367 Jenn Drummond

Jeffrey Feldberg: [00:00:00] Jen Drummond is a mother of seven, a successful business owner and world record holder. As the first woman to climb the second highest summits on each of the seven continents, Jen now spends her time inspiring others to create a thriving business and lasting legacy of their own. She shares her story and strategies for success through her book, Quit Proof:, Seven Strategies to Build Resilience and Achieve Your Life Goals, and her Seek Your Summit podcast, as well as programs and signature talks. Jen is devoted and determined to help entrepreneurs to go beyond a life of success to a life of significance.

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The idea shared forever changed the trajectory of the business and best of all, the experience was fun. And we'll round things out with Stacey. 

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Welcome to the Deep Wealth Podcast. Well, you heard it in the official introduction. Wow. Do we have a guest today? The places we're going to take you, the stories you're going to hear, but I'm going to put a plug in it right there. Jen, welcome to the Deep Wealth Podcast. An absolute pleasure to have you with us.

And I'm curious, there's always a story behind the story. What's your story, Jen? What brought you from where you were to where you are today?

Jenn Drummond: Yeah, my story really starts with a shift in plans. I got into a horrific car crash in 2018 that should have taken my [00:03:00] life and didn't. Thankfully, it didn't and I'm still here today enjoying the world, but that shifted my perspective on everything. No longer was I trying to achieve things, I was now trying to experience things and make the most of this life so I can say I got a little less serious and a little more fun and my life has started to reflect that journey.

Jeffrey Feldberg: Thank you for sharing that. And offline, you and I were talking about this. I was saying half joking, but not really that when the listener heard the bio that you're a mother of seven, we could have stopped it right there. That could be the entire podcast, a mother of seven. Let me ask you this, how has that been?

So being a mother of seven children, I mean, what a blessing from the outside looking in. I'm sure there have been challenges and sleepless nights and everything that goes along with that. How did that shape you though with your journey for the person that you've become?

Jenn Drummond: you know, I think the beauty of having children, especially when you have seven, is you realize you have seven people that you're modeling life to. And they're watching. And if [00:04:00] you're enthusiastic and happy, it gives them permission to be enthusiastic and happy. And if you're doing hard things, they think, oh, that's normal.

We do hard things. And so whatever life you're living, you're normalizing for them. And so with all these kids watching all the time, I'm like, okay, what kind of mom am I demonstrating? What kind of life am I giving them? What kind of life am I letting them know is possible? And that has really stepped up my game.

Because I know that they're watching and it's a big accountability factor for me.

Jeffrey Feldberg: It must be huge. And I know legacy and living that fulfilling life. That's one of your focuses. We can talk about that. And by the way, for the listeners in the show notes, we'll have a link to Jen's book, Break Proof, Seven Strategies to Build Resilience and Achieve Your Life Goals and How to Reach Your Life Goals.

And that's a point and click over the show notes. And I really recommend that you get that book. And so with the kids and with that accident that you had, I mean, wow, that must have really put some things in perspective for you.

Jenn Drummond: It really did. I mean, I had a business that was quite successful that I'm [00:05:00] thankful for in the financial service sector that I built from scratch and did all the things of cold calling and building and, the sleepless nights and when the markets went down, feeling more responsible than I should have been, but whatever.

And that life, I was double fisting. Okay, I'll just do it harder, or longer, or double down, and that's how we'll continue to grow. After that car accident, I realized, you know what? I only get one shot at this gig of life, and do I really want my whole story to be this version of double downing, doing everything as hard as I can, not really enjoying the journey?

And so after that car accident, I decided I'm going to shift things up. I'm going to start living a different way and allowing success to be defined on my terms instead of society's. And things changed, for sure.

Jeffrey Feldberg: And it's interesting, I know today you're sharing that you're speaking to different corporations and leaders and teams. You're also having people do some tours with you in terms of what you went through and what you did. [00:06:00] And really, as you're climbing some of the tallest mountains, I thought that's really appropriate for the entrepreneurial journey.

Not necessarily in the best way for most entrepreneurs, because we get to the top of one mountain at Great. I've done it. And instead of celebrating, okay, I see the next mountaintop and that's what I'm going to be focusing on. That's what I'm going to be doing. That's where I'm going to be heading. And we just missed the entire journey.

And so I'm sure for each of the continents that you went to and each of the journeys that you went on that, again, that's an episode in and of itself. If you look back though, is there the good old 80, 20 rule or Pareto's law that, you know what, 20 percent of my experiences in this area or when that happened, that really shaped.

80 percent of how I reacted or 80 percent of the situations in my life. Anything that comes to mind?

Jenn Drummond: So one of the big aha moments was early on in the quest. So I survived this accident. I decide that I'm gonna climb a mountain for my 40th birthday. My son ups it to climb Mount Everest. My coach ups it to set a world record and climb the second [00:07:00] highest peak on each of the seven continents.

I hadn't even slept in a tent before. So this was a huge reach in a different realm. Luckily, I was pretty fit and I adapt well. But one of the earlier climbs for me was Mount Everest because Mount Everest was actually training ground for K2, which is much more difficult mountain. And I had trained 1, 238 hours.

to climb Mount Everest. I was on the summit for 10 minutes, and I remember hiking down from that summit thinking, holy cow, how much is this real life, We're on these summits, for how long do we allow us to be up there? We celebrate for a second, or we're on to the next And that 10 minutes was just so significant because it was such a contrast to the entire pursuit.

And when was climbing back down, I was reflecting on the whole journey. And I realized that these goals that we set for ourselves, these businesses that we wanna build are these things that we want to achieve. So you can hear myself talking about the gym. [00:08:00] They give us direction. They allow us to say yes or no to opportunities that show up in our lives because those opportunities will bring us closer or farther from that pursuit.

However, our life is truly lived in trying to get to that thing and that thing is just Direction. Our life is lived in these little moments every single day. Like these are the good old days that we're creating. And it allowed me to just check in more, multiple times a day, to be honest, and say, Okay, I'm never going to get this moment back again.

Am I making the most of it? Is this the person I want to show up as in this circumstance? Is this great? Is this a sign that I need to pivot? And allowing myself to check in and ask how I feel has really been a game changer.

Jeffrey Feldberg: And as you're talking about that, what's amazing to me, Jen, I guess as an outsider looking in, you're saying, oh yeah, I was training on Mount Everest so I can figure out K2 and for most people, Mount Everest, that's really It's, I mean, books and movies have [00:09:00] been all about that, but that's something, okay, Mount Everest was my training ground to really go to something that's even higher than that.

And so at the peak, not only of Mount Everest, but of K2 and really all the others. So how did that change in terms of how you soaked in that moment of all those thousands or perhaps tens of thousands of hours now of the training and for each mountain? How do you really take in the moment? We see it in the movies, we read about it in the books.

But in real life, there's not really an instruction manual for that. So what did you do? What were you thinking or how did you approach that?

Jenn Drummond: I mean, I think we unpack these moments for a long time. I don't think it's a one time unpacking. It's kind of like when you have a baby. You've been cooking this thing. You've been celebrating this thing. You've been planning for this thing. And then all of a sudden the baby comes and you have this rush of emotion.

And in these pursuits, we have this rush of yay. There's also a bit of sadness. Because now the thing's here or the thing's done or now I have this next level that I have to get prepared for and mentally go forward on. But [00:10:00] I still look back on that memory and that experience and digest and recall and learn from it and use that to carry myself forward.

Jeffrey Feldberg: So it's really looking back so you can look forward if I'm hearing what you're saying.

Jenn Drummond: Yeah.

Jeffrey Feldberg: And then if I'm going to the book for just a moment, and I promise you there is a method to the madness here, Jen. So chapter one, you're talking about cast your vision wider and deeper, and you really alluded to that when you first said, after that horrible accident, you came out of that, you know, maybe I'll climb something or I'll have something monumental.

And then your family or others are saying, well, climb this or do Mount Everest or, hey, why not do seven of these one after the other? And so it's a great example of how you began to think bigger and going deeper with all that. So with that said, when you're in chapter two, fully commit or don't climb the mountain.

Jenn Drummond: Yeah. You know, There's a couple of different examples that I use in the book, but one that I don't use in the book that kind of applies to this principle I graduated [00:11:00] from college and I took a job in finance and I graduated a year early to take this job. So I was pretty young and I went home all excited to tell my parents and my parents were a little less excited.

They're like, Jen, you're pretty young. So if you take this job, like you can not quit no matter what for that first year of work. I was like, okay. I'm like, why would I be worried about quitting? I just got hired. I'm going to be fine. You know, I'm all optimistic and ecstatic. So this is 2001. so I graduate and I go to show up for this job and I'm like, hi, I'm Jen, I'm the new financial advisor, so excited to be here.

And I remember this lady like showing me around the office where the bathroom was, where the kitchen was, all this stuff. And then she brought me into a room that looked like a call center. And she said, here's your desk, and there's a phone and a phone book or whatever, and everybody will be coming into the office soon, and you'll meet your manager, and you'll go from there.

I'm like, oh, that's kind of funny, this kind of feels like a call center room. I signed up to be a financial advisor, am I in the right spot? And she's honey, a financial advisor is [00:12:00] call center, because how are you going to get your clients? And I had never thought about that, I mean, I don't know, I just didn't.

And so all of a sudden, my first week of work, I am cold calling five hours a day. And I'm getting told no, I'm getting hung up on, like, all this terrible stuff that I had zero experience to manage. And so I went home every night sobbing my eyes out. And so the second week I go to work, I'm like, I cannot do this.

This is the dumbest job ever. I cannot even believe this. So I called my college. I said, hi, this is Jen. I recently graduated. I was kidding. I don't want to graduate. I want to come back to school. Can I come back in? And they're like, no, you can't. I'm like, okay. And calling my parents was not an option. So I bought a calendar.

I circled a day that was 365 days away from this day to day. I'm like, okay, I just have to get through this period. And because I stopped putting energy into how do I get out of this thing, I was How do I quit? How do I do whatever? Now my energy could be, [00:13:00] how do I make this successful? How do I make this fun?

How do I use this to my advantage? And so I actually learned how to run the stats on calling and realized like every no, I was still making money because it was getting me closer to a yes. I bought the mirror. So I smiled and dialed. I bought a little snap gun. So every single time somebody hung up on me, I pretend shot them and felt like I was even and I could get my energy back to call the next person.

And because I stayed at this job for a year, and because I did the things I was supposed to do, and because I was consistent, I actually had a lot of success. My first year out of college, I made more money than my parents did combined. It was unbelievable. And I would have never had the benefit of that compounding, or the benefit of understanding how important it is to commit to something.

Had I not been forced into it at first. And so now when I'm in situations, I'm like, oh, wait, what is my commitment to this so that I can start using that energy to make it work?

Jeffrey Feldberg: Love that story so much [00:14:00] there. Actually, you take me back to my early days in business and the cold calling and the nose and the mirror and the smiling. I guess we're old school for some of the listeners like what are you doing with that? But Jen, let me ask you this because I've always struggled and I've personally made the mistake of, okay, I'm not going to quit.

I'm going to see this through. In your book though, chapter six, and you're talking about K2 here and chapter six is appropriately titled recognize when it simply isn't your mountain and you're talking about, okay, perhaps this isn't going to be the one.

So I've always struggled with that because sometimes, yes, it's that grit, it's that persistence. Like what you did in that first year, it got you through, you're successful. I'm sure some of your colleagues who started didn't make it through or like you, they're frustrated. They gave up and they never stuck it through.

That said though, other times I've stuck in and I shouldn't have. And if it's been in business, it's been really good money going in after bad that I just should have pulled the plug on it, not move forward. It's not working out. This isn't going to happen. So when do you [00:15:00] know it really isn't your mountain, that it's really not quitting, it's actually winning because you're stopping something that there really isn't a future or it's not meant to be to have that mental

Jenn Drummond: Yeah. Yeah. I think what really helps me is, have you ever played Texas Hold'em?

Jeffrey Feldberg: Sure.

Jenn Drummond: Okay. So you're playing Texas Hold'em and you have pocket queens and you have pocket queens. And it's been like, you've had crappy cards for a while and you finally, you're like, yes, I have pocket queens.

And then on the flop. It's a king, a ten, and a six. Okay, your pocket queens are no longer winning if somebody has one king in their hand. Because now they have two Kings, which beats your two Queens, but it's hard to put down those two Queens because you know, the odds of being able to get that is so slim, right?

And so I think a lot of times we get married to our hand and we get married to that excitement that we finally have this thing, but if we really look at the entire game, And what's going on outside of ourselves? We can decide, oh, wait, is [00:16:00] this really the card to hold onto anymore, or is this not what it was before?

Before the flop, it was excellent. After the flop, it's not. And so you always have to be checking in with yourself and being insane. Is this still the hand? That is going to win the game based on the external circumstances. And for me, I have to do like in the mountains, you really have to do it because your life's on the line.

your business could be on the line and things like that. So I think when I look at it as a poker game, it allows me to distract myself from my emotional connection and lets me look at it from a more, Neutral standpoint and be like, Hey, am I going to win based on what's going on?

And it helps me turn around faster than what maybe I would otherwise.

Jeffrey Feldberg: And so let's take that and continue it as much as it could be business, as it could be life. And the quote I was thinking about is Vince Lombardi, which is very black and white. And I don't necessarily agree with it all the time because the quote goes, winners never quit and quitters never win. And sure, there is some truth to that, but there's also times where that isn't true. [00:17:00] And so you've shared both sides of it. What would be some strategies or some insights from climbing these mountains, literally, or also in your life with some of the struggles that you went through? Well, how do I know what are the telltale signs that, you know what, I'm still going to be a winner because I'm deciding to quit now as opposed to a year from now or five years from now, whatever the case may be.

Jenn Drummond: Yeah. I think, the reason why mountains are such a good example for this is because the summit's only halfway. You have to make it all the way home, right? Just because I summited and if I die on the descent, I didn't win. I lost the game. And so I really think whatever we're doing, we have to be aware like, am I going to make it all the way home?

Do I have the energy to continue to do something else? Is this the way if my life were to end in two years from now, is this how I want to be spending my time? Another thing that I had happen in my life is I was enamored. With flying private, I went with a girlfriend to a shopping trip, she had a private plane, it was like the most amazing thing ever, we didn't have to do TSA, you know, like [00:18:00] all the garbage that you normally have to do when you go fly.

And so I came back from that trip and I'm like, hey, I'm gonna get my pilot's license, I'm gonna buy a plane, this is gonna make things so much easier, this is gonna be magic, like I had all these ideas running in my head because I didn't really fully know what was involved behind the scenes. So I hire a coach, I go work with him, and I'm not a quitter.

So I'm like, I'm gonna get my license this is gonna work. And so I go to lessons, and the interesting thing about flying is that when you're in the air, 99. 9 percent of the time, you're evaluating what to do if something goes wrong. Where am I going to land the plane? What would it look like? Are all the gauges working?

Is everything laying out like it should? Do you look at the horizon for two seconds? You're like, oh, wow, it's beautiful. And then you're like back onto work mode of what happens if something goes wrong and how do I survive? Well, I would come home from flight lessons and all of a sudden I would be scanning my environment for things that were going wrong.

Well, you have seven children. You cannot operate a house like that. There's things going wrong every [00:19:00] moment of every day if that's what you want to look for. Okay, so that was like my first time, but I was like, no, I'm not going to quit this. I'm determined. So I decided to take two of my kids on a flight with me.

I'm like, oh, we're going to fly over the house. They'll think it's so cute. Blah, blah, blah, blah, blah. And it was part of my idea. We were going to be able to fly on vacation and not have to do, eight flights everywhere and all the story that I sold myself on. We get into the airplane. The minute we take off, somebody has to go to the bathroom.

Okay, well, there's no bathroom on a four seater airplane, so I'm sorry. There's no television. And guess what? You're thirsty? We don't have a stewardess either to get you a drink, so you're just gonna have to sit there. So then my kids like, start swatting each other for this entire flight like, over my house.

And so I land this thing, I'm exhausted, and I'm driving home, I'm like, this is nothing like I imagined it to be, right? It was the total opposite, but again I'm gonna stick with this this is what I said I was gonna do. And I, then I started learning, like, how many times you need to fly each month to keep your license up and all this kind of stuff.

Well, the final straw was, I had taken The flight [00:20:00] part. So now I needed to take the written part and I would have my official license. Well, my instructor says, hey, it's time to call your insurance company because you're going to pass this thing and you're going to be done. But you need to let them know that you're a private pilot.

So I call the insurance company and tell them I'm going to be a private pilot. Apparently that's a very risky thing to become. Because my insurance premiums were like 7x what they were prior to this pursuit. And I'm sitting here thinking like, I'm starting to go through my pros and cons list, and this cons list is way longer than my pros list.

And my pros list no longer applied because everything had been negated during the pursuit. And so I didn't end up taking it. Because it didn't make sense and it took me that long to get there and so when you have these examples in your mind of times that when you took things too far or times when you turned around at the right time, you have to like look back on those and compare your current experience to a past experience to help you navigate what's best for you based on what you understand.

Jeffrey Feldberg: It's [00:21:00] actually, as you're talking about that, the wheels are turning here, it's actually a wonderful segue. We're jumping all over the place, but there is a method to the madness. So in chapter seven, you're talking about understand that the goal is not the goal. And so I know, Jen, look, hindsight's always 20 20.

It's perfect. That's why it's called hindsight. So understanding the goal is not the goal. What would you share from that chapter to anyone in business or their personal life, even with the story that you just shared with us? Knowing what you now know, how perhaps you would have gone a little bit differently of how you looked at, well, I'm going to fly private, I'll become a private pilot, my own pilot, do all these things.

What's going on with that, that the goal really isn't the goal. And one of the reasons I also ask this, I hear this constantly on the podcast, all kinds of leaders, thought leaders. Folks like yourself are coming on and it's, Hey, Jeffrey, it's not about the end goal. It's really about this, and that. And they're talking about the journey, but what's going on with that from chapter seven, from your own purview, your insights, what do you want our listeners to know?

Jenn Drummond: You know, I think we think it's the goal. And then once we get to that [00:22:00] goal and we're there, we're celebrating in our success, but I believe that true success flips into significance. And significance shows up when we're able to share that success, give frameworks, like what you do, right? You give frameworks for businesses to say, okay, I had this great thing happen to me.

I am so grateful for the experiences and the things that I learned and how I will navigate situations in the future. I want to help you. I think that's our natural instinct. I want to help that next person climb the mountain easier, sell the business at a rate that it deserves, like all those different pieces.

And so the goal gets us there, but once we get to that goal, we realize, oh, this was just so I could learn this thing and help somebody else.

Jeffrey Feldberg: there's a lot of introspection and just really thinking that through. And. Enjoying the journey. And so we started at the beginning, we kind of went to the end. Let's go back now to chapter five, The Messy Middle. And again, I love what you're doing with the book and the analogies and the different mountains and [00:23:00] what you're going through with that.

And so often in our journeys, isn't it always the case that We start off, we have some kind of success, it feels really good, we get excited, but then we do get to that messy middle and wow, it's more complicated. I'm not getting that success that I did at the beginning or what's happened, something's changed and it becomes more of a struggle.

So what's going on with that? What do you want us to know with the messy middle? And more importantly, how do we deal with that? How do we get through that in a way that honors our mental health, our physical health, our family, our loved ones, our colleagues around us? What's that looking like?

Jenn Drummond: Yeah. I mean, I think when we understand that everything has a messy middle, right? The messy middle is what shows up after the excitement of the pursuit is worn off and the end is not in sight. So you're in this area of space where, am I making right decisions, am I not making right decisions, and whatever.

I find for me, personally, it's helpful to look back and say, look at how far I've come versus looking forward and look how far I have to go. It just feels more overwhelming when I look that other [00:24:00] direction. And then it's very important in this stage to make mini milestones and to really focus on things that you can't control.

If we get back to the cold calling, I couldn't control the yeses. But I could control a hundred dials, and if I did a hundred dials, I knew statistically speaking, 97 people would say no, two would say follow up in a week, and one would say yes. And so if I could just focus on those 100 and measure that and just do that piece over and over, it was giving me a sense of progress, and it was giving me something that I could measure that kept me in the game long enough to get to the top.

Jeffrey Feldberg: That's interesting how it's really knowing what your KPIs are and separating yourself and just looking, okay, this isn't personal. This is just how it goes. Let me figure out the rules of the game so I can actually win at this game. And so when you're climbing these mountains, as you pointed out earlier, it's not just climbing a mountain.

It's your life on the line. And as you say, so true, Hey, I can get to the top, but if I don't make it back down, what's the point? It's [00:25:00] really all for naught. And so this might be a tough question. It might be as tough a question as which one of your seven children is your favorite. When you look at the seven mountaintops and many lessons along the way, but would there be one or maybe two or even three that really stand out for you as you now, not only for your own life, for your business, for the businesses that you're helping, for the business leaders that you're speaking with, anything that stands out for you that really yeah, I didn't know this before I started the client, but after it's really changed how I view the world or how I take my actions or how I think about my strategy.

Jenn Drummond: Yeah I think I assign way less things as bad or good, and I just accept them as different. Then I anticipated. And by not assigning something bad or something good, you're not putting yourself in a negative situation or a situation that's temporary. You're just looking at things. And so when you learn to emotionally detach and just [00:26:00] be, oh, this experience has taught me this.

That is getting me closer to my thing so I'm going to try it again or that got me further so I'm going to try something different and it just allows you to iterate a bunch of different versions until you find the winning formula that works for you. And when you allow that space to be different or experienced or learned from, you have a longer time to stay in the game.

So I really think it boils down to a deeper lesson of being kind to myself. Makes me stronger.

Jeffrey Feldberg: It's interesting. So if I'm hearing you, what I'm hearing you say is it's not that not to have expectations, just don't assign some labels and whether it's good or bad, just remove that, be kind to yourself. It's a journey, go through the journey, give yourself the space and the time to get through it. And then always re evaluate, where am I, where do I need to be?

What's changed here, perhaps? What are some of the rules that maybe I don't know that I should know? And so from there, I wanted to ask you, Jen, [00:27:00] because it's fascinating. I mean, not many people have done what you do and you have a world record that goes with that. And it really, your life was on the line and it was a life altering event.

And so you're now taking from really the challenges of life into the boardroom when you're speaking with companies, you're giving some keynotes or some talks with the leaders and the company and helping them get from here to there, or even in some of the tours that you're doing. So how are you taking what you went through with your journey and now imparting that on to entrepreneurs will never do what you did.

They'll never do the seven climbs more than likely, but they can learn from your system of what you've learned. And so. What does it look like? What's your secret sauce? Hey, Jen, come to the company and talk with us. All right. Hey, let's go on a tour. What's this going to look like? So walk us through that.

What should we

Jenn Drummond: Yeah. Yeah. So like, for example, I've taken teams to Kilimanjaro. Kilimanjaro is the highest point of Africa. It's a seven day climb. It is challenging. [00:28:00] But there's so many valuable lessons in living hard. And having a safe environment to experience that and metabolize that and see how you actually respond in those environments.

Because doing something hard on a mountain is going to trigger the same response as doing something hard in the boardroom. And it allows people to actually embody the experience, not just take in the information Metabolize it and try to repeat it out. So it's been a very humbling and rewarding and fun thing to witness with people.

When I go into companies and talk to them about what's going on or what they're struggling with, a lot of times it's. Resilience, the product didn't launch, didn't go as it planned or something. They had a bad quarter and they're trying to recover and, everybody's getting down on them.

So everybody's got this negative energy of, I don't want to go into work because well, this is what it feels like. Well, that's your environment. You're a component of that environment. So if you want that environment to change, that's on you. So you need to look at that environment and say, Hey, what can I do [00:29:00] to make this better?

And if you do one thing and then your friend does one thing and everybody else is inspired to one thing, all of a sudden that environment shifts from toxic to profit. And there's a lot of change that can happen. And I've had those experiences on the mountain. And so when I share those in an environment that's totally non threatening because it's not theirs.

And I say okay, let's think of who these different people are in your office that were similar to my team. And what can you do to help make that situation better? And it's amazing the phone calls you get months later and the people are like, okay, come back. This worked. We want to do it again.

Jeffrey Feldberg: So what do you think it is as the teams leaving the corporate boardroom, they're out in nature now on this mountaintop, seven days in this case for this one particular journey that you're taking them through. What is it fundamentally that's changing within them from they may be, these tough corporate people and all of a sudden it's humbling that you're out there yet they're changing it as people easier said than done.

It doesn't happen a lot, but they're doing it with you and your system. What's going on with that?[00:30:00]

Jenn Drummond: Yeah. You know, I mean, I think it's different for different people at different times. One memory that's coming up specifically is it was a hard day. Everybody was tired and things were going long and whatever else. And attitude was falling. Then all of a sudden, one of these porters comes by.

He's carrying 40 pounds, so like 30 more pounds than each one of us. He's in Crocs. We're like in the best gear you can possibly buy in the United States. And he's singing songs. I mean, he's basically the happiest human you've ever met. And we all had a talk that night at dinnertime, looking at, hey, listen, look at how important enthusiasm is in anything that you do.

And when you're around somebody that's enthusiastic, how that causes, when you're not, you can see and feel the contrast, and it causes you to reflect back on you. And at first you want to be like, push them away and be like, whatever. And then all of a sudden you look at it like, the guy's in Crocs.

He's carrying 40 pounds on his head and he's singing and he's happy and he's grateful. [00:31:00] Who am I not to be grateful right now? And those kinds of things happen and they shift and then you take it home because you have that memory. And when it shows up again, you're like, wait a minute, I'm doing the same thing.

How do I be the guy in Crocs carrying the more weight and be happy?

Jeffrey Feldberg: That's interesting. And so I'm wondering, you're talking about mindset now. So from the mountain or the mountaintop to the boardroom, talk to us about mindset of how that played a role for you to get done what you got done.

Jenn Drummond: Oh my, I mean, mindset's everything, right? And one of the biggest examples for me one day was we were climbing the Lhotse Face of Mount Everest. The Lhotse Face is about a 3, 700 foot ice wall that's exposed to the elements. So thinking of being on a Stairmaster and full on gear in a snowstorm and not being able to see in front of you, right?

Not your best environment. Well, when you're in that kind of environment and you don't have the sun out, You wear different color glasses, typically yellow or orange or pink because that lens [00:32:00] allows you to see depth and some different things that if you had sunglasses on would make it too dark. So, in this case, I was wearing pink glasses.

That's what I had. So, we're hiking for a couple hours, and this pink lens that I'm looking at life at makes the snow look like cotton candy. So, I'm thinking of a cotton candy machine, I'm thinking of that game Candyland and how much fun it is to play with my kids, and then all of a sudden, I'm looking at the rope that I'm attached to, and it kind of looks like a watermelon rind.

And so now I'm singing that song, Watermelon Sugar, hi. And I'm having this great time. Well, the alarm goes off. So we stop when you're at altitude, sometimes you can forget to eat, but you put an alarm on to make sure you're stopping and eating to fuel. So we stop and I go to get the snack out of my backpack and I'm kind of like in a loose, good mood, and then I bump my glasses.

And when I bumped my glasses, all of a sudden, I realized we're in this cold, gray, horrible snowstorm. It was like, instantly, the energy that I had was zapped out of my [00:33:00] body. And I looked at my teammates, and I'm like, guys, how long have we been in this situation? What is going on? And my teammates looked at me like I was eating mushrooms.

They're like, Jen, we've been in this thing for two hours. Where have you been? And I'm like, I have been here, but I had these glasses on, and here's where my mind went, and this is what was going on, and it was such an example of, hey, if you're going from point A to B, and it's getting hard, and what's another perspective that you can take that allows it to not be cold and miserable and a struggle bus?

Because that experience is entirely different, even though you're doing the same task.

Jeffrey Feldberg: That's amazing questions. We're asking how we're looking at things, where we let our mind think of instead of what's in front of us and mindset. Absolutely. Really is everything. Let me ask you this, Jen, we've really been all over the place from your journeys on the mountain to the boardroom, to everything else in between.

Before we go into wrap up mode, I'm [00:34:00] wondering, is there a question I haven't asked? Is there a topic we haven't covered? Or is there even a message that you'd like to share with the community?

Jenn Drummond: I think when we allow ourselves space to, B, instead of do, we become observers and notice more in our environment that make whatever we're doing more fulfilling or give us feedback on maybe pivoting to live something more fulfilling. And life goes fast. And the sooner that you can tap into what feels authentic, real, and re energizing to you, the better your life's going to be.

And you deserve it. And so does everybody else.

Jeffrey Feldberg: And Jenna, as you're saying that, you know, I'm thinking of a listener and they're saying, Jen, yes, I get that. We are human beings, not human doings. That said though, everywhere around that you have these to do lists and it's about productivity and you have to do more and less time and it's go. So with that in mind, for a listener who's struggling, that they want to be [00:35:00] in that flow state, they want to be in the being state, not in the doing and just going through the mechanics of everything.

On paper, it sounds really easy to do, yet in reality, it's not something that we're necessarily taught or those around us can actually show us because they're also caught up. In the doing and the to do list, and let me maximize the productivity and I'm burning the candle at both ends. And it just goes on and on.

And we're having a contest of who slept the least amount of hours. Just crazy. I know, but that goes on. So for that listener who finds himself in that kind of situation. Thoughts or insights of getting out of that into the better place that they have those pink colored lenses on and the cotton candy and they're just really enjoying regardless of what's going on that particular journey.

Jenn Drummond: Yeah. I mean, I think you have to pay attention to what you're defining as success. what helped me in the beginning, because I was not good at it, I actually set alarms on my phone. You know how you can label your alarms on your phone? And I would set them and at three o'clock in the afternoon, for example, my [00:36:00] alarm would say, magnificent mom.

And that reminded me that my kids were coming home from school, and it was now time to be the the magnificent mom, which is an entirely different skill set and persona within me than the athletic mom, or than the business mom, or, you know, right? So we have these different roles. So for me, I had to put alarms on during the day, define who that avatar was for that period of time, and then step into that person.

I have an alarm for going to bed. It goes off at 10 p. m. because otherwise I can get lost, doomsday scrolling or working on things or whatever, and at 10 p. m. that alarm goes off and it says serious sleeper. If I blow plaster that alarm and don't get ready like, go to bed, I'm not a serious sleeper anymore and I failed that part of my life.

So I think we have a tendency to do things that we're measuring and keeping track of, so it's really important to start balancing your life out and what are you measuring, what are you keeping track of, and how do you be good at other things than [00:37:00] just not sleeping.

Jeffrey Feldberg: Love that. And really it doesn't cost anything. It doesn't take any more time and it's taking certain segments of your life, Jen. It sounds like you're putting superhero titles. To that, whatever it may be, whatever floats your boat, whatever has you smile, that you're going to see this alarm. It's going to be whatever superhero title you, Oh, okay.

Yeah. Okay. Mode change. Yep. I'm going to be that magnificent mom or that super sleeper, that serious sleeper. And off you go with that. And it actually reminds me because one of the things that you focus on with entrepreneurs, and this is easier said than done, but you're doing it for many entrepreneurs.

It's all about success, but you're saying, Hey, get beyond the success. It's not about the success. It's a really, it's significance. Life is about significance. And again, for Deep Wealth Nation, for our listeners are saying, well, come on, Jen, what do you mean? It's all about success. It's all the accolades.

It's all the zeros in the bank. It's all the wins that I'm chalking up. What's this narrative about the significance and why they should really stop, listen, maybe even change [00:38:00] course and focus on the significance over success.

Jenn Drummond: know, I think when you've helped somebody else have their aha moment or climb their ladder or launch their business or have success, you realize like that's where real success lies. If you are still measuring success by zeros in your bank account, You haven't had success yet. You've only had it in one realm.

And once you get it in other realms, you start realizing, oh, wow, there's much more to life than just that one little piece. I just haven't hit it yet.

Jeffrey Feldberg: Interesting as you talk about that, in the 90 day Deep Wealth Mastery Program, we actually start at the very end, we put that at the beginning, and it's all about the post exit life. So when you exit your business, it could be two years from now, it could be 22 years from now, you could be in your 30s, you could be in your 60s, everything else in between.

It's the moonshot. So just like the astronauts, they went to the moon, they came back and they said, okay, now what? We just achieved the biggest goal, not only of [00:39:00] our lives, but of humankind. And so what are we going to do tomorrow? Because we're not going back to the moon. And for so many entrepreneurs, myself included, after the exit, my exit, I didn't find that happily ever after.

And one of the things that we focus on because of that, You're right. It's not about the zeros. You can have lots of zeros in the bank account, but it's true. It's that old saying, money doesn't buy happiness. It's got to come from within. Fulfillment, joy. That's not something that you can write a check.

It's not something material. Yes, money's nice and it can make things better. Smoother, it's like the oil of life. It can grease things and get things going along, but it's not going to be the end all and be all. So I really like your focus on the significance and part of your methods of the madness, whether it's in the talks or in taking people's on the journeys of really what is significance, what is really meaningful beyond the so called wins and the zeros love that in terms of what you're doing.

Jenn Drummond: Thank you. Thank you. Thank you.

Jeffrey Feldberg: And so it's a perfect segue for our wrap [00:40:00] up, and for me, I know I say this every podcast, but it's so true. It's a privilege, it's an honor, it's our ritual here where every guest, I have the privilege and honor of asking the same question. Let me set this up for you, it's a fun one, Jen. So when you think of the movie Back to the Future, you have that magical DeLorean car that can take you to any point in time.

So Jen, here's the fun part. It's tomorrow morning, you look outside your window, DeLorean car is there, it's curbside, the door is open, it's waiting for you to hop on in, What you do, and you're now going to go back to any point in your life, Jen, as a young child, a teenager, whatever point in time it would be, what would you tell your younger self in terms of life lessons or life wisdom, or, hey, Jen, do this, but don't do that.

What would that sound like?

Jenn Drummond: Yeah, I would tell myself to relax and enjoy. Because you will be successful. So stop worrying about being successful and putting everything at the expense of that and understand that with confidence, you will be successful, so have fun in creating it.

Jeffrey Feldberg: Wow. That was fast. That just came, boom, one, two, three. Is that something that you've just been living your life from what you've been [00:41:00] through?

Jenn Drummond: I think so, yeah, definitely. I realized it's been something that I always, I know I default going hard and I default going serious. And so since that's my default, I have to interrupt with the opposite to stay balanced.

Jeffrey Feldberg: I love that. So have fun, relax, enjoy. You're going to be successful. It's going to happen. Enjoy the journey. And really going back to what you said earlier, we define what success is, not somebody else, not social programming, not social media. It's us who define success. And from that perspective, when we're doing that how can you do anything but win from that perspective, have that significance, really have that fulfillment and enjoyment.

And let me ask you this, Jen, someone has a question for you. They want you to come in, give a talk, or they want to go on one of your journeys, perhaps on a mountaintop. Where is the best place online for someone to reach you?

Jenn Drummond: Yeah. I mean, my website's great. So JennDrummond. com, it has all my social media handles. So depending on your favorite platform, feel free to reach out on whatever one you like to use and say hi, and happy to connect. And it has access to [00:42:00] retreats that I host, the speaking engagements that I do, and you can even purchase my book.

Jeffrey Feldberg: Terrific. We'll have all that in the show notes, including your podcast, Seek Your Summit, subscribe to the podcast, listen, get the book, go through that, contact Jen, have her come in and do those talks, take your culture to the next level. Well, Jen, all that said, it's official. It's a wrap. Congratulations. As we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe.

Thank you so much.

Jenn Drummond: Thank You. 

Jeffrey Feldberg: So there you have it, Deep Wealth Nation. What did you think? So with all that said and as we wrap it up, I have another question for you.

Actually, it's more of a personal favor. Did you find this episode helpful? Have you found other episodes of the Deep Wealth Podcast empowering and a game changer for your journey? And if you said yes, and I really hope you did, I have a small but really meaningful way that you can actually help us out and keep these episodes coming to you.

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So all that said. Thank you so much for listening. And remember your wealth isn't just about the money in the bank. It's about the depth of your journey and the impact that you're creating. So let's continue this journey together. And from the bottom of my heart, thank you so much for listening to this episode.

And as we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe. Thank you so much. God bless.