Should you quit your job?

Don't quit your job. Express yourself on the side and grow.

I was forcing myself up to my 6th floor walk-up apartment in New York City. Those were the days when an elevator, and maxing out a ROTH IRA, was pure luxury. I hiked up nightly to an apartment that was positioned on top of a restaurant which now has changed hands a dozen times. I shared an apartment with an aspiring model called Elena who day hustled it at Jimmy Choo. I was the 75th person who had responded to her request on Craigslist to be her roommate at a discounted price. When I asked her why she chose me, she said that in the initial screening, I was the only one who didn't complain about the stairs.

Elena occasionally received gifts from her full time day job, including shoes so expensive that it exceeded my total operating budget for the month. While I barely saw her since she was working two gigs, I myself had my own overdrive mania as I was a full-time graduate student while working nearly full-time at the United Nations. I felt that if I rested for a moment, I would miss out on my own version of Jimmy Choo shoes.

I was making dinner for my family thinking back to these strange times. Not a lot of resources, but a time of high energy. That pace was truly unsustainable. I reflect back and realized I never cooked anything.

While I did escape the days of sharing bedrooms and eating cheap food, I wasn't able to dial down the work that lay ahead of me.

Within the context of American culture, every slice of gratifying life is about work and achievement. It's not good enough to have a job, there is pressure to have a career. It's not good enough to have a career, you need to also have a side gig. Even if you are a strict hobbyist, there is pressure to be not just a jogger, but a marathon runner!

We are conditioned to achieve, excel, and frankly, work. A lot. We spend a horrific amount of time also maintaining our ability to work, to the point where I often think about Vicki Robin's question "are you working for living or a dying?" In the modern West, your work is indistinguishable from your identity, which leads to supposed purpose and meaning.

I think it would do wonders for our mental health if we were profession agnostic. If fulfillment is the only goal that matters, then it would make sense to not obsess over the dream job, but rather a dream life.

Because I am conditioned from a work-first perspective, I have never thought twice about working hard and utilizing my skills within an economy which will reward me for it. After all, wasn't that a good thing, to be a productive member of society? Over time, I realized that we can do work that is "valuable" per se, but there is also the human desire to create, make, or express. Most careers do not allow for that.

This desire to learn, express, and create is something I felt most comfortable pursuing as a side gig without the explicit intention of profiting from it. The main case for avoiding pure profit on my side gig is that I want to be able to sustain it joyfully. I can think of no higher achievement that sustaining something joyfully over the course of my life. That's why quitting your career makes little sense. Start making on the side!

Some benefits...


A career allows you to have stable earnings. But it does something much more. It also serves as fuel for your creativity. Valuable insights that come by doing something useful for others can be integrated into a need for expression. According to Allen Gannett's The Creative Curve, most people who reach a creative breakthrough enjoy the counterintuitive coupling of both novelty and familiarity. The ability to have the right mix of this over time is characteristic in coming up with "new" ideas.

It likely has something to do with how the mind processes information in conscious and unconscious states. In Todd Kashdan's The Upside of your Darkside, the way of the creative is naturally found in the numerous pathways that the unconscious mind operates in as opposed to the limited number in the conscious mind. So it is hard to write something on a blank page if you are staring it. But if you are engaged in something else, you may know what to write, make, or do. It is not unusual to have lot of different ideas of expression when you are unilaterally focused on something else consciously different! The career and side gig are interdependent.


Musician and entrepreneur Derek Sivers is very prolific in this area, offering that your well-paying job will serve as a remedy to the inherent pain points of creating your art, whatever that is. Likewise, your art is the expression that you truly need in order to fill the void that comes from constant productivity and utility.

This speaks to the fact that nothing is interesting or enjoyable forever. There will be moments of pain and arguable worse, boredom. What are you going to do in order to stave off the pain and boredom? Utilizing each aspect of your life as a coping mechanism is a strengths-based approach in healing and sustaining.

True growth

Aside from a career fueling and healing you as necessary, there is a larger reason to make a clear distinction between what makes your money and what you do for pure joy. Personal growth is a human right. There is no shame in wanting to be better. But in what way? 

More money, status, achievement? As the genie in Aladdin says "so you want to drink from that cup?" - I watch my toddler laugh at the statement, oblivious to the accuracy of how funny that is.

What's wiser is learning something new and growing from that experience.

More reason not to care about profit from your creative endeavors is from the intense tension between professional and personal development.

As expressed in documentary The Zen Diaries of Gary Shandling the way to professional development is to be good at something specialized: 

"So what you do in life in order to be professional is you develop your brand, your way of working, your attitude, that is understandable to others. In most cases, it turns out to be something fairly narrow...and then you discover you have something to offer that is better than other people have or at least more distinctive."

Ultimately this leads to a boredom of sorts, because you do the same thing you are good at over and over.

"The consequence of specialization and success is that it hurts you. It hurts you because it basically doesn’t aid in your development."

There is instead a strong case to fail:

"People begin to get better when they fail, they move towards failure, they discover something as a result of failing, they fail again, they discover something else, they fail again, they discover something else. So the model for personal development is antithetical to the model for professional success."

Your need for expression and art making can follow this path of experimentation and constant learning. But the odds of keeping the lights on if you are dependent on your art solely for income are grim. In this model, personal growth is more meaningful than the drudgery of professional growth.

I sit around the dinner table with my family with the food that I have cooked. I enjoy that we do not talk about the events of the day. We are talking about the food and enjoying it. I feel rested and calm. I enjoy the sparkling water (which is now finally achieving price parity). A lot. I don't care about what anybody did that day. I didn't want to talk about anybody's goals. I was just so lucky to be in their company.

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