Alex Made A $500K Mistake So You Don't Have To

Last week, I found myself staring at my laptop at 1 AM, asking the same question that's probably haunted every entrepreneur.

“Should I keep pushing, or is it time to pivot?”

We glorify both persistence and pivoting in the startup world. "Never give up!" sits right next to "Fail fast and pivot!" in the entrepreneur's handbook of quotes.

But nobody tells you how to choose between the two when you're in the trenches.

I recently spoke with Sarah, a founder who spent two years building a B2B software platform. "Everyone told me to pivot after six months," she told me. "Thank god I didn't listen." Today, her company is valued at eight figures.

Then there's Alex, who admits he stayed too long in a dying market because "persistence" had become his identity. "I wasted a year proving I wasn't a quitter," he said. He lost 500K within a year.

Here's what I've learned from these conversations. The pivot-or-persist decision isn't about the market, your metrics, or even your competition. It's about answering one crucial question: Are you still solving the right problem?

See, most of us confuse the solution we're building with the problem we're solving. I did. When my first approach wasn't working, I kept tweaking features, changing the pricing, adjusting the marketing. But I was just rearranging deck chairs on the Titanic. The real breakthrough came when I stepped back and asked: "Is this still the core problem worth solving?"

The hard truth?

Sometimes persistence isn't courage – it's fear wearing a brave face. Fear of looking like a failure, fear of admitting we were wrong, fear of starting over. And sometimes, a pivot isn't strategic thinking – it's just running away when things get hard.

Want to know if you should persist? Look at your frustrations. If you're frustrated with the how – the execution, the timing, the approach – that's a sign to persist and optimize.

But if you're frustrated with the why – the core problem, the market need, the fundamental assumptions – that's your pivot alarm ringing.

Amazon started as an online bookstore. Twitter emerged from a podcasting company. Instagram began as a check-in app. They didn't just blindly persist or randomly pivot. They stayed true to solving a core problem while being flexible about how to solve it.

So tonight, if you're up late wrestling with this question, stop asking "Should I quit or continue?" Instead, ask yourself:

"Am I still obsessed with the problem I'm solving?"

Your gut already knows the answer.

Because in the end, the goal isn't to never pivot, nor is it to never give up. The goal is to be stubborn about your vision but flexible about your path.

What problem are you truly obsessed with solving? That's where your persistence belongs.

If you would like to connect on a deeper level, feel free to REPLY to this email and I’ll get in touch with you.

Be unstoppable,

Amos - Founder of The16hourclub