Originally Posted On: https://medium.com/@joseph.kenney212/charting-your-course-why-entrepreneurs-need-maps-mentors-and-messages-of-encouragement-8658ab3a2f3f
Charting Your Course: Why Entrepreneurs Need Maps, Mentors, and Messages of Encouragement
The Adventure Begins
At 14 years old, I stood nervously for a photo that would land me on the cover of Entreprenews. There I was, clutching a business plan I’d meticulously crafted, sitting next to Mickey Gomez — now the CEO of Lily Pad Resources in Kansas City. Neither of us knew then that we’d both take winding paths through the corporate investment world before circling back to entrepreneurship. That cover wasn’t just a moment of adolescent pride — it was the beginning of an adventure that continues to unfold.
My journey into entrepreneurship started even earlier, around age 8, when I discovered two loves simultaneously: “Choose Your Own Adventure” books and building businesses. I devoured those books, fascinated by how each decision point led to entirely different outcomes. Turn to page 65, and your character might discover hidden treasure. Turn to page 87, and you might face certain doom. These weren’t just stories — they were decision frameworks disguised as entertainment.
During those same formative years, I was building little ventures in my neighborhood — the classic lemonade stand, yes, but also lawn care services, and various other schemes that seemed brilliant to my young mind. By 14, I was identified by the University of Nebraska as a student with high entrepreneurial potential and selected to participate in a special program at their Center for Entrepreneurship that admitted only 40 high school students from across the state. This program recognized that some kids were simply wired differently — with an innate drive to create, build, and problem-solve through business.
Looking back, I realize something profound: entrepreneurship is the ultimate “Choose Your Own Adventure” book, except the stakes are real, the characters are actual people, and the rewards and challenges have tangible impact on lives and communities.
In the decades since that cover photo, I’ve learned that successful entrepreneurial journeys require three essential elements: Maps, Mentors, and Messages. Let me explain why each matters and how they’ve shaped my approach to building and scaling businesses.
Maps: The Expert Framework for Adventure
In those dog-eared adventure books of my youth, you always had some form of guidance — a map, a mission, or a framework for making decisions. The entrepreneurial journey demands the same.
Reid Hoffman, co-founder of LinkedIn, frames entrepreneurship as “jumping off a cliff and assembling an airplane on the way down.” While this captures the adrenaline of the journey, Hoffman also emphasizes that successful entrepreneurs don’t jump blindly — they calculate risks and have frameworks for rapid iteration.
My own entrepreneurial map came from various sources. Those early camps at the University of Nebraska taught me fundamental business planning. Later, I found guidance in Jim Collins’ “Good to Great” principles, particularly his “Who-Then-What” approach. Collins argues that getting the right people on your team before determining strategy is crucial for navigating uncertainty — something I’ve found consistently true across my ventures.
Sara Blakely, founder of Spanx, offers another vital element for entrepreneurial maps: reframing failure. In interviews, she’s shared how her father would ask at dinner, “What did you fail at today?” This trained her to see setbacks as waypoints rather than endpoints — a perspective that’s essential when your adventure inevitably takes unexpected turns.
These frameworks serve as decision maps when the path forward isn’t clear. When I’ve faced pivotal moments in building businesses — whether to expand into new markets, when to pivot products, or how to handle economic downturns — having these mental models has been invaluable.
But even the best map is insufficient without fellow travelers who know the terrain.
Mentors: Finding Your Fellow Adventurers
In “Choose Your Own Adventure” books, having companions often meant the difference between success and failure. The same holds true in entrepreneurship.
This is where organizations like Elevator have revolutionized the entrepreneurial landscape. Traditional business spaces — isolated offices, impersonal warehouses, or kitchen tables doubling as headquarters — rarely foster the connections entrepreneurs need to thrive.
I’ve watched firsthand as Elevator’s co-warehousing model has transformed startup ecosystems in cities like Kansas City, Des Moines, and Omaha. These aren’t just physical spaces; they’re incubators of shared wisdom. When an e-commerce entrepreneur struggles with inventory management, there’s likely someone two doors down who solved that exact problem last quarter. When a SaaS founder hits a roadblock with customer acquisition, mentors within the community can offer strategies that worked in similar scenarios.
Mickey Gomez — my fellow cover model from that long-ago publication — and I have taken parallel journeys through corporate America and back to entrepreneurship, though our paths haven’t directly crossed in recent years. Looking at where we’ve both landed, I can see how entrepreneurial communities have shaped both our trajectories. At Elevator events in Omaha, I’ve personally experienced the power of these connections — with the upcoming soft opening in Des Moines on April 1st and the Kansas City location later in 2025 promising even more opportunities for meaningful collaboration. These experiences have reinforced my belief that our greatest business breakthroughs rarely come from isolated brilliance, but from connections with peers and mentors who challenge our thinking and expand our possibilities.
The data supports this approach. According to research from the Founder Institute, startups with mentors raise 7x more money and have 3.5x better user growth than non-mentored peers. The adventure of entrepreneurship simply works better with guides who’ve navigated similar terrain.
But even with maps and mentors, the entrepreneurial journey can be emotionally taxing. That’s where the third element becomes crucial.
Messages: The Power of Encouragement
Entrepreneurship can be profoundly lonely. According to a Harvard Business Review study, 45% of entrepreneurs report struggling with mental health issues directly related to their founder journey. The psychological weight of responsibility, uncertainty, and constant decision-making takes a toll that’s rarely acknowledged in startup culture.
This is where seemingly small gestures of encouragement become disproportionately powerful.
I still have a handwritten note from my first business mentor, received just after a significant setback in my early twenties. “The adventure continues,” it read. “This is just one page in a much longer story.” That tangible reminder — something I could hold in my hands during moments of doubt as an owner of a small pet store — provided emotional fuel when my reserves were running low.
In our digital age, we’ve lost something important: the power of physical, tangible encouragement. Texts and emails vanish in the constant stream of notifications. Social media likes provide fleeting dopamine hits without lasting impact. But physical tokens of encouragement — a handwritten note, a meaningful card — create anchors in the entrepreneurial storm.
This is why I’ve developed an appreciation for companies like Ramona & Ruth, founded in 2009 in a spare bedroom in Omaha with a simple mission: creating beautiful, purposeful products that help people focus on what matters most. Their Next Adventure Sailboat Card perfectly captures the entrepreneurial spirit — acknowledging both the uncertainty and excitement of venturing into new waters.
I’ve started a personal practice of sending these cards to entrepreneurs in my network who are embarking on significant new chapters — launching products, expanding to new markets, or pivoting their business models. One recipient recently told me he keeps the card on his desk as a daily reminder that someone believes in his journey.
The simple act of sending tangible encouragement creates connection points that digital communication simply can’t match. It says, “I see you, I believe in your journey, and I acknowledge the courage it takes to choose this adventure.”
Your Next Adventure Awaits
As I reflect on that magazine cover from decades ago — that earnest 14-year-old with big dreams and a carefully crafted business plan — I realize that entrepreneurship has never been a linear path. It’s a series of adventures, each building on the last, each requiring maps, mentors, and messages to navigate successfully.
If you’re standing at a decision point in your entrepreneurial journey right now, consider these three elements:
- Seek expert maps: Find frameworks that help you navigate uncertainty. Whether from books, courses, or distilled wisdom from those who’ve gone before, having mental models for decision-making creates clarity when the path forward seems foggy.
- Find your fellow adventurers: Consider spaces like Elevator’s co-warehousing environments, where the infrastructure supports not just your physical business needs but your need for community and shared wisdom. The right mentors and peers will see possibilities you might miss alone.
- Exchange meaningful messages: Don’t underestimate the power of tangible encouragement. Send a Next Adventure Card to an entrepreneur embarking on something new. Keep encouraging notes where you’ll see them during challenging times. These physical reminders serve as emotional anchors when the entrepreneurial seas get rough.
Mickey Gomez and I couldn’t have predicted where our paths would lead when we posed for that cover 38 years ago. The corporate detours, the failures, the successes, the eventual return to entrepreneurship — none of it followed a predictable script. But that’s the beauty of choosing your own adventure: the story unfolds one decision at a time, shaped by the frameworks you follow, the companions you choose, and the encouragement that sustains you.
For more insights on building entrepreneurial communities that support business growth, check out Kauffman Foundation’s Entrepreneurial Ecosystem Building Playbook, which offers research-backed strategies for creating environments where entrepreneurs thrive.
What page will you turn to next?
