#16: It’s All About Perspective

newsletter Oct 29, 2023

Try Life On Community….

Recently, I've been traveling between Hawaii, New York, and Lebanon. Hawaii to reconnect with real estate business partners, New York to see an executive producer partner and Lebanon for philanthropy work.

I want to remind you that goals and passions are not always at home on the computer. Get out in the world and move. Live more. Geographic freedom is a great premise to focus on.

I realized in flight that October 2023 marks 2 years since leaving corporate and government work. After 25 years of working, I thought I'd miss it but I don't. I am, however, reflective.

Lots on my journey I think useful to you working to Try Life On your way.

Here goes!





I've held three parallel active careers over the past 2 decades...


Management Consulting Executive – 25 years

Military Officer – 22 years

Police Officer – 15 years


Yes, all at the same time. But that's another story.


I've also been a real estate investor and entrepreneur since age 26. It earned me financial freedom in 2014, and now I use it to help others and do philanthropy work with the proceeds.


Let me give you a sense of the following:

  1. What I got right
  2. What I understand better
  3. What college didn't teach me that books did
  4. What bothers me about the work world (in reflection)
  5. What steps you can take along your journey


What I Got Right


  • Didn't chase Partner, General, or Chief of Police titles. Wasn't concerned with titles.
  • Always prioritized roles giving unique life experiences (i.e., working in Portugal)
  • International travel came every 1-2 months, w/o fail, over 25 years
  • The experiences, relationships, and empathy gained fuel my life and mindset today
  • Used 9-5 pm skills during 5-9 am. Was always working on businesses or real estate
  • The risks were worth it. Failed a few businesses (i.e., coffee shops, nightclubs)
  • The failures were a blessing. Lessons learned led to a $200M business with partners
  • Earned financial freedom using pay, slowly buying small properties over 15 years
  • At an early age, recognized the 9-5 pm careers wouldn't last 24/7/365 for life
  • Learned over time investing and businesses built 5-9 am would last 24/7/365 for life


Here's What I Understand Better


  • Building outside income (real estate) since 26 was leverage for life
  • The life options I have (time + financial freedom) are because of my 5-9 am
  • Being an entrepreneur is more about choices later in life than money
  • The 9-5 career does not suck. Our default approach to it does
  • My employers DO NOT miss me, nor should they. We are all replaceable.
  • Too many people are blindly loyal to employers and forget personal goals


Here's What College Didn't Say that Books Did


  • A major purpose of salary is to create income. 'Build' with your pay. Stop buying unneeded stuff
  • Income streams provide leverage. No one controls you.
  • Building + designing a lifestyle should be a goal of your career 


What Bothers Me the Most


And the major points I want to get across.


I was rarely stressed working 25 years because I knew why I was there. I was loyally executing the mission of my employers AND executing mine (Freedom Goals) at the same time.


Many would 'de-stress' if they were more intentional about leveraging work for life goals.


Then you would have that 'pressing repeat' rat race feeling getting up each day. People are blindly chasing titles.


People give major chunks of life for goals that are not theirs, blindly chasing titles


  • show up early, stay late
  • go to your 8th networking event
  • the 2-hour lunch middle of the day
  • the 3-hour happy hour after 5 pm
  • OK... my employer sees me looking busy


You have external passions and life goals yet LACK TIME?

Perhaps you lack commitment to yourself. Perhaps you're not leveraging your 9-5.


Loved my corporate career. Full-time 25 years but still...


  • built large real estate portfolios
  • failed several businesses along the way
  • built a real estate investment firm w/ partners
  • executed on passions like pro football and acting
  • built lifestyle no vacation needed from via lifestyle design


With passion, made my corporate employer $100s of millions. Was a very loyal employee. I loved what I did for sure, but recognized we've got one lifetime to live.


I want you to recognize this as well.


What Can You Do?


With intention, try to focus heavily on outcomes, not hours (I talked to my boss about this a lot).


  • do the 20% at work that gets 80-100% outcome (Pareto's law)
  • ignore gossip + meetings non-impactful to outcomes
  • use the protected time to build business, invest, travel, build skills, execute goals, quietly
  • build relationships outside of work supportive of your passions and goals
  • YES... work on your outside stuff, even if still at the office, as long as work outcomes met


Never lose sight of goals. Never fall into ego games.

That's how folks get caught in the rat race forgetting your time eventually runs out.

My career was USED purposefully. You can do the same.




I have so many colleagues still working afraid to give up what they've built (i.e., roles, titles), yet want to Try Life On differently. The corporate guy who wants to be an artist.


The in-office government worker who wants to work remotely but fears not being promoted. This kind of default thinking is keeping people from living as intended.

Fear of risks and what peers or family may think is causing people to miss life.


Stop chasing someone else's version of success. LIVE!

Two years after leaving, I'm glad I did it my way. Wasn't always comfortable, but it worked.


Hope this gives you some perspective for your journey.