It was 8 a.m. in Seattle. As the sun rose, my phone rang. My mother’s voice broke the silence—Dad was critical. That moment showed me why smart entrepreneurs fail.
We had just returned from the Consumer Electronics Show (CES), where we’d won a startup pitch competition. A venture capitalist had promised to lead our next funding round—but only if I could secure matching investments. I had tried everything but had come up empty-handed.
As I booked my flight to Cairo, reality hit me hard. I was likely days away from having to shut down my startup. As I sat on the plane, thoughts raced through my mind. My father, my mentor, was fighting for his life, and I was fighting to keep my company alive. But the question that gnawed at me was: If I had to close my company because I couldn’t secure the funding, would that mean I had failed?
The Truth About Entrepreneurial Failure
When discussing startup failure, the conversation usually revolves around market fit, funding issues, or competition. But in my experience mentoring hundreds of entrepreneurs, I’ve discovered something far more insidious: the true causes of failure often lie within the entrepreneur’s mindset and approach, not external factors.
Success in entrepreneurship is a complex puzzle, often comprised of pieces beyond your control. Factors like market timing, investor mood, sudden technological disruptions, or global economic shifts can sway your journey. They remind you that success isn’t just about what’s within your control but also about resilience, adaptability, and understanding that entrepreneurship is as much about the journey as the destination.
Ronald Wayne, a name many people might not immediately recognize, co-founded Apple with Steve Jobs and Steve Wozniak on April 1, 1976. Yet, just twelve days after starting Apple, he decided to sell his 10% share for $800 and later received an additional payout of $1,500. His rationale was rooted in a past venture that had failed, leaving him with debts. Today, Apple is a trillion-dollar company, and 10% of that would be worth billions.
But actual entrepreneurial failure isn’t about bankruptcy, market rejection, or falling short of revenue projections. The genuine essence of failure is when you cease to try—when you let go of that fire that once pushed you to innovate, adapt, and persevere. When failure takes its proper form, you decide to step back and quit the infinite game of entrepreneurship.
Let me share with you the four mental traps I’ve seen derail even the smartest entrepreneurs—traps I fell into and had to overcome.
Trap #1: Overlooking the Marathon Mindset
The half-year before diving full-time into my startup was a whirlwind by any measure. I was juggling a regular job while trying to get our startup off the ground, and it felt like I was constantly running out of time. When I finally transitioned to full-time, my feelings were a roller coaster. There was the undeniable thrill of finally stepping into the shoes of a founder, a rush I had never felt before. But alongside that excitement were moments of profound doubt.
I had imagined a burst of productivity, days when I’d achieve what once took months. Yet, the reality was a growing list of tasks. Each hour spent seemed to sprout more work.
Most entrepreneurs treat their journey as a short sprint, going full speed and exerting unnecessary energy quite early. The intoxication of the sprint, with its short-lived thrills, can create a mirage of progress. However, without a prolonged, sustained effort, burnout lurks ominously close.
It’s easy to be swayed by quick wins. They offer a temporary ego boost and can paint a rosy picture, making you feel invincible. But this can be a dangerous illusion, providing a false sense of security.
Sprinting, charging forth without pause, can deplete your mental, emotional, and financial reserves at an alarming rate. When these resources are exhausted, many passionate entrepreneurs regrettably have to bow out of the race.
The Marathon Mindset in Action: Sara Blakely and Spanx
Sara Blakely didn’t become the world’s youngest self-made female billionaire overnight. Spanx, now a household name, was a marathon in the making. After her initial idea to cut the feet off her pantyhose for a smoother look under white pants, Blakely spent two years researching, patenting, and developing her product while working full-time selling fax machines door-to-door.
She faced rejection after rejection—from manufacturers who wouldn’t take her seriously to lawyers who thought her idea wouldn’t work. Even when she finally got Neiman Marcus to carry her product, she still drove store to store, setting up displays herself and educating salespeople.
Blakely understood that building a successful business wasn’t about quick wins or overnight success. It was about consistent effort, resilience in the face of setbacks, and maintaining focus on long-term goals. She invested her life savings of $5,000 and didn’t spend money on traditional advertising, instead letting the product speak for itself through word of mouth.
This marathon approach—patient, persistent, and focused on sustainable growth rather than explosive success—is what eventually led to Spanx becoming a billion-dollar company and Blakely becoming one of the most successful entrepreneurs of her generation.
Trap #2: Venturing Without a North Star
Picture this: you’re excited as you prepare for a challenging hike through uncharted territory. The thrill of adventure bubbles up within you. But suppose you are embarking on this journey without a compass. The prospect suddenly becomes much more daunting.
In the world of entrepreneurship, this scenario isn’t too far-fetched. Entrepreneurs without a clear sense of “why” can drift like a hiker who loses their way in the wilderness. It’s not just about losing sight of why you are doing it; it’s about the repercussions of meandering without direction. Without a clear North Star, growth opportunities might pass you by, hidden behind the thick foliage of startup complexities.
In 2004, Kevin Rose launched Digg, a social news website where users could vote stories up or down, determining their place on the site’s front page. Digg was one of the pioneers in user-curated content and quickly became a sensation, with millions of users and a peak valuation of over $160 million.
However, as the platform grew, Rose and his team faced increasing pressure from investors and advertisers. They began to make significant changes to the website, arguably drifting away from their original vision and the community-centered ethos that had made Digg popular in the first place.
The most notable shift came in 2010 with the launch of Digg v4. This version drastically departed from the original platform, prioritizing publisher RSS feeds over user-submitted content. The Digg community felt betrayed, believing the platform was now favoring mainstream publishers over its dedicated user base.
By 2012, the decline was so severe that Digg was sold in parts for a mere $500,000, a stark contrast from its once-lofty valuation.
Finding Your North Star: The Google Story
In contrast, consider Google’s unwavering commitment to its mission: “to organize the world’s information and make it universally accessible and useful.” This North Star has guided the company through massive growth, industry disruption, and technological transformation.
When Larry Page and Sergey Brin founded Google, they had a clear vision of creating a superior search engine. Even as they expanded into email, maps, mobile operating systems, and countless other products, they maintained this core purpose.
This clarity of purpose helped them make strategic decisions, like turning down early acquisition offers that would have made them personally wealthy but might have compromised their vision. It also guided them through difficult transitions, like reorganizing under Alphabet to better focus different business units.
By maintaining a strong connection to their founding purpose, Google has been able to navigate the complexities of tremendous growth while still delivering on their promise to users. This North Star has been fundamental to their sustained success over decades of industry evolution.
Trap #3: Losing Sight of the Vision
Engaging in entrepreneurship is akin to navigating a vast landscape. The saying “losing sight of the vision” captures a common pitfall. It speaks to moments when we become so engrossed in the details that we lose sight of the bigger picture. In business, succumbing to this trap can drastically stall your progress.
Consider the journey. Picture yourself driving on a long road and suddenly hitting a small pothole. Do you abandon the journey, or do you press on, understanding that a minor jolt shouldn’t derail the promise of the destination ahead? In the same way, as an entrepreneur, you’ll face hiccups. However, if you dwell excessively on each minor setback, they can morph into perceived insurmountable obstacles.
This isn’t just about the challenges you’ll face but how you perceive your journey. In the expansive tapestry of your business endeavor, these setbacks are mere threads. They might seem jarring up close, but you must maintain your venture’s overarching beauty and purpose.
Maintaining Vision Through Crisis: Airbnb’s Pandemic Pivot
At the beginning of 2020, Airbnb was preparing for its long-anticipated initial public offering. Then the COVID-19 pandemic hit, and global travel came to a standstill. Bookings plummeted by 80%, and the company was forced to lay off 25% of its staff. It seemed like the end of a dream.
However, instead of getting lost in the devastating details of the crisis, CEO Brian Chesky maintained focus on the company’s broader vision: to create a world where anyone can belong anywhere. Rather than viewing the pandemic solely as a catastrophe, Chesky saw it as a catalyst for evolution.
Airbnb quickly pivoted to focus on domestic travel and long-term stays as people sought escapes from lockdown and new remote work possibilities. They implemented rigorous cleaning protocols to rebuild trust and launched Online Experiences to maintain host income streams and user engagement.
By keeping the long-term vision in sight rather than fixating on immediate setbacks, Chesky not only navigated Airbnb through its existential crisis but positioned it for stronger growth. The company went public in December 2020, and its stock doubled on the first day of trading—a remarkable turnaround from near-disaster just months earlier.
This ability to see beyond immediate challenges to the broader vision is what separates entrepreneurs who persevere from those who falter when confronted with obstacles.
Trap #4: Neglecting Life Beyond Business
We’re in an era where the “hustle culture” is often celebrated. Everywhere you look, you’re urged to push harder, dream bigger, and let nothing stand in your way. But let’s step back and reflect. Can you genuinely savor success if it’s at the expense of everything else in your life?
Elon Musk, the magnate behind Tesla and SpaceX, is no stranger to intense dedication. His commitment to his ventures is legendary, with tales of him spending nights at the Tesla factory. Yet, this level of commitment has had its costs. Musk has spoken openly about the challenges and strains on his relationships, including multiple divorces.
Arianna Huffington, the brains behind The Huffington Post, learned the importance of health the hard way. In her chase for success, she pushed herself to the brink, leading to a physical collapse from exhaustion. This wake-up call led her to redefine her life and start Thrive Global, a venture focused on well-being and health.
Relationships, health, and personal passions aren’t mere background elements; they form the very fabric of a fulfilling life. As you climb the ladder of success, it’s easy to leave behind what truly matters.
Finding Balance: Jeff Weiner’s Compassionate Leadership
Former LinkedIn CEO Jeff Weiner offers a compelling counterexample to the all-consuming entrepreneur stereotype. Throughout his tenure, Weiner was known for his deliberate approach to balancing work and personal life, famously blocking 90 minutes to two hours on his calendar each day for reflection, strategic thinking, or simply catching up on industry news.
Weiner believes that taking this time makes him more effective as a leader—more thoughtful in his decision-making and more present in his interactions. He calls this “creating space” and considers it essential not just for his personal well-being but for his effectiveness as a CEO.
His approach extends beyond personal practice to company culture. Under his leadership, LinkedIn embraced compassionate management practices that recognized employees as whole people with lives beyond work. This philosophy helped create sustainable growth rather than the burnout-inducing cycles common in tech.
Weiner’s success—guiding LinkedIn through tremendous growth and eventually a $26.2 billion acquisition by Microsoft—demonstrates that prioritizing life beyond business isn’t just personally beneficial; it can be a competitive advantage. By maintaining balance, he brought fresh perspective and sustainable energy to his leadership role, allowing him to make better long-term decisions for the company.
The Path Forward: Transforming Failure Into Growth
After navigating my own startup journey through near-failures and eventual success, I’ve come to understand that the entrepreneur’s greatest asset isn’t their business plan, funding, or even their product—it’s their capacity to transform potential failure into growth.
When that AWS bill threatened to sink our company, I was paralyzed for weeks. But that experience forced me to develop a framework for breaking the thoughts-emotions loop that had trapped me. That single skill—learning to separate myself from my emotional reactions—became invaluable throughout the rest of my journey.
The acquisition deal that fell through two hours before signing taught me about resilience and the importance of having multiple paths forward. Instead of giving up, I leveraged that near-miss to create leverage with other potential acquirers, ultimately leading to a successful exit on better terms.
Each “failure” was actually upgrading my entrepreneurial operating system. And that’s the mindset shift I want to leave you with today.
Your Entrepreneurial Evolution Starts Now
The most successful entrepreneurs I know aren’t those who’ve never faced failure—they’re the ones who’ve failed productively, extracting maximum growth from each setback. They’ve learned to:
- Embrace the marathon mindset – Pace yourself for the long journey, building sustainable habits that prevent burnout and keep you in the game.
- Connect with your North Star – Regularly revisit your fundamental “why” to ensure all your decisions remain aligned with your core purpose.
- Maintain perspective on setbacks – Train yourself to see obstacles as temporary and situational, not permanent and pervasive.
- Build a life beyond your business – Invest in relationships, health, and personal growth with the same intentionality you bring to your venture.
- See “failures” as upgrades – Transform each setback into capabilities and insights that make you stronger for the next challenge.
The entrepreneurs who achieve lasting success aren’t just building businesses—they’re building themselves. They understand that the company may be their creation, but they themselves are their masterpiece.
Your journey isn’t just about the business you build—it’s about who you become in the process. And when you shift your focus to this deeper path of growth, something remarkable happens: both you and your ventures begin to thrive.
What “failure” are you currently facing that might actually be your next great upgrade? The answer to that question could be the beginning of your most significant breakthrough yet.
Ready to transform your approach to entrepreneurial challenges? Download our free Mental Resilience Workbook and join a community of founders who are mastering the inner game of entrepreneurship.
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