“What would you do if you knew you couldn’t fail?”

It’s one of those aspirational quotes.

It’s totally fine. In the self-helpy ways. But, you start thinking about it and - there are almost as many issues as the genie “3 wishes” problems.

Jason Buck brought it up in his Infinite Loops appearance which is must see modern TV, aka YouTube, for points exactly like this.

After saying the Target wall art quote he, characteristically said, “f*** that quote. What would you do if you knew you WOULD fail, right? That’s what we’re compelled to do.”

Amen.*

If you couldn’t fail, you could do anything. You could wish for infinite wishes. You wouldn’t quit your boring job in the accounting department and start a real business out of your Etsy side hustle. You would jump out the window and start flying around. If anybody had that type of power - I mean, this is why The Boys is such a powerful cautionary tale.

The question to ask yourself is: what is it that would you do anyway, despite risk of failure, because you are compelled to do so.

It doesn’t have to be rational. It doesn’t have to be smart.

My only request is that whatever you choose, let it be both good for you and not harmful for the world.

Jason and Jim get into more of that in the rest of the conversation, but let this point stand.

Whatever you would do anyway, despite the chance of failure, is worth pursuing.

*Speaking of amen, this is my image for the episode (thanks AI)

Full episode here:

And if you want more Buck and O’Shaughnessy backstories, I’ve got you covered via BOTH of their Intentional Investor appearances: