Last month won one of my monthly challenges, so here we are in the spotlight talking about Substack, love and so much more.

Judith writes The Love Stack. She is 69. She grew up in a family of teachers, as I did. She started her career writing press releases on Madison Avenue in New York, then studied education and human development, taught children, parents, and teachers, and published four books. Now she writes on Substack about aging. But not the way most people write about aging.

She calls it entirement. It’s a word she invented. And the reason she needed a new word is at the heart of everything she’s built.

Before I get to that word, I want to give you the single sentence that shapes how we should think about creator authenticity.

It’s Judith’s motto and it goes like this: “You have to live it to give it.”

She said it about her writing. She said it about her rebrand. She said it about why she waited to introduce a paid tier. And every time she said it, I found myself thinking about how many Substack creators are trying to skip this step.

You can’t write about a life you haven’t lived. You can perform it. You can research it. You can borrow it from those who did. But when your readers get to the other end of the page, they can feel whether the writer is standing where they’re pointing.

Judith’s whole Substack is built on this rule. Here’s what it actually looks like in practice.

The rebrand that only happened when she became who she was writing about

Judith started her Substack calling it “The Treasures Within”. She’s an introvert. She does everything from the inside out, as she put it. That felt like an accurate description of her writing at the time.

Then she read a book. Bell Hooks’ All About Love. And she came across a definition of love in that book that reframed everything for her.

“Their definition of love is that it’s supporting the spiritual development in the other. And I never heard a definition like that. That means it’s an action. It’s a verb. It’s not a noun.”

That reframe didn’t just change what Judith thought about love. It changed what she thought her Substack was actually about.

So she started calling it “The Love Stack”.

She’d come to understand that love, as an active verb-based support of another person’s growth, was the actual through-line of her writing, her teaching, her books, her grandmothering, and her life.

Most people do the opposite. They pick a positioning first and try to grow into it. Judith grew into her positioning and then updated the label to match.

The word she invented

Now to entirement.

Judith’s Substack is about the wisdom years as an opportunity to return to the authentic self we were in childhood.

Her exact words:

“It’s the person we were before we learned to perform, pretend, or please others.”

Sit with that for a second. If you’ve ever noticed how much of adult life is spent maintaining various performances (the professional self, the parent self, the online self), you know how important that sentence is.

Entirement is her word for stepping back into the version of you that existed before the performances started.

It’s a play on retirement. But she’s not talking about the end of work. She’s talking about the return to wholeness. The full circle.

“I decided to bring it all together, and it all makes sense as a whole,” she told me.

Here’s why this matters for creator positioning. Judith could have written about aging using any of the standard vocabulary. Retirement. Senior years. Third act. Wisdom years. Golden years. Every one of those phrases has audience overlap and existing search volume. Any SEO expert would have told her to pick one and commit.

She invented her own word instead.

And the invented word is what makes her Substack stand out in a crowded niche.

Why she waited to introduce paid

Judith didn’t turn on paid subscription until she could deliver on it authentically.

She now offers three tiers. Free subscribers get the weekly posts. Paid subscribers get an entirement manifesto she just updated, the opportunity to write an “Ask Omi” letter (Omi is what her grandchildren call her) that she may publish with permission, subscriber chats, and bonus writing when it shows up. Founding members get a copy of her book Where Wisdom Meets Wonder plus everything above.

Every tier maps to something she can actually provide.

She said this explicitly on the call:

“I don’t want to overpromise and underdeliver. Whatever I say I’m going to do, I have to be sure I can do it. I know a lot of people say jump in there and say you’re going to do it, but unless I really know I can do it, I’ll feel stressed about it.”

Most Substack advice tells you to turn on paid immediately, and I do too, but only when you have enough of it already published. For Judith this was a bit later.

The right question isn’t “am I ready to charge?” The right question is “can I keep the promise I’m about to make, immediately after purchase?”

If your paid tier requires four posts a month and you can sustainably deliver two and you haven’t published anything yet, don’t turn it on. If your paid tier requires a monthly workshop and your energy doesn’t sustain that, don’t offer it. If your paid tier requires you to be someone you haven’t become yet, definitely don’t announce it.

The gardener metaphor she extended to Substack

Judith mentioned a book by Alison Gopnik called The Gardener and the Carpenter. Gopnik argues that parenting isn’t like carpentry. A carpenter has tools, wood, and a blueprint, and produces something that matches the plan. Parenting is more like gardening. You plant seeds without knowing what will come up. You tend the garden. You wonder.

Judith extended this to Substack:

“I think that’s kind of like what writing on Substack is like. It’s tending your garden. You go in and give it some water. Tend to it, take care of it. And then see what develops.”

That’s the whole model for growing a Substack.

Most creators approach their Substack like a carpenter approaches a build. Blueprint. Plan. Execute. Deliver. And when the numbers don’t match the plan, they conclude something is broken.

Judith approaches it like a gardener. Consistent tending. Some things bloom. Some don’t. The overall garden gets richer over time. She’s not forcing it, she just keeps showing up.

Both approaches produce results. But the carpenter approach burns creators out. The gardener approach sustains them.

The TLDR version

If you take one thing from this spotlight with Judith, take this.

You have to live it to give it. Your writing on Substack will always land with the emotional weight of whether or not you’re actually living what you’re writing about. Readers can feel this. It’s the difference between a piece that resonates and a piece that reads well but leaves nothing behind.

Rebrand when you outgrow your positioning, not when you’re chasing a better market. Judith moved from The Treasures Within to The Love Stack only after she’d embodied a new definition of love. The name change followed the transformation. It didn’t manufacture it.

Invent your own vocabulary in saturated niches. Entirement isn’t a better SEO play than retirement. It’s a signal to readers that the writer has a specific worldview worth understanding. That signal is worth more than search volume in a crowded category.

Don’t turn on paid before you can deliver on it. The right question isn’t “am I ready to charge?” It’s “can I keep the promise I’m about to make?” Small promises kept build more trust than big promises broken.

Tend your Substack like a garden, not a construction project. Consistent care. Some blooms. Some don’t. The overall garden gets richer over time. This approach sustains creators. The other one burns them out.

Watch the full spotlight session above for the parts I couldn’t fit in here. Judith goes deeper on the Bell Hooks reframe of love, her “Ask Omi” letters, how she stopped comparing herself to other creators, and how she uses AI as a check-in tool for her drafts.

Subscribe to Judith here:

Subscribe to Judith

Watch on YouTube here:

Yana

P.S. Judith shared three books that shaped her, plus her own four (affiliate links):

The Secret Life of Bees by Sue Monk Kidd: The multi-million bestselling novel about a young girl's journey towards healing and the transforming power of love, from the award-winning author of The Invention of Wings and The Book of Longings
All About Love by Bell Hooks: Here is the truth about love, and inspiration to help us instill caring, compassion, and strength in our homes, schools, and workplaces
The Gardener and the Carpenter by Alison Gopnik: What the New Science of Child Development Tells Us About the Relationship Between Parents and Children

Judith has also written four books of her own:

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