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    Home»Founder Fuel»Overcoming the Fear of Failure: My 10-Year Journey to Starting a Business
    Founder Fuel

    Overcoming the Fear of Failure: My 10-Year Journey to Starting a Business

    A true story of facing down family, friends, and the fears in my own head.
    John HillBy John HillNovember 5, 2025Updated:November 13, 20256 Mins Read
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    • The 10-Year Foundation
    • The Day the Dream Met the Doubters
    • What Happens When You Listen to Fear
    • The First Attempt (And the Big Failure)
    • The Real Lesson: Smart Risk Has a Process
    • The Payoff: The Day It All Became Worth It

    It’s 1:30 AM. Fueled by coffee and urgency, I need to share the heart of my entrepreneurial journey—not about sudden success, but the grinding, 10-year struggle with doubt that almost stopped me before I began.

    If you’ve ever had a dream that everyone in your life told you was a mistake, this is for you.

    The 10-Year Foundation

    My journey didn’t start with a business plan. It started in 2001 as a bookstore clerk in my hometown. It was a simple job: 8:00 AM to 5:30 PM, every day. Because I loved books and wanted to learn everything, I asked my manager in 2004 if I could also work the part-time evening shift (7:30–9:30 PM) in the printing department.

    That printing shop became my world. I still remember the smell of fresh ink and the hum of the Heidelberg machine. For six years, I balanced both roles—bookstore clerk by day, printing assistant by night. I wasn’t just working; I was learning the entire business.

    The Day the Dream Met the Doubters

    By 2010, after nearly a decade of experience, I felt ready. I had a new dream: to start my own small bookstore that also published local authors.

    I was excited. Terrified, but excited.

    First, I pitched the idea to my coworkers, the people who knew the industry. We were having coffee in the break room. Their reaction hit me like a wall of ice.

    “It’s too expensive,” one said. “We’re too young for that, and it’s way too much work,” the other added.

    Their words stung, but I thought, “They’re just my coworkers. My family and friends… they’ll be different. They believe in me.”

    They weren’t different. They were worse.

    I told my three closest friends over dinner. They looked at me like I’d said I wanted to join the circus. “In this economy?” one said. The third just changed the subject.

    But the final, crushing blow came from my parents. I finally worked up the courage to tell my mom. There were no congratulations. No curiosity. Just immediate, undiluted fear. “Why would you throw away a stable job?”

    My dad joined in. It became a full family intervention. The things they said that night stuck with me for years:

    • “Regular jobs are less stressful. Why make life harder?”
    • “What will relatives say if you fail?”
    • “Remember your cousin who tried starting a business? He lost everything.”
    • “Why can’t you just be normal like everyone else?”

    That last one hurt the most.

    What Happens When You Listen to Fear

    I didn’t start the bookstore. I let their fear become my fear.

    I stayed at my job for another year and a half. I stopped talking about my ideas. I stopped sharing what excited me. On the outside, I was a “smart, secure” employee. On the inside, I felt like I was suffocating.

    The First Attempt (And the Big Failure)

    So in April 2012, my co-founder and I finally did it. We ignored the fear, quit our jobs, and started our dream bookstore.

    And… it failed. Completely.

    My family’s worst fears came true. After just one year and three months, we had made too many mistakes, we ran out of cash, and we had to close it down. My partner left, and that failure was the most painful moment of my life. But it also wasn’t the end. It was the real beginning of my education.

    The Real Lesson: Smart Risk Has a Process

    After that first business failed, I finally understood what my family’s fear was missing. They only saw the risk of failure; they didn’t see the process of learning from it.

    I’m not saying you should jump off a cliff blindly. I learned from my failure that smart risk-taking has a plan. This is the 6-step process I used to rebuild and restart my business, which became the Wardoh Books you see today.

    1. Check if the Upside Is Bigger Than the Downside. For my bookstore, the worst case was: I lose my savings, have to get another job, and feel embarrassed for a year. The best case was: I build something meaningful, support local writers, and wake up excited about work. Was the potential reward worth the potential cost? For me, yes.
    2. Get Clear on Your Passion. Opening a bookstore meant long hours and financial stress. But I loved books. I loved the idea of creating a space for readers and writers. That passion is what gets you through the hard months when you aren’t sure you’ll make rent.
    3. Understand What You’re Really Getting Into. I didn’t just wake up and rent a storefront. I spent months researching: How do bookstores actually make money? What are the margins? How much does publishing cost? Knowledge doesn’t guarantee success, but ignorance almost guarantees failure.
    4. Use What You’ve Already Learned. My 10 years in the print shop weren’t a waste. I knew how to manage budgets, talk to suppliers, and run a printing press. Those skills transferred directly to running my own business. Look at your past experiences. You know more than you think.
    5. Build Real Skills, Not Just Ideas. Ideas are easy. Execution is hard. I took a weekend workshop on small business management. I volunteered at another bookstore for a month just to see how they operated. Skills are what turn a dream into a reality.
    6. Be Honest About What You Can Actually Do. This was the hard one. I had to admit I couldn’t afford to publish dozens of books. I couldn’t compete with Amazon. So I started smaller. Three author partnerships. A focus on community events. Smart risk-taking means being realistic about your resources.

    The Payoff: The Day It All Became Worth It

    I did restart Wardoh Books. Alone. It was harder, slower, and lonelier than I ever imagined.

    But it was mine.

    Years later, one of those same friends who told me I’d fail walked into my bookshop. He looked around at the shelves, at the local authors we were featuring, at the small crowd gathered for a reading. He looked at me, shook his head, and just said,

    “Wow. You actually did it.”

    That was the moment I knew. The journey isn’t about proving your doubters wrong. It’s about proving yourself right.

    Your Next Step: What’s one dream you’re pursuing, even if others doubt you? Share it in the comments below—your story might inspire someone else.

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    John Hill

    Founder of TheTipsLab. My failure with my first bookstore—and the success I found building the brand as Wardoh Books—is the fuel for your success. I share hard-won lessons on mindset and resilience from the trenches of entrepreneurship. My mission is to empower you to start your journey. Let's build together.

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