WHAT 75,000 PEOPLE REGRET

Are you haunted by missed opportunities? Here's how to let go and move forward in 2026—by hearing the raw, personal, and honest regrets of others.

- JASON FEIFER

I've been plagued by a professional regret, which I've kept to myself for years.

But I'll tell it to you now. Why? Because it's helpful to share. As we start a new year, it's important to let go of what anchors us to the past-and hearing other people's regrets can help us do that.

I'll explain. But first, here's my regret.

Outside of my job as editor in chief of Entrepreneur magazine, I have spent years building a personal newsletter where I share the best lessons I've learned. (Find it at jasonfeifer.com/newsletter). A few years ago, I met a fellow newsletter writer who'd built an impressive audience, and he made me a nice offer:

He would add me to his recommendations list-which is to say, whenever someone subscribed to his newsletter, they'd get a popup recommendation to subscribe to mine. But he was on one newsletter platform, and I was another. To make this work, I'd need to switch to his.

That sounded like a hassle. So I thanked him, but passed.

Then his popularity exploded. He has more than 1 million subscribers. Meanwhile, I have 75,000-which I'm proud of, but it's a fraction of what he could have gotten for me.

I've kept this story to myself for years, because it seems silly and frivolous. Like, Oh, woe is me. But it really eats at me! Newsletters drive significant financial opportunities, and my entire business could be bigger today...if only I'd said yes to that guy.

Recently, as I texted with a friend who also writes a newsletter, I shared this with him. He was the first person I'd told. And his response took me back:

“Here's the worst for me,” he wrote. “A client told me to invest in Bitcoin in 2015.”

Oh, no, I said.

“It was about $250 a Bitcoin,” he continued. “Don’t do the math. It’s painful.”