Cal Newport would facepalm if he found out I was working on a startup. The life of a founder trying
to get their startup off the ground has all the qualities that a disciple of the deep life would want to avoid. Cultivating a deep life, as defined by Cal, is to focus with intention on things that matter to us in each bucket
of life - not just work. An example of how you might think about what matters to you:
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Community (family, friends, etc.)
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Craft (work, quality leisure)
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Constitution (health)
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Contemplation (matters of the soul)
Knowing what's in each bucket isn't straightforward. You have to spend a lot of time reflecting on your own thoughts.
Reflection, or solitude, is the time during which you make sense of all the stuff happening in your life, construct your
sense of self around those experiences, and begin to identify what matters to you, what doesn't matter to you, and how
you actually want your life to progress.
The best way to do this, as far as Cal can tell, is to introduce as much autonomy as you can into your Craft. Doing so
gives you the space to be intentional about your other buckets. For Cal, that means he focuses on two pursuits in his
professional life: computer science professorship and writing. Cal gained tenure at Georgetown in six years, laying the foundation for a lifetime of writing on his own schedule, choosing when to engage with his publishers and seriously pump out a book. Being in control of his work schedule, minus the occasional mandatory faculty meeting, allows him to make space for the other important buckets in his life.
But being an entrepreneur doesn't have to be completely at odds with the deep life, does it? In his book Company of One, Paul
Jarvis argues that focusing on building a sustainable and profitable small business can lead to greater freedom and
personal satisfaction compared to the stress and complexities of scaling up. For example, one case study examined a
burnt-out web developer who, after acquiring a lot of career capital, left his job and moved to a much lower cost of
living area, where he could focus on his family and take on freelance work as needed. He ended up as a pretty successful
freelancer. He only took on projects when he felt like he had room, and he built strong relationships with his clients.
He was so successful, in fact, that he considered hiring an assistant and even another developer to match his growing
list of clients. After some deliberation, he decided that instead of adding to his plate, he could simply raised his fees with his existing clients. And that's what he did.
That sounds ideal. But what stops me from turning my startup into a small business is because being at Stanford, I’m influenced by the infectious startup environment, which constantly pushes me toward building something ambitious. At the same time, I lack confidence in my ability to secure a predictable income stream as a small business owner, which makes the startup path feel less risky in some ways.
So far I've put on blinders and assumed that I'm going all-in on my startup. But man, it's exhausting. This past quarter, I could
only get myself to go on a run a handful of times. I barely read any books. My phone conversations with my parents were
brief. And to be fair, being in an MBA program is a lot of work as it is.
Now that the quarter is over, I have some breathing room. I'm trying to be intentional about how I enter the winter
quarter, as I don't want to make the same mistake again. I want to bring back my Constitution bucket from zero to... not
zero, and start running again. It's actually less about making entrepreneurship work with the deep life and more about making
entrepreneurship while being a student work with the deep life. Entrepreneurship is hard and because entrepreneurship is hard, my other deep life buckets will undoubtedly be affected.
"The deep life is not necessarily an easy life, but it is a life that you have chosen because you believe it is worth
living."