Lessons on Grit, Grace, and Growth from an Unexpected Challenge

The humid morning air on Portmore Hill is one of those familiar foes that somehow feels like an old friend. I had just resumed my morning walks, determined to conquer that treacherous incline only locals truly understand. The road is rough—imagine the worst road in Jamaica, then multiply it by ten. That’s Portmore Hill. It demands commitment.

Unfortunately, my “trusty” walking shoes had been left outdoors, victims of the elements. So that morning, I slipped into an old pair of sneakers that hadn’t seen the light of day in months.

The journey started normally—breathing steady, pace consistent—until a good way up from my starting point, something strange began to happen. My right shoe developed an odd wobble. A glance confirmed the horror: the entire sole had begun its slow, deliberate farewell from the shoe’s body.

In that moment, the temptation was real. Turn back. Pack it up. There’s a perfectly good excuse to quit—a textbook case of what Seth Godin calls The Dip: that inevitable stage in every pursuit when the thrill fades and the grind begins.

But almost instantly, a braver voice answered: “Shoe or no shoe, I’m getting to the top of this hill.”

So I did what any determined Jamaican would do—I kicked the broken shoe to the side of the road, muttered, “Mi shoe lef mi a road, mi a lef it a road,” and continued my journey in thick, white cotton socks (thankfully the thickest pair I owned that morning—a small act of foresight disguised as grace).

As I walked barefoot-in-socks over stones that felt like razor blades, my fellow walkers looked on with curiosity and sympathy. I laughed with them as I explained the situation, fully aware that every sharp rock underfoot was chiselling a leadership lesson into my soul.

The Hidden Advantage of a Slower Pace

The uneven terrain forced me into a slower, steadier rhythm. Gone were my sprint-and-recover bursts. Every step required full awareness. Paradoxically, that slower pace made the climb more effective.

What I experienced in that moment was Kaizen—the Japanese principle of continuous, incremental improvement. By focusing only on the next step (not the pain, not the incline), I achieved a more consistent, enduring workout than any high-intensity burst could offer. The obstacle became the teacher.

Destiny Helpers and Visible Commitment

If the climb had been humbling, the descent was downright punishing. With gravity and grit working against my tender feet, each step became a test of endurance. Just then, a gentleman who had passed me earlier reappeared—this time carrying a clean, thick pair of socks.

He said, simply, “Here, these might help.”

That moment exemplified something powerful: visible perseverance attracts support. When people see you staying the course, even when it hurts, they’re moved to help. Your visible commitment signals your worthiness to the world—and it draws your destiny helpers.

Salient Leadership and Life Lessons

1️⃣ The Mission Is Non-Negotiable (Grit):

True leaders don’t let small inconveniences derail major missions. Whether it’s a broken shoe, a budget cut, or a missed deadline, perseverance transforms problems into stories of triumph.

2️⃣ Embrace The Dip:

Every meaningful endeavour will hit “the dip.” It’s the crossroads where most people quit, but achievers persevere. That’s the doorway to mastery.

3️⃣ Consistency Outperforms Intensity:

Steady, persistent effort always outlasts flashy spurts of energy. Leadership is built step by step, not sprint by sprint.

4️⃣ Preparation Builds Hidden Strength:

Those thick socks represented subconscious preparation. The little things you do today—self-care, planning, rest—become the foundations of tomorrow’s resilience.

5️⃣ Visibility Attracts Support:

Your open commitment inspires others. People are drawn to those who keep going when circumstances scream, “stop.” Show up visibly, and the world will meet you halfway.

Podcast Reflection 🎙️

From Mop Bucket to Multi-Millionaire: The Journey of Paul Martinelli

This week’s featured episode of The Entrepreneurial You dives into the incredible story of Paul Martinelli—a man whose relentless faith and perseverance turned a $200 cleaning business into multiple multi-million-dollar companies. From overcoming a stutter to becoming the Founding President of The John Maxwell Team and sharing stages with Seth Godin and Les Brown, Paul’s journey embodies transformation through action.

Listen here:https://henekawatkisporter.com/from-mop-bucket-to-multi-millionaire-the-journey-of-paul-martinelli/

Scripture Spotlight ✝️

“Let us not become weary in doing good, for at the proper time we will reap a harvest if we do not give up.”

— Galatians 6:9Sometimes your “harvest” is one step beyond where you almost quit.

Recommended Reading 📚

✅️Daring Greatly by Brene Brown – https://amzn.to/3E7o68V

✅️Dare to Lead by Brene Brown – https://amzn.to/3BPC3rk

✅️Atomic Habits by James Clear – https://amzn.to/4bYM3L74

✅️Start with Why by Simon Sinek – https://amzn.to/3PqY6ra

Fun Fact of the Week 🤔

Portmore Hill has humble beginnings—once a regular walking trail—and has since become a favourite fitness spot for Jamaicans who enjoy community, conversation, and the occasional roadside sermon of encouragement. 

Perhaps our hills really do build more than muscles—they build mindsets.

Interactive Poll 📊

How do you handle your own “Portmore Hill” moments?

● Push through the pain—finish strong.

● Pivot, adjust, and keep moving forward.

● Accept help when it’s offered.

● Turn the failure into a story for someone else’s inspiration.

Share your climb—and your lesson below!

Bulletin Board 📢

LeadHERship is only 2 weeks away! Join this transformative experience aboard Royal Caribbean’s Liberty of the Seas!

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• PWD Credit Union
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Final Thoughts

Every broken shoe, every unplanned obstacle, strengthens your resolve and reveals fresh wisdom. When the road roughens, remember: the point isn’t the speed—it’s the stride.

Persistence, purpose, and preparation will always see you to the top—shoes or no shoes.

Keep climbing,

Heneka Watkis-Porter*

Podcast Queen | Leadership Visionary Architect | Coach | Grace to Grow Mentorship Founder

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