It’s Courageous Sunday! I’m here with your 4-part newsletter.

Make today the day you take your next courageous step.

I’ve shared pieces of this story publicly before, but today I want to share it directly with you, because it’s the foundation of why I’m building DailyCourage, and why I’m writing to you now:

In January 2024, after five years at Apple, I quit my job, sold my home, and moved to Mexico City.

It was a bold move, but not a sudden one. This decision was years in the making, inspired in large part by Steve Jobs’ philosophy, life story, and wisdom.

There are 5 specific quotes from Steve Jobs that particularly resonated with me. The one above came from his 2005 Commencement Speech at Stanford. He had cancer but hadn’t yet publicly announced it. He knew he was dying. That context adds so much gravity to the sincerity of his words; “have the courage to follow your heart and intuition. They somehow already know what you truly want to become.”

I knew I was called to do more with my life. I had more to give the world. I knew that if I didn’t build the courage to follow my heart and intuition I would end up dying with the #1 regret of the dying; that I didn’t have the courage to live a life true to myself.

Here are the 4 other quotes from Steve that impacted my life. I’m passing them along in hopes that they may impact your life as well.

While working at Apple, I was gifted a physical copy of Make Something Wonderful, a book filled with Steve Jobs’ insights and philosophies. This quote stood out to me, practically leaping off the page.

The irony wasn’t lost on me, this book was given to me by the very company I was part of, yet it felt like Steve was speaking directly to me. I had reached a point where my work, as rewarding as it was in many ways, felt like a “career” in the way Steve warned against. It had become a structure, a ladder, and a series of steps that, while successful by many measures, left me wondering: Was I truly living a life aligned with my deeper values and aspirations?

Although I had a great role at one of the world’s most respected companies, surrounded by smart people and working on projects that many would dream of, I felt a growing pull to pursue something more meaningful…something that could touch people’s lives in a direct and personal way. I knew I was capable of more. A lot more. I knew I had something unique to give the world, and I couldn’t continue down a path that might leave me living a life of regret.

Still, the fear of leaving such a secure, respected position was real. It’s easy to stay within the comfortable boundaries of a stable career, especially in a company as established as Apple. The idea of stepping away felt both exciting and terrifying.

But as I wrestled with these feelings, I leaned into Steve’s wisdom. I knew he was right. I didn’t want to be so caught up in building a career that I missed the chance to create a life of meaning and impact. Leaving Apple wasn’t about rejecting what the company stood for—it was about embracing what Steve himself exemplified: following my dreams and intuitions and having the courage to write, direct, and star in my own life’s movie.

This quote is perhaps one of Steve’s most iconic, representing his deep desire to make an impact that truly touches people’s lives. Working at Apple was great, but it meant supporting a company that had already transformed the world. I wanted to make my own “ding”—one that was personal, unique, and driven by my passion to directly impact people’s lives.

At Apple, I was proud of the work I contributed to, but I often found myself feeling distant from the lives I was helping to improve. I realized that my heart was calling me to something more—to create meaningful change through direct connection and purposeful work.

Leaving Apple wasn’t just about pursuing a new path; it was about answering the call to make my own mark, my own “ding in the universe,” in a way that felt authentic to who I am and the values I hold dear.

As humans, we are social creatures, hardwired to care about the opinions of others. It’s natural to want approval, to feel validated by those around us. I’m no different. Performance psychologist Dr. Michael Gervais believes the Fear Of People’s Opinions (FOPO) “is the greatest constrictor of human potential.”

I believe he’s right.

When I began to think seriously about resigning, my mind raced with questions:

What will my friends think? My family? My colleagues?

The fear of their potential judgment felt overwhelming.

The truth is, leaving a prestigious job at a company like Apple doesn’t always make sense to those looking in from the outside. People often equate success with stability and status, and walking away from those can seem foolish.

Why would you leave such a great job? Do you really think you’re going to be more successful on your own?

This quote reminded me that while others’ opinions might feel important, the most critical voice is my own. I didn’t want to look back years later and regret letting fear—or someone else’s expectations—keep me from taking the leap and fully pursuing my potential. Steve’s words gave me the permission I needed to trust myself. They reminded me that intuition isn’t just a whisper; it’s a compass, pointing us toward the life we’re meant to create.

Leaning into that inner voice wasn’t easy, but it was necessary. I realized that the opinion I valued most wasn’t anyone else’s, it was my own.

Steve closed his 2005 Stanford commencement speech with these iconic words. Today, I pass that encouragement on to you.

If you’re in a role that feels safe but unfulfilling, and you’re wondering if there’s more; you’re not alone. I’ve been there. The fear of stepping into the unknown is real, but so is the reward of pursuing a life that feels true to you.

The journey won’t be easy, but it will be worth it. So as the new year approaches, take a moment to listen to your inner calling. Stay hungry for growth. Stay foolish enough to take the calculated risks that matter.

Whether it’s leaving a job, starting a new project, or simply taking the first step toward your dream, I hope my story inspires you to live boldly and make your own “ding in the universe.”

In thinking about your 2026 goals, what role will courage play in achieving them?

Identify the ONE goal you want to achieve most in 2026. Now think about if you weren’t to achieve that goal, what would the most likely reason be? What can you do to proactively decrease the likelihood of that happening? This process of inversion thinking has been incredibly useful for me in increasing my odds of success in every area of life. Hopefully this helps you as well.

That’s it for today.

Stay courageous!

— Jonathan