The Happiest Man in the World is retiring. Or rather, I’m retiring this blog. In its place, I’m launching a weekly email newsletter called Refilling the Cup. Refilling the Cup will focus on sharing practical lessons on how to live a better life that come from philosophy, history, science, literature and more.

Unlike The Happiest Man in the World, which was a mix between self-help advice, quippy aphorisms, and self-indulgence, Refilling the Cup will be more focused. You’ll get a view into my notes on the absurd quantity of material that I read, watch, and listen to about how to live a better life.


I launched The Happiest Man in the World right after my 30th birthday. Its goal was to act as a reminder of how lucky I am, and to enjoy the journey. There was no reason at that point in my life to think that I should be anything less than The Happiest Man in the World.

Since then, a lot has changed.

Many of the things that have changed in my life have been amazing: I married the love of my life; we had a child; I checked off every single one of my career goals (Literally. There was a checklist. Probably not healthy.).

However, some of the events of the last few years have also been the most difficult in my life. I lost my father unexpectedly. I realized that for some reason my dream job wasn’t fulfilling me the way I thought it should. I found out that being a parent is really, really hard (or at least trying to be a good one). I flirted with burnout and depression. Oh, and there’s this global pandemic thing that happened that you might have heard of.

So, I went looking for answers and help. I started counselling, and I looked to faith (I’m a baptized Catholic, but have had a hard time identifying as such in decades). In both cases, the first few conversations felt like they were helping, and then over time, they started making me feel worse. Therapy left me frustrated. And trying to be religious made me feel like a fraud.

So, I turned to books. Not self-help books written by self-professed gurus (although I’ve read more than my fair share of those as well). But rather, I started reading research-backed Psychology books and papers. I explored Eastern and Western philosophy looking for answers. After a few months, I noticed that I was looking at everything I read from this lens, and finding practical lessons in everything from biographies of Leonardo da Vinci to fantasy novels.

It dawned on me that so many of the questions we ask ourselves on a regular basis have already been answered by other smarter and more articulate people who came before.

And so, I used research as my therapy.

However, there was still a piece missing. When I said earlier that both counselling and faith helped me early on, I think the reason they were helpful was that for the first time in a long time I was sharing.

Finally, there’s the fact that it’s well-documented that the best way to learn something is to share that information with someone else.

That brings me to this newsletter.


There’s a Zen parable about a “learned man,” who seeks out a Zen master. When they meet, every time the Zen master starts to speak, the man cuts him off and tells him about his own experiences and opinions instead. As the learned man is speaking, the Zen master starts to refill his tea cup. Even as the cup is filled, the Zen master continues pouring until tea is spilling all over the table. The following exchange goes something like this:

“Umm… Mr. Zen Master, Sir, the cup is full. You’re spilling tea all over the table,” said the know-it-all.

“You are like this cup,” said the Zen Master. “How can you hope to accept new knowledge when your cup is already full?”

The man in this story is me, and if we’re honest, it’s probably most of us. We get to a stage where we get so caught up in that which we believe we already know, that we become closed to new lessons. When we approach life like an empty cup, it’s incredible how much more we realize that there is to learn.

So, the goal of this newsletter is to refill the cup, even though we know that the cup will never actually be full.

If any of the above resonates with you, if you think that you might find the contents of these letters helpful, or if you’re just curious, go ahead and sign up.

I won’t:

  • Sell your info
  • Send you an email from me in a few weeks trying to push you into a comprehensive course about how to become the happiest man in the world for the low, low price of $499 (on sale for a limited time for $9.99!).
  • Offer to become your life coach
  • I won’t even promise to show you how to become The Happiest Man in the World.

All you’ll get is a weekly email with sharing practical lessons about living a better life that come from people much smarter than me.