#12: What Does it Mean to Try Life On?

newsletter Aug 12, 2023

The Try Life On newsletter has some 2000+ subscribers. Thank you!

A lot of you are new, so it’s time to take a step back and speak at a high level. We’ve been in the weeds for the past few weeks on principles, tactics, and examples to Try Life On.

Let ground again. What is the TRY LIFE ON concept and what’s the purpose of the newsletter?

To help you plug into planet and earth as intended
To help you develop habits to achieve the five freedoms
To help you create lifestyle you don’t need vacation from
To help you break the system and steer away from status quo
To help you learn how to leverage the 9-5 more than it leverages you.

I’ve done it over 25 years using trial and error, and a mindset of doing and course correcting along the way. The newsletter (along with the Podcast) explains how and why, as well as exposes you to people who’ve done same in their own unique way (I don’t have the market cornered).

Plain and simple. ‘Try Life On’ is a philosophy and approach, a Mindset, Skillset and Soul-set that leading to lifestyle you don’t need vacation from.


Life is something you can practice and ‘TRY ON’, constantly. We’re here to thrive, not exist… not just do status quo stuff neighbors, coworkers, family, and society seems to solicit from us.

As a priority, folks who want to Try Life On should give energy, research & time to actions leading to five freedoms, generally ignoring society's definition of "success". Genuine success revolves around:

  • Time Freedom
  • Financial Freedom
  • Geographic Freedom
  • Freedom to Execute Your Purpose
  • Freedom to Build Meaningful Relationships

You can build lifestyle you don’t need vacation from. Done it, helped >100 do same via coaching. Money plays a role but it's not that... Here’s the general formula…

  1. What’s your dream day look and feel like
  2. What’s the personal blueprint that enables it day to day
  3. What work or business blueprint supports it. If current job doesn’t, pivot to new. Don’t default.
  4. You now have tools for that day. Practice it. Try It On.

Been ‘Trying Life On’ a long time. Involves mindset + skillset.

Many don't realize 20 years of formal education sets us up for the status quo. We forget to dream. Yet we build the dream of others all the time.

On average we have 28,000 days in a lifetime. I have approximately 10,045 days left, if I’m lucky. I don’t have time for the status quo. Neither do you. The status quo sucks.

Once I realized it, I got aggressive about designing life, intentionally having work and personal experiences that would fill my life book with memories and joy. Money plays a role, but there are ways to hack the pursuit of it such that it supports your life, and doesn’t consume it.

I'm 48 now, retired from the W-2 world, with absolute time, financial and geographic freedom. I’ve learned how to make the planet very small to have worldwide experiences regularly. Planes are just Uber when you learn how to travel hack. Frankly, I beat the system. I’m still beating it. I want that for you (however it makes sense for you).

My goal was a lifestyle we don’t need a vacation from, creating experiences and relationships that enrich along the way…

  • acting on TV shows
  • trying out for the NFL
  • 25-year corporate exec
  • earning my way to Lt. Colonel
  • buying thousands of apartments
  • becoming a special agent in charge
  • serving in Africa, Mideast, and Europe
  • travel hacking to 100 countries, 350 times
  • opening several clubs, restaurants, and businesses
  • living & developing real estate in the Mediterranean
  • private equity firm founder (really proud of this one)
  • 33-year-old rookie police officer serving the local community
  • philanthropic projects across Washington DC and the Mideast
  • OUTRIGHT financial, time, and geographic freedom for anything.

Did most of the above for 15+ years, many at the same time. I love when people say it’s not possible, there’s no time.

No… It’s not possible for them. I’m still doing it.

The list will grow. Not trying to be everything, go everywhere. Just never liked the idea of pressing repeat because life should constantly evolve. I keep the beginners

I see Trying Life On as constant learning because I have just one fear...


Everyone should Try Life On, we have just one. Don't default to the status quo. Do or learn that thing you've always wanted to. Attack work and personal life with reckless abandon.

When we graduate from high school or college, we’re given a set of rules to operate by – get a job, climb the ladder, get a home, buy stuff, and be happy with what you got. That’s called status quo, and it’s a garbage default approach to life. I don’t operate by those rules. I figured out a different set and I’m going to share them with you. I call them TLO principles. To name a few…

  • Five freedoms (time, financial, geographic, purpose, relationships)
  • Asking better questions
  • Try Life On Trial Runs
  • Climb one mountain, go down, and climb another
  • I feel good when
  • Leverage 9-5 more than it leverages you
  • The ‘And’ not ‘Or’ approach
  • Make your investing life easy, day-to-day life hard
  • Being selfish now to be selfless later
  • Make the world smaller
  • Freedom = time + mobility
  • Finding your tribe

And the key to Try Life On…

Designed lifestyle = your dream day + personal life blueprint + work life blueprint

My 100+ coaching students know all this stuff and are using it to radically shift their lifestyles for themselves and family, building business and financial freedom while stacking experiences and relationships to fill their life book.

There is a lot more. We’ll get into it more. I’m excited to do it.

But I wanted to go back to the well and re-explain Try Life On.

I’m going to continue helping you Try Life On, your way.