Jason (00:27)
Shelley, welcome to The Wisory, The Wise in 5.
Shelley Paxton (she/her) (00:31)
Thank you! I'm excited to be here.
Jason (00:34)
Not more excited than me. Always great to see you.
Shelley Paxton (she/her) (00:36)
⁓
thank you. Likewise. And we match.
Jason (00:40)
We do match as as Shelly said, we're going to take the take a sip of wisdom, right?
Shelley Paxton (she/her) (00:43)
Mmm. Yes.
Mmm. I feel smarter already.
Jason (00:47)
delicious wisdom.
So ⁓
why don't you start by just sharing a little bit about your journey and you know, what you've done and how it kind of brought you to this point. So the folks who are engaging on the Wisory, you have a sense of who you are.
Shelley Paxton (she/her) (01:02)
Yeah, I love it. Well, thanks again. I love what you've created and it's such an honor to be a part of the platform and to be one of your first guests on this. So the short story, and you can learn a lot about me off this platform, but the short story is I spent 26 years in the advertising and marketing world, working for a lot of incredible global iconic brands like McDonald's and Visa and Intel and
Probably the one I'm best known for is Harley Davidson. At the pinnacle of my career, I became the chief marketing officer of a little brand, sort of a sexy brand called Harley Davidson. And yeah, and what's really interesting is, you I was in this incredible place, like stewarding a brand that's
you know, well over a hundred years old that has such a rich legacy and history. It was an unbelievable honor to have my fingerprints, you know, on the, the, the pages of the history of this brand. And I'm riding motorcycles around the world, leading hundreds of people and really creating the future of the brand. One of the things that we did while I was there was announced the new first
ever Harley Davidson electric motorcycle that's now known as the Livewire. It's its own company. It's its own thing. But I say that all his background is that you'd be like, yeah, so you're nodding along going, that's unbelievable. Like you had it made like that is success in a nutshell. And the truth is, and the real thing I want everybody to know about my story is that's the point at which I personally felt my lowest and inside I felt incredibly empty.
I felt alone, I felt unfulfilled, and the world's looking at me like, girl, you've got it made. I'm like bowing at the altar of success. And that was the beginning of a really, really intense and profound journey for me. We're at a wake up call. It's my nightmare. where my book starts. If you want more detail, you can read the book. But in essence, I sort of had my own awakening. I kind of had my breakdown to break through, as our friend Brene Brown would say.
where I realized that I had been living my dad's success script. And so it was my call, I decided to walk away voluntarily from the peak of my corporate career to better know myself, to learn who I am, to reconnect with my soul, to understand, I always say, rebel for who I am, what I want and the impact I want to have in the world. And little did I know that it would lead to...
this mission that I'm on and become the foundation of all of the work that I've been doing for the past eight years.
Jason (03:53)
It's incredible. mean, the wisdom that you've gained in probably those valleys, right? That took you to this next peak is invaluable, right? And I know that's something, you know, I've read your book. It's amazing. I've been fortunate where you've spoken to my class, the entrepreneurship class at Indiana, and they're always blown away.
Shelley Paxton (she/her) (04:04)
Absolutely.
Jason (04:15)
it's incredible. It's incredible. So why don't we dig into the wise in five? And I'm sure we're gonna have a couple of things to talk about off that, but something I always think about you, like the passion and creativity that just like oozes out of you. Where do you find
Shelley Paxton (she/her) (04:16)
Mm.
Yeah, I love this question and you know me, I'm a rebel. So I am going to give myself permission to tweak the questions slightly because I think the real insight is not only in where do I
Jason (04:39)
Feel free.
Shelley Paxton (she/her) (04:45)
find it, but how and the how is so important to me. And so I don't think we talk enough about how we create the space, how we create the pause in our lives. Right? So I talk about this concept of choosing pause over push, which is simply creating these, you know, this space in our lives for rest, for creativity.
for play, for inspiration. I think we subscribe to this crazy busy. This is something I joke about, but that was my favorite phrase when I was in the corporate world. And we wear all too often busyness as a badge of honor. And I'm saying that as somebody who is hugely guilty of that. And so I really want to start by saying, first think about how you create these moments where you literally give yourself
permission to say, I'm walking away from my computer. I'm giving myself a pause in my schedule. I'm creating time and space for me alone. It might just be to walk in nature because I believe that's where creativity happens. Create the time to lay in the hammock and read the book. Go walk in nature. Have lunch with somebody who inspires you. Go to the museum and stare at art from, you know, decades and generations ago. Like,
Jason (05:57)
Absolutely.
Shelley Paxton (she/her) (06:12)
Allow your mind, there's an awesome TEDx talk about idea sex. I don't know if you've ever seen this, it's incredible. But it's this idea that, you know, real true creativity and inspiration comes from like the most unexpected places and from just allowing. It's why we have ideas in the shower, just allowing ourselves to be. So I'm so much more intentional about
creating those places to play and those connections to invite those people into my life to listen to the thing to read the thing or just to plant my feet in the mountains or the soil or whatever it is. So that to me is the most important part the how versus the what.
Jason (06:57)
I love it. And I think the next podcast you've inspired me, I'm going to do from the shower. mean, so I think that's, I think that's a great suggestion. no, we probably do audio for that. No one wants to see the video. That's for sure. So second question, right? We're two out of five. What's been your greatest learning over this incredible career that you've created?
Shelley Paxton (she/her) (07:02)
Yes! Is it gonna be on video though?
Oof. I alluded to it in my introduction, but I would say at the most, like, macro level, it's the idea that success defined on anyone else's terms or script or values is always going to leave you feeling empty, not full.
And that was my biggest learning I had when I described being at the peak of my career, having this sexy job title and this big paycheck for this global iconic brand. And yet, you know, I ticked all the boxes and I still felt incredibly empty. And I'll be honest, you know this, I say this all the time. That was my dad's script and it served me very well for decades. So I have zero regret. And at the same time,
I got a big old cosmic kick in the butt to wake up to who am I really and how do I want to define success? think so often we're like, when I get to that place, when I get to that place, when I get to that next place, I'll be happy when instead of really pausing again, this is what I'm teaching my students. I'm teaching at Northwestern. As you know,
learned so much from you as a professor and from guest lecturing in your class. And I'm really teaching my students that we get to define success from the inside out. And that is truly what leadership is about. And so I talk about this idea, we bandy about this word successful, but so often we land success empty. And successful is really courageously defining success on our own terms and in a way that feels
energizing and fulfilling from the inside out.
Jason (09:11)
I love that. I love the juxtaposition. I love everything behind it.
I mean, as a leader, I mean, you've led in a variety of ways at a number of different places. I mean we're in a strange period of time right now. What do you think a leader's greatest challenge is right now? What are they facing?
Shelley Paxton (she/her) (09:29)
Yeah, it's I'm gonna keep pulling the threads through because this is my greatest passion in the world is that we define success Where we are able to celebrate it with more humanity and well-being and soul. Let me say that again Well, you know, I I am an advocate for defining success that celebrates our humanity our well-being and our soul
period. Our well-being is suffering. Our mental well-being, our physical well-being, our emotional well-being, even our spiritual well-being. I mean, in my keynotes, I talk about the headlines, but the headlines are frightening. From the C-suite, like 75 % of C-suite leaders are just considering walking away.
because the stress of their job is having such incredible physical and mental impact and creating that stress. And Mercer's Global Talent Report that says 82 % of all employees, all employees, regardless of level, are at risk of burning out this year. So we can go on and on, but to me, that is the greatest thing. It's like,
At some point, we're going to break and we are the soul of business. So how do we start to really think differently about the way we individually approach leadership and success? And how do we create the cultures that support those values? That's what I'm super passionate about because of what I see.
Jason (11:06)
And when you think about the stress and anxiety that's being created right now at a macro level, right? And we're just seeing the ripple effect of it. And we're going to talk about our two most talked about letters right now, AI in a little bit. But so you have macro, you have AI and the technology innovations that are happening where people are just questioning.
What am I doing today that I won't be doing tomorrow? And what do I need to prepare for? So I think all those things together are exactly what you're saying.
Shelley Paxton (she/her) (11:38)
I know you want to move on, but just I want one last sort of like nugget of truth. I really think that we are in an environment. I mean, it's incredibly uncertain. It's lean times. There's so many pieces that are moving in our world at large and in our business environment. So we're being asked to do more with less, but when we're trying to do like with less energy, with less fulfillment, you know, with less
Jason (11:38)
Go ahead.
Shelley Paxton (she/her) (12:04)
health and well-being, not gonna work. We're not gonna be able to show up powerfully for ourselves, our teams, or our work. And so that's why I really believe that we've kind of got to start with us.
Jason (12:16)
Yep. I agree. So I think people can kind of feel it as we're having this conversation, but we've talked about, you know, superpowers before and in other places in other conversations. So, know, for the folks that are thinking about engaging with you on the Wisory what would you say your greatest superpower is? What is the thing that people say when I think of Shelley Paxton, it's this, and there's no one better than Shelley at that.
Shelley Paxton (she/her) (12:32)
You
I always say my superpower is my energy, my superpower is my passion, but I also understand that people want to engage with me for something much more specific, right? A skill set, whatever. And so as I was thinking about this word, I wrote down four Cs that I think are very true and all connected. One is courage.
I inspire courage in you. And I think that's the core of my work. So if you're not feeling the courage to make some bold steps, some bold decisions, whatever you need as a leader in that moment, borrow some from me. I can help guide you through that. And I think that's crucial because sometimes we just do need to borrow courage and confidence from others to get to that next place and bridge it. So that's one piece. And the other three are
connecting the dots I'm great at seeing big picture how to connect the dots on a particular challenge like brand strategy, marketing strategy, business strategy, executive leadership, all of that and creativity and the three C's are courage, creativity.
the dots and coaching. Those are four C's actually. I love it. There we go. Me too.
Jason (13:55)
Four C's, I love the four C's. You know, I love alliteration, so I think that's wonderful.
I can't imagine there's a topic more discussed than this, but AI, right? And it's seemingly everywhere in every conversation. I don't care if it's a business conversation or just at a cocktail party, everyone's talking about AI. So, you know, my question is how do you see it impacting the people that you work with?
Shelley Paxton (she/her) (14:05)
⁓
Jason (14:20)
And what would you say their biggest questions and concerns are related to AI?
Shelley Paxton (she/her) (14:25)
Here's the thing, like as I think about AI, I was always really struck. I don't know if you follow a Esther Perel.
⁓ I'm a huge fan of Esther and she talks about, relationships and also work relationships. And she says AI is artificial intimacy. And I know that's not what AI stands for, but I think it's giving us this sense of like, well, we can sort of use it for everything. And the truth is we can't because what it will never be able to deliver is our intuition.
Jason (14:33)
I don't.
Shelley Paxton (she/her) (15:01)
Right? It'll never be able to deliver our insight, the nuance that we as humans provide from our experience. And it certainly isn't a substitute for our connection. So when I go back to those three words that I said earlier, this idea that, you know, success is, you know, it celebrates humanity and wellbeing and soul. really think about the role of AI in that. AI can be a thought partner.
AI can be a creative catalyst. AI can help us get started on a blank piece of paper with ideas and as a way to get emotion around something. AI can respond and be a mirror in some ways, but there's so much it can't do. And so that's.
Jason (15:29)
us.
Shelley Paxton (she/her) (15:50)
the thing I just, the leaders I work with in the conversations that I'm a part of, I keep reminding everybody, like there is a place for AI and I use it this way. I use AI as my thought partner. I have AI as like my creative director. I ask for AI on input to some things. like, hey, help me get my head wrapped around X, Y, and Z. Maybe it's about a project or a proposal I'm starting.
but it is not the final output. To me, it's an input. It is a place to start. It is a co-pilot, but it doesn't replace what's in here. And if you're not watching the video, I'm sort of like, you know, touching my, you know, like pointing to my soul, like heart and soul. Like that to me is something AI can never replace. So I don't know if that addressed your exact question, but that's how I'm thinking about it.
Jason (16:43)
absolutely. Yeah.
And I totally agree. And, and I feel like it's an, an and versus an or when it comes to things. And, you know, I get this question a lot, especially with what the Wisory is and what's important to you, to me, which are these connections and helping people get to the next level. The piece for me is when you search for information on pick your AI tool, you're getting the outcome.
Shelley Paxton (she/her) (16:52)
Mmm.
Jason (17:11)
but you don't know why. And there's wisdom in the why. Why certain decisions were made, why certain paths were decided to go down or not go down. And you can only get that talking with people that have been in the room, that have sat in that chair, that have really understood the context and the strategy and the specific business need at that point in time. And so I feel like you said it great, it's an input, right? But it's not the only input.
Shelley Paxton (she/her) (17:34)
Mm.
Jason (17:38)
There's a number of inputs and I feel like we have this saying within the Wisory which is AI plus AI equals AI, which is the artificial intelligence plus advisor insights give you actual intelligence. And I think it's having those things together with that human component, along with what technology is giving you that will help you get to the next level.
Shelley Paxton (she/her) (17:45)
Ha!
Yes, I absolutely love what you said. I think that's so powerful because nothing, absolutely nothing replaces that insight and wisdom from our lived experience coupled with our own intuition and that with the machine learning.
is, you know, that that's a very interesting combination, but not one alone. So yeah, I love that.
Jason (18:25)
This is
why we're simpatico. This is why there's a Shelley Paxton on the Wisory, and the Wisory needs Shelley Paxton. And for people that are watching and listening to this, this is why you need Shelley Paxton. So Shelley, I just want to thank you for making the time, answering our wise in five questions. You're awesome. Thank you. And we will talk again soon.
Shelley Paxton (she/her) (18:31)
I love it.
Mm.
Thank you, my friend.
Jason (18:49)
All right, be well.
In this week’s episode of the Wise in Five, we sit down with Shelley Paxton, former Chief Marketing Officer of Harley-Davidson turned acclaimed author, speaker, and soulful voice on leadership. Shelley shares how leaders can navigate uncertainty and technology disruption, especially AI, while staying connected to their inner purpose, mission and culture.
This episode is ideal for listeners who:
- Seek to lead with authenticity and purpose
- Feel disillusioned by traditional definitions of success
- Are navigating the pressures of modern leadership
- Want to understand how to integrate AI with human-centered strategy
- Appreciate real talk about burnout, courage, and growth


