2019 personal review: lessons, losses, victories, and books

2019 was a year lived in the extremes. On one hand, for the first time ever, I feel firmly on my path. I experienced a flow, joy, and ease of life that used to be alien. On the other hand, returning to school has been tedious and extremely time consuming. Far worse, five people close to me died.

As always, I’ll end the year with a personal review of what I learned, what went poorly, and what went well in 2019. I’ve also added a section on my favorite books of the year. (If you really want to see what’s changed, these are my reviews of 2016, 2017, and 2018).


That moment when you realize you forgot the part about the rings…. Photo credit: Pat Cori

It is life’s imperfections that make it beautiful: in October I flew to Virginia to officiate a close friend’s wedding. I worked for months on the ceremony and was proud to deliver it, especially since my new girlfriend was going to be there, too. As I started to say, “I now pronounce you man and wife” the bride interrupted me, saying, “I want my ring!” 

First, I was confused. Then, my stomach twisted in knots. Despite months of preparation I forgot the part where the bride and groom exchange rings. Yeah, that part. The part that the entire ceremony builds to. I literally walked off stage, half as a joke, and half because I needed to recompose myself before completing the ceremony. 

Earlier this week I hung out with the bride and groom. They were recently interviewed for an article about their wedding. When the interviewer asked, “What was your favorite part of the wedding?” they responded, “The officiant forgetting the exchange of rings. It was funny and it reminded us that life doesn’t need to be perfect to be beautiful and fun. It also made our wedding unique.”

We are pressured to be perfect, but our beauty and humanity shines most brightly when we are imperfect. More on the beauty of imperfection here.  

Life is a lot better when you’re on your path: changing careers and going back to school while still working full time is the opposite of fun, and huge parts of 2019 were defined by things I disliked. And yet, I found myself mostly feeling happy and playful. I think this happened because I took the time to find the right path for me, and then did the hard work of redirecting…everything… so I could step onto it. Not only did I feel happy against the odds, I had one of my most successful years in business ever which I suspect is an artifact of getting on the right path. 

How to be a productivity wunderkid: More than anything, 2019 was defined by a relentless stream of work. I took on:

  • An accelerated Masters program to become a therapist that requires 66 credits and 1200 internship hours 
  • A 2.5-year training in Buddhist psychology and meditation that requires multiple practicums and retreats
  • A full client load all year long

In any given week I had limited hours of free time. To pull it all off I focused intensely on the basics. I:

  • Stopped using social media as a form of distraction or entertainment (article on how to do this coming in 2020)
  • Spent 45 minutes meditating 6 mornings / week
  • Made sleep a priority
  • Hit the gym at least 2x / week
  • Scheduled everything
  • Developed a strong organization system
  • Attempted to take one full day off every week (I succeeded at this less than 50% of the time)

The real trick to productivity isn’t some fancy hack, it’s getting the basics right. Everything else flows from there.

Note: I still think that a good life is one with plenty of white space. I’ll go back to living a balanced life immediately after completing my Masters.

Sometimes you have to move down if you want to move up: 2019 created a weird dual reality between my professional and academic life. As a consultant I worked with some of the most esteemed and recognizable people of my career. But when I wasn’t doing that, I was a student and unpaid intern.

In one half of my life I was treated like an expert whose time was valued. In the other half, I was treated as a beginner whose time was worth little to nothing.  

It was harder to keep feet in both worlds than I expected, and it was extremely humbling.

And yet…there’s no other way.

I have no desire to pretend to be an expert on mental health. I want to be able to read and produce the research that shapes the field. I want to be able to implement evidence-based practices with precision and style. I want a licensure board and world class supervisor holding me accountable. Doing that requires going back to school. And while the academic path is slow and tedious, I’m absorbing tons of important stuff along the way that will make me a much better therapist, researcher, and innovator.


Five people I cared deeply about died this year. Five. I miss you. 

Many of my relationships floundered. The demonic levels of productivity in 2019 came at a cost. I spent less time with my family, friends, and my girlfriend than I wanted to. I have a perpetual backlog of unreturned calls, voicemails, and emails from people I adore.

Though I’ve done my best to communicate that my absence is a reflection of the career change and not apathy, I worry that I’ve been gone too long. The busyness ends in May of 2020 which is when I intend to make up for lost time in my relationships, though it feels shitty now. Sorry guys. I love you. Forgive me.  

This blog. Woof. I published fewer articles in 2019 than any other year. Instead, the majority of my writing time was spent on papers for school. While this is a necessary evil, and one that I won’t need to deal with after May, I still miss writing here. Thank you for your patience.


Business. This was my best year as a consultant, by far. Most of my competitors missed a significant shift in the market last year. I didn’t. Consequently, my clients soared while my competitor’s clients flagged. That feels good.

I also made a subtle change to how I decide whether or not to work with a client or not. I ask myself: do I adore this person? Am I confident I can knock it out of the park for them? If the answer to either of these questions is “no” then I don’t take them on as a client. This strategy has worked extremely well.

For those of you in the beginning stages of your business, keep in mind that this is a late stage strategy. I started working for myself by doing 100 cold calls/week and charging less than my competitors. The trick is to consistently do your best, always strive to improve, be honest, and be fun to work with. Start there and things will go well.

Meditation teacher training. Holy shit has this been cool. I’ve learned more about the mind and the spirit than I ever imagined possible, and I’m not even halfway done. Of course, this is largely due to my teachers Jack Kornfield and Tara Brach, as well as my teaching mentor P*. While there have been countless highlights from the training, two stand out:

1) RAIN partners. RAIN stands for Recognize, Accept, Investigate, Nurture. It’s a psycho-spiritual approach to identifying the blocks in your life and weakening their hold. While you could do this practice on your own, it’s more powerful with a partner. I started doing RAIN meditations every other week(ish) with a guy friend and can’t recommend it enough. It’s transformative. Instead of attempting to explain the process myself, I’ll let my teacher Tara do so here

2) In October I started teaching meditation classes in Denver’s jails. Doing so has been one of the most educational and rewarding things I’ve ever done. While my thinking on working with incarcerated people is still developing, I will tell you this: the punitive approach to criminal justice is cruel and almost certainly deleterious to everyone involved.

Vacation! I took a real vacation this year for the first time in four years! I went to a small surf town on the Pacific coast of Mexico. I left my computer at home, kept my phone off, and spent my days sleeping, reading, surfing, journaling, and walking along the beach. The world slowed down. Eating a popsicle or taco felt like a spiritual experience. If you haven’t been on a real vacation in a while, do yourself a favor and prioritize one in 2020. You deserve it.


Most years I read a lot of psychology and spirituality, but this year, between grad school and meditation teacher training, I was drawn in different directions. In no particular order, my favorite books of 2019:

The Stormlight Archives by Brandon Sanderson: I spent a huge amount of time in Brandon Sanderson’s Stormlight Archive series, and OMG is it amazing. The series starts with “The Way of Kings” and continues across 2.5 other books with several more in the works. My personal favorite so far is “Words of Radiance”, but honestly, every book in this series is great. If you’re a fantasy fan this series is a must read. 

Macbeth by William Shakespeare: earlier this year M* and I saw “Sleep No More” (if you find yourself in NYC, I highly, highly recommend). In preparation I read Macbeth. Though I remember hating Shakespeare in high school, I loved Macbeth. Turns out Shakespeare is pretty legit. Who knew?! Protip: if you’re like me and struggle to read Shakespearean English check out “No Fear Shakespeare”. It makes understanding the text infinitely easier.

What it Takes: How I Built a $100,000,000 Empire Against the Odds by Raegan Moya-Jones. I don’t read many business books anymore; they’re mostly redundant. However, “What it Takes” stands out. The author has an unusually human and transparent approach to entrepreneurship, leadership, management, and innovation. This was the first book on business that I’ve read in years that felt fresh. One of the things I loved about “Shoe Dog” was how transparent Phil Knight was about building Nike. Raegan Moya-Jones generously offers the same transparency about how she built aiden + anais while also explaining how she thinks about leadership and innovation.

Here is Real Magic: a Magician’s Search for Wonder in the Modern World by Nate Staniforth. If I have a spiritual cousin out there, I’m pretty sure it’s Nate. Both Nate and I fell in love with magic at a young age, became working pros, burnt out, and travelled the world trying to find whatever it is we lost. “Here is Real Magic” is Nate’s memoir about what it’s like to be a working magician, what happens when something you loved becomes a chore, and travel. Though I left professional magic much sooner than Nate, reading this book felt like coming home. In many ways it echoed another favorite, Paulo Coelho’s “The Alchemist.”

Fair warning: I bribed my book club into reading this by promising to do magic for them if they selected the book. While they took the bait, they didn’t love the book. If you don’t have a background in live entertainment (especially as a kid) or interests in magic or travel this book may not be for you. But then again, my book club also disliked “The Alchemist”, so… maybe they just have bad taste.

The Art of Stillness by Pico Iyer. This was a suggestion from my RAIN partner and good lord did it resonate. I read it three or four times during a silent retreat. Though Iyer is a travel writer, in this book he talks about the beauty, challenge, and adventure of being still. It’s accompanied by beautiful photography and great storytelling. Did you know that when Leonard Cohen wasn’t busy being a rock star, he lived as a monastic? Neither did I. If your life is filled with noise and motion, I can’t recommend this book enough.

The Stand by Stephen King. A mishandled chemical weapon kills almost everyone. The survivors who are mostly good move to Boulder, CO. The survivors who are mostly wicked move to Las Vegas. Both parties become aware of one another and battle for control. Like the Stormlight Archives, this book kept me up at night and I ended up missing the characters when I finished the book.

The Murderbot Diaries by Martha Wells. Murderbot, a lethal military robot hacks his governor and becomes self-aware. Along the way he becomes socially awkward, self-loathing, and kinda lazy. In other words, he undergoes a crash course in becoming human. But also Murderbot can kill and out maneuver pretty much everything. The Murderbot Diaries, which starts with “All Systems Red”, is a collection of short and fun books that walk the line between thriller, sci-fi, and entry level existentialism. They’re excellent for when you need a thrilling escape.

Sign up to receive Jason's expertise in your inbox.

Thank you for reading. Sign up to receive the Self-love & Self-Compassion Checklist. You’ll also received articles on the latest strategies and tactics for improving your mental health, mindfulness, and well-being.

I take your email privacy seriously.