Balancing the Grind with Calvin Rosser, Director of Business Operations at Mechanism Ventures

Calvin Rosser is the Director of Business Operations at Mechanism Ventures, a startup studio that helps founders fund, launch, and scale companies.

1) To kick things off, could you tell us a little about your career background and current role?

Hi, I’m Calvin Rosser! I grew up in Florida with a single mom who made less than $15,000 a year, so I spent my early life figuring out how to improve my circumstances. I ended up getting a full scholarship to Princeton University and graduated with a degree in public policy.

After college, I joined a big investment bank in New York to find my financial footing. I worked on mergers and acquisitions for private equity firms across the automotive, healthcare, and consumer retail sectors. Wall Street offered a steady paycheck, but I didn’t enjoy spending 15 hours a day in a cubicle doing grunt work. 

I knew there had to be more to life, so I looked for a new path. I ended up joining Toptal, a fully remote staffing company, in a growth marketing role. That experience hooked me on remote work and scaling companies. I spent the next few years growing Toptal, leading teams, and traveling to dozens of countries. I recently paused my travels to settle in Southern California.

For the last year, I’ve been the Director of Business Operations at Mechanism Ventures, a startup studio that helps founders fund, launch, and scale companies. I work on everything from launching growth channels, to improving internal operations, to hiring great people. I’m also the Founder of Life Reimagined, an organization dedicated to helping 10 million people live a more fulfilling life.

While I’m not sure where my career will take me, I’ve found a nice sweet spot for the time being. I spend most of my time writing, podcasting, and helping early-stage startups with growth and operations. It’s a lot of fun.

2) What does a day in the life look like for you? Can you take us through a recent workday?

I typically wake up between 7am and 8am without an alarm. I drink a few glasses of water and read a nonfiction book until my body and mind feel alive. Then, I make some coffee and head to my desk. 

After quickly glancing at my email and Slack messages, I write down the three most important objectives for me to accomplish that day. This list gives me the clarity I need to have a focused and productive day.

I spend the first half of my day bouncing between calls and focusing on my top three priorities. Once I start to lose energy around 1pm, I take a break to run, read, nap, do errands, or hang out with my girlfriend. I pick up work again around 3pm and stay heads-down until I go for a sunset surf.

The rest of my day varies, but often includes making dinner, chatting with friends, working on my website, and planning my priorities for the next day.

3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?

With the exception of my stint in investment banking, I’ve worked only in fully remote roles. While I enjoy visiting colleagues in person from time to time, I don’t think I could go back to a traditional office arrangement.

Above all else, remote work has allowed me to design life on my terms. So whether it’s exploring my interest in traveling the world, surfing in the mornings, or napping in the afternoons, I’ve had the flexibility to build the life that works best for me. 

On the whole, this flexibility has allowed me to live a more balanced, productive, and fulfilling life as I define it.

4) What does work-life balance mean to you and how do you work to achieve that goal?

I rarely make a distinction between work and life.

After losing my mentor to sudden death and my mom to suicide, I realized how precarious and impermanent life really is. So instead of creating rigid boundaries around work and life, I focus on enjoying my day to day, living by my values, and helping others create the life they want to build.

With both work and life, I make sure that I’m learning, building meaningful relationships, and contributing to something bigger than myself. If I start to feel that these variables are missing in my equation, then I re-adjust so that I don’t end up on my deathbed with too many regrets.

5) In the past 12 months, have you started or stopped any routines or habits to change your life?

I’ve been an avid and structured goal-setter for my entire life. But about 6 months ago, I gave up goal-setting entirely. I felt that I was spending too much time planning and tracking my life and too little time enjoying life in an unstructured way. It’s been nice to have fewer goals and more fluidity.

Recently, I turned back to a lighter form of goal-setting to make sure that I’m still going in the direction that makes sense for me.

The best habit I’ve picked up in the last year is surfing. Surfing is difficult to learn in adulthood – it’s incredibly mentally and physically demanding. But once you surf 50 or 60 times and start to feel comfortable out there, it’s such a rewarding and spiritually enriching sport.

When you surf, you’re yielding to something more powerful than yourself. The ocean is this simultaneously beautiful and frightening place. You have to approach the ocean with humility and respect, and when you start feeling in sync with its rhythms, there’s no better feeling.

6) Do you have any favourite books, podcasts or newsletters that you’d like to recommend?

I love reading books – it’s the most important habit I’ve developed as an adult. The knowledge and lessons I’ve learned through reading have made me a better thinker, communicator, friend, and professional.

I publish summaries and lessons for all of the best books that I’ve read, but here are a few of the most influential reads and what they taught me:

Man’s Search for Meaning by Viktor Frankl: A lesson in the power of choosing your response to every situation and learning how to create meaning in your life.

When Things Fall Apart by Pema Chodron: A wonderful guide about how to thrive in a fundamentally groundless and difficult world.

The Life You Can Save by Peter Singer: A compelling moral argument for why and how we can all do more to help alleviate unnecessary suffering and death in this world.

The War of Art by Steven Pressfield: An inspiring book that prepares creators for the lifelong, difficult journey of producing great work.

Give and Take by Adam Grant: Fantastic research that has helped me get comfortable with being a more generous and contribution-oriented person in my work.

7) Are there any products, gadgets or apps that you can’t live without?

I’ve lived most of my adult life out of a backpack while traveling the world, so I unintentionally fell into a minimalist lifestyle. I’ve found that my soul feels a bit more at ease when I have fewer possessions and products in my life.

I get most of my work done with Slack, Zoom, and G-suite applications. With products, I always have my Airpods, Kindle, and Macbook by my side. 

Now that I’m living in an apartment full-time, I’ve enjoyed having a Fully Jarvis Standing Desk, Topo Standing Desk Matt, and a RumbleRoller Gator Back Roller. These items have helped me develop more sustainable working habits and alleviated most of my back pain.

Coda is a tool that I’m really excited about as well. I started learning it about a month ago, and I see a lot of potential for making it my go-to place for task and knowledge management.

8) If you could read an interview about work-life balance by anyone, who would that be?

I’d love to hear from Richard Feynman. He’s no longer with us, but he seemed to lead a life filled with genuine curiosity and passion. I’m curious about how he spent his day to day life.

While I’m not a big sports fan, I think it’d be awesome to hear more about how top-tier athletes manage their time. There are a lot of business folks talking about what they do, but I bet athletes have a lot of interesting habits that apply to performance at the highest level in the traditional business world as well.

9) Do you have any last thoughts on work, life or balance that you’d like to share with our readers?

With both work and life, follow your energy and personal truth. 

Life is too short to work for people who you don’t respect. It’s too short to build a career that sounds good on paper, but that doesn’t fulfill you. It’s too short to focus on yourself and not think about how you can serve others.

It’s up to you to figure out what works for you. Lots of people will give you advice, but it’s usually them telling you what they would do, instead of them thinking about what makes the most sense for you and your goals. It can take decades to carve out a great path for yourself, but it’s certainly worth the effort of inching closer to living your truth over time.

We’re all just making this up as we go, so don’t beat yourself up if you’re feeling a little lost. I’m still figuring it out too, and I’ve stopped trying to predict what will happen. I’m focused on what makes sense today and for the next few months, and if that stops working, I make a change.

Don’t be afraid to make a change – it often works out in the end.

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