What is Try Life On?
A Lifestyle You Don’t Need a Vacation From
Try Life On is not about escaping life. It is about designing and living one that feels aligned, intentional, and fully owned.
Most people focus on changing external circumstances. Location, career, income, relationships. Those changes matter, but they are only the beginning.
Try Life On supports the full arc of change. Building a life that fits, navigating the identity shift that follows meaningful change, and learning how to live inside that life without recreating pressure, urgency, or old patterns.
This work is practical and deeply personal. It blends structure, environment, financial awareness, and identity so change becomes sustainable instead of temporary.
The goal is not constant reinvention. The goal is coherence, freedom, and the ability to move through life from choice instead of default.
My Freedom Journey
My journey to freedom was lonely at times. I struggled with what I call ‘entrepreneurial depression’—that feeling of being different from peers in both life and business. But through 20+ years of trial and error, I built a personal and professional lifestyle that works for me.
You don’t have to take that long. I’ve proven through coaching that you can shift your mindset—and in doing so, transform your external world much faster. But before diving into tactics, let’s step back and look at the bigger picture.
The Purpose of Try Life On
Try Life On exists to:
- Show you that the status quo is just a default—you don’t have to accept it.
- Help you reconnect with the planet and your true nature.
- Develop habits that lead to the Five Freedoms.
- Create a lifestyle you don’t need to escape from.
- Leverage your 9-5 rather than letting it leverage you.
- Unwind 20-30 years of societal programming and replace it with an expansive, fulfilling mindset.
I figured out how to Try Life On by simply doing—course-correcting along the way. That’s how I managed to hold three careers at once, build businesses, travel to 100+ countries, try out for the NFL, act on TV, and chase adventure instead of a corporate ladder.
Life is Something You Practice
Contrary to popular belief, life isn’t something you just arrive at—it’s something you actively shape and refine. You can always Try Life On in new ways. We weren’t meant to simply exist in the status quo. Yet, many of us get trapped in routines dictated by employers, coworkers, and societal expectations.
But here’s the truth: You can shift to fulfillment and satisfaction at any time via intention and effort. The key is focusing on the Five Freedoms.
The Five Freedoms
Those who embrace Try Life On prioritize actions that lead to freedom, rather than chasing traditional definitions of success. In my experience, personal fulfillment comes from achieving:
- Time Freedom – Control over your schedule and how you spend your days.
- Financial Freedom – Resources to support your ideal life without stress.
- Geographic Freedom – The ability to live and work where you choose.
- Freedom to Execute Your Purpose – Doing meaningful work that aligns with your values.
- Freedom to Build Meaningful Relationships – Prioritizing deep, fulfilling connections over transactional ones.
These freedoms aren’t easy to attain, but they are possible. The problem? No one ever gave us a framework to pursue them. So I created one.
The Framework to Try Life On
If you’re serious about designing your life, here’s the process:
Write your perfect day in extreme, emotional detail.
Break it down into goals within the Five Freedom areas.
Identify blockers stopping you from reaching those goals.
Create solutions to overcome those blockers—through actions, information, relationships, or mindset shifts.
Execute. Reevaluate. Iterate. Execute again.
I’ve been using this framework for years, and once you see its power, you’ll never unsee it. This is the point where the status quo world loses you forever. For me, that moment was 2013. Your moment can be today.
But the Lifestyle Blueprint is just the beginning.
Once you have clarity, we build your Financial Blueprint, where we reverse-engineer the numbers, assets, and buildable income streams required to support that lifestyle in the real world.
Vision without funding is fantasy. This is where life becomes executable.
Finally, we lock everything in with the Try Life On Principles. These are the identity shifts, mindset frameworks, and operating rules that help you inhabit what you’ve created. This is where you stop drifting back to old patterns and start living from your new self-concept.