2018 Annual Life Review

Reading Time: 9 minutes

2018 was a wild ride.

I navigated the devastating loss of my mom to suicide, started and scaled my mission to empower 10 million people to live a more fulfilling life, ignited my career as a writer, gave my first big public talk, conquered months of anxiety and self-doubt, and began leading a full-remote team of community builders at a $1B+ organization.

Below is my 2018 Life Review, a big picture reflection on my year. In it, I celebrate victories, break down challenges, and distill key learnings.

This annual review is one of my favorite exercises. It allows me to see how far I’ve come, clarify and overcome challenges, and digest what I’ve learned.

I publish my review publicly for three reasons: to hold myself accountable, to give you a candid look into my evolving and imperfect life, and to encourage you to conduct a similar reflection.

I hope you enjoy the insights and stories you find in the review.


First ski season in Colorado.

Friends and family

After two years of traveling to 30+ countries and meeting new people, I slowed down in 2018 and focused on deepening relationships with close friends and family. Some of the highlights include living in New York with good friends, hanging out in Florida with my grandparents, spending a week in the desert with a good friend, living in San Francisco with my college roommates, and moving to Denver with my best friend.

While investing in the “old” limited my exposure to the “new,” I cultivated a new appreciation for the importance and meaning of prioritizing the vital few relationships that matter.

My mission

On January 1st, I set out on a mission to empower 10 million people to live a more conscious and fulfilling life.

On my mission, I experimented with many endeavors – writing articles and weekly newsletters, coaching people through life challenges, launching my career as a public speaker, bootstrapping a leadership retreat in Nicaragua, and building relationships with other thoughtful, contribution-oriented entrepreneurs, to name a few.

Along the way, I made many mistakes and learned about my interests, skills, and weaknesses. The most rewarding part of the journey was interacting with the hundreds of people who have chosen to engage with my work.

The group included a diverse and thoughtful range of folks, including burned-out professionals looking to find meaning in their careers, creatives seeking the courage to pursue their passions, entrepreneurs scaling their businesses, college students traveling abroad for the first time, finance professionals craving an escape from the cubicle, recent college graduates looking for more out of life, and mothers who have lost their children.

These interactions provided meaning to my work, deepened my interest in serving others, and inspired me to continue finding ways to deliver more value.


I began my career as a writer in 2018, and it’s been an intense, challenging, and immensely rewarding journey since then. Throughout the year, I wrote 30 blog posts, 136 answers on Quora, and 42 editions of my Sunday newsletter, Life Reimagined.

To improve as a writer, I completed a writing course on Udemy, incorporated feedback from readers, read books on writing, and developed my expertise in storytelling. I still have a long way to go, but I’m incredibly proud of the progress I’ve made.

The three articles that I’m most proud of are:

12 Practices That Have Improved My Life

How to Use Fear as Fuel for Growth

My Mom’s Path to Suicide: Battling the Darkness in a Broken System

In 2019, I will continue writing articles, sharing useful thoughts and recommendations in Life Reimagined, and begin writing my first book. If you’d like to receive my weekly articles, ideas, and recommendations designed to help you live a more fulfilling life, you can enter your name and email below.


For my entire life, I’ve been plagued by extreme social anxiety about dancing. Tired of feeling uncomfortable and anxious on dance floors, I confronted this anxiety head-on in 2018.

While I was living in New York, I ventured alone to my first ecstatic dance class. Ecstatic dance is a judgment-free, free-for-all dance practice that allows participants to express themselves through movement. My first class was not only incredibly fun, but it left me feeling a healthy dose of gratitude for and connection with the other participants.

After that first experience, I realized how ecstatic dance could help me overcome my lifelong fear of dancing. And while I was at Burning Man in the Nevada desert, I participated in two more sessions. I was able to loosen up, liberate myself from my fears, and begin moving my body to the rhythm of the beats.

I left Burning Man and 2018 with the worst of my social anxiety about dancing behind me. It’s been a lot of challenging work, but the newfound lightness and joy I find through dancing are well worth the effort.


In late June, I joined Toptal’s executive team as the Head of Community, and for the last 6 months of the year, I led and managed a fully remote, global team of community builders. The team organizes events around the world and creates initiatives designed to add value to the lives of the freelancers in Toptal’s network.

This role has taught me invaluable lessons about the art of leadership and strengthened my ability to drive impact through leading a team.

Travel and adventure

While I slowed my travel schedule in 2018, I still made it to 10 countries outside of the United States, including Albania, Bosnia and Herzegovina, Costa Rica, Croatia, England, France, Montenegro, Nicaragua, Poland, and Spain.

Over the past few years, travel has been an indispensable driver of my personal growth and increasing understanding of the complex and infinitely interesting world we live in.

During my travels in 2018, I had the opportunity to engage in many activities that excited and energized me, including canyoning, hiking, skiing, skydiving, and surfing.


Thinking in Budva, Montenegro.


At various points throughout the year, I let my emotional, mental, and physical health slip. The most significant contributors to the problem were too little sleep, too much alcohol consumption, and failing to exercise, meditate, and journal consistently.

The shortcomings with my health were the direct result of prioritizing my entrepreneurial endeavors over my health. In 2019, I’m fully committed to my health. Without it, I’ll never achieve what I’ve set out to do.


2018 started the day after I lost my mom to suicide, an event that changed my life. For the first few months of the year, I confronted night terrors, felt waves of sadness, dealt with immense guilt, and struggled to experience joy.

While I navigated these challenges, I pushed myself too hard in my work and failed to practice self-compassion. The result was multiple periods of burnout and an unstable mind. Although I ended the year in a healthy frame of mind, my mom’s passing was a big driver of many of the challenges I faced in 2018.


At the beginning of the year, I quit my job and began my mission to help 10 million people live a more fulfilling life. On this pursuit, I explored many different avenues to maximize my impact – building calvinrosser.com, learning new skills, starting new social media channels, writing, coaching, speaking, and connecting with others, to name a few.

While this period of exploration taught me about what I enjoy doing, it also left me feeling constantly overwhelmed and unsure about where to focus. Without a narrow set of priorities to ground me, my time and energy were fragmented in too many directions.

In 2019, I have set a narrow set of goals to better guide and prioritize my efforts.

Self-doubt and confidence

After months of working on my mission and a series of relationship and business failures, I lost my confidence and experienced extreme self-doubt. Every day, a little voice inside my head told me that I wasn’t good enough and that I was wasting my time.

Tired of listening to this voice, I took action and found a way forward. After a few months, I carved out a path that brought back the joy, confidence, and meaning in my life.


Consistently reading books is the most valuable practice that I’ve adopted since graduating from college. Books soothe the soul and allow you to tap into centuries of knowledge and wisdom from the world’s greatest thinkers across every discipline.

While I picked up over 35 books in 2018, I failed to finish many of them. Throughout the year, I struggled to focus on the book at hand, and I too quickly jumped to the next book. Ultimately, this inability to focus and finish books led me to extract far less value out of the books I read.

In 2019, I’ve decided to read fewer books, at a slower pace. I now recognize that it’s not about how many books you read, but rather the quality of time you spend with the books worth reading. If you’re interested in reading more this year, check out my detailed book summaries and notes for ideas on what to read.


Playing a Tibetan singing bowl in Durmitor National Park.

Surround yourself with good people

In the first quarter of 2018, I entered a business partnership that ended very poorly. In addition to learning what to look for in a business partner, I also gained an appreciation for surrounding yourself with people who want the best for you.

Whether it’s with friends, family, clients, or business partners, it’s important to avoid people who want to change you, people you can’t trust, and people who don’t make you a better person. If you find yourself with these types of people, quickly remove them from your life and move on.

Life is better spent with the few people who you enjoy spending time with, who value you for who you are, and who want you to succeed. These people will help you live a good life, endure the hard times, and identify valuable opportunities.

Know your risk tolerance and relationship with money

In 2018, I decided to pursue my passion for helping people on their path to fulfillment. I took on this pursuit with the condition that I did not need to make money for a year. And while I had enough capital to sustain myself for the year, I quickly learned how having a stable income was an important factor in my own journey of feeling secure and fulfilled.

After a few months of working on my mission, which was by far the most rewarding work I had done in my life, I began to feel uneasy about not having a consistent stream of income. Specifically, I felt a growing and irrational fear that I would end up on the streets without anyone to help me.

Reflecting on the experience in the months after I solved my income problem, I realized that my fears stemmed from my experience growing up in poverty. In short, the realities of my childhood had conditioned me to have a lower tolerance for financial risk than I had anticipated.

While I still want to spend my life doing meaningful things without focusing on money, I now know that I can’t completely ignore money in the equation. If I do, my well-being will suffer.

If you want to do something, then do it

I started writing this year. I didn’t have any formal training or evidence that I would be any good at writing, but I started anyway. And while I’m still new to the craft and have a lot of room to grow, I’m regularly told by people that they enjoy my writing.

What this experience taught me is that whatever you want to do in life, just start doing it. Don’t wait for the right time or for someone to confirm that you can do it. The time may never come, and people may never encourage you.

Once you start, you’ll learn what it takes to be good at your craft and whether you enjoy it enough to do the hard work that mastering a craft entails.

Whatever you want to do, stop waiting and making excuses. Get after it, and surprise yourself with the results.

It’s never about you

It’s so easy to go through life taking everything personally. If someone is rude or fails to understand you, it’s easy to write them off as an asshole who just doesn’t get it. But if you want to be successful and have healthy interactions with people, it’s essential to remember that not everything is an attack on you.

Every person has a different background and set of experiences that drive their perceptions, attitudes, and actions. Further, most people are going through something that you’ll never fully understand. Perhaps they are incredibly insecure, just lost a parent, or had their heart broken. You really don’t know, and it’s both self-centered and naive to believe that you do.

So while it’s easier to castigate people for being shitty, take the noble path of remembering how people’s different experiences and the events happening in their lives may influence the way in which they interact with you. Almost no one is out to get you. Everyone is too consumed with their own problems to care about what you’re doing.

No one knows what they want to do in life

The big secret of adulthood is that no one really has life figured out. Most people will tell you well-crafted narratives about who they are and what they want, but many of these narratives are untested regurgitations of what people have been pressured to do by society, their parents, or their peers.

So if you’re confused or uncertain about your life, welcome to the club! Once you accept this reality, you can get started with the fun and rewarding work of experimenting with the many ways in which you can spend your limited time in this world.

If you’re completely lost, listen to my second podcast episode, “Deciding what to commit your life to.” In it, I explore how I’ve used a mission to begin moving my life in a direction aligned with what brings me joy and fulfillment. I suggest a messy process of exploring different paths that, over time, gets you closer to a world in which you’re excited to live.

And that’s it! Thanks for reading my 2018 annual life review. I’m incredibly excited to continue exploring, learning, and contributing in the next year. I wish you a phenomenal 2019.

If you want to follow my journey and receive regular updates with articles, resources, and recommendations to help you live a more fulfilling life, please feel free to subscribe to my weekly Sunday newsletter, Life Reimagined, in the big box below!

Finally, if you learned anything valuable in 2019, leave a comment below!

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