‘If It’s Not a Hell Yes, Then It’s a No!’ Can Be Dangerously Bad Advice

If you’re saying ‘Hell No!’ out of fear of the unknown, you’re robbing yourself of truly getting to know yourself

Michael Thompson
Published in
5 min readFeb 14, 2022


Judeus Samson

If you’ve spent any time on the internet, the odds are high you’ve come across the phrase made famous by entrepreneur and author Derek Sivers — “If it’s not a hell yes, then it’s a no!”

Like a lot of highly tweetable phrases, it was birthed into the world on The Tim Ferriss Show a few years ago. Even though it’s pretty self-explanatory, it means that if you don’t want to immediately do something when presented with an opportunity, your default answer should be “Hell No!”

As soon as Sivers said it, the world went nuts. Five or six years later, it feels like the phrase is just growing legs. From recent college grads to a ridiculous number of podcasts and articles, the phrase is everywhere. I even saw a dude wearing a t-shirt with the words on it this week in small-town Spain, hence why I’m writing this article.

On the surface, it sounds like good advice.

For some people, and for many basic decisions, it is.

But for most people though, it can be dangerously bad advice.

In fact, Mr. Sivers himself, when discussing it in a recent interview, struck me as a bit embarrassed that the phrase has become part of his legacy.

This is for the simple fact when the host, Robert Glazer, brought it up, Siver’s immediate response was a massive — “Uggghhhh!

The words around a phrase are just as important as the phrase itself

One thing the new world knows how to do really well is to take things out of context and wrap them up into sound-bites.

We hear the juicy parts of a story and disregard the rest because it’s not as entertaining, spicy, or inspiring when jammed into 130 characters.

The reality though, is that when Sivers introduced this phrase to the masses — and the masses decided to run with it — Sivers was in a place that not many of us are in.



Michael Thompson
Writer for

Co-creator of two cool kids with an equally cool woman • Word strategist • Storytelling coach • Free "story" guide: https://bit.ly/3h1KZeT