Q2 2019 Life Review

Reading Time: 7 minutes

Welcome to my Quarterly Life Review, a big picture reflection on the victories, challenges, and learnings from the quarter.

This review is one of my favorite exercises. It allows me to measure progress, identify challenges, and solidify what I’ve learned.

I publish my review publicly for three reasons: to hold myself accountable, to give you a candid look into my life, and to encourage you to conduct a similar reflection. Let’s get to it!


Calvin and group of people surfing.
Surfing Lesson in Lisbon, Portugal.

Surfing in the Azores Islands

I first fell in love with surfing while living in Nicaragua. When I’m in the ocean on a surfboard, I’m like butter that has finally found its stack of banana pancakes. My restless soul feels at ease.

In May, I headed to the Azores Islands for a surf vacation. Wanting to take my practice to the next level, I worked with a private instructor every morning. He helped me read waves, improve my takeoff, and feel more comfortable in the water. Not only was it an energizing trip, but it confirmed that I’d like to live near an ocean and surf more often.

Craft + Commerce

For the last two years, I’ve worked on my mission to empower 10 million people to live a more conscious and fulfilling life in isolation. Although I’ve connected with a few other creators digitally, it’s mostly been me sitting alone at my computer.

So in June, I headed to ConvertKit’s Craft + Commerce Conference for creators in Boise, Idaho. I wanted to see what it would be like to attend in-person events in my industry.

I had an incredible experience. Not only did I come away with new ideas to improve my work, but I connected with dozens of creators with shared values and interests. I felt like I found a tribe of people on a similar path. I’m looking forward to doing more in-person events.

Lisbon Leadership Summit

This quarter, my team and I organized and hosted a week-long leadership retreat in Lisbon for entrepreneurs and freelancers from a dozen countries. It was an incredibly rewarding experience, both personally and professionally.

In addition to learning about how to create a meaningful week of content and organize a retreat, I connected with a smart and thoughtful group of people. I also had the opportunity to lead two guided meditations, share my love for surfing, and show people around Lisbon.


Calvin in metro station
Metro Station in Lisbon, Portugal.


Travel nearly killed me this quarter. I visited 11 cities, flying 21,000+ miles and spending 5%+ of my waking time at airports and on airplanes. My quality of sleep and physical health suffered, and I consistently felt exhausted and disoriented.

As much as I enjoy the adventure that comes with travel, I’m going to slow my pace in the second half of the year.


Early in the quarter, I read Just One More by Nick Maggiulli. In the article, Nick, a Stanford graduate and classicly successful young professional, explains why he quit drinking. His story resonated and inspired me to become more conscious of my alcohol consumption.

Like Nick, I have enjoyed drinking socially since my teenage years. And even when I drink frequently, I’m still able to perform at a high level in my personal and professional life.

But lately, I’ve felt that drinking alcohol is no longer serving me. In adulthood, I’ve embarked on a journey of higher consciousness, and the reality is that alcohol brings me into a lower state of consciousness. 

Instead of giving up the dirty juice cold turkey, I decided to track my drinking behavior this quarter. To better understand my drinking patterns, I kept a simple spreadsheet that tracked how many drinks I had each day and the context in which I had those drinks.

Measuring and analyzing my behavior led to some interesting insights:

  • I drank alcohol on a higher percentage of days than I would have estimated.
  • I drank more during periods of heavy travel. Friends and new acquaintances often wanted to have a drink to catch up.
  • Drinking reduced the quality of my sleep.
  • Drinking more than 5 drinks in a night impaired my emotional regulation the next day.
  • You cannot rely on memory to accurately understand your habits and behaviors.

These insights aren’t particularly surprising, but they are helpful. In becoming more conscious of my alcohol consumption and getting an accurate picture of reality, I’ve been able to shift my behavior to align with my goals. By the end of the quarter, I said “no” much more often and put myself in fewer situations in which I would be encouraged to drink heavily.

Too many of us are binary with our views on using substances. We think you either have a problem or you don’t. But it’s not binary; it’s a sliding scale. And just because you’re successful and have your shit together doesn’t mean it’s not worthwhile to consciously examine your consumption of substances like alcohol.

Moving forward, I’ll continue tracking my drinking until I fully understand the role that I’d like alcohol to play in my life.


Between managing a full-time job, a long-distance relationship, writing, traveling, and so on, I felt consistently overwhelmed this quarter. Even with robust prioritization frameworks, I fell into the classic trap of trying to do too much.

Doing too much, coupled with significant life changes and not getting enough sleep, led me to have many ups and downs during the quarter. Moving forward, I’ll do less. I’ll also better protect my mind and body by making sleep, meditation, and exercise non-negotiable activities.


Calvin in Porto, Portugal at bridge.
Porto, Portugal.

There is no “right” path in life

The ambiguity of adult life is a mind-fuck. While most of us obsess about making the “right” decision, there often is no “right” decision. There are a series of potential paths that you can take, and rather than being “better” or “worse,” these paths are just different. And you can’t predict with any accuracy how any given path will play out.

This quarter, I made decisions that shifted the trajectory of my career and romantic life. Both situations were ambiguous. There was no clear answer. I couldn’t think my way into the solution. So I listened to my wise mind, made a call, and moved forward.

The difficult part of making decisions in life is that there is no way to test the path you choose against the alternative paths. Navigating life is like being an actor going on cold with one shot to make the scene perfect. We have no rehearsals and no re-dos. So we do what we can – we do our best to make a good decision and move forward.

Instead of getting trapped in the paralyzing pursuit of trying to predict the future and make the right decision, make a call, see how it goes, and pivot if necessary. In all likelihood, it will be okay either way.

Do you hear the birds chirping?

In the Azores Islands, I was struck by the omnipresence of birds chirping. Day and night, birds sang the song of life. As I left, I thought it’d be years before I returned and heard the birds again. 

But then something weird happened. As I traveled to Denver, Boise, and New York over the next few weeks, I still heard the birds chirping.

I realized that hearing the birds chirp had very little to do with where I was. It was more a function of my internal state of being. When I was calm, clear, and present, the birds chirped. When I was trapped in my head with an endless to-do list, there were no birds. 

Hearing the birds chirp is an excellent measure of your presence, the awareness that you bring to each moment in your life. When you hear the birds, you’re on the right path. When you don’t, consider slowing down, taking a breath, and noticing the beautiful world that’s always around.

Do nothing, just stand there

In college, I led week-long wilderness trips for incoming freshman. These excursions were designed to help new students integrate into the university. As a leader, I needed to keep the participants safe. No parent wants to hear that their child was mauled by a bear during the first week of college.

In my health and wilderness safety training course, we learned that if someone has a seizure or falls, we should resist the urge to act immediately. Instead, we should,

“Do nothing, just stand there.” 

Practically speaking, this means observing the situation fully to understand what’s happening. From a place of understanding, we can act appropriately to help the person in need. We can also avoid being blinded by our panic and doing things that will make the situation worse.

This quarter, I realized that “do nothing, just stand there” is a useful tool for many parts of life. In navigating challenging career and romantic changes, my instinct was to start hustling and filling the void so that I could numb the painful emotions that began to consume me.

But I fought this impulse and consciously did nothing. I just stood there, sitting with and observing all of the difficult emotions – fear,  sadness, loneliness, and so on. And while it’s been painful to do this in the short-term, it’s best for my long-term well-being.

By resisting the urge to mask my pain, I’ve been able to see the situations and decisions more clearly. And instead of filling the void with temporary external solutions – substances, another person, work, and so on – I’ve focused on rebuilding internal peace and happiness.

Living by the principle of “do nothing, just stand there” is not easy. It requires patience, courage, and a willingness to look the darkness in the face. But it might just be the antidote you need.

And that’s it, thanks for reading! If you had any wins, challenges, or learnings from the quarter, feel free to shoot an email to [email protected] to let me know.

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