Hard choices now prevent harder problems later

Easy choices, hard life. Hard choices, easy life. I often find that anytime that I'm making the easy choice, my life gets hard. And when I make the hard choice to shut down the business, fire the person, say bye to a project that I was excited about, it's almost always the right choice.

"This" and "something different" refer to Shape Up, Ryan Singer's product development methodology that replaces traditional Agile/Scrum approaches with 6-week cycles and upfront "shaping" work.

I would say wait until it hurts more. If the unfamiliarity is the big problem with it, then maybe the things are fine. Because it's not like this is the only way. It's more like, changing is really hard, and if there's a good reason to do it and it's like, look, we've done it the old way. We've tried different experiments. We've even already churned through a new head of product, or we've got a different CTO in and we're still having the same problems, then there comes a point where it's like, I know that this is uncomfortable, and I don't know somebody who's done it, but I think we need to try something different because we can't continue this way.

If you keep doing what you're doing, you keep getting what you're getting.

If you do the hard path and it doesn't work, actually you still win because you've now done something hard. You've probably worked with smart people. You've learned something along the way that is valuable.

You should tell everyone this story... I will always come down harshly on people who do not take risks, and you did not take a risk in this case.