The Manifista Podcast with Portia Mount

Bold career moves with Jen Gresham

December 17, 2020 Portia Mount Season 1 Episode 8
Bold career moves with Jen Gresham
The Manifista Podcast with Portia Mount
More Info
The Manifista Podcast with Portia Mount
Bold career moves with Jen Gresham
Dec 17, 2020 Season 1 Episode 8
Portia Mount

“We are wired to want simple” - Jen Gresham

Jennifer Gresham is the executive director of Work for Humanity, an organization that is making bold moves to fundamentally rethink the nature of employment and solve one of the biggest challenges the US economy faces today, rebuilding the middle class. If this sounds like a big, audacious goal, well it is. And you will hear why Jen is the perfect person to tackle it. Jen is a graduate of the Air Force Academy and a scientist with a background in human performance. In this episode we trace her career from her early days as assistant chief scientist in the Air Force to her bold decision to leave the Air Force just a few years short of retirement. We also explore her journey from successful blogger and business coach helping thousands of professionals achieve their career aspirations. Jen shares her ups and downs along the way and what finally led her to found Work for Humanity. In this episode you will learn about why we need to embrace complexity, risk taking and why you should bet on yourself. The future is female, let’s get started!

Have a question or comment? Email us at

Topics discussed in this episode:

Embracing complexity and being comfortable not knowing

  • We often don't solve a complex problem, we evolve with a complex problem.
  • There's untapped human potential, which is something I'm really interested in.
  • We need the intellectual and emotional capacity for complexity, because we are so wired to want simple.
  • The importance of being comfortable not knowing and having to experiment and find your way. 

Work for Humanity and envisioning a better future 

  • Income inequality is the highest it's ever been in 50 years.
  • My vision for the future of work is that everyone has a job that enriches them financially, intellectually, emotionally, socially and spiritually.
  • We need to upskill the workers and employers in small businesses, so they can start to work together as a strategic team.
  • Our system is inhumane by design. We all need to really understand that we are part of that system, and therefore we are part of the problem. 

Resources Mentioned 

Jennifer Gresham (link)
The report: Reimagining Inclusive Economies (link)
Work for Humanity (link)
Peter Diamandis (link)
Winners Take All by Anand Giridharadas (link)
Humanocracy by Gary Hamel and Michele Zanini (link)

Show Notes Transcript

“We are wired to want simple” - Jen Gresham

Jennifer Gresham is the executive director of Work for Humanity, an organization that is making bold moves to fundamentally rethink the nature of employment and solve one of the biggest challenges the US economy faces today, rebuilding the middle class. If this sounds like a big, audacious goal, well it is. And you will hear why Jen is the perfect person to tackle it. Jen is a graduate of the Air Force Academy and a scientist with a background in human performance. In this episode we trace her career from her early days as assistant chief scientist in the Air Force to her bold decision to leave the Air Force just a few years short of retirement. We also explore her journey from successful blogger and business coach helping thousands of professionals achieve their career aspirations. Jen shares her ups and downs along the way and what finally led her to found Work for Humanity. In this episode you will learn about why we need to embrace complexity, risk taking and why you should bet on yourself. The future is female, let’s get started!

Have a question or comment? Email us at

Topics discussed in this episode:

Embracing complexity and being comfortable not knowing

  • We often don't solve a complex problem, we evolve with a complex problem.
  • There's untapped human potential, which is something I'm really interested in.
  • We need the intellectual and emotional capacity for complexity, because we are so wired to want simple.
  • The importance of being comfortable not knowing and having to experiment and find your way. 

Work for Humanity and envisioning a better future 

  • Income inequality is the highest it's ever been in 50 years.
  • My vision for the future of work is that everyone has a job that enriches them financially, intellectually, emotionally, socially and spiritually.
  • We need to upskill the workers and employers in small businesses, so they can start to work together as a strategic team.
  • Our system is inhumane by design. We all need to really understand that we are part of that system, and therefore we are part of the problem. 

Resources Mentioned 

Jennifer Gresham (link)
The report: Reimagining Inclusive Economies (link)
Work for Humanity (link)
Peter Diamandis (link)
Winners Take All by Anand Giridharadas (link)
Humanocracy by Gary Hamel and Michele Zanini (link)

Transcript Jen Gresham 

Portia Mount  1:00  

Jen, how has your concept of success changed for you over the years? I'm curious, like, what does it mean for you now?

Jen Grisham  1:09  

You know, this is a question that I dealt with a lot. When I started my coaching business, I'd been in the military for 16 years. So I think at that time, I had a very traditional sense of success, you know, promotions, how much money do I make? Where do I live? Those kinds of things. And when I made this shift over to coaching and running my own business, and was talking to people all the time, who were really unhappy in their career, I think it gave me a different perspective and actually created a course called define success for yourself.

Portia Mount  1:42  

Oh, I love that.

Jen Grisham  1:43  

Yeah. And it just really hit me how important that was. And that it's not that promotions of money and where you live isn't important. But if you don't have the quality of life, if you aren't living in accordance with your own values, those things aren't all that meaningful, right? We know that that makes people unhappy. But then I went through another shift again, when I decided to start my nonprofit Work For Humanity. And now it's become all about impact and justice. I'm still living in accordance with my values. And now I'm having to balance my desire for impact and justice with that quality of life. Because those don't always work so well together. I haven't figured out how to do that. It's a balancing act. I think over the course of your lifetime, your definition of success changes.

Portia Mount  2:37  

I love that you say that. And I think that's very consistent with the women that I interviewed for Kick Some Glass, who said, really along the lines, the exact same thing you did, which is around just aligning the work that you do with your values, wanting to make an impact. And that I think it particularly, as we go on in life, we realize the measure of our success in life isn't about the paycheck or the title, but it's much deeper than that. And we're going to touch on the incredible work you're doing in leading and starting Work For Humanity. But I have to ask you a couple of other things, because I was, you know,  it's always fun to prep for these conversations, because I get to rediscover why I wanted to talk, you know, talk to the luminary I'm speaking to and on your LinkedIn bio, you have a certification. You are a certified wrong thinker. And that actually just I just kind of stopped and I was like, whoa, what is that? So what is a certified wrong thinker?

Jen Grisham  3:40  

Yeah, that was really, it was such a good time. So I deal in complex problems. And I think this is really helpful for people to understand the distinction between a complex problem and a complicated one. So a complicated problem is what most of us are familiar with. These are problems that are well defined, you know what the problem is, there's usually some best practice for solving it. Right? You can break it into its component parts independently, solve those and then get a solution. So complicated problems can still be really hard, like putting a man on the moon was a complicated problem. But by and large, we know how to approach those. 

Portia Mount  4:17  

Distributing a vaccine right, now we're in the middle, we're talking and at this point in time, there are probably two COVID-19 vaccines that will likely be approved very soon. And one of the most complex problems now that they developed, the vaccine is the logistical distribution of that really interesting, complex problem to solve globally. Right?

Jen Grisham  4:41  

Yeah. So that's interesting, right? So vaccine development for example, developing the vaccine is a complicated problem. We know how to do that. 

Portia Mount  4:48  

Very much so.

Jen Grisham  4:49  

But how you distribute it, how you decide who gets the vaccine first, all of those things, that's a complex problem. So a complex problem. If we were to define that is usually an interrelated set of problems. It's really difficult to get to the root cause, how you frame the problem will depend on how you approach it, you cannot break those problems into their independent parts and solve them, they have to be treated as an entire problem set. And as you start to try to solve them, the problem itself changes. So we often don't solve a complex problem, you evolve with a complex problem. So what I find is that most people don't understand the distinction between those two problems. The fact that a complex problem requires a very different set of skills, a very different approach. And so you can't come at it the same way. And so I got this certification in wrong thinking to help me deal with complex problems. And it's just a series of exercises that really helps you get out of the traditional way we think about problem solving. 

Portia Mount  5:53  

And it sounds perfect for what you're trying to do now with Work For Humanity, too. So I'm excited to get to that. But I'm sure as people are starting to hear it's like, wow, who is this woman? You are a scientist. And I want to go back a little bit in time with your career, which is your military veteran, you graduated from the Air Force Academy, with a BS in biochemistry, and you have a PhD in biochemistry as well, what specifically led you to the Air Force Academy? And what drew you to biochemistry and you've talked about problem solving? So I suspect there's something in there about that. But talk a little bit about that?

Jen Grisham  7:01  

Yeah, you know, the truth is, I joined the military to escape an abusive home, and maybe not as rare as many people might believe. But I grew up in a very controlling household. And it was clear to me that I could not allow my father to have financial control over my future. So I only applied to three schools, it was incredibly risky. But I applied to the Air Force Academy, Naval Academy and West Point. 

Portia Mount  7:32  

I was gonna say, did you apply to West Point in the Naval Academy as well? 

Jen Grisham  7:36  

I did. 

Portia Mount  7:37  

So those were your three schools. That is it?

Jen Grisham  7:39  

That's it. I mean, honestly, like, I look back now, I would never tell anyone to do that. But to me, it felt like the only way.

Portia Mount  7:48  

You had a goal. And you had to get out.

Jen Grisham  7:52  

Yeah. Because it was just, I won't go into all of that. But it was, that was the only way I was gonna get my freedom. And so yeah, so I was very lucky, I got into all three, I ended up going to the Air Force Academy. And I ended up pursuing biochemistry for a couple of reasons. One, because I had been doing summer programs in high school, that actually allowed me to work in our chemistry labs, it was like a really great state summer program that you could get into and learn all about science. So in some respects, it's just sort of it's what you know, right? If I had done a writing camp, maybe I would have become an English major.

Portia Mount  8:32  

And you are, you are a writer as well.

Jen Grisham  8:34  

I am also a writer, yes. That was actually a very difficult decision for me, part of me wanted to do biochemistry, part of me really did want to become an English major. But I think what, what kind of tip that balance is, I love understanding how things work in all the gory detail, right? So the idea that you could go from I just ate this piece of food to I can watch the electrons move in your body, to me was just mind blowing. And so it was kind of irresistible for that.

Portia Mount  9:08  

Well, and the access to the technology that you get in the military can be second to none from a, you know, from an educational standpoint, right?

Jen Grisham  9:17  

It is. And I mean, interestingly, I wouldn't say that I personally had a lot of exposure to technology and it was more science than technology. Although there are plenty of scientists in the military that do that. I was more on the sort of basic research, understanding how things work. That was definitely a theme for me throughout my career.

Portia Mount  9:42  

So one of the things that you've talked about in your, and I saw this in your bio, was that you had a career changing moment when you became Assistant Chief Scientist for human performance in the Air Force. So what was that role about and why was it such a game changer for you professionally?

Jen Grisham  10:01  

Yeah, that was such an amazing job. So the human performance wing, we were all about how do we up level human performance in a variety of contexts. So we always like to say we tried to augment human performance, using biology, sex, psychology and technology. 

Portia Mount  10:20  


Jen Grisham  10:20  

And that was really the first time that I've thought about this idea of augmenting human performance. Most of us are familiar with medicine, where the whole idea is to take performance that's been somehow decreased and bring it back up to baseline, right? So you have an illness or injury, right? The whole idea is to bring you back up to baseline. But what we were doing was how do we take people who are already at baseline and augment their performance, and it just has never occurred to me that that was even possible outside of, you know, athletes who were illegally taking performance drugs.

Portia Mount  10:55  

Which we’ve heard a lot about right?

Jen Grisham  10:56  

You can do this legally.

Portia Mount  11:01  

You get paid to do it.

Jen Grisham  11:03  

Yeah, you can get paid to do it. And it's interesting, too, I think, because it was clear to me that most people outside of our lab didn't know about this, right. And there was this really negative perception around performance enhancement because of what had happened in sports. And so I think, too, especially in the military, you get people who worry about creating super soldiers.

Portia Mount  11:29  

And we know there's a lab somewhere underground in Colorado, that's creating super soldiers, it has to be true.

Jen Grisham  11:39  

In these days of conspiracy theories I worry about even suggesting it.

Portia Mount  11:41  

We shouldn't even joke about it. But honestly, if you told me it existed, I would be like I knew it. 

Jen Grisham  11:50  

And I think this can be as mundane, as you know, working with, for example, people who are on the flight line, it's a very noisy environment, but you still have to be able to communicate with your teammates. So how do we do that, right? When we, and part of that was understanding how sound traveled and how we could mitigate that that was world class research that we did. We looked at, for example, how do we understand the determinants that happen to people when they lack sleep, right? And how do we get them to understand when their performance has declined due to sleep loss.

Portia Mount  12:27  

I think a lot of mothers right now know what that feels like, during a pandemic era. It's not the same as a fighter pilot, but...

Jen Grisham  12:38  

Actually, most people underestimate how much the performance has declined. And so they keep working, thinking that, oh, I've got to get this done. I've got to get this done, when actually they would be much better served, getting some rest, and then coming back to the problems. Anyway, I could go on and on, right, we did all of this great, great stuff. But that was what planted the seed that there's more that we can do in terms of enhancing our performance. And I think it laid the groundwork for this idea that there's untapped human potential, which is something I'm really interested in.

Portia Mount  13:14  

Well, and it's so interesting, because there's for sure, for me, and again, thinking about in preparing for this conversation, there's very much a red thread, from your days at the Air Force to what you're doing now. I don't know if you see that? In terms of, you're just talking about human performance. I actually want to maybe do a little pivot here because you leave the Air Force and you go on a journey. And you become a coach and you launch a really successful blog that's engaged, you know, literally thousands and thousands of people around the world, No Regrets Career Academy. How did that happen?

Jen Grisham  14:01  

It was really interesting. So let's pull a number of threads together now. Like we just talked about. So you remember, I thought I wanted to be an English major as well. So when I decided to leave the Air Force, which was primarily for family reasons, although I was frustrated at the time with the lack of innovation that happens inside a large bureaucracy, so you know, it's no slam on the Air Force. That's just the way large organizations happen. And even being in a lab, it was really hard to innovate. And so I made this decision. And everybody said, I was crazy, right, because I left the military four years short of retirement. 

Portia Mount  14:44  

Oh, wow. That's kind of a big deal, right?

Jen Grisham  14:47  

It's a huge deal.

Portia Mount  14:49  

And your husband was also or is he still in the Air Force? 

Jen Grisham  14:52  

No, he's retired. He's retired from the Air Force. 

Portia Mount  14:53  


Jen Grisham  14:54  

But yeah, most people don't realize that the deal in the military is that you have to serve for 20 years. If you do that when you retire, you get half of your base salary for the rest of your life. 

Portia Mount  15:06  

Oh, wow, that's a good deal.

Jen Grisham  15:08  

It's a super good deal. In the past 15 years like nobody walks away from that. 

Portia Mount  15:17  

Except for, except for Jen Gresham.

Jen Grisham  15:20  

And, you know, I think part of it was that I had had a couple of miscarriages, which was really bringing home the preciousness of life in that moment. And I was noticing that when I took a day off, I was thrilled, you know, despite having a terrific boss and a terrific mission, like there was nothing wrong with the job. And I was thrilled every time I took a day off.

Portia Mount  15:46  

That's a sign of something, right? It's a signal

Jen Grisham  15:50  

Right? There's nothing that they could do to make me happier. And I still wasn't happy. And so I was lucky. My husband was really supportive. I made the decision to get out. I had all of my former bosses call me to say, are you okay?

Portia Mount  16:04  

Was your phone just ringing off the hook whit people saying like, are you feeling okay, you know, take some extra days off and think about this. And, all of that

Jen Grisham  16:12  

Yeah, yeah. And I mean, just coming from a place of love and wanting the best for me, and I'm really feeling like I was making a huge mistake. Because it's not like I had something to go to right? And so...

Portia Mount  16:26  

That's right, because you were leaving and you didn't have any thoughts about what you were gonna do yet?

Jen Grisham  16:33  

And they're like, what are you gonna do? And I'm like, I don't know, I'm gonna have to figure that out. So I kind of coached myself. I mean, I read a book, you know, called the Pathfinder, and did all these exercises and coached myself through that process. And finally, you know, I decided that I'm going to be a writer. And so I started my blog truly as an experiment, it was not meant to go anywhere or be anything. And I was just talking about my experience of wanting to change, wanting more fulfillment, not even knowing why or what was possible. And so I made that shift. It was very difficult, it ended up being more difficult than we thought. My husband got reassigned, we thought we were going to be staying in the same location. So we ended up having to put our house on the market while the recession was still going on. At the same time, our renter for our place that we owned in Washington DC, lost her job and could no longer pay rent. So all of a sudden, we had three houses that we had to pay for and half the income.

Portia Mount  17:47  

A series of unfortunate events. 

Jen Grisham  17:49  

Yeah. And so, you know, I'm doing this little blog thing on the side, and I'm loving it. And I'm just like, Oh, I think I really want to be a writer. But  not only does it not generate money, it takes money. So I went back to my old boss, and I said, Hey, you know, is there any position for me here? You know, I'm looking for something. And so I originally started off as a consultant, kind of doing what I was doing for them before, but I was on the plane right back from that first assignment. And I said, I can't do this.

Portia Mount  18:26  

Oh, wow. 

Jen Grisham  18:28  

Yeah, it was...

Portia Mount  18:29  

They hired you back and you're like, I can't do it?

Jen Grisham  18:31  

I can't do it. All the same reasons that I left are still here. So I had to go, I think that was the hardest call I had to make. 

Portia Mount  18:40  

My heart actually is sinking for you. Because I can only imagine how torturous that call was, could have been. 

Jen Grisham  18:46  

Right? Especially because I loved my boss and was so grateful to him for, you know, the opportunity that he'd given me. And so he said, Jen, what do you really want to do? And I said, I want to be a writer. And he said, Well, then why don't you write for us? And I said, What? That's an option? And so, you know, overnight, I became one of the highest paid writers ever.

Portia Mount  19:16  

What were you going to write, because you said you want to be an English? You want to be like a writer. So you're, is it like, technical writing that you are going back into or?

Jen Grisham  19:28  

Actually writing thought leadership pieces.

Portia Mount  19:30  

Oh my gosh, right up your alley. 

Jen Grisham  19:33  

So this was trying to overcome the stigma, human performance augmentation, and really educating people about what this is, here's why we need it. Again, really foundational for what I'm doing now. I ended up having tremendous success. Doing that I was able to get pieces published that people said Oh, you're never going to get into that journal. In fact, I got the cover story in the Armed Forces Journ al. Ended up writing book chapters with some really big name people on this topic. But then that catalyzed my book and so I'm telling people what I'm doing and all of a sudden people say, Hey, can I hire you? And I said, What for? Do you want me to write something for you? I'm here, xxx performance augmentation? And what they said is no, I want you to show me how to do what you've done. I want to understand how to make a career shift like you've done. And I said, I don't know anything about that. 

Portia Mount  20:32  

You just did it. But you didn't really know how to teach it?

Jen Grisham  20:35  

No. I mean, I really felt like I had done it very awkwardly, and almost unprofessionally, right? Like, who would have you know, the advice? Well go get a job with your old employer, then, you know, after the very first day on the job, you tell them, You can't do it. And then you're lucky enough that they're open minded enough to give you a better job and what you really want to do, that wouldn't work, right? So for a long time, I said, No, I can't do that. But after enough people kept asking, and the blog was taking off.  

Portia Mount  21:07  

We will link to it because the posts are, the posts aren't just great. The conversation after the posts are equally great and illuminating as well. And you engage with the reader in such a great way and people engage with one another. So I can't wait for people to read some of your posts.

Jen Grisham  21:28  

It was such a great community. And we did have really good conversations. And so I basically, you know, at that time, I probably had fewer than 1000 subscribers to the blog. And so I sent out an email, I said, Look, a number of you have asked me to put something together. I don't know what I'm doing. I have not created this. But I am a scientist, and I'm willing to run an experiment. If you want to go through a program like this, with the caveat that I have no idea if it will work. Let me know. And that's sold out in 24 hours. 

Portia Mount  22:01  

Wow. No, were you charging at this point? You said sold out? So did you just say look, I'm going to put a price out there and see?

Jen Grisham  22:09  


Portia Mount  22:11  

See what sticks? 

Jen Grisham  22:12  

Yeah, so I put a price and I set a limit. So I was going to take 10 people at $200 a person, you know, easy peasy. I ended up taking 13 people because people begged me to let them in. They said, Please, I need this so much. It was honestly really scary. Because I thought, well, here are people who really need this. And I don't know what I'm doing.

Portia Mount  22:38  

You sort of stepped out there, right? Because you sold a product that you didn't really have yet.

Jen Grisham  22:43  

No, I created every lesson the week before I sent it out.

Portia Mount  22:47  

Oh my god. This is both inspiring, and also terrifying. 

Jen Grisham  22:54  

We would work together for one week. And I would just be really present to what do I think needs to be done now? Where are people at? What's missing? And then I would create that. So it was really tailored to that first group. And then you know, that went really well, people were really pleased with it, we had good results. So I decided to offer it again to a wider audience. And it just kept growing, right? It's just every time I offered it, it got bigger and bigger.

Portia Mount  23:22  

And so, did that become your full time work at that point? Were you still doing the writing for the Air Force at the time, but launching your Career Academy, as well, and this kind of grand experiment that you're on?

Jen Grisham  23:41  

So this is interesting. So I was doing both for a while, at some point I fell in love with the coaching, I really enjoyed it. To me, it was like, Oh, now I get to do the human performance augmentation. 

Portia Mount  23:54  

Yeah, you're doing all the stuff that you've been studying for all these years, right? 

Jen Grisham  23:58  

Rather than leaving it right, because I had been in a management position. So now I'm actually getting to do it. So I quit my writing job. I went full on with the No Regrets Career Academy, but I never figured out how to make it financially viable as a sort of using online marketing. So you know, lots of people have this impression, like, Oh, you just create a course. And then you know, tons of people stumble across it and sign up for it. 

Portia Mount  24:30  

It's a ton of work to promote.

Jen Grisham  24:33  

A ton of work and I was paying subcontractors to do all of these things for me. And so basically, I wasn't making enough to even pay myself most months. So this is again, no one would advise this, but this is how it worked out. I went back to my old boss and asked for my job back again.

Portia Mount  24:53  

So this is now, let's count, the second time you've quit and asked to come back, I just want to make sure I'm keeping track. Okay, we got it straight. 

Jen Grisham  25:05  

But here’s the other crazy thing is I said, Hey, here's what I'm getting paid now as a coach, I also want to raise.

Portia Mount  25:14  

So you come back the second time. Like, I need to make more money?

Jen Grisham  25:20  

Yeah. And they said, Okay.

Portia Mount  25:26  

All jokes aside, it speaks to how highly they thought of you, and the skill that you brought that you could leave and come back like that. And the relationship that you had, with your boss

Jen Grisham  25:45  

Yeah, I think the thing is, the people that I was working with, they did not have the time and the space to do what I was doing for them. But what I was doing for them was critical to the success of the mission, right? So everything that we were doing had a direct impact on the reputation of the organization, the amount of money that was allocated. What's interesting is that from the time I started working there from, you know, kind of bringing people back up now to where we are now, the reputation of that organization did a complete 180. And so, yeah, it had a huge impact. And honestly, no one else, I don't know of anyone else who could have done what I did for them.

Portia Mount  26:36  

So part of what you were doing in your coaching was helping people define and achieve their personal moonshots. Is that the right way to frame it?

Jen Grisham  26:51  

Yes. So that was an evolution of the coaching, eventually, I did figure out how to make the coaching financially viable.

Portia Mount  26:59  

Talk about how you made the business viable once you figured out that I'm doing all this work to promote the course, fill it, and there's not enough money for me to pay myself? So now, but I like the coaching, so I'm going to go back and ask for you know, go back to my old boss. So talk a little bit about how you scaled, you're able to eventually scale the business?

Jen Grisham  27:26  

Yeah. What's fascinating is that scale is in some ways the wrong word. I actually descaled it. In the online marketing world, right, your goal is to get lots and lots of people. That's how you make that work financially viable. I never figured out how to do that personally. So I ended up getting a coach myself. In fact, I had a couple of coaches who worked with me on money, mindset, and marketing in a way that really worked for me. And so this was, here's how much I want to make. Here's how many clients I really want to work with. So now I need to figure out a way to help people with an issue that is valuable enough that they can pay me enough to get there. In some ways, it's really simple, right? And so I basically said, I don't want to work with more than six clients at a time. So rather than working with hundreds of people, I want to work with six people, but I want to do something really life changing for them. And so what was great is that a number of people who had gone through the No Regrets Career Academy, were looking for more personalized service. And so it was just that those were my first one-on-one clients, and it grew from there. And what's awesome is that I didn't have to do any marketing. They all came through referrals and just conversations that I was having with people. Even today, I haven't written on the blog in a long time, I still have people who get pointed there who asked me for coaching, so that was really pivotal. 

Portia Mount  29:00  

When you read the post, it still feels very relevant, even though you haven't written on it while.

Jen Grisham  29:12  

Yeah, yeah. I mean, all of the same issues are still relevant. And we're still still dealing with them. And yeah, so that was an important moment when now I'm making even more money now as a coach than I was in my writing job. Loved it. And so an evolution of that was this idea of moonshots. And this is where I came across this term reading Peter Diamandis’ book. He gets it from Google, of course, who has their moonshot factory, and it actually comes from putting a man on the moon, right? John F Kennedy's speech. So a moonshot is a near impossible goal that, if achieved, would have enormous impact either out in the world or personally and I was fascinated with this right? And so I went to a few of my clients that I had at the time, none of them had asked for a moonshot. And I just said, Hey, I've read about this thing. I'm really interested in it, would you be interested in transforming what we're doing into a moonshot? And they all said, Sure, okay.

Portia Mount  30:21  

Why not

Jen Grisham  30:22  

I don't really know what that means but okay. And I'm telling you, the results were so extraordinary. It blew my mind. I couldn't believe what we were able to achieve. And so, then I really did start reaching out to people saying, hey, like, I've got this thing, if you want to give it a try. It'll probably blow your mind too. And I worked with a number of people who specifically said they wanted to do moonshots.

Portia Mount  30:51  

So not to give away your secret sauce. But I'm curious, what did you learn in helping people figure out and achieve their moonshot? Are there some principles or sort of core steps one takes to think about and begin to work towards achieving a moonshot? And then we'll talk about the moonshot that you're working on right now.

Jen Grisham  31:22  

Yeah, so the first principle, and this is often hard for people to believe until they've experienced it, is that bigger and bolder, are often easier.

Portia Mount  31:34  

So counterintuitive.

Jen Grisham  31:36  

It's so counterintuitive, but a lot of what would happen, right? The people who were working with me, they were highly successful, yeah. But they've gotten to a place where they could not get where they wanted to go, just by working harder. That wasn't an option. But that's what they knew, you know. And so it was, it was saying, okay, we're gonna pick something that feels completely impossible for you. But by doing so, you have to think wrong, right? You can't do this the same way. And then I think the other piece to this is really taking time to understand what you want, and understand the barriers to getting there. And again, we often think our intuition is right. And we'll follow that without spending a lot of time thinking about it. And so, a lot of times, what I'm having to do is to disabuse people of their intuition on how to solve complex problems.

Portia Mount  32:31  

Oh, that's, that's also kind of counterintuitive, because you, you know, so much business literature is like, gather the data, then trust your gut.

Jen Grisham  32:41  

Yeah, and it's not that your intuition doesn't have a role to play. So, as you know, I was a poet, I published a book of poetry. And one of the things we say in poetry is when you're trying to come up with the simile when you're trying to come up with a comparison, whatever you come up with first will be bad, like, it will be cliched, it will be really common, it won't spark interest. So you're going to have to go through that several times before you get a good comparison that you can put into a poem that anybody wants to read. The same is true of complex problems. The first intuitive, most obvious approach is bad is not really the wrong approach, right? And so it's just being willing. And if there was anything that I could do for society at large, it would be to give people the intellectual and emotional capacity for complexity, because we are so wired to want simple. And I think this is one of the biggest problems we're seeing in our political environment right now. We take very complex problems and you've got everybody who's suddenly an expert, for example, on epidemiology. 

Portia Mount  33:56  

Oh, my gosh, it's maddening.

Jen Grisham  33:58  

Maddening, right? If they would just do this. Or they would just do that. And this was true before, right? I can't tell you how many times I would just want to pull my hair out when somebody would say like, Oh, if you just did this. Or if you just did that. That's like a sure sign somebody doesn't understand complexity. And they're really uncomfortable with not knowing. So that's, that's another piece is being comfortable, not knowing and having to experiment and find your way. And then I think the other big principle is that moonshots are so big, you can't do it alone. There's no way to get there by yourself. This often requires high achievers to operate in a very different way. 

Portia Mount  34:42  

To give up some control maybe.

Jen Grisham  34:45  

To give up control, to realize it's not all about you.

Portia Mount  34:47  

To collaborate.

Jen Grisham  34:49  

Right. And so that also is very powerful. When you start to say, I can't do this by myself. I don't know what I'm doing. And bigger and bolder, are easier.

Portia Mount  35:00  

That's hard for overachievers to, like you're sort of putting together all the things that make overachievers want to throw up.

Jen Grisham  35:09  

You know truly, I love Anand Giridharadas book Winners Take All, and one of the things he says in the first part of that is if you look at our society today, we've got all of the valedictorians and the Ivy League school graduates, right? They're all running the country. And we're not doing a good job. 

Portia Mount  35:31  

It's so true when you think about that, and I love his writings, and I love to hear him speak, because he just, he really cuts to the heart of things, doesn't he? 

Jen Grisham  35:43  

He does. And I come back to that again, and again. And I think it's really important, you know, including for people like me to remember that my training, by and large, did not prepare me for this moment. And so I've got to constantly work against my natural instincts.

Portia Mount  36:02  

So let's talk about Work For Humanity, because that is a big idea. What is Work For Humanity about?

Jen Grisham  36:12  

So our mission is to create a more equitable and enjoyable future of work so that workers, businesses and communities can thrive together. And just to unpack that a little bit, we already know that most people aren't happy in their jobs, they're not engaged. And that's true, regardless of how much money you're making. In fact, I always, at one point, I was going to write a book about overachievers. And I was going to say, if parents knew truly what the statistics were on depression, anxiety and suicide for doctors and lawyers, they would never push their kids into those fields. I mean, just it's horrific. So we know that work isn’t enjoyable, but we also know it's highly inequitable, right, income inequality is the highest it's ever been in 50 years, the United Nations has actually deemed the United States, one of the most unequal places in the developed world.

Portia Mount  37:08  

And we are seeing that really starkly right now with schooling for kids like give you for that. It's really drawing a line between the parents who can afford to, you know, figure out their pod schools and homeschools and tutors and kids whose parents don't have those means are literally falling behind every day.

Jen Grisham  37:34  

Right. And we know, for example, like what essential workers are going through, and the lack of support that they get, and the lack of some financial support that they're getting is just, there's so much there. 

Portia Mount  37:45  

There's so much there. Yeah, it's like a multi front war isn't it?

Jen Grisham  37:49  

Right. I mean, talk about a complex problem with lots and lots of root causes. And so what we realized is that's going to require a transformation of the economy. But in order to transform the economy, we have to transform the way we work. And so I spent 18 months in a collaboration with the Foundation For Inclusion, who are experts in systems thinking and systems mapping, trying to understand our labor market, to really see why economic mobility was failing, despite the fact that we've just been through the longest economic expansion in the history of our nation. And we had literally invested billions of dollars in higher education over the last several decades. So why didn't that work? And that ended up being an incredible research project, we actually just put out a report on that on inclusive economies. And it was a bit of a surprise that education is not only not the barrier that we think it is, but it's not the equalizer that we think it is either. And so the real problem is a lack of good jobs. And so that has really shaped our entire perspective and approach to this issue.

Portia Mount  39:05  

So I want to follow that a little bit because there's been a big debate about the value of a college education for all the reasons you've just said, right? And we've got unbelievable student debt. That is that hamstrings young people for years, if not their entire lifetime. I live in a manufacturing state and textiles that essentially left the state of North Carolina gradually getting replaced by industries like biotech. But there's been a big debate about do we do something like Germany does where you have apprenticeships and you have continuous certifications, do people need a four year college degree? Is two years of community college and certifications the right way to go? And I'm curious if you have a point of view on how you're thinking about this through Work For Humanity?

Jen Grisham  40:09  

Yeah, I mean, the future of education is huge. In fact, I did a series of keynote talks last year on this topic.

Portia Mount  40:20  rr

It's such a big topic. I know, we could spend probably two hours just on that.

Jen Grisham  40:24  

Right. Yeah, so I have a whole hour long talk on this, but I'll try to distill it down. So one lifelong learning, it's going to be incredibly important for everyone. So we have got to get away from this idea that we can front load education and so much of that discussion around, is it college? Is it an apprenticeship? Is it to your community college like, all of that still makes the assumption we can front load education, which is wrong. We also have to get faster at education, right? So the idea that you can continually go back to college and get another degree that takes several years to obtain is not going to work. But I think more fundamentally, this goes back to this issue of complexity. I think we misunderstand what education is required. So what I talked about are the need for specialists and what I call agilus. So specialists are really well suited to complicated problems. No, no problem there. There's plenty of complicated problems that need solving, right? We need people to develop vaccines. But the world is increasingly complex, and specialists are not well suited to complexity. And so this really requires a completely different education model, where what you're doing is you're teaching someone how to teach themselves anything, and apply it in completely different and new contexts. And so luckily, we're already starting to see some of those. I'm really excited, we have a couple of potential collaborations that we're pursuing on this front. But that's starting to spring up. And I think, more importantly, colleges are in trouble.

Portia Mount 42:02  Big Time.

Jen Grisham  42:04 I mean, they're not going away. And then in the really immediate future, but pretty much everyone's unhappy with college right now.

Portia Mount  42:17  

Well, the value proposition has fundamentally changed and we saw that this year, right? Where, especially for, you know, especially the Ivy's were they had to be virtual, and you had parents saying What? You want me to pay $50,000 to be sitting at home in my basement, taking you English 1-on-1? Hell no.

Jen Grisham  42:38  

And I think it's been fascinating, right? Because it really starts to speak of what is the value of that Ivy League education? Is it just the fact that you're on campus? And you're networking? It turns out, that's actually a big piece of it.

Portia Mount  42:50  

It is yeah, I was gonna say, it turns out that that's actually exactly what it is. Right?

Jen Grisham  42:56  

What that tells us right, is that again, not and we know this fundamentally, but not all college degrees are equal, because not all college degrees give you that same kind of access, and labor market once you leave. And so there are inequities, again, that are built into the system that we're going to have to deal with. And I don't, personally, I don't think colleges are doing a really great job of addressing those or even acknowledging them. So you know, my expectation is that colleges will stick around for specialist education, they're still going to have to get better at getting faster, in order to keep with changing technologies. But there's a whole different kind of education system that's going to develop, we're already seeing this. But I think how fast that happens depends on how well employers realize how the world is changing and how they need to respond in their hiring practices and employment practices accordingly. And so far, we're not seeing that in the US very much outside the tech industry.

Portia Mount  43:56  

So talk more about that. Because, you know, we started this conversation with, it's not about education, it's about the lack of good jobs. And so what's your hypothesis about how we get better well paying jobs?

Jen Grisham  44:16  

First, I want to say when I say a good job, what do I mean? 

Portia Mount  44:20  

Yeah, what do you mean?

Jen Grisham  44:22  

Yeah, so I think, you know, my vision for the future of work is that everyone has a job that enriches them financially, intellectually, emotionally, socially, spiritually.

Portia Mount  44:36  

That's a tall order. Oh, there's a lot of people probably making six seven figure jobs that don't get that out of their jobs. 

Jen Grisham  44:45  

I know exactly. I mean, that is exactly the point right? So we are really looking at a whole sale transformation of how we work. This will require us to really get at many of these assumptions and narratives that define how we work. And I think we, as a society, we just, you're starting to hear this in the education field, right? The education that we have today was largely designed for the industrial era, right? So we needed to teach, you know, how to read and write so that you could follow instructions and work in the factory. We don't really need you to think that much. We need to give you knowledge and tell you how to do things. It's not that education hasn't been evolving from that, it certainly has. But the underlying assumptions haven't fully been challenged. And the same is true in work. So really, I think the big thing that employers need to think about is that the world is becoming more complex. It's becoming more unpredictable. I think COVID has really reinforced that, I hope. 

Portia Mount  45:51  

Yeah, I hope so right? Like, we'll see, we tend to have short memories. But I hope you're right.

Jen Grisham  45:59  

Yeah, I think that the danger is thinking that COVID is a one off, that once we get past COVID, everything goes back to normal. Not only will it not go back to normal, I don't think there's such a thing as normal anymore.

Portia Mount  46:14  

And also normal was not working for most people. That's the thing, normal was working for only a small group of people at the top of the pyramid. And so why would we want to go back there? 

Jen Grisham  46:27  

Exactly, exactly. And I guess what I would also say is that a lot of what we're seeing in terms of really bad leadership and management practices, because, frankly, the leaders of our companies are not succeeding in this complex world. So they're having to resort to, you know, strategies that drive up shareholder value, without creating any real value in the company. So when you see a lot of these mergers and acquisitions, when you see stock buybacks, right, or you see companies who are what's called the financialization of the market, so when Facebook wants to get into a cryptocurrency, what that tells you is that there's something wrong with their model, right? They've already saturated the market. So the only way for them to grow is through financialization. And there's a, that's a whole field, but in any event, the companies are increasingly getting their products through credit. So our economy is so much more fragile than you would think, looking at the stock market gains and the unemployment figures. And that is not sustainable. And I like to believe that many business leaders know that, they just don't know what to do. 

Portia Mount  47:44  

So how do you? So you've laid out the field of the problem and I'm curious, you know, how do you eat an elephant? I guess, one bite at a time. How do you get started on this? Are you rapid prototyping, experimenting with a small group of companies?

Jen Grisham  48:48  

Yeah, so this is fascinating to our working hypothesis. And that's what it is. Okay. It's a hypothesis. But what we think is that the place in the system where we can intervene and make real change is actually with small businesses. So...

Portia Mount  49:04  

Which actually employs the majority of Americans anyway, a lot of people don't realize that. But yeah...

Jen Grisham  49:09  

Yeah. And they're responsible for about half of our national GDP.

Portia Mount  49:14  

I did not know that. But that makes sense. 

Jen Grisham  49:16  

Yeah. So they are a huge driver of the economic engine for this country. And they are geographically dispersed. So this is another big issue, because most jobs when you look outside of the small business industry, recreated in large metropolitan centers, but we know that that's also where the cost of living is the highest. So what we're seeing right, this urban rural divide is real, but it actually fails both parties, right. So we have a lack of jobs being created in sort of more rural areas. And then the jobs that are being created in more urban areas aren't good jobs either. And so those people also aren't making enough to really have a good quality of life. So what we hypothesized is that if we can help small businesses deal with this complexity and uncertainty and a way that drives business growth, and having worked with small businesses for now, almost 10 years, and having a team that has tremendous experience in working with small businesses, what we know is that oftentimes, it doesn't take very much to help a small business get new customers, roll out new products, increase their prices, so on. So if we can do that, and if we could create just one good job per small business, there are 30 million small businesses across the US, we would completely rebuild the middle class. I mean, it will be transformative. 

Portia Mount  50:45  

Wow. That's a moonshot. 

Jen Grisham  50:49  

That's a moonshot, right? So we're really looking to create 30 million good jobs to rebuild the middle class. And what for me is exciting about that is that again, we get to start to address that urban rural divide. We are specifically focusing on women and minority owned businesses, so we can start to address racial and gendered inequities. And most business owners, most small business owners would really welcome this change because they are overwhelmed and maxed out. So what we're talking about is a real shift. And so this means we need to upskill the workers. And we need to upskill the employers in these small businesses, so they can start to work together as a strategic team, where everybody is responsible for the business growth and success of that business. And as the revenues increase, that now gets put into employee salaries. And so not only do they have more autonomy, they have a greater input on the policies and the practices that impact their health and well being, but they're earning more.

Portia Mount  51:56  

So how do you get the scale of this right? Because, you know, to get back to your point about moonshots, it's something, it's a big problem. It's a complex problem. It's one you can't solve on your own. So I'm curious, is the thought that you kind of experiment with small businesses and then teach other organizations, nonprofits how to do this so that they can scale it?

Jen Grisham  52:32  

Yes. So there's a couple of things here. I mean, the first point is, again, being comfortable not knowing how to solve it. And scaling is the hardest part, right? So this is true of lots and lots of interventions where you can get something to work on a small scale, but as soon as you try to take it larger, it falls.

Portia Mount  52:51  

It's a yeah, it's a different ballgame. 

Jen Grisham  52:53  

Totally different ballgame. So in my mind, first, so we're actually fundraising for this project right now. We're hoping to launch this pilot program in early 2021, after the small businesses have hopefully gotten through the holiday season and have some space to breathe. But what we want to do is to kind of figure out the principles and the content that needs to happen, you know, what are the transformations? It really is like designing the No Regrets Career Academy, right, you start with a group of people, right? And so what you're generally looking for is, what are the changes that need to happen? What are some things that work, and then not holding on to that too tightly. So you're exactly right, we're going to essentially, take what we learn for this, share it with the world, encourage people to take it and make it their own. So maybe we would train people, but we would actually encourage them to make it more specific for their communities for the businesses that they're working with. And really, they become scientists in the field. So the idea is that then you create a community that's all trying to do this. And you're sharing knowledge of what's working, where, what are the conditions that change that make this other idea better, right? So we ourselves are not going to come up with a perfect solution. So you have to be willing to take it out to the crowd and let them iterate and refine and evolve. Right? That's the complex part. But I have full confidence that that can happen, right. I think this is a really important point. Because it's essential to the future of work that we've got to start trusting in the capacity of people to do complex work. 

Portia Mount  54:50  

Yeah, yeah. I am so inspired and excited and I can't think of a more important mission right now than what you're doing. Because structurally, something has to change in our economy, and how we work and how we educate people and how we allow people tomlead, meaningful, fulfilled and productive lives. So I'm super excited to follow. And I, you know, to follow you, Jen and I believe that you will do this, I actually, I believe that because it is ambitious, and the vision that you're driving to make this happen, I think is really exciting right now and timely. I want to ask you. So, you know, 2020 has been a rough year for all of us. But I think we also have some really big opportunities, and you've laid out a number of them. Personally, I think we have the opportunity to rethink the kind of society that we want to have, which is what you've been painting a vision of. So lofty question, but what's your hope for 2021? Personally, professionally and for society?

Jen Grisham  56:25  

Yeah, I really hope that what we take away from COVID is that what we had before is unacceptable. It's not just inhumane which it is, right? Our system is inhumane by design. But I think we all need to really understand that we are part of that system, and therefore we are part of the problem. And so all of us need to change in order to repair the system. Otherwise, the systems are designed to produce the results they produce. So I really hope that business owners, Wall Street, the foundation's that are funding philanthropic work, boards of directors all start to say to themselves, we are part of this problem. And we need to do something about it. And we can't just scratch the surface, right? When I saw the response, for example, to the murder of George Floyd and many large businesses were making philanthropic donations. It's not that that's bad. But it's so not enough. 

Portia Mount  57:46  

Yeah, it's just, it's beyond not enough, right? It's, you hate to say it, because the intention is good, but it's insignificant to the scale in relation to the scale and depth of the problem.

Jen Grisham  58:04  

I haven't seen yet this sort of click of understanding in many of our leaders, that it's not enough. And that requires, I don't think people fully grasp. But this requires a really big change in our beliefs and assumptions about our economy, about how things work about society about people. Right. And so I think a big part of what we're trying to do is to liberate human potential at scale. And that involves believing that there is potential there to unlock.

Portia Mount  58:46  

Frankly, is going to be increasingly on the minds of so many leaders. I know it is where I work. And I know it is among some of my colleagues who are thinking deeply about how we transform society, because this is the window, right? This is the time to do it. I don't think we're going to get another COVID hopefully not soon, because we're barely gonna recover from this one. But this is the time to make those big structural changes that can make our society better for everyone. I want to ask you just on a more personal note to maybe wind things up. Do you have a motto or credo or saying that you live by? 

Jen Grisham  59:46  

Hmm. Yes. So the motto that I have to constantly remind myself of and is really helpful is to think bigger and bolder.

Portia Mount  59:55  

I love it. What are you reading or listening to? That's either for let's say for pleasure. We probably get a sense of what you're reading for work but what's on your nightstand right now or what are you listening to on your phone? 

Jen Grisham  1:00:17  

Yeah, this is, I hate to say this right, this goes back to our very first question. I don't have reading for pleasure anymore other than I take pleasure in my work but I'm currently reading Humanocracy by Gary Hamel and Michele Zanini, which is all about this topic. It's a great book.

Portia Mount  1:00:35  

Okay, we're going to link to that. And then finally, Jen, what advice would you give to 20 year old Jen?

Jen Grisham  1:00:45  

Oh, gosh, I think one I would tell myself to trust myself and to focus on the kinds of problems I'm excited to solve, rather than thinking about things as a career.

Portia Mount  1:01:01  

Jen, it has been a pleasure. Thank you.

Jen Grisham  1:01:05  

Thank you so much. This was really great.