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Calvin Rosser: “Practicing gratitude”

Practicing gratitude. While navigating a stressful time in my career in 2016, I stumbled across Shawn Achor’s Ted Talk, “The happy secret to better work.” Shawn details a 21-day positivity challenge, which includes writing down three things for which you are grateful every morning. After doing this exercise for a month, I kept going. This […]

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Practicing gratitude. While navigating a stressful time in my career in 2016, I stumbled across Shawn Achor’s Ted Talk, “The happy secret to better work.” Shawn details a 21-day positivity challenge, which includes writing down three things for which you are grateful every morning. After doing this exercise for a month, I kept going. This simple gratitude practice takes two minutes, and it transformed how I thought and felt about the world. It helped me stop focusing on what’s wrong and instead become aware of the good in my life. Whether it’s warm clothes, a cup of coffee, or being healthy, the good is always there — it’s up to me to find a way to see it.


As a part of my series about “Mental Health Champions” helping to normalize the focus on mental wellness, I had the pleasure to interview Calvin Rosser, an infinitely curious writer, speaker, and community builder on a mission to empower 10 million people to live a more fulfilling life. After growing up in poverty in Florida, Calvin graduated magna cum laude from Princeton University. He began his career as an M&A banker on Wall Street and later joined a $1B+ startup in the talent space. While scaling one of the company’s business units, he traveled to 25+ countries. He now leads a fully remote, global team of community builders and writes at calvinrosser.com.


Thank you so much for joining us! Can you tell us the “backstory” about what brought you to this specific career path?

My story begins in Orlando, Florida. My dad disappeared early in my life, and while my mom did her best, we lived an unstable existence with very little money. I didn’t know it until later, but my mom struggled with severe anxiety and depression for most of my childhood.

After enduring a string of violent boyfriends and moving elementary schools multiple times, I became angry at the world. I didn’t know how poor we were or how well other people lived, but I did know that I wanted a more comfortable and stable life. I despised the world of scarcity, and I committed to finding a way out. Instead of letting my anger cripple me, I channeled it into an insatiable drive to stand out in the classroom. I couldn’t control my living conditions, but I could control how hard I studied in school.

Eventually, my dedication to my academics paid off. With hard work, luck, and support from a generous mentor, I was accepted to Princeton University on full financial aid. This was my opportunity for a better life, and I wasn’t going to waste it.

At Princeton, I focused on securing a job that would help me escape the poverty of my first two decades of life. After graduating, I landed a high paying job at a big investment bank in New York. Within months, I could afford afternoon coffees and weekly dinners with friends. This was immensely liberating.

But while I had finally achieved the financial comfort that I craved for my entire life, I still felt unfulfilled. As a banker, I was spending 15 hours a day in a cubicle doing work that didn’t excite me for people who didn’t inspire me. No paycheck was worth that existence.

Hoping to create a better life, I left Wall Street and joined a fully remote startup in the talent space. Within weeks, I packed my life into a small backpack and bought a one-way ticket to Cartagena, Colombia, beginning a new life as a digital nomad.

Over the next 18 months, I grew one of the startup’s business units from 0 to millions of dollars in revenue while traveling to over 25 countries. It was a wild and immensely rewarding personal and professional ride. For the first time in my life, I felt a deep and enduring sense of calm, gratitude, and joy.

After spending so much of my life angry at the world, I was astounded by how much better life could get. I also knew that millions of people, including my mom, were stuck in the cycle of anger, anxiety, fear, resentment, and self-doubt. I felt called to start chipping away at this problem. I wasn’t sure how I would do it, but I knew that I wanted to spend my time helping others find balance and fulfillment.

So I left my job and started a mission to empower 10 million people to live a more fulfilling life. I began working on the mission by writing about my story at calvinrosser.com.

Two weeks after making this career transition, my mom committed suicide. This was a soul-penetrating blow. After years of trying to help my mom get to a better place, it was devastating to see her life end in this way.

Instead of hiding from my pain, I channeled it into my writing. I openly shared my experience knowing that I wasn’t the only one suffering. When I shared the eulogy I wrote for my mom, three strangers reached out to me to say that they were not going to commit suicide because of what I had written. Those messages were deeply moving and motivated me to keep going on this uncertain, but meaningful path.

I now work on the mission every day.

According to Mental Health America’s report, over 44 million Americans have a mental health condition. Yet there’s still a stigma about mental illness. Can you share a few reasons you think this is so?

Mental illness is difficult to understand. My mom suffered from severe depression and anxiety for decades, and even though I knew her better than anyone, it wasn’t until the end of her life that I began to understand the complexity of her battle with mental illness.

For years, I tried to help her by using the rational, problem-solving lens that I had learned in school. If she was in a rut, I’d tell her to be grateful that things weren’t worse, to take responsibility for her problems, and to start taking action. That’s how I had solved problems in my life, so it seemed like a reasonable response.

The issue is that mental illness doesn’t work like this. Not only is it immune to rationality, but it’s incredibly complex and different for every individual. My mom had been abused, raped, and bullied. Every day, she felt shame and self-doubt, and she was on a new cocktail of medications every month. Her struggles were deep-rooted and didn’t come with a quick or easy solution.

My mom didn’t need a list of self-help advice. She needed non-judgmental, compassionate professionals with the time, training, and resources to work with her on a comprehensive plan.

If we want to break down the stigmas about mental illness and create a healthier environment in which we can discuss and solve mental health challenges, we need need to transcend our culture’s obsession with rationality and individual responsibility. To do this, we need to replace judgment with understanding and blame with compassion.

Can you tell our readers about how you are helping to de-stigmatize the focus on mental wellness?

In 2018, I ignited a mission on calvinrosser.com to empower 10 million people to live a more fulfilling life. On that mission, I write, podcast, and speak around the world about how we can all find balance and meaning across all areas of life — our career, finances, health, relationships, personal growth, and leisure.

The most impactful piece that I’ve written is about my mom’s path to suicide and what we can learn from her life. I hope that this story will help people understand how complex, important, and painful mental health issues can be, especially if we don’t work together to find better.

In all of my work, I focus on telling stories, instead of handing out prescriptions. I don’t have it all figured out, and I don’t believe anyone does. But in candidly sharing my struggles, experiences with mental health, and lessons learned, I hope to help others feel less alone and better equipped to solve the challenges in their lives.

Was there a story behind why you decided to launch this initiative?

Like so many people, I grew up angry at the world. The odds were stacked against me, and that seemed unfair. But thanks to a compassionate mom who believed in me, I believed in myself. Thanks to grandparents who taught me good values, I set ambitious goals and worked hard. And thanks to a mentor who took me under his wing, I knew that I could create a better future. I’m so fortunate to have had these people in my life.

So when I had the opportunity to study at one of the nation’s best universities, achieve financial stability, and carve out a meaningful career at such a young age, I felt not only immense gratitude and joy, but also a deep obligation to give back. I may have worked hard to get where I was, but without the people who helped me along the way, I could have just as easily ended up on the streets or in prison.

My mission to help others live a fulfilling life started from this deep desire to pay it forward. There are millions of people suffering, and I wanted to find the best avenues to give back and help soften that pain. And after growing up with a mom who faced crippling anxiety and depression and ultimately decided to take her life, I knew just how deep this suffering could be.

Everyone gives back in different ways, but for me, writing about my story and lessons learned made the most sense. I realized that some of the ways in which I had learned to find meaning, perceive the world, pursue goals, conquer obstacles, and engage with others could be incredibly helpful for other people.

If nothing else, I want people to believe in themselves and the opportunity to create a better reality. My mom taught me the power of belief, and belief is everything.

In your experience, what should a) individuals b) society, and c) the government do to better support people suffering from mental illness?

Individuals, families, psychiatrists, therapists, universities, governments, and society need to stop working as fragmented units and start working as a unified team. To start working as a team, we need to create an environment in which everyone involved can safely and comfortably discuss their challenges and ideas.

Individuals need to express their struggles without being criticized or misunderstood. Families need to discuss the unique challenges of helping a struggling family member. Psychiatrists and psychotherapists need to be more open about how they struggle to help patients. Governments need to provide more funding for research and better institutional support. Universities need to create healthier campus environments and dialogue. It’s essential that everyone involved has the space to voice their perspective.

As a society, we need to stop perpetuating the “everything’s good” message. Life is difficult. It’s not an easy ride with happiness around every corner. Every person struggles, whether that’s with fear, anxiety, self-doubt, a difficult boss, depression, and so on. Life is full of challenges, and we need to stop sweeping that reality under the rug.

With increased openness, awareness, and candor about life’s universal struggles and the difficulties of mental illness, we can accelerate progress. Individuals will see that they are not the only ones who are struggling. More bright and capable minds will focus on finding better approaches. And we will be able to throw away unhelpful solutions and adopt the ones that work.

Over time, the stigmas associated with mental illness will lose their power. When we bring the darkness to light, it will slowly fade. People will realize that to struggle is human, not a weakness.

What are your 6 strategies you use to promote your own wellbeing and mental wellness? Can you please give a story or example for each?

There’s definitely no one-size-fits-all solution, but here are a few practices that have worked with for me.

Meditating: I started meditating in 2015. After having severe heart palpitations in a Buenos Aires nightclub, a friend took me to a public park and guided me through a short breathing exercise. Shortly after, I started meditating regularly. I use the Headspace and Waking Up apps. Meditation is a practice that enables you to become a more conscious observer of your thoughts. And in doing so, you develop a healthier relationship with the tape that’s constantly playing in your head. You become less reactive, less entrenched in destructive thought patterns, and more grateful for the human experience. It’s amazing.

Practicing gratitude. While navigating a stressful time in my career in 2016, I stumbled across Shawn Achor’s Ted Talk, “The happy secret to better work.” Shawn details a 21-day positivity challenge, which includes writing down three things for which you are grateful every morning. After doing this exercise for a month, I kept going. This simple gratitude practice takes two minutes, and it transformed how I thought and felt about the world. It helped me stop focusing on what’s wrong and instead become aware of the good in my life. Whether it’s warm clothes, a cup of coffee, or being healthy, the good is always there — it’s up to me to find a way to see it.

Asking perspective-expanding questions: If I feel myself going down a negative mental spiral, it’s often because I’m not keeping a problem or situation in perspective. I get lost in the difficulties of the moment. When I recognize that this is happening, I ask myself questions that expand my perspective and help me stop the negative spiral. Some of my favorite questions are: Will this matter in 10 years? Have I overcome this emotion in the past, and if so, how? What’s the smallest action I can take to make progress on this problem? What can I learn from this situation?

Taming my iPhone: In the few years, I’ve consciously built a healthier relationship with the technology in my life. Three practices have helped significantly reduce phone-related anxiety:

  • Airplane mode morning: To prevent checking my phone and receiving distracting emails or notifications when I first wake up, I set my phone to Airplane mode before going to bed. Then, I spend the first 20 minutes of my day journaling, meditating, and reading without any distractions.
  • Turn off social media notifications: You don’t ever need to know when someone tweets or comments on an Instagram post. These notifications are nothing but dopamine hits contributing to our increasing inability to focus.
  • No phone Saturday: When possible, I do not use my phone on Saturday to give my brain a break from being constantly plugged in. I always feel more recharged, focused, and productive after the hiatus.

Exercising: Exercise is one of the most important parts of my mental wellness routine.If I’m feeling down, the first thing I do is get up, jump, and wave my hands in the air. Motion creates emotion. I don’t like all forms of exercise, but I do enjoy yoga, swimming, running, and weight lifting.

Sunday Life Review: Every Sunday, I spend 30 minutes reflecting on and writing about my prior week. I detail progress towards my goals, celebrate key victories, break down challenges, and determine my focus for the upcoming week. This weekly review calms my soul and grounds me. It allows me to see how far I’ve come and to quickly solve any problems I might be having.

What are your favorite books, podcasts, or resources that inspire you to be a mental health champion?

Read Man’s Search for Meaning by Viktor Frankl. I stumbled across this book while traveling through South America. At the time, I wanted to navigate the creeping nihilism in my life and find ways to help my mom with her anxiety and depression.

Viktor Frankl was an Austrian neurologist and psychiatrist who spent years suffering from extreme hunger, brutality, and cold in Nazi concentration camps. His wife, mother, and father died in the camps.

Despite his tragic and dehumanizing experience, he emerged an optimist and later founded logotherapy, a school of psychotherapy contending that humans are motivated by the search for meaning.

Frankl’s story and theory helped me see that meaning is what moves us forward and allows us to endure the inevitable tragedy, malevolence, and existential concerns of life. I’ve used Frankl’s theory to combat nihilism in my life and to help others who are struggling. Often, helping someone find a source of meaning in their life will help them tremendously.

I also recommend It’s All Your Fault by Bill Eddy. One of the ideas in the book is to “seek to understand, not judge.” If we all applied this principle to our daily interactions, the world would be a much better place.

Thank you so much for these insights! This was so inspiring!

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