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“Is there enough to keep you going?”

Lauren Graham empathetically asked this simple, yet profound question in response to a 12-year-old aspiring actress in the audience of her book tour1, as if Lorelai Gilmore herself had stepped into the room with a blossoming Rory after a big, bad day with Mitchum Huntzberger.

I’m telling this story in reverse because I don’t like to bury the lede, but as you may have guessed, the initial question posed to her was, “How do I know whether I should keep acting?”

So, how does one know?

I didn’t think much of this seemingly insignificant moment at the time, nearly three years ago. After all, I wasn’t an actress. And my writing career was thriving as an SEO book blogger who’d reached approximately the top 10% of my field.3

I’d made it through the early stages of imposter syndrome and sneers from those with whom I shared my hopes and dreams. (Why is it always this way?!)

I also navigated the administrative shock of running a full-fledged writing business, from taxes and payroll to contracts, hiring, intellectual property issues, and being a Jill-of-all-trades all day, every day. And I earned a “Google” degree in everything from coding and email marketing to digital product sales, website security, graphic design, and more social media platforms than I can count.

Often, I tackled any combination of the above even before my first jumbo coffee of the morning. Heck, I’d even reached the mountaintop at which all those who once sneered were waiting, just to tell me they “always knew I could do it.” (Again, why is it always this way?!)

You get the point.

So, for some reason unbeknownst to me, Lauren’s (Can I call her that?) advice stuck with me. Maybe it was because she was so visibly taken aback by such a life-altering question from a preteen in her formative years. Maybe it was just because the preteen was as sprightly as season one Rory.

Shortly thereafter, I hit my own writing wall—one with the power to take down every Huntzberger: AI. Writers were the lowest-hanging fruit gobbled up and spit out by these evil little bots, and we can tell you just how quickly things became bleak.

Many of us lost almost everything.

I worked twice as hard to stage a comeback that would never come, then pivoted to Substack in summer 2025, where I now focus solely on Gilmore Girls-inspired content.

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(And, yes, I do think this platform is where Rory Gilmore would be today, too.)

While I became a bestseller in about six months (100+ paid subscribers), this whole “writing career in the age of AI” thing is still very much a work in progress, a chipping away at the iceberg day-by-day kind of thing—not a shot to the moon.

Lauren Graham confirmed as much in the commencement speech she published, In Conclusion, Don’t Worry About It:

“I’ve had ups and downs. I’ve had successes and senior slumps. I’ve been the girl who has the lead, and the one who wished she had the bigger part. […] Eventually, I was lucky enough to have the career I wanted, but it wasn’t a straight shot. It was a series of ups and downs, of steps forward and then back again. […] Satisfaction is a state of mind.”

Throughout each of my lows (and there have been many), I found myself asking those seven other words she shared:

“Is there enough to keep me going?”

It’s like I’m always looking for a sign—a compass outside myself with an arrow that says that, yes, I’m going in the right direction.

Somehow, that answer has always been yes.

In fact, just last week, I asked myself the question, then opened Instagram, where up popped a video of Lauren Graham recounting how she almost didn’t join “the union” (which allowed her to work as an actor) because she didn’t have the money. Against her instincts, she borrowed the money from her dad.

(If you, too, immediately picture Papa Graham saying, “So you need money,” in his best Richard Gilmore tone of voice, then, hi, we should be friends.)

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So began Lauren Graham’s famed acting career, the one that eventually earned her a star on Hollywood’s Walk of Fame, and the one that her father ceremoniously sent her off on when she wasn’t sure there was enough (literally) to keep her going. And so, there, too, was my sign to keep going, again—all of which leads us right here.

Nearly a year into running this Substack, it’s grown beyond a new home for our 6th annual Rory Gilmore reading challenge to read the books on Gilmore Girls.

So, I expanded from reading like a Gilmore to also living like a Gilmore with posts like this one:

But it’s time to expand even further. I’ve been teasing for about a month now, a new Substack section called “Room to Write.” It’s not just about reading and living like a Gilmore anymore. It’s writing like a Gilmore, too.

Here’s how I describe it:

“These are the highs, lows, and messy middles I've lived through as a former lawyer turned full-time writer who wants to see you achieve a sustainable creative business, too. I'm building in public on Substack, sharing the most and least impactful strategies I've implemented, and keeping it authentic and transparent along the way. In A Room of One's Own, Virginia Woolf said, "A woman must have money and a room of her own if she is to write[.]" Nearly a century later, Rory Gilmore found her own room to write on the reboot of Gilmore Girls. And here, I'm going behind-the-scenes on mine. This is our room to write.”

And this is the first post in this section. Some of it will feel insightful, and some of it will feel tactical (because as an Enneagram 6w5 and an INFJ, I’m a strategist at heart4). I’m doing the things and sharing my pivots as time passes and technology changes.

It’s something I’ve been doing quietly with friends for some time now.

And now, it’s in the open.

Little did I know that Lauren Graham’s uncomplicated advice about acting would be the thing that drove my writing career for years thereafter— the one that would keep gnawing at me.

“Is there enough?”

“Is there enough?”

To this day, yes, there has been enough to keep me going. And I want there to be enough for you, too. In her published commencement speech, Lauren Graham further advised: “Let joy be the thing that drives you. Give yourself permission to make mistakes. […] You already have the most, and you’re already one of the best.” Those are the vibes I’m bringing to the function.

And, lastly, in the words of her most beloved character:

So, are you with me?

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