First voice: Get up, let’s do something, get up.
I roll over and curl into my sheets.
Second voice: Fuckkk. What is there to do today? You don’t need to get up. You have passive income. The rentals are there. You have a good life. You played ball for 20 years man. Just chill.
I shut my eyes again, but slowly, the chatter starts again, except louder this time. I try to block out my thoughts, but the voices get louder. I had never felt such apathy inside me. Such a lack of motivation. Such anxiety to be something. I miss knowing. I miss having something passionate to do.
First voice: Let’s go. Let’s go. Let’s go. C’mon man. Early bird gets the worm. You can find it. You can do this. Just put in the effort. You will find it. You will find something.
Second voice: The early bird does not get the worm, why does it get the worm? Explain that. The early bird probably gets picked off by a hawk. The accounting can wait. The paint can be dropped off later. The workers will be paid when you want. The taxes are still waiting. Are you going to be in foreclosure soon?
I want to be something, again.
I wrap the goose down comforter around me even tighter and think of my therapist appointment later, my ex-girlfriend leaving me, the sound of horse hooves on Brugge cobblestones, and the leather orb that used to be part of my life. I thought of the money coming in and the shots going in and the crowd roaring in my head. Being a pro athlete was the best feeling in the world — like someone had hooked a crack-opiate IV to my arm and fed me for 20 years.
But now, the IV was ripped out and I was a real estate property manager in Flint, Michigan*. Every morning, my brain was cracking open and my body tingled in a state of continuous anxiety and panic. The pressure inside me is a tea kettle shrieking. I pull the pillow over my head.
Second voice: I know, I know, just a little while longer. Just give me sleep. I need sleep. They can wait. Life can wait.
Something licks my hand. I open my left eye.
It’s 11am you lazy bastard — says Bear telepathically, my tricolor Jack Russell dog, his shining, round black eyes a few inches from my face — get your ass up.
I know my dog can’t talk to me like that, but he is right.
First voice: Just don’t fucking give up. Suffering is supposed to be part of the path. You will find something you love to suffer in again. Believe me. Trust me. Get up.
Having tons of money doesn’t mean you’ll be happy. Trust me. Money represents freedom for me, but freedom doesn’t mean anything if you are wired like me.
Here is my shitty job of investing, what you don’t see is I lost 3k on trying to loan money to high default type people. But I grew. I got better. When I started, I had no idea of what an A, B, C, D, or E rated loan was, but after a year, I’ve filtered the investments to only default on nine A-rated loans in my entire LendingClub.com existence.
LENDINGCLUB.COM — MY FIRST ATTEMPT AT DIVERSIFYING FROM REAL ESTATE IN PASSIVE INCOME
Let me first explain how to get to passive income sustainability.
With LendingClub.com, I lend $25 dollars in a very strict filter that limits who I give my money too. I buy real estate properties, do flips, and I use PeerStreet.com, Fundrise.com, Prosper.com, TDAmeritrade.com Roth IRAs, an Acorns.com app that invests automatically every month, I rent my third bedroom on Airbnb.com, and I do anything that gives me back what I value the most:
FREEDOM TO DO WHAT BRINGS ME MORE JOY, USEFULNESS, OR PURPOSE.
Creating my own life through minimalism and less consumption helps me get freedom. But freedom doesn’t inherently mean you’ll be happy. I know millionaires that are unhappy (like really, do the rims make you feel more special?)*
But I get it, I was able to semi-retire at 36. I didn’t need to work. But I also didn’t live like a king. And I didn’t want too.
I drove a shitty Hyundai Sonata.
I rode my bike too much.
I lived on $500 a month in Mexico.
And every dollar I saved, I invested in either something I love to do, something that gives me more freedom, or something that increases my passive income. Why? Because passive income is the measure of true wealth.
True wealth, to me, is when you lose your job, or income making ability, how long will you survive?
How long can you live with your current lifestyle and expenses per month?
Yeah, but I have a 100k in the bank, bro.
Okay, so your expenses are 10k a month. That gives you 10 months until you are broke.
Enjoy the foreclosures, and giving that sweet ride back, bro.
Like a Texan that has a big hat and no cattle, your investments are passive income. The more you diversify, the more income streams you have. But most people never get to investing. If you value the wrong things, you will be on a rat raced looking hamster wheel that never gets you any closer to being happy.
Joy isn’t in things, it’s in doing what you are strong, useful, and find passion or purpose in doing.
I am trying to lower my addiction to new things, to my phone, to my car, to my technology, and live more like a nomad. Western philosophy has it wrong. You don’t need more stuff to be happy, you need more of what brings you joy.
And if you need more of what you love, or brings you joy, you need freedom from distractions, from things, from expenses, to do more of it. You need to be useful and connected to people you care about and enjoy being around.
BUT MOSTLY YOU NEED MONEY, TO MAKE MONEY. AND THAT STARTS WITH SAVING (OR WORKING MORE, OR SMARTER).
In 2015, I retired from professional basketball after 13 years of living and traveling through Europe as a paid mercenary. People paid me anywhere from $60,000 to $100,000 every season to win their basketball club games. Let me tell you what I didn’t do when I was younger.
Save 1.3 million dollars.
But what I saved, I invested in real estate or passive income assets. I bought a Subway (that failed). I tried to invest and learn. It taught me the importance of investing, of creating a life of freedom and autonomy, but what I didn’t realize is the soul, body, and brain still need to have something to feel useful, to be content, and know my purpose. When I told my soul I was done playing professional basketball, a myriad of mental health problems started.
I was anxious AF.
Dude, you are retired, people would say.
Well, fuck retirement.
I’m 39 and ready to live again, and feel alive again. Anxiety hit me like a MAC truck. I value autonomy, connection, teams, growth, adventure, travel, and laughter. Anything that didn’t align with my values was cut from the team.
That went for people.
Places I chose to live. To be ruthlessly honest with yourself, you have to cut the values and things from your life that slow you down.
Life feels like a race, sometimes.
A rat race.
If you want off the rat race, you need to challenge your thinking. Your fears. Your life. Your idea of right and wrong. Good and bad. Instead of listening to my fixed mindset second voice, I challenged it. I challenged my version of what I thought my rat race would be and I literally went on a walkabout for authentic happiness:
Authentic Happiness Tip #1: Find your strengths and cultivate them in a field that you are curious about.
“I do not believe that you should devote overly much effort to correcting your weaknesses. Rather, I believe that the highest success in living and the deepest emotional satisfaction comes from building and using your signature strengths.” — Martin Seligman 
Thanks Marty. You may or may not know what your strengths are. If you do know, cultivate those strengths. God, the Universe, the Creator, the Genetics, the Energy, or the Life you were given, whatever you call this experience, has bestowed some sort of rubric of strengths inside you.
Inquire curiously about that strength, and realize the story you tell yourself is what fuels who you become.
Are you listening to a voice that feeds you a stale, old, rotten glass of milk every day?
List five of your strengths or take a Strength Finder’s test**:
What kind of jobs, careers, or fields would be interesting to me? Start walking towards that curiosity. Practice learning and practicing in those realms you find most purposeful or useful in doing.
Authentic Happiness Tip #2: Go on Your Version of a Walkabout and Find Your Values, Strengths, and Where You Can Be Useful
One way to find your values, your strengths, and change your direction is to go on a spiritual passage; an awakening of values and principles, daily epiphanies of learning which voice you will become and listen to.
We all have those voices of resistance in our head.
Are we going to choose the growth mindset or the fixed mindset voice?
In Australian Aboriginal society, a Walkabout is a rite of passage during which males undergo a journey during adolescence, typically ages 10 to 16, and live in the wilderness for a period as long as six months to make the spiritual and traditional transition into manhood.
That day I woke up, like so many others, when my whimpering dog licked my hand, I decided it was time to go on a rite of passage. I went slow traveling through the Caribbean on a shitty sailboat I bought for $5,000. This scared the shit out of me, but I knew it was time to challenge myself. My brain, my body, my habits, and which voice I should listen to.
It was on my walkabout, I decided it was time to what I’m doing now.
Be an entrepreneur. Be a minimilist. Coach kids. Adults. Start writing every day. Practice growth. Sell the things that I didn’t use (or give them away). Lower my expenses, pay off all debt as quickly as possible and live free from typical Western consumption.
This has all led me to where I am today, a work in progress.
*I always bust my friend Charlie’s balls about the rims. I mean, there are debates about why people have nice looking rims, but in the end, it comes down to egos.
**The Strength Finders test is a good way to figure out what you are naturally inclined to be good or like doing. But they also do a good job of figuring out different fields for you to be in: marketing, journalism, writing, startups, etc., were some of my options.
- Prout, S. (2008). “On the Move? Indigenous temporary mobility practices in Australia” (PDF). Centre for Aboriginal Economic Policy Research. Retrieved 21 November 2015.
- Authentic Happiness Using the New Positive Psychology to Realize Your Potential for Lasting Fulfillment BY MARTIN SELIGMAN