The Entrepreneur’s Paradox: Why “It Always Gets Worse, First”

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Ever feel like things are falling apart just when you’re chasing a new dream? You’re not alone. I’ve been there, and it’s a pretty universal experience for entrepreneurs.

My “Worse First” Moment

When I pivoted from training angel investors (the peak of one mountain, as I saw it) to leadership development (suddenly at the foot of a new one), uncertainty hit hard. Doubts swirled: Would my perspective resonate with this new audience? How would I win clients in this space? It honestly felt like everything was getting worse.

The Entrepreneurial Trap

Many entrepreneurs face this: doubt creeps in, and it feels like “things aren’t working.” But here’s the key insight I want to share: sales & marketing are DIFFERENT skillsets than delivering your core service or product. Your product can be incredible, world-changing even, but if it remains your little secret, no one benefits.

That journey to get your product out there, to build awareness and generate sales? It always seems to get worse before it gets better. It’s like the universe is testing your resolve.

Lessons from the Descent

What kept me going? My certainty that I was (and am) a great facilitator. I know I can create interactive, inclusive, thought-provoking experiences for people. But getting into the room, getting that initial opportunity? That requires a different skillset entirely.

The key takeaway: every ending holds valuable lessons that shape a new beginning.

History’s “Worse First” Club

Think about it:

  • Walt Disney was told he was unimaginative.
  • Steve Jobs was fired from Apple.
  • Oprah Winfrey was fired from her first television job.

Let’s take a look at Oprah Winfrey.

Oprah Winfrey’s story is a true testament to resilience and the power of perseverance. After being fired from her first television job as an evening news reporter in Baltimore, where she was told she was “unfit for TV”, Oprah didn’t give up. Instead, she leaned into her unique style of empathetic storytelling and connection, which would become her signature.

Today, Oprah is widely regarded as one of the most successful and influential media personalities in the world. She is a billionaire, philanthropist, actress, producer, and entrepreneur. Her impact spans across television, publishing, film, and social change.

History is full of examples of those who hit rock bottom before achieving greatness. That initial turbulence is often the cost of admission to fulfilling your vision.

Embrace the Discomfort

Remember, adversity is a crucible. What you endure ultimately becomes your strength. Discomfort isn’t weakness; it’s a bold decision to grow and push beyond your comfort zone.

I truly believe that it always gets worse first because that’s where we are made, conditioned, adapted and grow. That’s where we answer the important questions, like “do I really want this?”

Your future self will look back at those pivotal moments and smile at the decision you made to face into the reality that although it got worse, it got a lot better later.

The Takeaway

Don’t give up. Your breakthrough could be just around the corner. Keep pushing, keep learning, and keep believing in your vision.

Onwards and upwards.

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