I Fell Down the #Hustle Rabbit Hole. Now I'm Climbing Out.

TL;DR: I fell into the hustle culture trap—building audiences, creating digital products, publishing weekly—all because the bros selling courses told me this was the path to financial freedom. When they started selling AI tools to help me keep up with the content machine they built, I realized: I got trapped in the system again. Time to climb out.

Hey there 👋

When I made the jump from school leadership to EdTech, I was hired to be an in-house K12 SME. But before long I branched out into content creation and writing. Because I was new to this, my manager (now work bff) sent me to take a digital writing course. I chose Ship30for30—a program where you’d learn to write for what was then Twitter, posting a threaded, long-form tweet once a day for 30 days.

I loved it. I thrived. I learned a ton. I got myself noticed in a cohort of 500.

At the time, the founders—Dickie Bush (yes, really) and Nicolas Cole—were just starting to build their business. In the intervening five years, it morphed into what I can only describe as a near-cult of hustle culture. And I drank the proverbial Kool-Aid.

Per the endless emails and “free” offerings, I learned that one must have a personal newsletter. That the newsletter was to “build a list” and create “lead gen” which could then lead to monetizable digital products. That with just 23 emails, one would start raking in the bucks. Look at the two of them! Earning millions!

I bought in. A year ago, I paid for Cole’s newsletter course and started my newsletter. “Niche down,” he instructed, “but this only works if it either makes the reader money or helps them save money. Anything else, no one cares.”

So I picked the most monetizable topic I could think of: leadership guidance, help with the workplace codependency and people-pleasing that holds women back from their full earning potential. Was this my area of expertise? Yeah, no. But it fit the formula.

“If you publish every week, you win Substack,” Cole counseled. Okay. I’m super competitive and driven. I can do that!

“For this to work, you must have a social following of over 10K.” I chose Threads. I gave myself a year to hit 10K. I reached it in just shy of three months.

Then I paid for another course on digital products. I made my first one. Posted it on Stan. Another $30/month. So now I’m maintaining a social platform, publishing a weekly newsletter, and making digital products.

Oh, and I work full-time (and I work really hard), have four kids (three still at home), and cook and clean and fold laundry every single day.

I am really so fucking tired.

Here’s what hustle culture sells to women: You have valuable knowledge. Turn it into a business. Build your personal brand. Create passive income. Achieve financial freedom.

It sounds empowering. It sounds like taking control of your career and your worth. It sounds like the antidote to watching Steve get promoted again (which, by the way, he did last week).

But here’s what it actually is: a system that takes women’s unpaid labor—the mentoring, the coaching, the emotional support we’ve been giving away for decades—and tells us the problem is that we haven’t figured out how to monetize it yet. The solution to workplace inequity, apparently, isn’t structural change. It’s a side hustle.

The pattern works like this:

First, they identify your expertise. Maybe it’s something you’re actually good at, or maybe it’s just something you’ve been doing for free that other people find valuable. Mentoring younger colleagues? Helping friends navigate difficult conversations? Perfect. That’s your niche.

Then, they sell you the system. Newsletter course. $497. Digital product course. $997. Platform subscriptions. $30/month here, $79/month there. You need all of it to “win,” to “build your empire,” to “create the life you deserve.”

Finally, they exhaust you with their own demands. Post every day. Publish every week. Engage with your audience. Create lead magnets. Build your funnel. Optimize your conversion rate. And when you’re too tired to keep up? Well, here’s an AI tool for $79/month that will do it for you.

The real genius of the system is this: it takes your legitimate frustration with workplace inequality and redirects it into individual entrepreneurship. Tired of not being valued at work? Build your personal brand! Watching less qualified men get promoted? Create your own income stream! The system that’s holding you back at your job? Just work around it by working more.

When women feel stuck in their careers, we’re told to:

“Invest in yourself.” Take courses. Build skills. Get certifications. All of which costs money and time—resources you may not have—and puts the burden squarely on you to fix a broken system.

“Build your personal brand.” Post consistently. Show up on social media. Share your expertise. Create content that “provides value.” In other words, perform unpaid labor in public in the hopes that it might lead to paid opportunities later.

“Create multiple income streams.” Because one job isn’t enough anymore, apparently. You need a side hustle, a newsletter, digital products, a course. Never mind that you’re already working full-time and managing a household.

Here’s why this advice fails: It treats systemic problems as individual deficiencies.

The reason Steve keeps getting promoted while you don’t has nothing to do with whether you have a personal brand or a digital product line. It has everything to do with how organizations value (and compensate) men’s contributions differently than women’s.

The hustle culture solution doesn’t address that. It just adds more to your plate and calls it empowerment.

And here’s the really insidious part: the only people consistently making money from this system are the ones selling it. They’ve figured out the actual passive income model: create one course, sell it to thousands of exhausted women, then sell them the next course on why the first course didn’t work.

Yesterday, I got another email from Dickie and Cole. They’ve built a new AI-powered program to generate content for people exactly like me—people who are exhausted from all the content production they told us we needed to do (!!!!!) For $79/month, I can use their platform to spit out content that sounds just like me.

This one pushed me over the edge. I joined the cult of hustle culture, and I want out.

Two people sent me this article from The New Yorker this week (s/o Vic, the fab artist for this newsletter and my ever-inspiring MIL Myrna.) The piece traces how feminist self-help has become “a mirror in which our financialized society admires its reflection.”

So, here’s what I’m doing differently:

Instead of: Publishing every week because the algorithm demands it
I’m Gonna Try: Writing when I have something to say

Instead of: Building an audience to convert into customers
I’m Gonna Try: Sharing insights that might actually be useful

Instead of: Paying for platforms and tools to “optimize” my content
I’m Gonna Try: Using what I already have and what actually serves the work

Instead of: Treating my knowledge as something to monetize
I’m Gonna Try: Treating my knowledge as something to share

This isn’t about abandoning ambition or giving up on growth. I appreciate that at 59, I continue to evolve and learn new things. I want to keep at that. But not because it’s monetizable, and not at a cost to my energy level and bank account.

This is about recognizing that the system—the one that underpays us, undervalues us, and promotes Steve again—has figured out how to sell us the solution to the problems it created. And the solution is: work more, for less, and call it a side hustle.

This week, I’m doing three things:

1. Unsubscribing from Dickie and Cole’s email list

2. Canceling my Stan Store subscription

3. Committing to share only when I have something to say

If you’re feeling the weight of hustle culture, I invite you to pick one subscription, one “should,” one optimization tool you’re using because someone told you that you had to—and let it go.

Notice what happens when you stop performing productivity and start protecting your energy.

• Hustle culture sells women the idea that the solution to workplace inequality is individual entrepreneurship—more work, more optimization, more content.

• The only people making money from this system are the ones selling courses on how to make money.

• Climbing out means recognizing the trap: your value doesn’t need to be monetized to matter.

With you all the way,
- Kara

P.S. I’m not sure what I’m writing about next week! I’ll see what happens this week that feels worth sharing with this audience, whose plates are already very full.