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    How to Handle Disappointment as an Entrepreneur: Building Grit That Lasts

    August 1, 2025
    5 mins read
    My Journal
    Obafela Killa

    Obafela Killa

    3x Founder helping Entrepreneurs & Professionals Maximize their Potential and Dominate

    Recently, I had a couple of bad experiences. Disappointments, if you may. It was annoying, and I wondered what I was doing wrong. Why me?

    Then I remembered something: disappointment isn't the enemy of entrepreneurship. It's the curriculum.

    Running NexusData Intelligence, NexaVida Plus, and Africa Development Summit has taught me that disappointment comes in countless flavors. The investor who seemed excited, then went silent after three follow-up emails. The client who shook hands on a deal in the morning, then called that evening to say they'd "reconsidered." The sponsor who pulled out two weeks before your big event, leaving you scrambling to fill a budget gap. The quarterly KPIs you missed despite working 16 hours per day, and sacrificing weekends. The pitch meetings where you poured your heart out, only to receive that popular "We'll be in touch" message that never comes.

    Then there are the quieter disappointments—the ones that eat at you from the inside. The days you stare at your laptop screen wondering if you're smart enough, connected enough, or just simply enough. The moments when imposter syndrome whispers that everyone else has figured out some secret formula you're missing. The nights you lie awake questioning whether this venture is worth the stress it's putting on your relationships, your health, your bank account.

    It's tough. And if anyone tells you it gets easier, they're lying. What changes is your relationship with the toughness.

    Here's what running three ventures simultaneously has taught me: resilience isn't about avoiding the fall, rather, it's about what you do when you hit the ground. And make no mistake, you will hit the ground. No matter how strong you are, how mentally tough, how well-prepared, there will be days when you kneel. Days when the weight of building something from nothing feels impossible to carry.

    When those moments come—and they will—it's okay to feel the hurt. I'm sorry it hurts. I know it does. The pain is valid. The frustration is real. The desire to quit? Completely understandable.

    But here's the thing about entrepreneurial grit: it's not about being invincible. It's about being antifragile; growing stronger from the stress, learning from the setbacks, adapting to survive another round.

    The game-changer isn't your ability to stand alone; it's having the right people in your corner. Not necessarily with money—though that helps—but with presence. The friend who listens without trying to fix everything with hollow optimism. The family member who believes in your vision even when you've forgotten why you started. The mentor who shares a connection that could change your trajectory. The colleague who reposts your content when your reach feels pathetic. The person who simply says, "I see you fighting, and I'm proud of you."

    These people become your oxygen when entrepreneurship feels like drowning.

    I've learned to be strategic about building this circle. It's not about networking for networking's sake, it's about genuine relationships with people who understand the journey. Some will offer advice, others connections, some just presence. All are invaluable.

    There's a saying from one of Nigeria's TV legends that affects me in the best way: "Let the young man in his desperation go out and hunt. If he kills the elephant, his poverty ends. If the elephant kills him, his poverty ends." It's dark, yes, but it captures something true about the entrepreneur's dilemma; sometimes you have to risk everything to change everything.

    The desperation isn't weakness, it's energy. It's what drives you to take calculated risks others won't take, to persist when logic suggests you should quit, to innovate when conventional wisdom says it can't be done.

    But I prefer this saying instead: "It's not over until I win!"

    This mindset shift changes everything. Every setback becomes data for your next attempt. Every closed door becomes redirection toward the right opportunity. Every "no" becomes practice for delivering the pitch that finally gets a "yes." Sometimes you'll need to close one business to start another. Sometimes you'll need to completely pivot your approach. Sometimes you'll need to swallow your pride and start smaller than you'd planned.

    The key is that you keep moving. Forward, sideways, even backward sometimes; but never completely still.

    Your disappointments aren't always evidence that you're failing; sometimes they're proof that you're trying something worth doing. They're battle scars that demonstrate you're in the arena, not in the stands criticizing others who dare to play.

    To every founder reading this who's carrying their own disappointments: you're not alone in this fight. Build your circle intentionally. Honor your struggles without letting them define you. Remember that the elephant you're hunting today might be tomorrow's victory story.

    The journey is hard, but you're harder. The market is unforgiving, but your dreams are stronger. The odds are against you, but that's exactly what makes success so sweet when it comes.

    Keep hunting. Keep fighting. Keep going.

    Also; Happy New Month!

    Till next week. Cheers! 🥂

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