About

From Burned Out Teacher To Thriving Digital Entrepreneur

Hi, I'm Jonathan Milligan 👋

I help writers, coaches, and speakers transform their message into multiple streams of income. But my journey didn’t begin here. It started with a leap of faith and a lot of uncertainty.

Years ago, I walked away from a secure teaching career with a big dream and zero business experience. I had a young family to provide for, and every decision felt heavy riddled with self-doubt.

I spent nights working for a call center while trying to build something meaningful during the day.

Exhaustion and information overload became my norm, and I constantly questioned if I was making the right choice.

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The Turning Point

One frustrating evening, I hit a breaking point. I was overwhelmed by fear of failure, but something shifted inside me. I realized that waiting for the perfect moment was holding me back.

On a whim, someone recommended I read an old-out-of-print book by Russell Conwell titled Acres of Diamonds.

That book taught me that my purpose wasn’t somewhere out there—it was within me all along. I already had the skills, passions, and experiences needed to build something meaningful.

But I still had to figure out what was unique about me? What was my unique gift?

A New Path

I uncovered that my strength was in being a resourceful, practical teacher. But not the kind of teacher that is in a traditional classroom.

So, I turned my love for teaching into a blog, sharing lessons I had learned about business and life. Step by step, I created a framework for helping others turn their ideas into thriving online businesses.

Today, I’m a serial entrepreneur, 7-Figure+ Online Business Earner, and the author of 12 books (and counting).

But what truly matters to me is helping people like you find clarity, confidence, and recurring income streams with their message.

I Understand Where You’re Coming From

If you’re full of ideas but unsure where to start, if you’re overwhelmed by options or stuck in self-doubt, I’ve been there.

I know what it feels like to be stretched thin and questioning every move.

My mission is to show you that you don’t have to stay stuck.

You can build something meaningful—even while balancing life’s demands.

The Monday Messenger Newsletter

Grow Your Writing or Coaching Business into Multiple Streams of Digital Income in Just 5 Minutes Per Week

Get It Weekly in Your Inbox

How I Can Help You

Over the years, I’ve helped thousands of writers, coaches, and speakers:

Build their audience and grow their email list.
Launch online courses, books, and memberships.
Create recurring income streams that lead to freedom.

I do this through proven frameworks, step-by-step guidance, and a deep understanding of what it takes to succeed in today’s digital world.

Whether you’re just starting or looking to scale, my goal is to give you the tools and clarity you need to move forward with confidence.

Why Trust Me?

I’m not just teaching theory—I’ve lived this journey. Here are a few highlights that might help you feel confident in working with me:

Built a 7-figure online business from scratch.
Authored 12 books on platform growth, recurring income, and personal development.
Featured on major platforms as an expert in digital entrepreneurship.

But beyond the credentials, I care deeply about helping others succeed. Your success is what fuels my work every day.

LET'S TAKE THE NEXT STEP TOGETHER

If you’re ready to take action and turn your message into a thriving digital business, I’d love to help.

Start by joining my free weekly newsletter, THE MONDAY MESSENGER.

It's designed to give you a clear roadmap for getting started.

Your message matters. Let’s bring it to life.

You're safe with me. I'll never spam you or sell your contact info.