Hour seven of the Write for Money and Power 12-hour livestream book launch was a masterclass in what happens when you refuse to flatten your thinking for the internet.
I was joined by ashley ray — a comedian, freelance TV critic, and cultural commentator whose work has appeared in Vulture, The A.V. Club, Elle, Variety, and more. She’s also the creator of Deep Trouble, a Substack that goes far beyond hot takes — publishing smart, funny, deeply researched essays and cultural deep dives that refuse to fit into a tweet-sized box.
This conversation was about why going deep still matters — and why chasing constant reaction is quietly hollowing out culture.
Here are a few ideas from Hour 7 that deserve a slower reread:
Hot Takes Flatten People
Ashley named something we all feel but rarely articulate:
When everything is reduced to hot takes, we lose the fullness of people.
You get frozen in one moment. One opinion. One clip.
Nuance disappears — and with it, curiosity.
Deep work gives people room to be complicated again.
Don’t Say Something Just to Say Something
One of the strongest throughlines of the hour:
You don’t need to have an opinion on everything.
If someone else has already said it better — let it go.
Writing only when you have something new to add builds trust. It tells readers you’re not here to farm engagement — you’re here to think deeply and offer them nuanced takes. In short? You respect them and their time.
Substack as Creative Autonomy
Ashley talked candidly about why Substack matters so much to her.
On Substack, the rules change:
You choose the topics
You define the tone
You own the audience
That autonomy isn’t abstract. It’s felt — in how you write, how you rest, and how much risk you’re willing to take creatively.
Your Perspective Is the Niche
Ashley’s career is deliberately multi-hyphenate: comedy, criticism, TV, podcasts, cultural analysis.
And the advice she gave writers struggling with “niching down” was refreshingly blunt: Make your own lane.
The internet no longer needs you to fit a single box. Younger audiences don’t care about legacy hierarchies — they care about whether your work is interesting.
Depth beats branding.
Cross-Training Makes Better Writers
One of my favorite metaphors from the hour:
Comedy, criticism, podcasts, essays — they cross-train the same creative muscles.
A joke can become a 5,000-word essay.
An essay can turn into a podcast segment.
A cultural obsession can become a career pillar.
None of it is wasted.
Say No So You Can Say Yes Better
Ashley was honest about something many freelancers learn the hard way:
Saying yes to everything doesn’t make you stronger — it makes you scattered.
Being selective with your time lets you bring your best self to the work that actually matters.
Every yes is also a no to something else.
If you care about cultural criticism that’s smart, funny, rigorous, and genuinely curious — you’ll want to spend time inside Ashley’s world:
And if this conversation lit something up for you — about originality, ownership, and refusing to contort yourself for the algorithm — the philosophy behind all of this lives inside my book:
The ebook is $0.99 because ideas that matter should be accessible.
More to come.
Thank you Mary Beth Kaplan🪶, Megan Gilbert, Amy Benavides, Joni Chan, Kristine Vince, and many others for tuning into my live video with ashley ray!
-Amy
