⛰️ Trail & Error: Chappell Roan is Right

Welcome back to ⛰️ Trail & Error, your guide to building a life on your terms.

At the Grammys, Chappell Roan called out a brutal truth: the system isn’t built to support the people creating the most value. The same is true in tech—companies keep cutting jobs, but the smartest founders are finding a better way. Let’s talk about it. 👇

Houston, We’ve Got a (Work) Problem

Chappell Roan stood on the Grammy stage last weekend and said what so many independent professionals already know:

💬 “I felt so committed to my art and so betrayed by the system… Labels, we got you, but do you got us?”

She was talking about the music industry. But this isn’t just a music problem.

It’s a work problem.

Companies profit off top talent—until they don’t need them anymore.
Workers give everything—only to be left scrambling when the market shifts.
The system isn’t built for independent workers—even though they’re the future.

This isn’t just an artist’s struggle.

It’s the same story for:

🎶 Creatives who drive culture but don’t get security.
💻 Fractional executives who scale companies but don’t get benefits.
📊 Consultants who build businesses but don’t get a safety net.

The talent economy runs on independent builders—but who’s building for them?

The False Promise of Stability

For decades, the assumption was simple: You either work full-time for one company, or you’re on your own.

I used to believe this, too. I spent years in high-growth startups, climbing the ladder, thinking that full-time work was the safest bet.

But after seeing layoffs hit even the most successful teams—and experiencing firsthand how companies prioritize their balance sheets over people—I started questioning everything. I realized that real security doesn’t come from a company. It comes from building leverage on your own terms.

And yet, we still tell people that the only way to survive is to put all their trust in one employer.

Except… we all know what happened next.

The layoffs just keep coming. Last week, Okta announced its third round in three years. Meta’s layoff is happening today.

Even profitable companies aren’t immune—when the numbers don’t line up, employees become an expense to cut.

The people who built the company are suddenly left to figure things out alone.

But what if we flipped the script? What if security wasn’t about one company? What if independence—done right—offered more stability than any full-time job ever could?

Smart Founders Are Already Making the Shift

The best operators—marketers, product leaders, finance experts—aren’t sitting on job boards. They’re choosing independence.

Some founders are starting to tap into fractional, high-impact talent—because full-time hiring is:

❌ Too slow
❌ Too expensive
❌ Too risky

They’re not building teams the old way. People like Sahil Lavingia at Gumroad.

He’s working with world-class fractional operators—on flexible, high-leverage terms.
He’s getting more done—without the overhead of full-time hires.
He’s moving faster—while others are stuck in hiring cycles.

This is where work is going & founders like Sahil are showing us the way.

📩 If you’re a founder, what’s your biggest hiring challenge right now? If you’re an independent operator, what’s the hardest part of finding great work?

Hit reply and let me know, I’d love to share the learnings with the rest of our Trail & Error friends.

We’re on the precipice of a better way of working—let’s build it together.