2018 Q1 Life Review

Reading Time: 11 minutes

On November 1, 2017, I was living in Chiang Mai, Thailand.

For the last year and a half, I had been traveling the world and working full-time for a startup. I had scaled a business unit to millions of dollars in revenue, explored 25 countries, built a global personal and professional network, and felt more joy and gratitude than any other period in my life.

I was living a fantasy.

But while my fantasy had served me for a long time, it no longer felt fulfilling. I wasn’t excited to wake up in the morning. I didn’t feel a deep sense of calm when I finished my day. I had everything I needed and felt happiness on a day to day basis, but something deeper was missing.

So instead of continuing to live this narrative that no longer fulfilled me, I decided to make a change.

I knew that I wanted to spend my time and energy helping others. That was the work that excited me most and gave me a lasting sense of joy.

I didn’t know exactly what a career in helping others would look like. I didn’t know what I would be helping with or how I would make a living. I just knew it felt right.

Of course, I went through the logical motions of listing out pros and cons, writing down my fears, and toiling over the different outcomes. But ultimately, I went with my gut.

I decided to make a bet on myself and start creating a path more aligned with my purpose. I decided that life was too short and fragile to do anything different.

I called my boss on November 1st and resigned. My last day would be December 31st.

I said goodbye to a good paycheck. I said goodbye to a promising career path. I said goodbye to the security of the life I knew. All of this was remarkably easy to do once I was clear on my purpose and what I wanted out of life.

Throughout November, I started mapping out my new path and transitioning off of my responsibilities at work. I started getting excited about the future.

And then life happened.

I woke up on the morning of December 1st in a haze. I was in Bali, Indonesia. I had spent the last 48 hours curled up in the top bunk of a hostel bed trying to survive a vicious case of food poisoning.

As I left my room to enjoy some sun, I got a call from my grandma,

“Cal. I’m so sorry, but I found your mom in her room and she was unresponsive. I called the ambulance. I think she took too many pills. Her heart has stopped multiple times. I don’t think she’s going to make it.”


That call marked the beginning of my mom’s thirty-day battle with death.

I’ll spare the details for now, but things got really complicated and intense during that period.

And on December 31st, I turned 25 years, wrapped up my last day at work, and held my mom’s right hand while she took her last breath.

The next day, my new journey began. In an environment of extreme change, pain, and suffering, I had to find the courage to get out of bed and start building my new path.

I started with a mission.

I set out to empower 10 million people to live more conscious and fulfilling lives.

I did not know how I would get there, how long it would take, or if I would earn a living from this pursuit. I simply committed to the mission and the uncertain journey of making it happen.

That’s how my 2018 began. It’s been a wild ride since then. My first 90 days have been an immensely rewarding and uniquely frightening roller coaster.

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

This review is one of my favorite exercises. The structured reflection process gives me an opportunity to see how far I’ve come, digest what I’ve learned, and gain clarity on what’s stopping me from being where I want to be.

I am publishing 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.

I hope you enjoy the insights and stories you find in the review. Feel free to use this structure to reflect on your own life.

4 Victories

My mission

At the beginning of this year, I set out to empower 10 million people to live more conscious and fulfilling lives. It has been extremely challenging and rewarding so far. A big focus has been exploring the different avenues I can pursue to reach more people.

I spent significant time building out calvinrosser.com, which is the home of my work. I have focused on writing, creating resources, and building a community through my newsletter, Life Reimagined.

I’ve also been working one-on-one with select individuals for life and business coaching. I really enjoy working with folks who want to make career moves and entrepreneurs who are looking to scale their businesses.

I have also spent time connecting with other values- and impact-oriented entrepreneurs to identify opportunities to work together. Near the end of the quarter, I partnered with a friend and well-accomplished entrepreneur to lead a personal and professional development retreat on the coast of Nicaragua.

The whole journey has been incredibly exciting, challenging, and inspiring. The most rewarding part has been the connections and feedback that I’ve gotten along the way.

Here are a few things that have landed in my inbox:

“I’ve been truly inspired by your story.”

“Between your Quora answers and our meet up, I have been thinking about my future non-stop this past week. I have experienced a break-through.”

“Calvin, I think it’s awesome that you’re doing this man. I really appreciate the truly human side of what you are saying. I’m used to hearing this type of language in Christian circles but with only a few exceptions not from my secular friends.”

“I’m more pumped to read your email than just about any other email I receive. Great job Cal and great poetry.”

These short notes are humbling and provide meaning to the work I’m doing. They give me signals that I should keep going. They help me get through the periods of self-doubt. They inspire me to continue sharing and putting myself out there.

I’m honored and inspired to keep working on this mission.


I set out to become a better writer in 2018. Writing is a timeless way to reach and motivate more people, and it’s an important part of making my mission a reality. During the quarter, I wrote 57 answers on Quora, 11 blog posts, 9 newsletters, and various resources on my site. I also took a Udemy course on writing and did various writing and journaling exercises to get my creative juices flowing.

Writing has been a lot of fun and a big challenge for me. I had to overcome my limiting belief that I wasn’t ready to write yet and go for it. I had to get comfortable putting myself out there in a very personal way.

I wrote about a diversity of topics on calvinrosser.com: finding meaning in death, using fear as fuel, the psychology of building relationships, things I want to do before I die, how to travel the world with one backpack, my life story, and more.

I wrote about even more things on Quora, including how to overcome procrastination, lessons learned from college, and how to quit your job and travel the world.

During this period, I’ve learned about the art of storytelling, crafted my voice, and clarified my beliefs about important topics. The positive feedback I’ve gotten thus far has built my confidence and gotten me excited to continue improving my writing.

Physical Health

I made my emotional and physical health a priority this quarter after losing my mom and making a big career change. I did particularly well with my physical health, exercising 80% of days during the quarter.

I gained a lot of momentum after doing a 30-day challenge of running at least 1 mile every day. This challenge helped me build the habit of running, and I developed a craving for my daily run.

When I arrived in Nicaragua in February, I also started swimming laps once or twice a day. I’ve always had an affinity for swimming, which is a form of meditation for me, and having a pool available has been a tremendous asset to keeping me physically healthy and emotionally grounded. On the whole, the consistent exercise has left me feeling good and mentally sharp even when working long hours and processing my grief.

Family and friends

I spent significant time with family and friends this quarter. I was at home for a few weeks and took a trip to New York to visit with my closest friends.

After being on the road for most of the last 2 years, I’ve really grown to appreciate and value the time that I spend with close friends and family. And even though I’m on the road again, I’m not letting that get in the way of staying in touch.

I’ve found ways to connect more with email, messages, and video calls. It’s amazing what a quick email or message can do. I feel much more connected now, and that’s something that I want to continue prioritizing in the future.

4 Challenges

My mom’s passing:

Losing my mom to suicide and watching her take her last breath was a very intense experience. The grieving process has been unpredictable and a big part of my life during the quarter.

I’ve faced night terrors, sudden waves of sadness, and mountains of guilt. I’ve had to sort through all of our possessions and decide what to do with them. It’s been heavy and something I’ve needed to grapple with daily while trying to make progress on my mission.

I’ve found some peace through writing about my experience and sharing it with others. In mid-January, I delivered a eulogy at my mom’s funeral to 150+ people. The funeral was a very emotional experience, but there was a tremendous amount of support there to celebrate my mom’s life and be there for my family.

I also gave a presentation to 20 entrepreneurs on how to find meaning in death. The presentation was born in my own pain and experience coping with death in my life.

On multiple occasions, people experiencing deep pain have read my writing and reached out for support. It’s been a humbling experience to connect with these people and to offer some insight into how to work through some of the challenges.

Losing a parent is never easy, and I know that I still have more processing and grieving to experience moving forward.

Overextending myself

This has been a lifelong challenge for me. I have always set lofty goals and worked hard to achieve them. While this is an asset in most instances, I sometimes end up working on too many things and sending myself into overdrive.

This quarter has been particularly challenging. To make progress on my mission, I’ve had to learn a lot of new skills and be accountable for charting my own path without any direction.

I’ve been writing, building a website, coaching, co-creating a retreat, freelance growth consulting, and exploring new opportunities and mediums to collaborate with others and scale my impact. Working on such a diversity of things spreads my focus in many directions and requires me to use very different skills on a daily basis.

Although I’ve tried to prioritize efficiently and give myself more breaks, I can still focus on fewer things and work in more time to relax.

The challenges of entrepreneurship

While being an entrepreneur can be very rewarding, it comes with a unique set of challenges. For every victory, you need to stomach four loses. For every achievement, there are 150 more things you want to get done.

And while there are certainly some feel-good moments, the journey comes with a healthy daily dose of isolation, self-doubt, and wondering if you’re spending your time wisely.

I’ve improved at working through these challenges by building better habits and empowering mindsets, but I’m still adjusting to the entrepreneurial life.  

As I move forward, I’d like to adopt the approach of Sam Walton, the founder of Walmart,

“Celebrate your successes. Find some humor in your failures. Don’t take yourself so seriously. Loosen up, and everybody around you will loosen up. Have fun. Show enthusiasm.”

There’s always more to be done, but it will be important to celebrate progress and have some fun along the way.

Emotional equilibrium

Between losing my mom, the uncertainty of my new entrepreneurial path, and the many endeavors I’m working on, I’ve struggled to find the right balance and emotional equilibrium.

Daily exercise, journaling, meditating, and writing has been immensely helpful in keeping me grounded, but at times, I’ve struggled to feel the sense of joy and fulfillment that makes life so beautiful.

An important part of moving forward will be prioritizing more opportunities to have fun and to continue working through my grief without putting too much pressure on myself.

4 Learnings

Depth matters

In my last 2 years on the road, I’ve had the opportunity to meet many interesting and inspiring people, explore 25 countries, and accelerate my personal and professional growth. These experiences have been wonderful, but they’ve lacked depth.

Over the last 3 months, I’ve stopped pursuing the “new” and instead worked on appreciating and deepening the “old.” I spent lots of time with family, made more time for friends, and housed myself in Nicaragua, a place where I am comfortable and have spent time before.

One of the most rewarding parts of this last three months was working with my grandpa to improve his walking. He had a stroke 1.5 years ago and has been working on his mobility ever since. While I was at home, we set big goals together and started with walking every day.

In one week, he went from walking 275 meters to 500 meters. That’s an 81% improvement in one week! At the same time, his spirit and engagement with the world improved. It was awesome, and the best 15 minutes I spent each day.

In shifting away from chasing the temporary highs of always doing new and exciting things, I’ve deepened my relationships with close friends and reconnected with my family.

Creativity is born in action

To make progress on my mission to help 10 million people, there are an unlimited number of avenues I can pursue. I could have easily gotten paralyzed in research and thinking through the choices.

But instead, I took action. I built a site that wasn’t perfect. I wrote when I wasn’t ready. I started with a newsletter format that I changed the very next week.  

In the process of taking action, not only did I learn a ton, but I got an influx of ideas on new things to try. All the ideas that weren’t clear in my head became much clearer once I started working on them.

And because I put things out there, I benefited from having other people reach out to let me know how I can do things better. This feedback has been tremendously valuable towards improving my work.

When you take action, the idea factory opens, feedback comes in, and you start finding motivation and inspiration in your progress.

Collaboration elevates your work

During most of my life, I have embraced challenges on my own. But over the last quarter, I’ve attempted to shift that mentality and way of being. I’ve started to ask for more help and looked for ways to collaborate with others.

This shift has led to a number of rewarding benefits, including being able to help others elevate their work, new ideas to improve and scale my mission, and opportunities to collaborate on impact-driven projects.

For example, this openness to collaboration led me to start working on a 6 day personal and professional development retreat in Nicaragua with another entrepreneur.

When you find and work with other smart people with similar values, your work becomes better and you have more fun in the process.

If you bury your grief, it will eventually bury you

After losing my mom, my instinct was to hide my pain and protect myself from the emotions. Instead of accepting that instinct, I’ve attempted to pay closer attention to my feelings when they arise and start to understand how they flow into how I think and what I do.

I’ve started to be present with my grief. I’ve listened to it and sat with it instead of forcing it down like I want to. It’s sometimes more painful in the short term, but it has helped prevent me from letting things bottle up and go deeper.

There’s no one right approach for processing grief, but I do believe that burying your grief is when you get yourself into trouble.

And that’s it!

Although I’ve faced a number of challenges this quarter, I’m feeling alive and very aligned with my purpose. I feel excited to work on my mission every day and pumped for the future. And until that changes, I’m going to keep going.

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