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How to Stay Productive as an Entrepreneur Working On the Road


Lisa Ellis

Marketing Specialist - 30 Mar, 2018


Productive people can be found anywhere. We’re inspired by Calvin Rosser, aka "Positive Cal,” a Princeton graduate, entrepreneur, and writer on a mission to empower 10 million people to live more fulfilling lives. During his career in high finance and building businesses, while traveling to over 25 countries, Calvin has developed an impressive productivity routine.

We’re speaking to him directly to dive into his routine and figure out how he creates wins and stays highly productive while on the road.

When you left your job on Wall Street, what changed for you in your productivity routine?

I left Wall Street to travel the world and work remotely for a startup. Overnight, my world shifted from spending 100+ hours a week in a cubicle in a hyper-structured and top-down environment to working out of Airbnb's in Colombia in a role with very little guidance and structure.

On Wall Street, my routine was set for me.

I was guaranteed to spend most of my waking time in the office and to have my work handed to me with clear expectations by people above me in the rigid hierarchy. I just had to show up and work hard to succeed.

My new role was completely different. It was ambiguously defined and required me to direct my own time and work. It didn’t matter how much I worked, what I did, or where I was. All that mattered was that I brought in more revenue each week. To succeed in this new environment, I needed a routine that allowed me to operate with extreme ambiguity, be highly self-disciplined, and adapt to living in countries I had never been to.

What really helped me thrive was developing a morning routine.

After experimenting with lots of different things, I settled on a routine that included reading, journaling, meditating, and exercising every morning. These four things grounded me. They put me in the right headspace to focus and operate at peak productivity no matter where I was or what I had to do.

Although this routine worked for me, it’s not for everyone. With productivity, there’s not a one-size-fits-all solution. Finding the right routine is about understanding your personal preferences and learning how to adapt to changing environments and needs.

You talk about building the right habits. Can you explain your philosophy for this?

Whether it’s writing a book, building a big business, running a marathon, being a better parent, or feeling more fulfilled, we all have goals that we want to achieve. And while it’s tempting to look for ways to get to our desired outcome more quickly, success takes time and starts with building the right habits.

Habits are the compound interest of achievement and personal development.

They are the small, automatic decisions and actions of daily life that seem trivial in the moment, but that compound over time and determine our success.

Eating a glazed doughnut every day may not seem so bad for our health. Then we realize it’s an extra 91,000 calories a year. Reading for 10 minutes may not seem like it will make a difference in our learning until we realize that it equates to reading 15 books a year.

On top of this compounding effect, habits are even more powerful because once we form them, they are built into our brains.

When our motivation fades and willpower fatigues, our habits endure and keep us progressing forward. And as our habits allow us to get small, concrete wins towards our goals, we often find additional inspiration and motivation in our progress.

When we learn how to leverage the power of building the right habits, achievement becomes an easier and more enjoyable process.


Working poolside is all part of the job for Calvin Rosser.

What’s the best advice you’ve ever received about productivity?

Rest and play more.

It may seem counterintuitive, but rest and play are indispensable to productivity.

In order to achieve more in less time, you need to protect your body and mind. Rest is the best way to do that. But for many high-achievers, this is a big challenge. There is always more to do. We falsely believe that we will achieve more if we sleep less and work harder. This may work in the short-term, but in the long-run, it leads to burnout and a creative vacuum.

Along with rest, integrating more play into your life can significantly increase your productivity.

Play expands the mind. It sparks creativity, increases engagement, and allows you to see old problems in a new light. We often associate play with children, but it’s a really underappreciated productivity hack for adults.

In my life, play comes in the form of surfing, embarrassing dance moves, and cooking dinner with friends. In relaxing my mind and having fun, I’m often able to tap into a creative flow that helps me solve problems and generate new ideas.

Calvin Rosser's Shift account and a Life Re-imagined email.

What are your go-to productivity tools? 

There are endless productivity tools out there, but the three that I use every day are Evernote, Grammarly, and Shift. Together, these three help me focus on the right things, streamline my work, and ignore distractions.


I’m a big note taker and often need to access my work on the go. Evernote is a great tool for this. I use it to take notes, organize my thoughts, and create daily to-do lists. Over time, I’ve built the habit of doing a monthly review of all my notes. My review always brings to light ideas and resources that I’ve forgotten but that I later use in my work.


Grammarly makes me a better professional and writer by saving me from many grammatical errors in my emails and writing. I love to write directly in their interface. It allows me to check my work in real-time and avoid the distractions of having multiple tabs open or spending too much time with unnecessary formatting.


I discovered Shift about a year ago. I recently upgraded to an Advanced account, which allows me to have my Gmail, WhatsApp, Slack, Evernote, and Spotify accounts all in one place. This centralized setup saves me about 10 minutes every day. Over the course of a year, that’s 2 to 3 days of my time back to do the things that excite me. Not a bad deal.

Calvin is on a mission to empower 10 million people to live more conscious and fulfilling lives.

What’s next for you?

I’m on a mission to empower 10 million people to live more conscious and fulfilling lives. This mission gets me excited to wake up every morning.

To tackle the mission, I write about big ideas, unconventional living, practical achievement frameworks, and the art of fulfillment on my website, Quora, and in my Sunday newsletter. I am also a life and business coach for entrepreneurs and professionals. I support those who want to grow their businesses, accelerate their careers, and get more out of life. The one-on-one work is really rewarding.

Of late, I’ve also been exploring new opportunities to collaborate with others who believe in contribution, personal growth, and paying it forward. I just partnered with another entrepreneur to bring a 6 day personal and professional development retreat to life on the coast of Nicaragua in May.

I’m excited to continue to scale my impact moving forward.


Like many other high-achieving entrepreneurs, Calvin uses Shift to achieve productivity greatness. Start your journey today by downloading Shift here.