Jenn Drummond is the first woman to climb the second highest summits on each of the seven continents. But beyond her mountain conquests, she’s a mother of seven and a successful business owner. Her adventures are not just about reaching the peaks, but about the invaluable life lessons learned along the way. The host of The Deep Wealth Podcast and post-exit entrepreneur Jeffrey Feldberg explores how Jenn’s experiences can inspire and guide entrepreneurs and leaders in their own journeys.
Jenn’s story starts with a dramatic pivot. In 2018, a near-fatal car crash shook her to her core. “I got into a horrific car crash in 2018 that should have taken my life and didn’t. Thankfully, it didn’t and I’m still here today enjoying the world, but that shifted my perspective on everything,” Jenn shares. This life-altering event pushed her from merely achieving things to truly experiencing life. She recognized the importance of seizing every moment and injecting more fun and less seriousness into everyday existence.
Jenn’s role as a mother heavily influences her approach to life and her legacy. “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,” she says. This constant observation by her children kept her accountable and motivated her to exemplify a life filled with enthusiasm and hard work. For business leaders, Jenn’s experience highlights the significance of leading by example and crafting a culture where challenges are embraced as opportunities for growth.
Jeffrey brought up Jen’s role as a mother of seven, pointing out the challenges and sleepless nights it must entail. Jen sees motherhood as an opportunity. “The beauty of having children, especially when you have seven, is you realize you have seven people that you’re modeling life to,” she said. “If you’re enthusiastic and happy, it gives them permission to be enthusiastic and happy.” Her children hold her accountable, pushing her to live the best life she can.
Jen’s story didn’t start on a mountaintop. It started with a near-death experience in a horrific car crash in 2018. “My story really starts with a shift in plans,” Jen recounts. “I got into a horrific car crash that should have taken my life and didn’t.” This accident shifted her perspective from just achieving things to truly experiencing life.
“I got a little less serious and a little more fun,” Jen says. Her zest for life radiates as she teaches others to do the same.
Lessons from Cold Calling Finance
A notable part of Jenn’s story is her early career in finance, which taught her the power of commitment. She recalls a tough start where her job involved cold calling potential clients. “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,” she remembers. Instead of quitting when the job got tough, Jenn focused her energy on making the best out of her situation. This dedication paid off, proving that perseverance and grit are essential components of success.
Jenn’s mountain climbing experiences taught her crucial lessons about goals and fulfillment. For her, the summits were not the ultimate achievements; it was the journey that mattered most. “These goals that we set for ourselves, these businesses that we want to build, give us direction…our life is truly lived in trying to get to that thing,” Jenn reflects. Entrepreneurs should take note: success isn’t just about reaching the top—it’s about valuing the process and the incremental steps along the way.
Knowing When to Pivot
One of the most profound lessons Jenn shares is recognizing when to pivot. She recounts her experience with flying lessons, pursuing a private pilot’s license, only to realize it wasn’t what she truly wanted. “I had to call my insurance company and say I was going to be a private pilot… Apparently, that’s a very risky thing to become,” she laughs. The drastically increased insurance premiums were a reality check. Reflecting on whether her efforts aligned with her real goals, she realized it was time to shift her focus. For entrepreneurs, this lesson is key: understand when a project is worth pursuing and when it’s better to redirect your energy elsewhere.
Her accident made her reconsider the kind of success she wanted. “After that car accident, I decided I’m going to shift things up,” said Jen. She no longer wanted to double down on just business success. Instead, she emphasized living a fulfilling and balanced life.
Jen has learned invaluable lessons from her climbs and applies those lessons to her career and personal life. One major takeaway? Recognizing when a certain path isn’t yours to take. “The summit’s only halfway,” she explained. “You have to make it all the way home.” In business, this means recognizing when an endeavor isn’t working and it’s time to pivot.
Jen advises fully committing to any goal. Once, after taking a finance job straight out of college, she had to cold call for five hours a day. Initially deterred, she realized the importance of commitment. “Because I stopped putting energy into how do I get out of this thing…my energy could be, how do I make this successful?” Commitment led her to turn those cold calls into a successful first year, proving the importance of tenacity.
Mindset: The Ultimate Tool
Throughout her journeys, Jenn emphasizes the importance of mindset. A powerful example was her experience climbing the Lhotse Face of Mount Everest under challenging conditions. By changing her perspective—literally, through pink-tinted glasses—Jenn transformed her grim surroundings into a joyful, Candyland-like scenario. “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 body,” she recounts. This story underlines that our outlook can vastly influence our reality. Entrepreneurs, therefore, must nurture a positive mindset to navigate challenges effectively.
One of the standout ideas Jen shares is the importance of mindset, especially in stressful situations. Jen climbed the Lhotse Face on Mount Everest, an ice wall exposed to the elements. Wearing pink glasses changed her outlook entirely. “The pink lens made the snow look like cotton candy,” she remarked. Her positive mental shift turned a harsh climb into a more bearable experience.
The Messy Middle and Mini Milestones
The “messy middle” is a phase every entrepreneur hits. Jenn advises looking back to see how far you’ve come instead of being overwhelmed by how far you have to go. “It’s very important in this stage to make mini milestones and to really focus on things that you can control,” she recommends. Breaking down tasks into small, manageable steps and celebrating those achievements helps maintain momentum and motivation.
Another key point Jen discussed was navigating the “messy middle,” the often overlooked phase of any journey where initial excitement has waned and the end isn’t yet in sight. Focusing on how far you’ve come, rather than how far you still have to go, is crucial. “If we get back to the cold calling,” Jen pointed out, “I couldn’t control the yeses, but I could control a hundred dials.” By setting and hitting smaller goals, you can find progress even in the messiest middle stages.
Seeking Significance Over Success
Jenn’s most compelling message is the shift from success to significance. “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,” she says. Real fulfillment comes from helping others achieve their goals, sharing success, and moving beyond personal accomplishments to make a broader impact. Entrepreneurs should aim not just for personal milestones but for contributing to something larger than themselves.
Jen emphasizes that significance goes beyond mere success. “If you are still measuring success by zeros in your bank account, you haven’t had success yet,” she said. True significance means sharing your knowledge and helping others climb their mountains. Helping others achieved what you’ve achieved, Jen believes, is the key to finding true fulfillment.
Wrap Up
Jenn Drummond’s journey from the boardroom to the world’s highest peaks is filled with lessons that transcend mountaineering. Her experiences teach us about the importance of perseverance, the power of mindset, knowing when to pivot, and seeking fulfillment beyond personal success. By applying these lessons, entrepreneurs and leaders can navigate their own “summits” in business and life, leading not just successful but also significant lives.
Jen uses her mountain experiences to teach business leaders valuable life lessons. She’s even taken corporate teams on climbs to instill these lessons in a tangible way. A standout moment? Watching a porter carry 40 pounds up Kilimanjaro in Crocs, singing and staying positive. This illustrated the power of attitude and how enthusiasm can uplift an entire team. “Who am I not to be grateful right now?” Jen questioned, highlighting how a positive mindset changes perspectives.
Jen’s story teaches us that no problem is insurmountable. She’s climbed the world’s second-highest peaks and emerged with wisdom she gladly shares. Her message is clear: fully commit, embrace the journey (even the messy parts), and strive for significance. Success, she believes, will follow.
In essence, whether you are scaling a mountain or building a business, the journey itself holds the real treasures. Remember to enjoy the climb, celebrate the mini milestones, and always aim for a life of significance.
To hear more about Jen Drummond’s incredible journey, her tips for overcoming life’s challenges, and her insights on achieving true success and significance, be sure to check out her podcast, Seek Your Summit. Pass on the lessons you learn from her to elevate your own life and journey.
Remember, life’s highest peaks are not just there to challenge you, but to shape you into a stronger, more resilient person. So go out, face your challenges head-on, and strive to turn your success into significance. Happy climbing!
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