Those whose lives revolve around adventure tend to have similar career goals: they want to do meaningful work that can be scaled down far enough to leave sufficient time for their adventures, while also earning enough to fund those adventures and enjoy basic financial security.
The term “dirtbag rich”—coined by Tim Mathis in The Dirtbag’s Guide to Life—is the closest thing I’ve found to this vision. Below is my own take on the concept.
Consider three elements of an enjoyable career:
High pay (e.g., $50+/hour)
High purpose (your work contributes meaningfully to the world)
High time flexibility (you can work part-time and take long breaks as needed)
How does these elements interact?
THE CONVENTIONAL RICH
With 💰 high pay but 😔 low purpose and ⏳ low time flexibility, you are…
financially wealthy but stressed
hard-pressed to find purpose through hobbies because you’re so busy
inclined to find purpose in “providing for my family” and “saving for retirement”
EXAMPLE: Well-paid employee of a soulless organization
THE SATISFIED BURNOUT
With 💰 high pay and 😊 high purpose but ⏳ low time flexibility, you are…
wealthy and satisfied, even if stressed and overworked
possibly sacrificing hobbies and relationships to your career
EXAMPLE: Executive of a world-saving startup
THE WEALTHY FREELANCER
With 💰 high pay and 🏖️ high time flexibility but 😔 low purpose, you are…
delightfully secure/free while simultaneously uninspired/resentful
perhaps finding sufficient purpose through hobbies and relationships to distract yourself from existential dread
EXAMPLE: Freelancers reliant on well-compensated but mind-numbing projects, the disillusioned self-employed, commercial fishermen
THE CLASSIC DIRTBAG
With 😊 high purpose and 🏖️ high time flexibility but 💸 low pay, you are…
satisfied and relaxed while living on the edge of financial security
doing what you love, long-term considerations be damned
EXAMPLE: Full-time climbers and world travelers, thru-hikers, clergy, gap year
THE STARVING ARTIST
With 😊 high purpose but 💸 low pay and 🕰️ low time flexibility, you are…
an overworked idealist/do-gooder
contributing to the world but likely stressed and financial anxious
EXAMPLE: Social workers, full-time activists, struggling writers working at Starbucks
THE DRIFTING UNEMPLOYED
With 🏖️ high time flexibility but 💸 low pay and 😔 low purpose, you are…
unoccupied, discontent, and lacking a sense of options
possibly supported by welfare programs or parental contributions
EXAMPLE: Adult children living at home without a plan, the recently laid off
THE MODERN INDENTURED SERVANT
With ⏳ low time flexibility and 💸 low pay and 😔 low purpose, you are…
sad, and rightfully so
EXAMPLE: Full-time service workers who despise their jobs
THE DIRTBAG RICH
With 😊 high purpose and 💰 high pay and 🏖️ high time flexibility, you are…
Doing work that matters, and not too much of it
Enjoying plenty of time for hobbies and relationships
EXAMPLE: Travel nurses who love nursing, self-employed people with a clear mission, and many artists, writers, coaches, consultants, and those in the skilled trades.
A little backstory.
I’ve long thought of a “good career” through the lens of passion, skill, and market. Find the happy space in the middle, and you’re set.
But this model (1) assumes full-time work and (2) doesn’t properly acknowledge the role of purpose (or assumes that it derives from passion).
The ikigai model nicely touches on purpose by separating “what the world needs” from “what you can be paid for,” but it still ignores time wealth.
For serious adventurers and others who value flexibility and free time over much else, we must acknowledge the value of work that can be scaled to part-time, done intensively in bursts, and abandoned for long stretches.
Like all models, this one is incomplete.
Where does frugality fit in, which affects how far money can stretch?
What about evolution over time? Those in the FIRE movement encourage the pursuit of high pay (paired with frugality) for a many years in order to purchase time wealth in the future.
What about high-purpose work that must be done full-time?
Finding purpose through work versus outside of work remains a blurry distinction.
Your thoughts are welcome.
I arbitrarily chose $50+/hour as representative of “high pay” in the United States in 2023. Adjust to your local economy.
Things that come to mind:
Are you familiar with Daniel Schmachtenberger? I was listening to a series he did recently on the Great Simplification podcast - and the summation of what to do next - he was saying exactly this, find meaningful useful work that you are paid well for, don’t work too much, and spend your spare time working on healing your shit - intergenerational patterns and trauma and all that (I’d consider going on a retreat with you Blake a healing intervention).
And the next thought was, Daniel was unschooled as a young person- he discusses this a little in that series - but I’d love for someone to interview him more on this - maybe you could Blake???
And then I wondered who is supposed to clean the public toilets, and take out the garbage of the dirtbags - or maybe those jobs need to be paid $50+ an hour....