1. Getting Started

Pete and Jen kick things off by exploring the question: How do you set yourself up for success when starting something new?

Peter: Hey Jen.

Jen: Hey Peter.

Peter: What's up? I guess we're doing this, right? We're recording a podcast right now.

Jen: I know that because it says "recording" on my screen here in New York City.

Peter: Oh, you're in New York? Yeah, I'm in Melbourne, in Australia, which is literally the other side of the world, and so I'm a little bit nervous because, you know, we've got some technology. We've got some time differences. We don't really know what we're doing to some degree, but we're starting now, and we're trying it anyway.

Jen: Yeah, we're starting. We're beginning, and we've been dreaming this one up for quite some time, so it's both exciting and terrifying that the day has come that we're actually recording the first podcast episode.

Peter: I think that leads us to the topic, right? It feels only fitting that we start by discussing this idea of beginnings - and so the question I would ask: how do you set yourself up for success when starting something new?

Jen: That's a good question. Let's unpack it. This is The Long and The Short Of It.

So Peter, I want to hear a bit from you about how you set goals. When you know you are starting something new, do you have practices in place that you use that help to set you up for success?

Peter: You know, goal-setting to me is one of those things where I want to be able to give you an answer that's like, well, yes, Jen, I have this perfectly-constructed process and I definitely go through it every single time, but the reality is sometimes I do, and sometimes I don't. And so when I think about goal-setting, I think about whether the goal is the point, or whether the goal can be framed in a way that it's a win-win. So to give you an example, one goal for this podcast could be to have ten thousand subscribers in twelve months time, right? That could be a goal, or the goal could be to record fifteen episodes of this podcast with Jen. They're two very different goals, while they're kind of related. The first one is out of my control to some degree. We could record the best podcast ever: we could crunch it for twelve months, and there's no guarantee that we will reach that end number. But the latter one, this idea of recording fifteen episodes, to me, A) that's within my control, and B) it's a win-win. If we record fifteen episodes, we've recorded fifteen episodes. I've got to work on a project with you for those fifteen episodes. I've got to develop my skills of podcasting, and at the end of the day I have those fifteen episodes which then we might seek to turn into a bigger podcast over the next twelve months, which may or may not result in those - I think I said ten thousand downloads. And so when I think about goal-setting in that context, I actually think the process of goal-setting is more important than the goal itself. What I mean by that is: a good goal-setting process ultimately uncovers a few things. The first is: you have to identify something that's within your control. I think too often people set goals or get goals mixed with dreams and have this idea of a goal in their head that is so outside their control. So that example that I mentioned of the podcast is one, or becoming famous as a goal - that's kind of another idea that's very esoteric and completely outside your control. So by going through a goal-setting process, you first have to identify what is within my control. Then you have to list why it's important to you. Most goal-setting practices or frameworks that you look at, it's a bit of a like, "what's in it for me?" "Why is this important?" And you have to get really clear on the intention behind the goal, because you might actually realize that, oh, that's actually not the goal - there's a different goal that I'm working towards because that's not actually that meaningful to me. So I think that's the other important part. The other two, which I mentioned, the obstacles, the roadblocks, the things in your way, the things that are going to prevent you from achieving that goal, if you like. So you have to list them. You have to write them down, you have to think about them. And then the other part of a good goal-setting framework I think is: who can help you? How will you get past those obstacles? Actually thinking about that and mapping that out upfront, again, is more important to me than the goal itself. And so while I say all this, I completely acknowledge that sometimes I don't do it well, but that's I guess how to answer your question, Jen, in a long-winded way. That is how I'm thinking about goal-setting at the moment. Tell me - tell me about you. How do you set goals?

Jen: Well, I just need to say that I've said this to you offline, but now I can say it for our listeners: we share the same brain sometimes, Peter, because so much of what you just said is what I practice as well. I really believe that dreams can function as traps: that dreams can be actually quite limiting. When I hear you say that a possible dream for this podcast would be to get ten thousand downloads, my initial impulse is, well, why not a hundred thousand? Why not a million? Now when we have a dream, sometimes we set boundaries because we're afraid of what success might look like, and so I've - not that I've given up dreaming - but I'm very aware that I can only dream about things that I think are possible. Even when I call it "the impossible dream," I was able to come up with it because I think it could happen. So I'm not the biggest fan of setting those kinds of dreams in place that feel out of my control. Similarly with goals, something that I've learned over the course of the last couple months - and just for a bit of context, I'm currently doing this really intense program with thirty-five extraordinary artists here in New York City who are looking to make major shifts in the kind of work that they're doing, and we talk a lot about goal-setting - and something that I've realized is that when these artists have been setting goals for themselves, many times it's just a task masquerading as a goal, and once we start sort of peeling back the onion on what that task masquerading as a goal is really about, they're able to reveal something much deeper, much more meaningful, much more impactful. But as you said, the process of setting the goal actually allows them to uncover what it's really about. So I believe in the process and I'm totally okay with giving up the end result.

Peter: So one idea I think linked to this is this idea that you and I have spoken about before, which is beginning with the end in mind. So my question is, do you think going through a goal-setting process is one way to begin with the end in mind? Do you think that's helpful in that context?

Jen: Absolutely. Absolutely. So let's use a really specific example here. I can just grab something from my own recent experience. I have a client who has come to the realization that the work she's been doing has not necessarily had the kind of impact that she believes her work is capable of having. And to that end, she set a goal for herself of "finding a new tribe": seeking out the future potential collaborators who are doing the kind of work that she also wants to be doing so that they could ultimately connect and possibly work together. That was the goal, and in order to identify the roadmap to get to that goal, we did have to come up with: what are the specific tasks that are going to allow the small steps of progress that will cumulatively become the large leaps of progress? Who are those people who can help you to find like-minded, potential collaborators? And what are the obstacles that are standing in your way, both internal and external, that you know you'll have to overcome, whether they are gaps in knowledge or lack of a network, or fear, so that you can start putting the systems and tools in place to help you overcome those things. Now, it's very possible that as she goes through the process that she set up for herself, checking off the individual small tasks along way, the goal could completely shift. Getting out of the gate with this idea of finding like-minded collaborators, you know in her mind that's going to take a long time, but what if tomorrow she runs into someone on the subway who she finds is a kindred spirit, and says, let's make something together? Well now she's met that goal. So that goal might shift, and become: create project that will transform the culture of riding the subway in New York City - who knows what it is. But the fluidity of the goal I think is something really worth attempting to wrap your head around; that sometimes the goal is less important than the actual steps you're going to take and the processes you're going to put in place in order to move yourself forward.

Peter: I couldn't agree more. I couldn't agree more; and I mean, this idea of failing along the way - I don't like the word failure, but I know it's very popular at the moment in a lot of circles to think about failing fast and failing often and trying things and failing and then you get up and you try something new - and I think that it rings true in this instance, which is: it's important to set goals, I think, and it's important to go through the process of setting goals, but there's also this degree of fluidity that's required in goal-setting, and you need to be open enough to flex and change your goals as opportunities present themselves. Exactly like what you mentioned, Jen. With that, I think there's actually a transition into a discussion about what sits behind this fear of goal-setting. And so I think there's a couple of different angles to this. One is, sometimes people I think actually hide behind goal-setting, and they might miss opportunities because of this idea that they think their goal can't change. And then at the other extreme, people don't set goals, or people don't think about the end in mind, they don't start with the end in mind because of this idea of fear of beginning. When I think about it, even at the start of this episode, in terms of being a little bit scared to begin something - like you physically feel so often when you start something new or you try something for the first time or you set a goal, you set an intention whether you write it down or say it out loud or whatever but there's some physical reactions to that. And I think, me personally, you know, my chest will tighten and I might get short of breath, or I might get sweaty palms and butterflies in my stomach, and that fear actually manifests itself very physically, which I think is confronting for some people and causes them to hide behind certain things. And so I wonder from your perspective, Jen, what role does fear play in beginning, and what role does that - does that tie into goal-setting at all?

Jen: Well I have a good friend who often talks about reframing fear and its physical symptoms, and I thought I'm going to borrow this from him for a moment and point out that the physical symptoms of fear that you just illuminated - the shortness of breath, the feeling physically tense, for some people it's clammy hands, or feeling unstable on your feet, or whatever it might be - these are the same physical symptoms of being excited. And so when you look at it that way, you have the power then. Instead of saying to yourself, "What am I afraid of?" you can say, "what am I excited about?" And so in the case of this podcast, for example, you know, we were - who knows if we're going to edit it out - but we were really dancing around starting because it's scary to say, "wow, we're actually doing this. We're actually going to create a podcast together." And people might like it, and people might hate it. What's exciting about that is that we're doing something totally new for us. We're sharing our ideas with a broader audience than either of us has ever had access to - you're in Australia, I'm in New York City. I'm going to have people who you know over in Australia listening and you're going to have people that I know over here in New York listening. And that's exciting that we're actually throwing our ideas across the globe at each other. It's also exciting to know that this may actually not be about a podcast. The podcast might be a warmup for something else that is inspiring and exciting that we both will get to make together. So I can list all the things I'm afraid of, and it's actually a useful exercise, like: I'm afraid that I'm going to make a fool of myself, I'm afraid that I'm going to destroy your career, I'm afraid I'm going to destroy my career, I'm afraid that I'll be exposed as a charlatan, I'm afraid that I'm going to say something that will offend my friends and family and then lose them forever, you know? I can go on and on about the fears, and all of those things are useful to put a voice to, and it's also useful to identify all the things that you're excited about that might happen because of what you're beginning.

Peter: I love that reframe about it being exciting as opposed to fearful, and so it reminds me that fear is a choice, and that fear is universal, and so hearing you play back your fears just then you couldn't see it, but I was like nodding along and raising my hand in the sense of I have all those exact same fears. And so I'm afraid that this might not work. I'm afraid that people might think we're crazy. I'm afraid that my ideas aren't going to resonate with people and that people are going to give me feedback, that this is a stupid idea. And I'm afraid I'm going to ruin your career and all of those things that you listed. I have the exact same fears. And what's interesting about that is this whole idea that fear is universal. It's not my fear. It's not your fear. It's just fear. And so the difference, because I think we all struggle with the same fears, and so the difference then, I guess, is what you do with that fear, where you put it, how you interact with it. And so I love that frame of reference that you provided, which is: what if you reframed it to be excitement, and started to think about all the things that are exciting about that particular fear.

Jen: For many years I have been practicing this very specific fear idea - which we could spend an entire episode talking about fear, and we probably should - but essentially it's based on my belief that in every single moment you have a choice, and that choice is fear or faith. Those are your two choices. So in every moment you must choose wisely, and there are some moments where choosing fear is actually wise. Like when you're crossing the street, for example, it's good to have a little fear so that you are able to get safely to the other side and assess danger when it's coming toward you. There are also moments where fear is not the wise choice, and instead having faith in whatever it is you need to have faith in is the wiser choice. So we could be fearful that our ideas are going to stink, but we could also have faith that we're doing this podcast because people have told us that our ideas have resonated with them and we want to share them with more people.

Peter: This leads me to I guess a more tactical conversation or question, which is how do you then set yourself up to distinguish between the two - between the good kind of fear that's literally protecting you from things that might danger you, versus the irrational kind of fears that can be confused with or reframed as excitement? And I know we've talked about a few ideas, and one of them in particular, which resonates with both of us (and I'd love to hear you talk about it) is this idea of a pre-mortem.

Jen: Yeah. I love the pre-mortem. The first time I heard about the pre-mortem was from Dan Pink, but it seems to me that many other people have done some version of this. So who knows where it originated, but it's really brilliant. And essentially the idea is that before you begin something, you determine all the ways that it could go terribly wrong. You envision the worst possible outcome or outcomes, and then ask yourself, how did we get there? So in the case of this podcast, let's say the worst possible outcome is that zero people ever listen to it, and we're doing it in a vacuum, and we never get a single download. And so after months of recording, we have to look at each other and say, how did we get here? Well, one thing that we might have done is never uploaded an episode because we were too afraid to. So that's one possible thing. Or that we failed to tell people that we were doing a podcast because we were too afraid to let people know what we were doing. Or maybe we failed because, well, in the case of getting no listeners, I mean, it really has to be like we just didn't put it out there. We didn't hold each other accountable for following through with what we said we were going to do. But another horrible outcome would be that a lot of people listen, and then start posting clips of our audio with comments like, can you believe these two morons? Have you ever heard such stupid people in your life? Where'd these a-holes come from? So that would be another horrendous outcome is that we're both publicly humiliated for sharing our beliefs. And so in that case, what would we have failed to do? How would we get there? Well we would get there because we didn't consider our audience, we didn't listen to feedback, we didn't seek feedback from trusted, reliable sources who we know would be in our audience, we acted with Hubris, you know, on and on and on. So then the question becomes what are the actual tasks associated with preventing the worst case scenario? So one of the things that you and I need to do is identify who are trusted early listeners so that we can share the early episodes and receive feedback. The other thing we need to do is figure out what is our system for processing feedback. So we can start to come up with tangible, actionable steps that we can take in order to prevent the worst case scenario when we do a pre-mortem.

Peter: Yeah, and what's amazing about that is the steps aren't that grandiose, or difficult, or hard, and what you realize by going through a pre-mortem I think is, oh, this is a little bit irrational - like you start to catastrophize these things like you said, zero people listening. Well, I mean the way to combat that is we actually tell people about the podcast, and that's not that difficult. It's actually quite an easy step to take. So I think the power of the pre-mortem is sort of tenfold, and by realizing that some of your fears are quite irrational, by writing them down - this worst case - what you also start to realize is avoiding that is actually quite easy. And so you can easily set yourself up for success, which I think is a really important part of that.

Jen: I'll tell you that my daughter just popped into my head. So several months ago my daughter had an appointment to become a part of this singing group. That's neither here nor there, but the point is that she was very fearful about going into this appointment, and she tried everything she could to get out of it, and ultimately, I forced her to go, and it worked out great, because this thing that she had really wanted to be a part of, they invited her to be a part of it and so she was happy. But we had to have a conversation about how fear was getting in the way of her actually getting to go after what she wanted, and the kind of fear that that was showing up for her was the kind of fear that was keeping her from being at her best. So that began a series of conversations around fear, which is kind of an amazing thing to talk about with an eight year old. So a couple of weeks after that, we were walking to our parking garage, and there was this gentleman on the street who was extremely intoxicated, and sort of flailing around dangerously, and at one point he came toward us, and he almost fell over, and she said, "Mommy, that made me feel really afraid. Is that okay?" And I said to her, "Yes, this is a time when fear really kept you safe. It was good to listen to your fear and know that something was not right and that you needed to cross the street. So that was a time when fear was helping you to stay safe." So this began the question that we came up with, which is: when she feels afraid, she asks herself, "Is this the kind of fear that is allowing me to stay safe, or is this the kind of fear that is keeping me from being at my best?"

Peter: So one thing that I would ask, which I try and ask myself when thinking about fear and thinking about beginning, to bring it back, is: What am I afraid of? And then writing it down, and then writing underneath that: So what? And so I think what you can do by going through that exercise is you can uncover: is the fear something real, something life-threatening, something dangerous, or is the fear just something irrational, something in your head, something that you're telling yourself? And I guess the beauty here, Jen, is there's no right answer. We don't have the right answers. We're just here to provoke thoughts, you know, ask questions, and - we've spoken about this - and hopefully spark some change in each other, and maybe in the listener as well. And at some point you kind of just have to begin. I mean we can sit here and talk about goalsetting, and we can sit here and talk about fear-setting, and all of these various things to unpack this. But there comes a point where once you've done all that, you just have to hit record.

Jen: And that's The Long and The Short Of It.

Jen WaldmanComment