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The Quarter-Life Breakthrough: A Millennial’s Path to Modern Elder Academy


* Chip’s Note: I’m excited by the idea of a Millennial/GenZ workshop at MEA. Brian makes a compelling case for it, but we need to hear from you to determine whether this kind of workshop would sell. *

My name is Brian Dubow, and I’m a 30-year-old graduate of Modern Elder Academy (MEA). I attended MEA in 2022, and at the time, I was the youngest person to ever take part in an MEA workshop. How does a 28-year-old end up at a place marketed for people going through their midlife crisis? Allow me to explain.

I’m an entrepreneur with a happiness coaching business based out of LA called Hit of Happiness. While going about my business and networking as usual, the name Chip Conley came into my life three times in the same week. First, someone sent me his Ted Talk. Next, executive coach Mark Goulston saw synergies between my message and Chip’s and suggested we connect. And finally, Chip was on my favorite podcast (Rich Roll). Who was this guy and why was he popping up everywhere in my life?!?

Nonetheless, I saw the signals as synchronicities and shot Chip a cold email. Chip, being as supportive and responsive as he is, answered all my questions and suggested that I attend the entrepreneurship mastery week at MEA (there’s another one coming up in September in Santa Fe). I appreciated the wisdom and offer, but was I really about to check myself into an elderly home for a week at 28-years-old?! I figured for Chip I could suffer through a week with elderly people talking about their midlife crises. 

As you can guess, this sentiment changed after my week in Baja. For me, the curriculum, the vulnerability, the people, and the collective effervescence were all invaluable to my personal growth, clarity, and life design going forward. For those interested, here is my blog post recapping my experience.

On the last day of the retreat, I asked Chip if he ever considered hosting millennial weeks at MEA. My argument was that those going through their quarter-life crisis would benefit just as much from the programming as those in their midlife, and the earlier we could help people on their journey, the longer they could live a consciously aligned life. Chip loved the idea and told me to keep in touch about it.

The “Unhappy” Generation

Here we are two years later, and the unhappiness of millennials and Gen Zers is at an all-time high. The World Happiness Report came out earlier this year, with the US dropping from the 15th to 23rd happiest country, which marks our first time out of the top 20. But it gets worse.  

If the World Happiness Rankings were based on the population of 30-year-olds and below only, the US would be 62nd out of the 143 countries ranked in terms of happiness. 62nd!!! So much for the U-Curve of happiness, times have changed. 

So, what do I mostly attribute this to?

  1. Social Media – Theodore Roosevelt once said, “comparison is the thief of joy.” With social media, today’s youth are constantly comparing their internal experience to the world’s glorified external experience. It makes them feel lonely, less than, and disconnected from reality.
  1. The Path is Broken – In past generations, if you worked at a corporate job for a couple decades, you were all but guaranteed to be able to afford the American dream. Two cars, a house with a white picket fence, the financial means to travel and send your kids to college, and a golden retriever. Between student loans, inflation and a recession, the younger populations struggle to visualize building a brighter future.
  1. Lack of Community and Connection – In an increasingly digital world, face-to-face interactions have diminished. Traditional community structures have weakened. This lack of real-life social support and community engagement leaves younger generations feeling isolated, disconnected, and riddled with social anxiety. 

Reason for Hope

As a happiness coach who works with many high-performing Millennials and Gen Zers, I meet a lot of people who have subscribed to the victim mentality and are driven by fear rather than hope. The reality is that we all have agency over our lives, and that happiness is an inside job. We can each take simple actions, like exercising, meditating, connecting, and journaling, to be the best version of ourselves. Once we get ourselves out of survival mode and into a flourishing state, we can then be lighthouses for everyone else, shining our light on all the ships lost at sea, guiding their way to a happier shore.

For this reason, the time is now to address the “quarter-life crisis” and turn it into a breakthrough. This is still hush-hush, but Chip and I are collaborating on a Millennial and Gen Z workshop at MEA for Summer 2025 on Building a Life that Matters, with a focus on helping participants define success for themselves and operate at their highest capacity. If you or someone you love is interested in joining us, fill out this form and shoot me an email ([email protected]). If you are a parent of a Millennial or Gen Zer, look no further than this session to give your child the gift of purpose! Or if you have some young high-performers in your company, think about sending them. 

-Brian

Brian Dubow is the CEO and Founder of Hit of Happiness, a coaching and corporate consulting company on a mission to make the world a happier place. Multi-faceted, Brian is also a blogger, a podcaster, a marathoner and Ironman, a Certified Happiness Trainer and coach, and a teacher at UCLA Business School. His UCLA course is a life design/self awareness course intended  to help students craft a personal and professional life that makes them feel alive. Brian constantly strives to test his limits and push his comfort zone while helping others do the same. 

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