The Netflix documentary The Social Dilemma explains how social media operates using a special algorithm. Mixed in with posts, photos, videos of your friends biggest to-dos, you’ll have a litany of “other” posts. Where do those come from? Why do I see certain posts over others? Well…if you pause on a post as you scroll through, the algorithm picks up on that as a sign that you are interested in seeing similar posts.

For me, this often means a heavy dose of clips from The Office, clips of dogs dressed up as people, or clips of amazing sports feats. While the algorithm can connect to content that is dangerous and misleading, it can also (based on the parameters I’ve mentioned) lead to some truly inspiring content. 

The algorithm introduced me to the work of a “serial entrepreneur”, someone who is a self described “spiritual billionaire.” His name is Jesse Itzler.  

Itzler, co-owner of the Atlanta Hawks, is so much more. He rapped in the 1990s, wrote a number of team anthems including the New York Knickerbockers “Go Knicks Go,” co-founded Marquis Jet, partnered with ZICO Coconut Water and sold it to Coca-Cola, married his incredibly successful wife Sara Blakely (founder of Spanx), and wrote two New York Times best-selling books, Living with a SEAL and Living with the Monks.

Yes, In 2015, Itzler had a Navy SEAL live in his apartment and train him in the most intense conditions for 30 days – just to “shake things up” in his life. As a 55 yr old athlete, he uses fitness to better his relationships and the world. He once ran 100 miles – nonstop – to raise $1.5M for charity. 

But most of his crazy journeys are communal in nature. Itzler started a race called 29029, an ode to Mt. Everest’s 29,029 ft of elevation. It’s an endurance event- a physical and mental challenge, that anyone could participate in. You don’t have to be a runner, swimmer, cyclist or “obstacle-course-type of person.” Everyone pushes everyone to the finish line. As the event website states, “overcoming obstacles reveals the best in each of us.” In May, Itzler recruited a dozen strangers to take a 2 week biking trip, some 3000 miles, from San Diego to St Augustine, raising funds for families who cannot afford cycling equipment. In both experiences, Itzler talks about the community bonds that form from being in those moments together. It’s the ultimate “bubble” experience that brings everyone who participates closer together, even for a short period, in the bonds of life.

Yes Itzler is a billionaire (in large part thanks to his wife’s empire), and he could just write a check to those charities that speak to him, but he describes himself as a “spiritual billionaire.” In an interview, Itzler explained 

“that his father was never a billionaire in financial terms, but his father was the ultimate spiritual billionaire, the only currency that really matters in life. This was profoundly represented to Jesse when he was researching retirement homes for his mother after the passing of his father. The evaluation process didn’t include analysis of bank accounts, connections or social status, but was based on a retirement grading system of wellness, known as “SIPPS”–social, intellectual, physical, purposeful, and as Jesse emphasized, spiritual. Jesse explained the value of being a spiritual billionaire is the ultimate multiplier in life. One can have billions of dollars in the bank, but if they don’t have anything else of value in their life, they ultimately have nothing. In other words, being a financial billionaire multiplied by zero spiritual wealth equals zero. He encouraged everyone to spend more time on the spiritual side of the equation, as that is the true multiplier of life.”

When speaking about the legacy he’ll leave his four children, Itzler says “One of the hardest things as a parent for me is recognizing that our kids are on a different journey than us. For example, I liked to play basketball in my driveway until midnight…my sons like to play Minecraft. And that’s amazing.

That said, I’ve learned to focus on certain things that matter most regardless of what our kids decide to do: self esteem, grit, empathy and compassion. We’ve found the best way to build those qualities in our kids is to show them. They are watching.”

This is probably not the first time you’ve heard some guru advice about appreciating the journey. It actually takes place in the second half of our double parasha, Masei.  

“These were the marches of the Israelites who started from the land of Egypt, troop by troop, in the charge of Moses and Aaron. Moses recorded the starting points of their various marches as directed by the Lord….” (Numbers 33:1-2).

Parashat Masei, the second of the two portions that we read this week, begins with the recounting of the Israelites’ itinerary, outlining their travels from Egypt through the desert, acting as a checklist before the “promised land moment.” I mean this is it- the end of Numbers is that threshold moment outside Israel. Deuteronomy is mostly a reprisal to get us to those final moments before we enter the land.

So the rabbis go back and forth as to why we have this listing of directions that reads more like an old printed Mapquest guide. 

Approach 1: Remember the miracles; show God’s power. Each stop represents God’s miraculous moments.  

Approach 2: Remind the Israelites of where they went wrong, both in the places they rebelled and in the fact that they are traveling so long in the first place.

Approach 3: The faith of the Israelites. Yes they had to walk around in circles, and they weren’t always compliant, but in the end, they maintained faith in God.

I’d like to add a fourth approach. By repeating the Israelites’ itinerary, we place value on life experience. Yes our faith wavered and remained intact, somehow, but I would argue that more importantly, we experienced all the ups and downs, the journey, together; and the bonds of that journey are everlasting friendship and community.

The journey is more than just for you– it’s for those who you take with you on the journey- family, friends, even strangers. It’s about finding that lucrative deal where one can maximize the quality AND quantity of interactions with loved ones. Which brings me to the first Jesse Itzler video to pop up on my social media feed. It’s the video that launched an algorithm of more Itzler videos. In a standard back and forth question sequence he has done in a number of interviews, Itzler asks the interviewer, Rich Roll, the following:

J: My parents are both alive. Are your parents alive?

R: Yeah

J: How older are your parents?

R: 76, 74

J: And where do they live?

R: Washington DC

J: How often do you see them?

R: like twice a year

J: Ok, so most people’d be like, “okay, you know I have…lets say your parents live until 80, so they have five more years, lets just say roughly, you would say “I have five more years of my parents” but I would say, “no, you have 10 more times with your parents if you see them twice a year.” You see them twice a year times 5, you have 10 more times to see them. WHen you start thinking of things like that, your first reaction is, “I wanna go see my parents.” At least that’s mine. So you change the way you approach it, and I’m like “I’m gonna go see my parents every other month, I’m gonna make it a priority”

Many of us prepare for retirement, or prepare for our ultimate retirement, our death. We do so in the hope that we have a financial portfolio that puts our loved ones at ease, thinking about the literal capital we leave for them. Rarely are we thinking in spiritual terms- we should aspire to be spiritual billionaires, leaving a legacy of a journey well taken. And while we can sometimes have a clearer picture of life as a Journey towards something- towards retirement,  towards death, towards the world to come, life is really a journey IN something. 

Take a moment to think about Itzler’s scenario: if you have 10 years, 20 years left on this earth, how does that equate to different journeys you might take? Is that 10-20 more times in shul? Is that a few dozen times seeing your friends for lunch? The question isn’t intended to freak you out, although I do recall kids at summer camp crying because that Tuesday was the last Tuesday french toast that they’d ever have as a camper. Rather, it’s a question to motivate us to live IN the journey, to make time for meaningful moments and meaningful conversations, to engage rather than dismiss. 

Rabbi Harold Kushner, of blessed memory, who guided so many on this path of life and loss as a rabbi and an author, wrote the following: 

“The purpose in life is not to win. The purpose in life is to grow and to share. “When you come to look back on all that you have done in life, you will get more satisfaction from the pleasure you have brought into other people’s lives than you will from the times that you outdid and defeated them.”

At our regular healing service, I often highlight a line from one of our healing prayers that reads “we celebrate the journey, this precious gift of life.” May we celebrate our journeys, enhanced because we walk them, with purpose, together. 

Our successes in life will be defined by engaging IN life, IN partnership with others, not towards something else- a journey well traveled, a life well lived.  

There’s a favorite quote of mine from Ralph Waldo Emerson that summarizes this idea:

“To laugh often and much; to win the respect of intelligent people and the affection of children; to earn the appreciation of honest critics and endure the betrayal of false friends; to appreciate beauty, to find the best in others; to leave the world a bit better, whether by a healthy child, a garden, a redeemed social condition; to know even one life has breathed easier because you have lived. This is to have succeeded.”

We are all on the ultimate endurance course of life. May we help others breath easier, lift others up because we are on this journey, together.