Rebel Rising Podcast

Creating Moonshot Projects & Pursuing the Impossible with Jen Gresham

Jennifer Gresham has helped hundreds of people around the world find greater fulfillment and financial success as a high-performance coach and business strategist. She founded Work for Humanity to help people see the future as an invitation to create a better human experience of work, rather than a dire problem to solve.

Today on the podcast Jen and I talk about moonshots, a near-impossible goal, that if achieved would produce an enormous positive impact, either for yourself or out in the world.

We cover why everyone should have their own moonshot, how to choose one specifically for you, and how it can quite literally change the world.

Tune into the audio:

Michelle: Welcome back Jen to the Rebel Rising podcast.

Jen: Thank you.

Michelle: I'm so glad you're back with us. The last time you were here we talked about money and money mindset and negotiating your fees and how to ask for huge sums of money, and now we're talking about something completely different, although still enormous.

We're talking about creating moonshots.

So to kick us off,

why don't you tell us what a moonshot is?

Jen: Yeah, I guess I should say when you said it like that I wanted to say it's not a drink. So don't try to order this at your local bar.

Michelle: Yes you can't drink your moonshot, although your moonshot may cause you to drink some.

Jen: Yes, yes.

So a moonshot is a near-impossible goal, that if achieved would produce an enormous positive impact, either for yourself or out in the world.

So it comes from John F Kennedy's original moonshot right to put a man on the moon at the end of the decade, and so generally speaking it just refers to anything that seems really hard, you're gonna need to galvanize people behind you to achieve it, you don't have to have your own governmental agency, you just need to be able to galvanize people with this compelling difficult call, with the end result being some positive impact out in the world.

Michelle: Wow. So it's like a big goal, huge positive impact for the world and potentially for yourself.

Jen: Right. That's right.

Michelle: Love it.

So tell us about, I know you've been working on your own moonshot project for a year and a half now.

Jen: Almost two years now.

Michelle: Almost two years. So tell us about your moonshot.

Jen: Yeah so I mean just a little bit of background about how I came into this. So I initially heard the term from Peter Diamandis. So he is the guy who … and we talk about moonshots, right? So he is a guy who launched the SpaceX … not SpaceX but you know, the … Oh Michelle. You know I know this and you know this. Peter Diamandis. XPRIZE.

Michelle: Yes, the XPRIZE, not SpaceX, the XPRIZE, yes.

Jen: SpaceX ultimately came out of the original XPRIZE, right? So the original XPRIZE was to design a rocket that could take people up into space and return with them, and then it had a number of other criteria for what it would solve. But it was essentially Peter Diamandis wanted civilian space travel. He tried really hard to get a flight on NASA, couldn't make it happen, he's like, “Fine, I'm just gonna create my own prize and send people into space.

So he talked about this concept of moonshots, but when he was introducing this and sort of the programs that he runs, many of them were originally aimed around growing a business that serves a billion people. Really awesome, but I was like that just doesn't motivate me, like that's just not me. And I said but what I am interested in is doing something that has an exponential impact out in the world.

It may not necessarily impact a billion people, but it dramatically moves the needle on something that's important to me or to the world.

So I said to my coaching clients at the time, I've been a coach, a career and business coach for the last seven and a half years. I said, “Hey, want to do a moonshot?” And they were like, “I guess.” And so it was totally unplanned but basically, I just started inserting moonshot ideas and coaching into the current client work that I had at the time. And the results were so extraordinary like just blow your mind extraordinary. I was like I have to have a moonshot like I made my husband get a moonshot too. I'm like, “Honey we need moonshots.”

Michelle: Wow. What kind of results were they seeing?

Jen: So that my favorite one, and I have to be a little careful here just to keep my clients identity anonymous, but basically this was someone who had been very successful in her career but had stalled, and so she'd been passed over for a number of positions, and she just came and she said, “I can't get where I wanna go just by working harder or doing what I'm doing.” Like something has to change, I've tried everything.

And so this whole idea of the moonshot, so we came up with her moonshot, and it was basically to take the research that she was doing academically and apply it out into the real world, because basically, her research was showing that the things that we were doing out in the real world, none of it worked, it was actually counterproductive. And so in order to do that, she's like, “Well I would need a center, and I would need a large amount of funding, and I would need a set of multidisciplinary collaborators.” And she's like … So that was her moonshot, was to basically create a center around her research and bring all of that together.

And so when we came up with it I said, “Well how do you feel?” And she said, “That's amazing and impossible like there's just no way that's gonna happen.” And I remember saying to her, “Well look, it's a five-year goal, it's way out in the future, don't worry about it, we're just gonna work towards it.” We had it done in nine months, the whole thing.

Michelle: Oh my. Holy crap that's impressive. Like that's amazing.

Jen: It was amazing right, but the thing about a moonshot is that it's so outrageous that it compels people to help you.

When I'm talking to clients about this I always tell people you'll know when you've got the right wording around your moonshot when people say, “Hey what do you do?” And you tell them and instead of just saying, “That's cool.” Or, “Uh-huh.” They say, “Wow, how can I help you? How can I help you?” That's the key.

Michelle: Wow I love that, like how can I help you. Because we were just talking right before this call about my troubled relationship with goal setting and how I don't like setting huge impossible goals because I like to win. And I gave an alternative.

So yeah, how do you deal with the fear around this?

Like for the people who are high achievers, high performers, they expect a lot from themselves, and now you're like, “Do this big impossible thing.” That makes them go … What do we do?

Jen: Yeah so it's funny right, it's very counterintuitive, and you know I like to say I'm an almost recovered overachiever. Not fully there. And so I struggled with the same sort of thing. But the thing about a moonshot is that it's so ridiculous that you don't really … It's nearly impossible. You don't really think you're gonna do it. In fact, no one really thinks you're gonna do it, and so it in some ways reduces the pressure because one, it's very long term, you do not … If you ever do it it's not gonna happen this year. And if you never do it, like people will simply admire you for being so audacious.

So it's kind of a win-win. If you do it you're a freaking hero, and if you don't you're just audacious and people admire you anyway.

So it's like what an awesome concept, I would love this.

Michelle: Oh, that makes sense on how to balance it. It's like okay reframe this as not like win-lose, it's like well you tried it and you probably learned a whole lot along the way and gained a whole lot of respect because you went off after this big huge thing.

Jen: Right.

And usually, I recommend anyway that your moonshot is something that's deeply meaningful to you.

And so where I've gotten with my own moonshot, and I'll talk about that in a bit, is I tell people I'm either gonna do this or I'm gonna die to try. And I'm perfectly okay with either one of those outcomes. This is so meaningful to me I can't not do it.

Michelle: So meaningful to me that I cannot do it. I love that. Oh my gosh, Jen, that's so inspiring.

Jen: Yeah because I mean you probably know, we talked about making tons of money right now. So I was at a place in my business where the natural thing is just to keep ratcheting up how much money I make in my business, and I could have done that, and I was sort of on that path of like all right, I'll double my revenue next year or whatever, right. But I was like that is so uninspiring to me, like it just didn't motivate me. And so I think that was the other piece. And what's ironic to all of this is that I've dramatically reduced my coaching. I only take maybe one or two, maybe three clients now, in fact, it's probably closer to one or two, and I can see at some point tapering that off altogether. Because I care about this moonshot so much.

Michelle: Yes. Yes yes yes. Okay, so I feel like we've teased everyone with the moonshot.

So tell us what your moonshot is because I'm sure people are like, “What is it?”

Jen: Yeah so what I'm really interested in is how we leverage what's happening technologically. Instead of seeing it as something like oh my god, the robots are gonna take all our jobs and humans are gonna become useless, it's how can technology and the advances that we're seeing enable us to transform work in a way that makes it something that is rewarding, not just financially but cognitively and socially and emotionally and spiritually.

How can we truly transform the human experience of work in a way that we would want to?

And so, as you know, I had no idea how to do that, I mean it's not like … It's a really big issue and there's like a thousand different solutions, and it wasn't clear to me at all where to kind of put my efforts. And so I convened a group of experts from business and tech and education and so on, and said, “Hey, will you explore this with me?” And these were fairly high-level people. We had the head of research from Google, we had the former deputy director from NASA, we had heads of different foundations that were involved. And that was really exciting. And so what came out of that was to produce a vision for what we want the human experience of work to be.

And it's called Work for Humanity, and as far as I know, it is the first vision of its kind for this topic.

And that seems extraordinary like that doesn't even seem possible.

But I think everyone's been so frightened, we've been so focused on trying to predict the future instead of trying to create it.

And so this is where the moonshot work kind of rolls right back in because what moonshots say is like I don't have to worry about predicting the future if I know how to create it. But first I have to know what I want to create. And so this version allows us to say like, “Here's what we want to create, hey, who wants to create this crazy audacious vision with me? Because I can't do it alone.”

Michelle: Yeah.

So can you give us a little taste about what the vision of work would look like in the future?

Because I mean I know, I mean I have a lot of people who listen to this podcast who have a side hustle and they're in a job that they hate, and there are so many people who hate their work, and oh my god the robots are gonna take over so we need a minimum income for everyone in the United States and blah blah blah, but at the same time we're gonna be totally bored. So there's like all of these issues around it. So can you share a little bit of the vision that you ended up creating?

Jen: Yeah I mean so we came up with seven elements, and I won't go through all of them in detail, but generally speaking work should be enjoyable. And so as you probably know from a historical context, jobs are a relatively new invention. And so I don't know what's going to happen with jobs and how we earn a living, but we made the assumption was that work is part of the human experience, but it should be rewarding and enjoyable. So it should have a positive connotation, it's something that people look forward to doing, and adds to their life rather than takes away.

The other big thing and this is a little bit radical, is that I think human work should always be of high value.

Right now we have humans doing relatively low-value work because it needs to get done, and so we create a rather elaborate system to incentivize work that's boring, that's meaningless, that's dangerous, all of those things. And so you know in my vision, humans only do high-value work. And that means that we are going to need to automate all of that low-value low skill work that we're having humans perform today.

People tend to get scared about that for a couple of reasons. One is that they can't imagine that people are capable of more. Just is utter hogwash. We are more alike than we are different, we all have the same anatomy, it all works relatively the same.

People are highly resilient and capable. So one I think is starting with an assumption that people are far more capable than the system believes, they're far more capable than they believe.

And two is that there's no shortage of high-value work to do. And I think that's the other thing is that if you look at like … I don't know about you but my to-do list runs over. There are all sorts of things I would love to do, but I don't have time. I simply don't have time. And I don't know anyone else who's like, “Yep, done for the day.” I mean unless you have a job that's just truly low-value.

So once you get up into higher value work there's just an immense amount of work to be done. So I think those are the other two big things and it's where technology will really enable us. But too, being an entrepreneur, I think work is going to be far more fluid and flexible than it is today. So people will have the ability to work when they want. That's again kind of a radical concept. Wanna take a year off? Take a year off. But you're doing such high-value work that you're getting paid enough that that becomes possible, or you'll find a way to make that possible.

And that goes along with the idea that work also becomes much more low risk. Right now we have to make decisions on our careers based out of mitigating risk. I have to stay in this job because I don't have the financial security to allow me to change directions or go back to school or whatever.

Finding a way to lower the risk both for individuals and for organizations I think will be really interesting, and again I think technology will enable all of that.

And then the last piece is that work should be … work should contribute to the greater good.

So you know right now there's not a lot of responsibility for either workers or organizations to think about the greater good, it's simply an economic transaction. And if I were designing the system from scratch that's a big piece I would change.

Michelle: Yeah, because I had a job once where I was doing market research for Microsoft and the whole study was just about making sure that the executives got their bonuses like literally, we were doing some ad tracking and it was just about making sure the executives got bonuses. And that was the most meaningless work I have ever done in my entire life because it wasn't impacting the greater good, it was useless except for getting a bonus.

Jen: Yeah and it's astonishing how many people feel their work is meaningless.

And it's worth saying that it's not necessarily that the work itself is always meaningless, but it's meaningless to the person performing it.

And so having done a ton of career coaching over the years, I think most people right now don't feel they even have the ability to pursue work that they would find rewarding and enjoyable and meaningful if they even know what that is because our whole system is not designed to do that.

Michelle: No our whole system's designed to make you a cog in a machine.

Jen: Right. Right, it was designed for the Industrial Revolution, which is fine, it made sense at that time, but I don't think it makes sense anymore, and I think what's really exciting is that technology is going to enable us to move closer towards this vision than we've ever been before.

Michelle: Yes. So as you were developing this vision and going through this process of the moonshot and gathering people together to help you achieve this vision, or develop this vision,

what were some of like the big insights you had from doing this work?

Big aha moments. I'm sure there are many.

Jen: Where do I begin? I think the first thing was, and you and I talked about this before, this idea of being willing to sit with the question.

So for the benefit of the people listening I'll just talk briefly about the distinction between complex and complicated problems.

So complicated problems can be very difficult, but the system is generally understood, and we all know what success looks like. So ironically actually putting a man on the moon was a complicated problem. You can break it down into its component parts. We've got thrusters and we've got life support and maybe we've got some trajectory work, whatever. Each of those can be solved relatively independently, and then they're all stitched back together and we produce something that puts a man on the moon, and when the man reaches the moon we know we're done. Success, bing.

So in a complex problem we often don't fully understand the system, it's often evolving over time, and we're not sure we agree on the rules of the system or what success looks like. So it becomes very difficult, and so anytime we're talking about like transforming education or social justice reform, those are moving targets. And in fact you never really reach success, you're just always trying to move towards it and to maintain the gains that you've already gotten.

And so what I realized, and so my background is as a scientist. And I have a Ph.D. in science, I was for 16 years. And what I realized is that I had been trained on complicated problems, not complex ones. That was really what I knew how to do well, and so in some ways, I was like wow, I am so ill-suited to do what I am about to try and do. And so that led me to learn more about systems theory and complexity theory, and to say it's okay to sit with this problem and to really think about what are the root causes? What are the different parts of the system and how do they impact and influence one another? What does collective success look like? Because often times what we want to do is we want something easy.

You see this in the news all the time for incredibly complex issues, for example like climate change. Oh, just reduce carbon emissions off of industrial plants and wham-o. Or we'll all go vegan. Those sound great, but there's this web of other things that come into solving these issues.

And so I think the biggest thing is just being willing to sit with that complexity and not knowing.

I hate not knowing, so I don't want to paint that as fun, but it's necessary and it's okay. And just as a hint, in the future of work will require us to become much more adept at not knowing and being comfortable in not knowing and dealing with complexity.

Michelle: Yes, because that uncertainty often provokes our anxiety, and we think … because I remember when you were first starting this project, like people would be like, “Oh yeah, so how are you gonna solve that?” And you're like, “No no no no no no.”

Jen: Let's just figure out what the problem is, right? And there are many problems, that's the point, but how do I articulate this in a way and allowing that to then guide what it is that I do. And so that's been one of the great things about this vision. I could still go a number of different directions, but I'm working towards something rather than fleeing a vision of something that may or may not ever happen.

Michelle: Yes, well it goes back to like you're actually creating the future instead of just letting it happen. Like it gives you … well in some ways it gives you that sense of control, like I'm creating this and it's fluid and it might change, but at the end of the day I know that I can basically roll with it.

Jen: Yes. Yes. So rather than having certainty around, I do this … If X and Y, right? If I do this then this will happen, and that's kind of like best practices. It's doing what's been done before. In a moonshot, you get that feeling that certainly gives us in our normal day to day life from clarity.

Clarity says here's what I want to do, I have no idea how to do it, but I know generally what I'm trying to do, and why it's important. And that clearly can provide that sort of warm fuzzy feeling inside, even when you don't have certainty.

Michelle: Yes, because at least you know where you're navigating to. You have this general vision. And one of the things that I've loved about knowing you, working with you, all of that, is for me, now when I have a problem or there's something that I want different, I'm willing just to kind of put that outside of myself and be like okay so this is the issue I'm having, this is the problem, let me get to know it, say hello and like unpack it instead of being like okay what's the best solution in here? This is the problem we have to solve it right away. Because I don't feel like we allow ourselves that time to be like alright, let me explore the problem.

Jen: Yeah and it's so true, I mean even for things that are just complicated. They're still hard. And you don't put a man on the moon right away, and so whether you're dealing with complicated or complex problems, that really miss to unpack a problem and understand it at a deeper level, I think is something that we don't teach people and therefore they're very uncomfortable.

Oh, since this is a podcast all about speaking, you will love this, I just gave a keynote talk on this topic, and for my opener, I came out and I did 30 seconds of silence.

Michelle: That probably made everyone uncomfortable.

Jen: So uncomfortable right, I can see people like turning their heads, like what's she doing, what's happening? And in fact, I was so nervous about it I told the organizer, I said, “I just want you to know I'm gonna do something a little edgy, everything's fine. Don't panic.” And I said to people after the 30 seconds, I said, “Well that was awkward wasn't it?” And I said, “And that was just 30 seconds of silence.” And we don't often appreciate how deeply uncomfortable and how quickly we get there when things aren't proceeding the way we think they should or the way they normally do.

Michelle: Yeah. Exactly, because it's like oh it should be going this way but it's not. Defying all my expectations.

Jen: Right and you and I have talked about this, in my view and I've come to believe that moonshots are something that everyone should do because it gives you the capacity to deal with uncertainty in a way that we've never learned before.

Michelle: Oh that's so interesting. It gives you the capacity to deal with uncertainty in a way that you've never done before. Which I really feel that is a skill that we need as speakers, business owners, parents, like for our entire life is being able to have that relationship with uncertainty.

Jen: Yes. It's coming for all of us, I mean the world is becoming increasingly complex, which means it's becoming increasingly uncertain, and most of us don't have the skillset to know how to deal with that.

And so you're seeing even large successful organizations panic about that, the stability of companies is very low compared to historical levels. It hasn't quite hit the workers yet so there's this wonderful cognitive dissonance. I love it, where people say, “Yes I think that technology is going to completely transform the world of work and it's going to take over much of human work in the workplace, just not my job.”

And so there's a kind of dissonance. And again, as you know, I don't think necessarily that computers are gonna take over all work, that's just I don't think that's happening. But what I can say is that there's a huge amount of uncertainty that's coming and that the world will continue to change and evolve at paces that will make us very uncomfortable.

Michelle: Yes, because … well, I even think about like the news these days, where it's coming at us so fast and so furious that it feels like you never know what's going on and what's going to happen next, and there's just a lot of anxiety and uncertainty.

Jen: So true, right? And so what is wonderful is to be able to step away from that and to sort of say, “Well, that's not my issue.” Like it's just going to keep coming, but I know what I'm trying to create, and I am gonna gather people together.

Another big thing that I've noticed recently, I know you're not supposed to do this but I got into an argument on Facebook.

Michelle: Yes!

Jen: I just could not help myself, I'm very passionate about the environment, as I think we all should be. And people were sort of saying, you know it was another link to another government report about how we're all gonna die soon because the planet is gonna explode or something like that.

Michelle: Yes.

Jen: And I was so frustrated because it's like can we stop talking about how bad it is and talk about what we want to do together.

And they kinda were like, “No, we need this, because we … the people need to change or the companies and organizations need to change.” It was all pointing fingers and they're the problem, they need to change, and there's very little we can do about it. That was the whole sort of encapsulated belief system.

And one of the things I think is important about moonshots is that it helps you see how powerful you are. With the right questions, with the right vision, you can compel great things to happen. And that's another good piece of this that I think is so important as the news keeps coming out, is like you are not powerless, you have agency.


You can create the future.

Jen: You can create the future, right. It'll be hard and you'll have setbacks and you won't know what you're doing much of the time or if it will work, and that's okay.

Michelle: Yes. So I have one final question, which I realize is probably a really large question, but for people who are listening to this conversation and they're like oh my gosh, maybe I need to do some kind of moonshot project,

how can people start finding their own moonshot idea?

Jen: Yeah so it begins with asking interesting questions. There's a wonderful book on this topic that I recommend, I'm like the evangelist for this book. It's called A More Beautiful Question by Warren Berger.

And there are some wonderful examples in there, but the general idea and what I do with clients is I usually will say if you could solve one problem in the world, what would it be?

And you can doodle on that, we usually come up with several different answers and play around with that.

But if solving world problems isn't your thing, if you really want to do a moonshot for yourself, then the other question I ask people is to say if I had a magic wand, turned out I'm actually your fairy godmother, I could make anything happen, only one thing, but anything you wanted, what would you want that to be? And then whatever your answer to that question is, ratchet it up several times. So imagine whatever your answer is that I laughed at you and I said, “No seriously, it's a magic wand, it's magic.” Because I actually have to do that to my clients all the time.

Because we're so used to doing what we think we can do. We're so used to doing what we already know how to do. And this is what you don't know how to do.

So if you come up with something and I ask you well how would you do that? And you start to tell me, you don't have a moonshot yet.

Michelle: Yeah. Yeah. Because the purpose of it is not knowing how to do it so you sit with the problem and gather people and inspire other people to want to help.

Jen: Right. So for example, my husband's moonshot. He did not want to go out and save the world, we decided one world saver per household is enough.

Michelle: That seems like a good role.

Jen: And so he also was a scientist in the military with me for many many years, so right around the age of 46 he decided to become a singer/songwriter, and he had zippo experience, he'd never sung a song, he'd never written a song. I think he could play one lick from Tube Snake Boogie on his guitar.

So that's where we started, and so he eventually got to the place where he had a few songs and was really getting into it, and so I asked him, “If I had the magic wand.” And after several iterations what we got to was well I'd like to do a sold-out show at the Moore Theater, which is here in Seattle, it's a pretty big venue. And for him, that's a moonshot. He doesn't get to start at age 25 and do what everybody else does in the music business. So you know, the question that we kind of came up with was what if I … At this point now he's 50.

What if a 50-year-old former scientist could change the world through music?

And so that's led him in really interesting places and it's produced really interesting connections. And so he's making his way. Yeah. So it's just a different version of, and I wanted to talk about these personal moonshots because they're equally valuable and meaningful. He doesn't know exactly how he's gonna get there, I mean how does any 50-year-old sell out a show at the Moore Theater when you're starting from Tube Snake Boogie?

Michelle: Exactly.

Jen: No one knows how to do that. And so we're having a good time with it. So he's evolved to where he's writing a lot of politically oriented songs. We said oh wouldn't it be fun, you could put yourself out there as a musician for politicians. Maybe open rallies and things like that to kind of get the mood right. And I think it'd be really cool. Will that work?

I haven't the foggiest, but what's cool about a moonshot is they're so ridiculous that you have to be innovative. You have to be creative. And so you try things out.

Michelle: Yeah it's all a big experiment to see if it works.

Jen: It is right? So really I'm still a scientist, I mean that's the secret.

Michelle: You're still bringing your whole self to this project.

Jen: I am, I'm just running human experiments, that's all.

Michelle: Oh my gosh, I love it. Jen, I want to thank you so much for talking to us about moonshots, and tell us where we can find you, where are you hanging out these days?

Jen: The best place to find me is So you can read a little bit more there, you can check out the vision that we created as a result of this effort, and yeah, shoot me an email, love to hear from you.

Michelle: Yeah. Thank you so much, Jen, this has been an amazing conversation for me, considering the podcast that's going to precede this one is all about how I don't like setting goals because I feel like a failure if I don't get them. And hearing about the possibilities around setting a moonshot and doing something that is like so ridiculous that it takes the pressure off, it's such a great reframe and I think it's gonna be a really good reframe for other people too. So thank you for being here.

Jen: Oh you're so welcome, yeah. And if you come up with a moonshot idea I hope you'll share it with me. I absolutely love hearing how people apply these ideas and where they take them.

Michelle: Yes, I will, I will. Thank you, Jen.

Jen: All right.

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