey go well.
Section 02
The Subtitle of an Upcoming Book
The “throw away line” I mentioned before comes from a colleague who’s a psychiatrist, and he was talking about yet another book that he’s working on.
I don’t recall the title he’ll be using, but his working secondary title is along the lines of
“I don’t know where we’re going, but I’m pretty sure I know how to get there”.
That sentence so resonated with me, and each time I’ve shared it with someone since then, I typically add “that’s the story of my life”.
It also reminds me of another colleague who states that he never wants to bring any client to a place that they haven’t already indicated they’re willing to go.
As advisors to families, while we can try to lead them to where we think they should go, we’re usually better off trying to guide them to where they’re trying to go.
Section 03
Leading from the Middle?
It turns out a very similar line,
“I don’t know where we’re going but I know exactly how to get there”,
comes from a book called The Lion Tracker’s Guide to Life by Boyd Varty. (I just ordered it).
While I don’t plan on tracking lions through the jungle, I do plan on continuing to guide families who face the challenges of transitioning their wealth or business from one generation to the next.
I like to refer to this as leading from the middle.
I use the guide analogy frequently, as I picture myself as a tour guide for a family.
Some members are running ahead and others straggle behind, and I’m responsible for keeping them together and getting them through the journey safely.
Remaining somewhere in the middle of the group makes sense in that context.
Section 04
Going Far Together, On a Journey
A decade ago, in Going Far? Go Together I shared my thinking on families slowly going together on a journey.
In 2018, in There Is No Destination we looked at the fact that in life, there is in fact no destination; life is all about the journey.
Living in the “now” is the key, and it requires me, as a guide to a family, to continually ask the same question, again and again.
“What does THIS family need, NOW?” (from 2025).
Section 05
Where Are We Going? I Don’t Know. But Follow Me!
Each family is different, and they need to be met “where they are”, and then we need to help them figure out where they want to go together.
Even though I don’t know where that is (because they aren’t usually sure themselves) I’m confident that their odds of going somewhere positive are greater with my guidance than if they were left to themselves.
I may not know “exactly” where that is, but I will help point out their progress along the way.




