Hey! I'm here with your 4-part newsletter.

• One courageous quote to set the tone for your week

• One personal story about courage

• One question to reflect on the past week

• And one weekly challenge for this upcoming week

One Courageous Quote

One Personal Story

November 28, 2023.

That's the day that changed my life forever. It's the day I submitted my resignation notice at Apple. My biggest regret from college was never studying abroad. My goal was to give myself the time and space to explore my entrepreneurial ideas while becoming conversationally fluent in Spanish in 18 months. 

In the weeks leading up to my resignation, I couldn't sleep. Every night, I'd wake up drenched in sweat, heart racing. I was terrified of leaving the best paying job I’d ever had.
I was terrified of failing. I was terrified of what my colleagues and boss would think.

But I was even more terrified of not living up to my potential. 

I Had the Talent. I Lacked the Courage. I was in prison. 

I knew I had the talent and intelligence. I’d held coveted roles at Netflix and Apple and turned down roles at Uber and LinkedIn. I had no shortage of start-up ideas. Many of them turned into real start-ups, like Intro, Winc, and PeakReservations. I had a shortage of acting on them. I had two previous entrepreneurial failures and had scar tissue from them not working out.

What I lacked was the courage to bet on myself (again). Yes, I was making great money at a great company with a great title. But I was hiding out in Corporate America as a back-up plan. I knew deep down I wasn’t playing to my potential. I had so much more to give and I’d regret not trying my hand at entrepreneurship again. I'd be settling if I stayed. 

One of the books that changed my life is The Top 5 Regrets of The Dying. It was written by a hospice nurse, who wrote the book based on her conversations with her dying patients. The #1 regret? “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

I knew working in Corporate America for the rest of my career wasn’t aligned with living a life true to myself.

I didn’t want to die with regrets, so I knew I only had one choice. 

IT'S TIME.

The 2023 Rolex Sky-Dweller you see in these photos isn't just a watch to me. It's a monument to the day I stopped playing small. I got it engraved because I want this watch to be an heirloom for my kids and grandkids. I want to change the future of my family for generations to come. I want them to be proud of their father and grandfather, and to know that courage is a family value.

The first line of the engraving says: "IT'S TIME."

It was time to stop playing small. It was time to level up. It was time to bet on myself. 

I’d read the books, I’d listened to the podcasts, I’d bought the courses, I’d gone to all the seminars, but there was no substitute for action. 

On November 28, 2023, at 10:32 AM PT I did it. 

I let my manager know I was resigning.

Boom. It was done. I felt excited, fearful and relieved all at the same time. 

The Ripple Effect

After I put in my notice, and told my friends, family and colleagues my plans, they all basically asked me the same question:

"Where did you get the courage to do this?"

That’s when I realized I could help others by sharing the same strategies that helped me. I created a 5-minute, unlisted YouTube video and sent it to friends and family to gauge interest. A dozen people said they were interested. That led to me creating a 5-week cohort-based course called Courage Camp. It was a success.

The feedback exceeded my expectations. One thing led to another, and now I have a clear vision: building DailyCourage, the world's #1 ecosystem of products, services, and experiences dedicated to helping people build more courage.

None of this would’ve happened if I had allowed fear to be my career coach.

My Life Today

I can’t believe how much my life has changed since I left Apple on January 3rd, 2024.

I’ve never made less money or worked longer hours, but I’m having a blast and know I’m on the right track. Every day I receive encouraging comments from people on social media and DMs from old colleagues, friends, and associates I hadn't heard from in years.

There’s a form of non-monetary compensation that comes from doing mission-driven work that directly impacts people in a meaningful way. This is my life’s work.

No, not everyone needs to quit their job, sell their place and move to a foreign country. Courage isn’t about taking unnecessary risks. It’s about giving fear the respect it deserves but never an ounce more. 

I wish everyone has the opportunity to experience this during their lifetime. And I’m on a mission to help as many people achieve this. It’s why this newsletter exists.

One Question

Looking back on this past week, where did fear play a role in your decisions? Remember: fear is simply the anticipation of an unwanted experience or outcome. It often hides behind perfectionism, procrastination, over-thinking, self-doubt, insecurity, and anxiety. The first step in changing your relationship with fear is identifying it. 

One Weekly challenge

This week's challenge: 

Remember that quote from Sahil Bloom? "The worst thing in the world is having the talent and intelligence to achieve something great but lacking the courage to go out and do it." 

Identify ONE fear that is suppressing your talent.

We all play beneath our potential. We’ll never reach 100% of it. That 's OK. But it’s not OK to operate at a small fraction of what we’re capable of. Fear is the #1 factor for why we don’t reach our potential.

Write down one thing you have the talent and intelligence to achieve, but haven't pursued because of fear. Be as specific as possible. What assumptions are you making? What is it costing you? How much better would your life be if you overcame this fear? 

My life’s mission is to positively impact 1B+ lives by helping people have more courage.

This is why I need your help.

Two favors:

1. Forward this to someone who would benefit from it.

2. Reply and let me know how I can improve. I read everything and respond to each one.This newsletter is written by me (not AI). 

Stay courageous!

— Jonathan