Habits and Routines of Writer and Speaker Calvin Rosser

Meet Calvin Rosser, a writer who has the courage to speak freely about how to lead a more fulfilling life.
Habits and Routines of Writer and Speaker Calvin Rosser

Meet Calvin Rosser. One of the most authentic and honest writers talking openly about how to live a more fulfilling life. I connected with Calvin some time ago and was inspired by his down to earth attitude and genuine desire to lead a life of service and contribution.

Here's my interview with Calvin Rosser where he shares his most influential habits, thought provoking questions, and life philosophy.

Who's Calvin Rosser?

Calvin Rosser is 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 about living a more fulfilling life at calvinrosser.com.

What Are the Most Influential Habits in Your Life?

Reading. Reading books is the most important habit I’ve developed as an adult. The knowledge and lessons I’ve learned through reading have accelerated my personal and professional success, making me a better thinker, communicator, friend, and professional.

Meditation. While I experienced severe heart palpitations in Buenos Aires in 2015, a friend took me to a public park and guided me through a short breathing exercise. This was my first formal meditation session. When I returned home to a grueling job as an investment banker in New York, I started meditating regularly to ease my anxiety and lower my levels of stress.

Since then, I’ve explored various types of meditation and read books to deepen my understanding of the practice. Through these efforts, meditation has become an invaluable part of my life. It’s enabled me to become a more conscious observer of my thoughts and experiences, allowing me to cultivate a healthier relationship with the tape that’s always playing in my head. I’ve become less reactive, less entrenched in destructive thought patterns, and more grateful for the human experience.

Weekly Life Review. Every Sunday, I spend 30 minutes reflecting on my prior week. I summarize progress against my quarterly goals and document victories, learnings, and challenges from the week. I then set priorities for the coming week. I send this review to a group of close friends to hold myself accountable and keep my friends updated.

The weekly review calms my soul. It allows me to track progress, clarify priorities, cement learnings, and solve problems in a simple and structured way.

Exercise. Ever since an uncle made fun of me for being a chubby teenager, regular exercise has been a vital part of my life. If I’m feeling down, the first thing I do is get up, jump, and wave my hands in the air. Motion creates emotion. While I don’t enjoy all types of exercise, I’m a big fan of yoga, swimming, running, and weight lifting.

How Do You Set Goals and Manage Time?

I’m a rigorous goal-setter. I use a variant of the OKR system to set quarterly and annual goals for my career, health, finances, learning, leisure, and relationships.

To track results and be accountable, I measure daily progress in simple excel sheets and write a weekly report to my friends with progress against my goals, learnings, challenges, and priorities for the upcoming week. At the end of each quarter, I review my weekly reports, evaluate how well I did against each of my goals, and set goals for the next quarter.

This goal-setting system provides me the clarity, accountability, and flexibility I need to move in the direction I want to go. For anyone interested in learning more about how to adopt and implement this system, I’ve written an in-depth goal-setting and achievement guide that includes examples and templates.

In terms of time management, I use Google Calendar. I schedule calls and meetings in blocks and ensure that I have at least a few consecutive hours of unstructured time every day. During my unstructured time, I focus on completing my top three objectives for the day.

How Are You Modeling Your Life?

After losing two of the most important people in my life to sudden death, I’ve learned to appreciate the precarious and impermanent nature of life. Life is short, and I believe in designing a life that brings you immense joy and fulfillment.

My joy and fulfillment come from learning, contribution, and relationships. As long as I’m consistently growing, helping others, and investing in relationships that I value, I know that I won’t be on my deathbed with too many regrets.

I also believe in living a principle-driven life, and I do my best to live by principles that improve the quality of my life and interactions with others. A few of the most important principles for me are: be present, choose your response, pay it forward, choose courage over comfort, and seek to understand, not judge.

Can You Describe Your Work Process and Thinking Behind It?

Every morning before I start working, I write down the three most important objectives for me to accomplish that day. For example, my list from yesterday was: draft the content plan for the leadership summit, meditate and exercise, and publish the goal-setting article. This list gives me the clarity I need to have a focused and productive day. Even if I have more to do at the end of the day, I can rest easy if I complete my three objectives.

I also try to structure the day around my productivity cycles. In the morning when I’m fresh and have a full tank of creativity, I write or do analytical work. Once I hit an early afternoon lull, I take a short nap, read, and cruise through administrative tasks and Slack messages. When I get a second wind in the evening, I switch to strategy work and begin prioritizing the next day.

What Do You Eat for Breakfast?

I keep my breakfast simple and light so that I can eat quickly and not feel sluggish. Most mornings, I drink coffee with milk and eat an avocado with pink Himalayan salt. If I’m feeling spunky, I’ll make scrambled eggs and bacon or a shake with milk, whey protein, and a banana.

How Do You Train Your Body and Mind?

For my body, I run, swim, or lift weights three to four times a week. On good weeks, I’ll do yoga at least once. I also get a massage once a month to relieve lower back pain and tightness in my legs from frequent travel and running.

For my mind, I meditate, read, and write. I try to meditate every day. I like to meditate a few hours after I begin my work day, and if possible, I do it outside while the sun shines. On the reading front, I don’t read every day, but I typically finish 30 to 40 books a year.

Writing has also been a powerful tool for training my mind. Whether I’m keeping a simple free-form journal or working on structured articles, writing makes my soul feel at ease. There’s something divine about finding the best way to clarify your thoughts and communicate those to other people. When I publish an article, I go for a run, and I feel liberated and amazing.

How Do You Meet and Connect with People?

I spend most of my time traveling, so on the personal side, I meet people in all types of situations and places. Professionally, most of the people I meet come through introductions from friends or colleagues. While traveling, two principles have helped me better connect with people from all walks of life.

The first principle is to “seek to understand, not judge.”

If I meet someone who I don’t jive with or who I disagree with, instead of judging and categorizing that person, I’ve trained myself first to understand them.

  • Where did they grow up?
  • What do they read?
  • What do they value?

When you fight the natural tendency to judge people and build the habit of being understanding, you have more interesting, meaningful, and pleasant interactions with everyone.

The second principle is always to ask, “What can I learn from this person?”

When you adopt this principle, no matter who you meet - big shot CEOs, recovering drug addicts, irritated Uber drivers, etc. - you approach the conversation from a place of curiosity. And when you’re curious, you judge less, listen more deeply, ask better questions, and learn a lot about how people and the world work.

With all of my relationships, I value depth over breadth. I’m happiest when I have long and meaningful conversations with one person or a small group. I typically don’t enjoy being in environments where I’m having lots of surface-level chats. Given this preference, I typically attend events and engage in environments that facilitate depth.

What Are Your Sleeping Rituals?

I don’t have a regular sleep schedule since I often work whenever I’m feeling productive, but most nights I go to bed between 10 pm and midnight and wake up between 6 am and 8 am. I also use binaural beats to take 30-minute naps on most afternoons. After a productive morning, I need to recharge before doing a second cycle of work during the evening.

What Are Your Investing Habits?

I grew up very poor, and for the first 22 years of my life, I committed myself to escaping the world of financial scarcity. As I began earning a steady paycheck, I read dozens of books and articles to understand the financial principles and practices that would enable me to grow and protect my wealth.

I now have a simple, automated system that allows me to spend freely and achieve my financial goals with minimal effort. I invest most of my capital in Wealthfront and Vanguard’s VTSAX index fund. I also keep cash in a high-interest online savings account and have a small amount of play money to put in stocks, cryptos, or other investments that I make for fun.

In terms of how I spend my money, I invest in learning, people, and experiences. I’d much rather buy 50 books or fly across the world to visit friends than own more expensive shoes or have more stuff in my apartment. When I lived out of a backpack on the road for a few years, I developed an appreciation for living with less, and that’s a principle I intend to live by throughout my life.

What Books, People, Experiences Shaped Your Thinking?

Books. Reading great books has allowed me to transcend the limitations of my direct experience and transform my life by tapping into the knowledge of the world’s greatest thinkers. I publish summaries, lessons, and notes for all of the best books that I’ve read, but a few of the most influential reads and what they taught me are:

People. So many people have helped me along the way. My now-deceased mentor, Howard Sherman, helped me understand the value of my difficult childhood, supported me financially, and guided me to getting accepted to Princeton University. He taught me the importance of paying it forward, a lesson that inspired me to live a life of contribution.

My paternal father was a raging drunk and gambler who left my life at an early age, but my grandpa stepped up to fill the gap. His optimism, integrity, and patience have guided me at every turn of life. Finally, my mom dedicated her life to giving me the freedom I needed to pursue my dreams. She committed suicide in 2017, but I carry her authenticity, belief, and compassion with me every day.

Experiences. After I left my unfulfilling job in investment banking, I had the opportunity to travel to 30+ countries while working full-time. This period of my life led to immense personal and professional growth. I came out of the journey with a clearer understanding of what I wanted out of life, deep compassion for the human experience, and a desire to continue learning and giving back in meaningful ways.

I’m a curious designer, marketer, and writer from Lithuania. Co-founder of Best Writing and Port Surfer, marketing advisor at App Idea and growth manager at saas.group. Love reading great books, building stuff online, designing systems, optimizing lifestyle, learning new skills, playing basketball, lifting weights, and traveling. If you like my writing, check out my newsletter.

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