Dear Mr. Higgonbottom: My family wants a legacy book, but they only want the “highlight reel.” How do we handle the hard parts?

Dear Mr Higgonbottom:

My family wants to honor my late grandmother with a legacy book, but we can’t agree on what to include. Some just want a highlight reel of the positive parts, but others think that’s like turning her life into a brochure. How do we handle the hard parts in a way that’s acceptable to everyone?

Dear Caught-in-the-Middle,

Many families have found themselves exactly where you are right now. Trying to honor a loved one’s legacy while accommodating various family members’ wishes is one of the trickiest parts of any legacy book project.

The good news is you’re asking the right questions.

The disagreement between your family members isn’t really about the book itself but about what they each believe will best honor your grandmother’s memory. Once you can name that and agree on it, it becomes a lot easier to move forward without anyone feeling like their opinion has been dismissed.

Here are some steps to navigate this challenge:

Start with a scope conversation, not a writing session

Get all your family members in the same room — or on the same call — to determine the book’s purpose. Ask each other: Who are we writing this for? What do you hope to feel after reading it?

Answering those questions will sharpen your focus as you decide what to include. For example, if the group agrees that the book is meant to inspire younger generations, that shared purpose becomes your filter.

Using that filter, a difficult chapter that shows resilience would definitely belong in the book while gratuitous, uninspiring details probably wouldn’t.

Separate “what happened” from “how much detail”

Acknowledging that your loved one went through difficult times isn’t the same as dwelling on them. If you’re still having disagreements, help your family understand this distinction. You can include the hard parts honestly without making them the centerpiece of your loved one’s story.

For example, there’s a difference between writing ‘Nora struggled with poverty for much of her early adult life, which shaped her fierce determination to build something of her own,’ and dedicating three chapters to describing that hardship. The first gives readers what they need to understand her; the second risks making the struggle the story, rather than the person.

Let the subject’s own voice be the tiebreaker

Despite your conversations, you might still see family members disagreeing. If so, ask them to think back to your loved one’s own stories. Did your late grandmother speak about her struggles? Did she write them down in letters? What stories did she tell?

When family members disagree, returning to what she said about her own life is the most respectful way to break the deadlock.

Agree on what “hurtful” actually means

Consider the difference between a story that might embarrass a living relative — say, one about an uncle’s financial mistake — versus a story about your grandmother’s struggle with grief after losing a child, told with care and compassion.

The first has an identifiable person who could be hurt. The second might make some family members uncomfortable, but discomfort isn’t the same as harm. Asking who this story would hurt and why can help your family move past instinctive resistance and make more deliberate decisions about what to include.

Finally, consider structure as a solution

If the disagreement is still irreconcilable, the book’s structure can sometimes do what negotiation can’t. A celebratory opening, a contextual middle section, and a forward-looking conclusion can honor both impulses — the highlight reel and the real story — without either side feeling overruled.

Imagine the book opening with your grandmother’s proudest achievements. Maybe it’s the business she built, the holidays she hosted, or the way she made everyone feel at home.

The middle section then provides a fuller picture, encompassing the hardships she navigated and the sacrifices she made — the details that explain how she became who she was.

Finally, the book closes by looking forward, sharing her hopes for the generations that follow and touching on the legacy she left behind.

Structured this way, the family members who want a highlight reel get one in the opening, but the behind-the-scenes context is present too, giving the narrative the weight and honesty it deserves.

These conversations aren’t always comfortable, but they’re worth having before the writing begins. They can help produce a book that feels true; one that future generations will return to not just for milestones, but for a deeper understanding of who your loved one was and where they came from.

Cheering you on,

Mr. Higgonbottom