Today, we’re sharing our interview with Calvin Rosser, a 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 Rosser graduated magna cum laude from Princeton University. He began his career as an M&A banker on Wall Street and later joined Toptal, a fully distributed, $1B+ organization in the talent space.
While scaling one of the company’s business units, he traveled to 25+ countries. He now leads a fully remote team of community builders and writes about living a more fulfilling life at calvinrosser.com.
How Does Your Remote Workday Look Like?
I don’t have a “standard” day. In general, I try to structure the day around my natural productivity cycles. When I’m fresh and have a full tank of creativity in the morning, I write and do analytical work. Once I hit an early afternoon lull, I take a 30-minute nap, work out, 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 planning for the next day.
What Tools Do You Use to Get Things Done?
With tools, I prefer simplicity. I get the majority of my work done with G Suite applications, Slack, Zoom, and Evernote. I also create to-do lists, take notes, and brainstorm with pen and paper.
What’s the Biggest Challenge of Remote Work?
Communication. There are many communication dynamics at play in a remote environment:
Information overload. Slack, Zoom, Trello, and other companies have made digital communication and collaboration frictionless and cheaper. While these developments have facilitated the remote work revolution, they have also created unique challenges. With so many tools, messages, and alerts, most of us experience information overload. As we try to keep up, we skim more often and respond more quickly. In this environment, we’re significantly more likely to send unclear messages and misunderstand messages we receive from others.
Cultural differences. In remote working environments, it’s common to work on teams of people who don’t share a common location, time zone, culture, or language. This environment is ripe for communication gaps and misunderstandings. The Culture Map by Erin Meyer is a great book that explores the many ways in which communication differs across cultures and how we can bridge the gap.
Intention and tone. Because we aren’t physically present with colleagues in a remote working environment, we have fewer cues to understand the intent of our colleagues. So when we receive a Slack message or hop on a Zoom call, we’re more likely to misunderstand the intention and tone behind the message. If we assume mal-intent when there is none, that can cause unnecessary strain on working relationships.
Uncomfortable conversations. Not being physically present with your colleagues also makes it easier to avoid difficult conversations. For example, if you find it challenging to work with someone, you don’t need to see that person in the office every day. You might only have to see the person on a 30-minute video call every week. So instead of delivering feedback or discussing the relationship problems, you might avoid the issue entirely.
What Are the Advantages of Remote Work?
Remote work allows you to design life on your terms. Whether you want to travel the world, spend more time with your newborn and husband, surf in the mornings, or nap every afternoon, remote work gives you the flexibility to create the life that works best for you.
In a healthy remote working environment, results matter more than hours spent in the office. So as long as you deliver results, you can escape the constraints and burdens of the 9 to 5 office model. In the long-run, you can create a more joy-filled and fulfilling life.
What’s the Future of Remote Work?
I think we’ll see more smart, motivated, and capable people choose to ditch traditional 9 to 5 office arrangements in favor of remote opportunities that pay well, offer career growth, and provide the flexibility to design life on your terms.
As the best and brightest talent shift toward the remote model, more companies will become comfortable with remote arrangements in order to attract top talent. This trend will accelerate as social norms shift and technological progress further erodes the necessity of being in an office.
As the remote working population grows, we’ll also see an increase in businesses focused on creating a sense of community and connection for remote workers. Remote work can be isolating, so there’s a vital need for high-quality coworking spaces, coliving experiences, and in-person events that engage people and give them a sense of community.
What Made You Consider Remote Work?
I unintentionally stumbled into the world of remote work. To find my financial footing after college, I began my career as an M&A banker on Wall Street. While I enjoyed the security of a steady paycheck, I despised spending 15 hours a day in a cubicle doing work that didn’t excite me for people who didn’t respect me. I knew there had to be more to life, so I began planning an escape from the cubicle.
As I explored different career options, I spoke with a good friend who had been traveling around the world while working remotely for a technology startup. His work and life sounded exciting, so I explored roles with the company and ended up landing a remote position as a growth hacker.
After an invigorating first week of onboarding with my boss in Cartagena, Colombia, I realized that I could travel and still be incredibly productive. So I moved out of my apartment in New York and began a three-year journey of work and travel.
I’m grateful I fell into the remote working model. It aligns with how I prefer to work and live, and it has accelerated my personal and professional growth. And in being able to design life on my terms, I’ve felt more consistent levels of joy and fulfillment.
What Are Your Favorite Destinations in the World?
Every place is charming if you approach it with patience and an open mind, but a few of my favorites from the 30+ countries I’ve visited over the last few years are:
Rio de Janeiro, Brazil. I first visited Rio in 2013 to study Portuguese and the city’s architecture. The city has an intoxicating romantic energy and blends city life and beach life in a fascinating way. It also has a thriving health and fitness culture that aligns with my values. In 2017, I had the opportunity to be in Rio with good friends for Carnival, and it was a highlight of my life.
The Azores, Portugal. This group of Portuguese islands sits in the middle of the Atlantic Ocean. Not only are the islands visually stunning, but they also have a diversity of fun activities – surfing, hiking, biking, bathing in natural hot springs, and whale watching. It’s a perfect place to take a vacation, work for a few weeks, or write a book. At every corner of the islands, birds chirp the song of life.
Lake Tahoe, California. I rented out a house close to the base of Heavenly Ski Resort last winter, and I fell in love with the area. It’s a charming town, and while you’re skiing, you have a full view of the beautiful lake below you. I’d love to spend time in Tahoe during the summer.
What People Who Want to Work with You Need to Have?
There are a few values that I look for in both friends and colleagues:
Integrity: Do what you say you’re going to do. Operating with integrity builds trust.
Empathy: Learn to take another person’s perspective, especially when you disagree with that perspective. Teams with more empathy achieve better outcomes and are more fun.
Extreme ownership: Own your results – the good and the bad. When everyone practices extreme ownership, the team orients toward results, creativity, and problem-solving. Instead of assigning blame, everyone takes responsibility. It’s a much healthier and effective way to work.
Growth mindset: We all have areas for improvement in our personal and professional lives. I appreciate people who look for ways to learn, grow, and better confront adversity.
Open-mindedness: Being open-minded means you approach problems, conflicts, and disagreements with a curious lens. Instead of fixating on being right, you’re focused on achieving the best outcome for the team.
