A Year of Making This Podcast & How Simplify Changed Us

We’re part where we grew up, part where we’ve chosen to make a home.
We’re six years at summer camp and the last four volunteering at the local library.
We’re the person who decided to stay in last night with a book as well as the person who stayed at work until 9 the night before—not because of a deadline, but because we promised ourselves we wouldn’t leave until the job was done.

We are the sum of our experiences, and as adults, work is one of the most consistent of them all. This also means that, more than nearly anything else in life, the work we do each day has tremendous potential to change us. For my part, I feel very lucky to have spent 2017 working on Simplify.

In a year, we’ve interviewed 14 people and produced 14 episodes of Simplify—a podcast that makes clear and applicable the big ideas from today’s brightest writers and researchers. We’ve learned practical things, of course, like the fact that a pinch of scripting trumps pure improv every time, and that if we’d just sprung for swankier mics, we’d have cut our editing time by 25%.

But from listening to our collective of rather incredible guests, Ben, Nat, Ody, and I have also learned things that have nothing to do with podcasting and a lot to do with life. Here are the ideas that have stuck with us from the last year of Simplify and changed the way we do things in our daily lives.

Ben stopped giving advice

Episode: Season 2, Episode 4: Michael Bungay Stanier
Ben says: “I copied a whole page-worth of transcript from the Stanier interview and sent it to the other content people at Blinkist,” Ben says. “The whole idea of waiting, being curious, staying with the question a little longer… that’s really important.”

From the episode:
Michael Bungay Stanier: “It turns out that most people are advice-giving maniacs. Like, they love to tell people what to do. And it also turns out that in general, advice-giving is an overdeveloped and less effective way of managing and leading than you might think…there’s times when advice-giving is exactly the right thing to do. I mean, Caitlin, if you come into my office, virtual office, and you go: “Hey, Michael! Where do I find the file?” It’s terrible for me to go: “So Caitlin how you feeling about the file?” You know, that’s not useful. So, it’s important people hear that I’m not saying “Never give advice.” But here’s why you should move to advice-giving more slowly.

The first is, most of the time you don’t really know what the challenge is. We get seduced into thinking that the first thing somebody tells you is the real challenge and the thing that needs to be solved. So, you’re too quickly solving the wrong challenge.

Secondly, honestly, people’s advice isn’t nearly as good as they think it is. So often now you’re offering up slightly crappy advice to solve the wrong problem.

And thirdly, even if you’ve got the right problem and your advice is amazing, there’s a dynamic that’s playing out: you’re training the people you’re leading and managing and influencing to come to you for advice, rather than helping them become more self-sufficient, more confident, more competent, more capable, more able to work by themselves.”

Hear the episode here!

Nat cut through creative paralysis

Episode: Season 1, Episode 1: Seth Godin
Nat says: “So, my favorite takeaway was from the episode with Seth Godin. Just like many other people I often get stuck and paralyzed because I believe I have so many good choices. And I waste too much time investigating each one, afraid that I could miss out on a great opportunity. His advice is to figure out if you’re paralyzed because you’re hiding or if you’re doing that because you actually need more time to decide.

And I followed his exact instructions for how to figure it out. I created a document noting four things/projects that are currently competing for my time and asked some smart friends of mine who also know me pretty well to pick one that I should focus on. When they gave me their feedback, based on my reactions to their choices, I realized that I’d already decided what I wanted.”

From the episode:
Seth Godin: “One of the easy ways to get paralyzed is to say, “I have so many good choices, I need to investigate each one, because I don’t want to walk away from the wrong choice.” And so we get this paralysis of doing an analysis of everything forever and we never launch.

And so my advice to people has been: figure out if you’re doing that because you’re hiding or if you’re doing that because you actually need more time to decide. And the easy way to figure this out is, let’s say there are five things that are competing for your time: write a one page proposal, the best possible vision that you have for each one of the five things and then hand it to some smart colleagues and say, “You guys pick. Whatever you pick is what I’m going to do.

And that’s frightening, right?

Caitlin Schiller: Yeah.

SG: You say, “No, no, no, no, I can’t possibly do that.” Well, because we’re calling your bluff. Because if they’re all good, then do whichever one we pick. And if you’re not willing to let us decide, then you decide. But you don’t need more time. You just need to decide.”

Listen here!

Ody stopped offering reasons

Episode: Season 2, Episode 2: Ryan Holiday
Ody says: “I took to heart the advice that Ryan Holiday gave us in Season 2. State your decision clearly, but say as little about your rationale as possible. Because your decision will remain the same, but the reasons for it can always change.”

From the episode:
Caitlin Schiller: “Yeah, I don’t think that in general people do well with uncertainty, especially not when you’re supposed to be the expert and you’re put on the spot. You want to have a facile answer.

How have you cultivated it for yourself? Like, are you in a conversation, and you go, “OK, Ryan, slow down”, and want to think about it more? Like, what have you been doing to make sure that you can nurture that habit in yourself?

Ryan Holiday: Yeah, that’s a big part of it. And being comfortable saying “I don’t know.” I think we tend to see it as a weakness but it’s not. And then I would say the other thing is like I’ve tried to just say less generally. There’s a line I like from William Tecumseh Sherman where he’s saying, “never give reasons for why you think what you think because the reasons can change.” And so it’s just like the less you say the more options you have. And so from a social media standpoint, I think realizing that just made me go like, “Oh wait, there’s very little upside for me in doing my thinking out loud here.” Like, if there’s a chance that I’m going to change this opinion in a month, why would I put it on record now?”

Listen here!

Caitlin stayed on the field

Episode: Season 1, Episode 1: Dan Savage
Caitlin says: I’m an only child and I’ve lived away from my home country—the US—for eleven years now, in three different countries. I’m an expert at being alone, and I enjoy it, so what’s much harder for me is being with someone. My inclination is to walk away rather than work things out when the going gets rough. But then I talked to Dan Savage earlier this year, and what he said about commitment really stuck with me. And I’ve stuck with my partner, too.

Caitlin Schiller: What does commitment look like to you?

Dan Savage: Continuing to not break up.

CS: I think that’s a great definition.

DS: Because sometimes people ask me and Terry, “What’s the secret to your success?” We both look at each other and say, “Well, we just keep not breaking up!” I mean that in a sort of joking way, but I’m also really serious, because, you know I have friends who are perpetually, you know, who are single, who get in relationships and break up and heartbreak and heartbreak. And they’ll come to me and they’ll, you know, bemoan their new, you know, their single status, their back-to-singledom, and they’ll say that they’re just so jealous of you know, what Terry and I have, and then I’ll ask them, “Well, what was the…why did you break up?” And tell me what the incident was. You know, what the fight was that led to the breakup, and I’ll laugh in their faces. It’s like, do you know how many times Terry and I have had that DefCon level of a fight and didn’t break up?”

The problem isn’t that you know, your relationship failed. You walked off the field because you had a big fucking fight.

And sometimes—this is a simplifying point, I’d like to make—people have it in their heads that they need to perfect their relationships, that if they just keep pushing at this issue, that they’ll have a breakthrough one day and then it’ll go away or it will be resolved to everyone’s satisfaction.

And you know there’s things in a long-term relationship and you just have to sidestep them. You know, things that person is never going to do differently or never going to do better. I like to call it paying the price of admission. And you pay the price of admission and you ride the ride. If it’s not a price of admission you’re willing to pay, don’t ride the fucking ride. If you pay the price of admission and get on that roller coaster, you don’t spend the entire time you’re on the roller coaster bitching about how much it cost. You just eat the cost and shut the fuck up and enjoy it. People can do that when it comes to restaurants and buying houses and riding roller coasters. They have a hard time doing that in relationships.

Listen here!

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I’m grateful every day to do this work, to speak with our bright, kind, across-the-board lovely guests, and to get to work with the rest of our team on the show.
I’d also be grateful to hear what you learned from the last year in Simplify! Email me at [email protected], or email all of us at [email protected]. We’ll be back soon with Season 3 of Simplify. Thanks for joining us!