Entrepreneur magazine Editor in Chief Jason Feifer on his favorite advice from a celebrity and how to flip the script on failure

The thought of failing stops many people in their tracks. After all, if you start something and it fails, what was the point in trying? According to Entrepreneur magazine Editor in Chief Jason Feifer, failing is actually the first step toward success.

Thanks to his position in business and publishing, Jason has been able to speak with many people running successful businesses of all sizes and tries to learn something new from each conversation. While most are inclined to talk only of their successes, Jason says it’s the mistakes that teach the lessons. Check out some of his favorite moments.

To be good at something, you have to be willing to be bad.

My favorite piece of advice from a very famous person came from Ryan Reynolds. “To be good at something, you have to be willing to be bad.” Those are Ryan’s words, and it made me realize that too often we think that if we try something new and we are not immediately successful at it, then it is just not for us. We should give up.

We look around and we see people who are much better and we say, ah, I’m never gonna be like them. But the point that Ryan is making is that everyone is bad at first. Everybody. And so the difference maker isn’t whether or not you are good at the beginning of something, but rather whether or not you are able to tolerate being bad long enough to get good.

Change before you must.

Change before you must. The argument is you could either wait for change to come to you, and then you’re scrambling and just trying to put out the pain, which means you’re not gonna be making the most sound decisions. Or you could do things on your own terms, which means making difficult decisions that don’t seem forced.

Are you looking at a door or an engine?

What are you looking at when you’re looking at a problem? Are you looking at a door or an engine? Imagine you’re driving down the street in a car, and the door falls off. Is that a problem? Yes. But can you still drive? You can. Car still goes. Now imagine you’re driving down the street and then the engine falls off. Can you drive? No, the ride is over. 

If it’s a door, then you can make small tweaks on the margins. You can try to improve the product, whatever it is. But if you’re looking at a problem and it’s an engine, and in three to five years that engine is going to fall off the car, then you have to start now. You have to.

Maybe their experience actually echoes lots of other people’s experience, and maybe this is just the only person who told you.

I think you need to take seriously anybody who is saying something in earnest, even if it’s angry, because they had an experience, and that experience was real to them. And maybe all you have to do is just show them that they were heard and they will calm down.

But maybe their experience actually echoes lots of other people’s experience, and maybe this is just the only person who told you. It’s vitally important to hear people out, hard as it is, and it can be very hard.

I always ask the dumb questions now, and often the things I thought were a detriment could be an asset if only seen a little differently.

The most surprising piece of advice anyone gave me was from a conversation I had very early in my career, which was when I started as a community newspaper reporter. I had this habit, which was that if I was talking with, let’s say the local mayor, and the local mayor is telling me the city just put out an RFP for something. I would write in my notebook, “RFP,” and I would circle it write a question mark, and that was so that I could go back to the office later and try to figure out what he was talking about (RFP by the way, is a request for proposal). And this was because I was afraid of revealing that I didn’t know what he was talking about because here I am trying to be this professional, absorbing and repeating information that he’s saying to the public. I’m supposed to be a filter for the public.

And if I don’t know what he’s talking about, then how can he possibly trust me to tell me anything? So I was hiding this, but then I was talking to an older reporter George, and George told me, don’t be afraid to ask what you think are dumb questions because someone would much rather you get it right than guess and get it wrong. They want to be helpful. If you don’t know what an RFP is, they want to explain it, so asking these kinds of questions shows your thoroughness that you’re not going to let something go by ‘cause you don’t understand it. And that’s a value that doesn’t make you look stupid. That makes you look smart.

Then also, frankly, if you ask really simple questions of things that people spend a lot of time with, they like it because you’re engaging at a deep level with something they care about. Not a lot of people care about RFPs, but if you’re the mayor, you probably have a lot of thoughts on them.

So being asked about it is not really a bad thing. I always ask the dumb questions now, and often the things I thought were a detriment could be an asset if only seen a little differently.

This interview has been edited for brevity and clarity.

These lessons come from an episode of Behind the Review, Yelp & Entrepreneur Media’s weekly podcast. Listen below to hear from Jason, or visit the episode page to read more, subscribe to the show, and explore other episodes.