Closing the Vocation Gap: Supporting Your Life While Doing Your Life's Work

A recurring theme in my philosophy practice centers on what I'll term "the vocation gap," which I will define as follows:

When sourcing a livelihood is misaligned with pursuing a vocation. 

I will explore the available approaches, starting with the most glamourized one: go all in. 

With this approach, a person endeavors to source their livelihood through a vocation. I referred to this previously as an “alivelihood,” something that makes one “come alive” while bringing enough money to support their life, which is contrasted to a “deadilhood,” an emotionally deadening job. 

Some individuals find success through the "go all in" approach, and the counsel from those who have closed the gap this way becomes the default guidance many people receive regarding their vocation. There are many examples of this, such as the "do work you love" advice from Steve Jobs.¹

Jim Carrey's 2014 commencement speech is an exemplar case in advocating this approach:  

Carrey contrasts his father's vocational "failing" in being an accountant to his vocational success as an accomplished comedian. The moral of the lesson: If he's capable, then all of us have the potential. The issue with extending this advice to everyone is threefold.

Firstly, Carrey's father made a career decision under specific conditions, and his sacrifice for his family and his perceived failure might have been the catalyst for Carrey's vocational commitment. If Percy Carrey had pursued the same path and achieved the same success as his son, Jim Carrey might have remained a relatively unknown name. He could have ended up living in his father's shadow as a trust-fund baby, lacking the necessary motivation to attain similar success.

Secondly, counsel like Carrey's often overlooks the concept of "survivorship bias," a cognitive bias that occurs when people focus on the success stories or individuals who have "survived" a particular experience while overlooking those who did not. It leads to a distorted perception because it only considers the outcomes of those who made it. How many people went all in and did not succeed? We do not know because self-help books or motivational speeches do not mention their advice.

Thirdly, the indirect shaming of such advice is an underlooked phenomenon. Many individuals whom I have inquired with are uncertain about their vocation, possessing only a faint sense of what their calling is, or they have a clearer understanding but find themselves entangled in complex situations with responsibilities toward others, making the "go all in" approach seem both selfish and foolish. These individuals may grapple with a sense of shame resulting from hearing this advice, believing they are deficient in some inherent way.

This approach should always remain an option, but examining the available options is prudent before going all in. The art of closing the vocation gap is a practical philosophical concern for everyone, and it's crucial to acknowledge that aligning one's livelihood with one's vocation is not the sole approach to achieving this.

Beyond the "go all in" approach, I see six options for closing the vocation gap: 

• Accomplishing financial independence

• Achieving "fuck you money."

• Creating a "muse"

• Making “small bets”

• Having a financial benefactor

• Being supported by "soul-safe" work

I'll explore these approaches in the next entry.

Thank you for reading Less Foolish. This newsletter is funded by its readers, and I endeavor to keep most of the content accessible to everyone. If you wish to contribute to my work, you might consider subscribing, whether for free or as a paid member, and sharing this post with those you sense will resonate.

Beginning in January, I will be resuming my philosophical practice. My approach will center on deep, ongoing collaborations with a limited number of individuals, in addition to offering single-session engagements. If this interests you, feel free to respond to this email for more details. These inquiries have proven beneficial in assisting many individuals close their vocation gap. You can read additional details in the entry below:

Lastly, consider joining Collective Journalling available to paying members of Less Foolish, where we can philosophize about closing the vocational gap together in silence.

What is Collective Journalling? This communal practice happens via Zoom and is 90 mins, with check-ins in the chat at the beginning and an opportunity to connect with fellow journalers in breakout rooms at the end. You do not have to stay the whole time. If you are in an antisocial mood, you do not have to interact with anyone, yet you can still enjoy the coffee shop-esque communal vibe. The session concludes with an optional sharing of a passage in the chat. Most of the time is spent in silence together, individually inquiring about what matters most. A lovely group of people has formed around this practice. The practice occurs on weekdays @ 8 AM ET. RSVP link is behind the paywall.