In my previous entry, I introduced the term “vocation gap” to refer to the all too common phenomenon of having a livelihood and vocation misaligned. There are at least seven approaches to closing this gap:
Going all in
Accomplishing financial independence
Achieving "fuck you money"
Creating a "muse"
Making “small bets”
Having a financial benefactor
Being supported by "soul-safe" work
Apart from the going all in approach, the common thread among all strategies is discovering a means to secure one's livelihood, alleviating the prevalent financial insecurity many feel today, and enabling a clear focus on one's vocation. Financial insecurity, even when relegated to the subconscious, instills fear in the body, hindering access to the creative disposition needed for vocational awareness.
I’ll go through each approach, discussing who should consider them.
Going All In
This approach occurs when someone drops everything and slavishly devotes themselves to their calling. This approach requires sacrifice, embracing substantial risks, and sometimes entails a degree of madness before leaping. It might be quitting a job, leaving a relationship, burning bridges, and removing optionality. The essence of this approach is perfectly expressed in Charles Bukowski's poem "The Laughing Heart."
I previously offered a critique of this approach, as it is the one that receives the most attention. However, one must possess the courage to go all in. Without this courage, one will never know if cowardice or wisdom is the place they are acting from. Courage fully allows one to feel the fear that comes with financial insecurity, embraces it with acceptance, and allows them to proceed undeterred. Although this approach might not be appropriate for everyone, possessing the ability to choose it is essential for wise living.
Who is this approach suited for?
This approach is suited for artistic souls who have difficulty switching to non-artistic modes of being, those receiving divine downloads beyond the sublunar realm, bohemian types with no dependents, and those who have “ten thousand hours”1 of practice in a marketable skill starting at a young age.
Financial Independence
Financial independence (FI) is the condition wherein an individual or household possesses ample financial means to sustain their lifestyle without the necessity of actively participating in employment. The FIRE (Financial Independence, Retire Early) movement is a financial philosophy that aims to achieve financial independence at an early age, often in one's 30s or 40s, with the aim of freeing someone from reliance on a monthly salary, aka "wage slavery."
“The three most harmful addictions are heroin, carbohydrates, and a monthly salary.” - Nassim Nicholas Taleb
Champions of the FIRE approach emphasize frugality, saving aggressively, and investing in low-cost index funds to receive enough passive income to support a modest lifestyle. My favorite example of FIRE is Jacob Lund Fisker's Early Retirement Extreme (ERE). This practical philosophy additionally encourages significantly living below one’s means and developing self-sufficient "Renaissance" skills: homesteading, auto/bike repair, carpentry, and making house products such as soap.
Who is this approach suited for?
This approach is suited for those who already have a stable 9-to-5, have patience and discipline, a good relationship with their “learn drive,”2 have family responsibilities, and do not have a clear sense of what their vocation is but desire liberation from wage slavery to attain the time and psychic freedom needed to explore it.
Fuck You Money
Fuck you money (FU) is financial independence with attitude. It is having enough financial resources that allows someone to say "fuck you" to undesirable situations, employers, or obligations, as they have the means to walk away and pursue their own interests or desires. How much money does one need for FU? In a recent thread on X, specific numbers were mentioned regarding the amount of money required to say fuck you: 10 million, 50 million, 100 million, etc. John Goodman’s character in The Gambler puts forth 2.5 million as the number, arguing that "a wise man's life is based around fuck you."3
Unlike the FI approach, the FU approach comes hard and fast. It commonly involves entrepreneurs launching a business venture, strategically growing it, and subsequently cashing in through a lucrative sale, often leading to a substantial financial windfall. This path to fuck you is the true north star for many startuppers, tech bros, and Silicon Valley denizens.
Who is this approach suited for?
This approach is suited for those who have youth on their side, little family obligations, are tech literate, have high IQ and conscientiousness, can survive and thrive in hustle culture, and have a psychological temperament to "eat glass."4
Muse
Tim Ferriss, the author who launched the lifestyle designer/hacker movement with The 4-Hour Weekend, recommends the "muse" strategy for freeing one from active employment. A muse is a self-sustaining enterprise that generates revenue without demanding substantial time or labor. Typically achieved by marketing a product (either physical or digital) that requires limited capital investment, is readily automated, and demands minimal ongoing maintenance. The core principle of this approach is that what one does with their time now is more important than making money for things to buy later.
“You can lose money and make it back, you can't do that with time.” - Tim Ferriss
Muse hunting doesn't begin with one's passion as the going all-in approach does. Instead, it starts with a monthly cash flow target that supports a desired lifestyle, subsequently reverse-engineering a product to attain that objective. The muse approach is the fastest way to escape wage slavery, requiring less time and work than the FI and FU. It applies the hacker ethos to one's lifestyle.
Who is this approach suited for?
This approach is suited for people in a life phase where lifestyle experimentation is desired, those disenchanted with societal scripts, practical hedonists, minimalists, aspiring “digital nomads,”5 those allergic to normie lifeways, haters of office culture, and those who dislike routine.
Small Bets
A compliment to the muse but more antifragile is
's "small bets" approach. Vassallo argues that when it comes to livelihood sourcing, there are "two worlds" in which people commonly operate: the predictable world and the stochastic world. The former guarantees success (or the illusion of success) with consistent effort, and success in the latter is mostly randomly determined.
The small bets strategy is needed to thrive in the stochastic world. A small bet is a business venture that aims to get a small win as soon as possible, leveraging the "Matthew effect,"6 with success begetting success. A small bet could be an ebook, a course, a physical product being sold, or some clever hustle that brings in money immediately. Much like Dave Snowden's concept of a "safe-to-fail experiment,"7 the aim is to conduct small experiments that unveil the adjacent possible. The best small bet is the one that gets you to the next.
Who is this approach suited for?
This approach is suited for people comfortable with uncertainty, those with complexity literacy, Nassim Nicholas Taleb fans, aspiring “solopreneurs,”8 the recently unemployed, someone desiring to make their first $1k outside employment as soon as possible, and people who are longing to quit their jobs.
Financial Benefactors
Closing the vocation gap doesn't necessarily demand a deliberate focus on money-making. Another way is money-receiving through a financial benefactor. The three common types are 1) family, 2) sugar daddies/mommies, and 3) patronage. Some individuals benefit from supportive affluent parents or inherit wealth from family members. Other individuals might have a romantic partner or arrangement that allows freedom from working.9
Patronage refers to the financial support an individual provides to a person's livelihood and vocational pursuits. Historically, patronage encompassed influential individuals' support, financial aid, or privileged assistance to artists. While this approach is underestimated, I've noticed a growing trend among acquaintances in the "wisdom commons,"10 where affluent individuals financially support them to pursue meaningful endeavors.
Who is this approach suited for?
This approach is suited for individuals who want to go all in without the downsides, those who do not have undue status anxiety, likable and trusting people (at least to the benefactor), and people whose vocations are highly time-consuming and too unconventional to align with the market economy.
Soul-Safe Work
In a recent conversation with my mentor, he introduced the term "soul-safe" work, referring to a job or career path that sources a livelihood, allowing one the time and energy to pursue one's vocation without compromise. The outcome remains consistent whether you interpret "soul" literally or metaphorically in this context. Some work tends to bend one out of their integrity, causing psychic anguish that hinders their ability to concentrate on their vocational aspirations.
“Most of the temptations that come to us to sell the soul come in connection with the getting of money.” - William Jennings Bryan
Some work is more soul-safe than others, and not all conventional employment needs to be considered wage slavery. 9-to-5 jobs can align with one's vocation or, at the very least, provide frictionless support for their vocational endeavors. Each person will experience specific jobs differently. For instance, being a doctor may feel like a vocation for some individuals, while for others, it might be a source of soul-suffering because they were pressured into the profession by their family.
Who is this approach suited for?
This approach is suited for those who like or need stability, have family responsibilities, do not mind office culture or working for others, have marketable skills and require a predictable cash flow to meet their obligations and lifestyle preferences.
***
The above list is incomplete11 and, given the rapid technological advancements, continually evolving. Since it might not be clear what option to choose, here are three principles to help:
Be ready to switch approaches: A particular approach may be more suitable depending on your current life circumstances. Nonetheless, maintaining the nimbleness to switch approaches regularly could be a perfectly wise thing to do.
It’s not you, it’s us: It is easy to personalize things, feeling shame for not following one's vocation like others seemingly do. However, we should not be too hard on ourselves. We are collectively transitioning; things are changing fast, and nobody knows what will happen. Feeling off-track in your vocational journey is entirely natural and understandable.
Stay with the bother: Closing the vocation gap takes time. Things are complex and confusing. Do not rush into choosing easy answers. Stay with the complexity, which always requires one to stay with the bother, as confusing complexity can be deeply bothersome. Yet, the more complexity one can hold in one's body, the clearer the path forward will become.
The most effective practice I'm aware of, which allows one to address the challenges of closing their vocational gap, is philosophical inquiry. I'm not surprised that this is one of the most common inquiries I encounter in my practice. The world is complex; to respond effectively, we must become complex ourselves, one inquiry at a time.
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If you have additional insights on closing the vocation gap, please share your thoughts by leaving a comment.
The 10,000 hour rule popularized by writer Malcolm Gladwell's Outliers states one needs 10,000 hours of practice to become an expert in something. While recent studies have debunked this number, I think the spirit of it remains true: more practice = more skill.
The "learn drive" is an innate, universal tendency in the brain to seek new information, activate reward centers when finding novel patterns in memory, and can be trained or suppressed. It was coined by educational reformist Piotr Wozniak, who contrasts this notion to the “school drive.”
I agree. However, I think the highest form of FU is “fuck you happiness.”
"Being an entrepreneur is like eating glass and staring into the abyss of death." - Elon Musk
Digital nomads are individuals who use technology to work remotely and live a location-independent lifestyle.
The Matthew effect refers to the tendency for individuals to accumulate more success, be it social or economic, based on prior advantage.
A safe-to-fail experiment is a small-scale, low-risk experiment designed to reveal emergent possibilities without significant consequences.
“A solopreneur is usually (not always) a digital entrepreneur who leverages automation, work flexibility, and creativity to develop ultra-lean business models.” Source.
I am employing the terms "sugar daddy" and "sugar mommy" in a broader context than their typical association with purely sexual arrangements. For instance, during a period of unemployment and creative exploration my wife was my sugar mommy, and when she decided to take a year off work, I became her sugar daddy.
Wisdom commons is the place that makes wisdom more common. See the wisdom commons presentations.
Other options could include homestays, monastic living, UBI, etc.