ART, AMBITION, CREATIVITY: How To Steal Like An Artist's Austin Kleon
Here are the top 10 key takeaways from Ryan Holiday's conversation with Austin Kleon on creativity, ambition, and the artistic life.
1. The value of being present versus documenting moments
Austin describes an artistic dilemma during a beautiful sunrise at Barton Springs. He debated whether to stop swimming to take a photograph or simply continue experiencing the moment. This highlights the tension between capturing experiences for later versus fully immersing in them as they happen.
The conversation explores how stopping to document can actually change the experience itself - similar to the observer effect in physics. They suggest that sometimes the memory and the ability to write about the experience later might be more valuable than an imperfect photograph that fails to capture its essence.
2. The importance of hobbies and creative outlets
Both speakers emphasize how crucial hobbies are for mental health and channeling energy in positive directions. They discuss how creative pursuits provide an outlet for people who might otherwise direct their energy in destructive ways.
They observe that hobbies seem to be disappearing in modern culture, replaced by passive activities or social media. They suggest that everyone should practice some form of art, regardless of skill level, because time spent creating means less time "out on the street bothering somebody" or "wreaking havoc."
3. The long game of parenting and cultural exposure
Ryan shares a story about buying his son a Kindle years ago that only recently became a regular part of his life. Austin relates similar experiences taking his children to heavy metal concerts. Both discuss the patience required in introducing children to cultural experiences.
They note how it might take years for seeds planted in childhood to bear fruit. The conversation highlights how meaningful it is when children finally connect with something you've introduced them to. Ryan describes it as "holding eternity in the palm of your hand" when his children finally wanted to attend concerts with him.
4. Music as a transformative and subversive force
The conversation delves into music's power to transform perspectives and open doors to different cultures and ideas. They discuss how music "hits your nervous system first" before becoming an intellectual experience, making it uniquely powerful compared to other art forms.
Both reflect on how music can be subversive, particularly for young people from conservative backgrounds. Austin shares how discovering that Judas Priest's Rob Halford was gay helped him question other assumptions he'd been taught. Music creates "portals" into different worlds and perspectives that challenge preconceptions.
5. Understanding historical and economic context of creative work
Austin emphasizes the importance of understanding the context in which admired creative figures worked. He points out that many revered writers and musicians operated in specific economic and cultural environments that no longer exist.
He cautions against simply trying to replicate someone's career path without acknowledging how conditions have changed. For example, he discusses how the economics of the music industry between 1965-1975 created conditions for great albums because "people bought albums." Understanding this context helps creative people make better choices in their own time.
6. The rising bar of professional performance
The conversation explores how the requirements for professional success have increased across fields. In the past, artists, musicians, and even athletes could be "bad at life" but still succeed through raw talent in their specific domain.
Now, creative professionals need skills in self-promotion, business, and public presentation alongside their artistic abilities. As Austin puts it, "What we're losing culturally is that in the old days, you could be bad at life." The increasing professionalization means fewer opportunities for eccentric or socially awkward people who might have thrived in creative fields previously.
7. The problem of ambition and the hole it tries to fill
Both speakers discuss how ambition often stems from an inner emptiness. Ryan suggests that what drives people to extraordinary achievement is often "a big hole in you" that can't be filled even by success.
They use Elon Musk as an example of someone whose drive keeps expanding into new ventures because solving real problems didn't satisfy his underlying needs. The conversation suggests that learning to sit with oneself might be harder but ultimately more fulfilling than constant achievement. As Ryan quotes, "It was easier for Hitler to conquer Europe than to be a painter."
8. The therapeutic function of art in society
They discuss how creative fields have traditionally served as a place for people with mental health challenges or difficult personalities to channel their energy productively. Austin suggests that the arts have functioned as a containment system for "maniacs" who might otherwise cause harm in other domains.
The conversation implies that society benefits when challenging personalities have creative outlets. Ryan jokes, "It's a healthier place to work out your enormous childhood wounds than in the stock market or geopolitics." This framing positions art as having important therapeutic and social functions beyond entertainment.
9. The problem of "cheap talk" and bullshit detection
Austin introduces the concept of "cheap talk" - the constant stream of low-value communication encouraged by media platforms and social algorithms. He connects this to education systems that reward students for filling space rather than saying something meaningful.
Both speakers lament the declining ability to detect bullshit and hollow rhetoric. They discuss how AI magnifies this problem, with Ryan sharing an anecdote about receiving confident but entirely wrong information multiple times. The conversation emphasizes critical thinking and media literacy as crucial skills in navigating information overload.
10. The enduring wisdom in old books
Both speakers express appreciation for classical texts that offer timeless wisdom. Austin mentions reading Montaigne's essays on prognostication that seem perfectly relevant to current times despite being written 500 years ago.
They discuss how reading older works creates connections across time, linking readers to generations of thinkers who've engaged with the same fundamental human questions. Ryan notes that ancient writers "knew what a demagogue was. They knew what truth was. They knew what virtue was," suggesting these fundamental understandings might be more valuable than the accumulation of facts and trivia that characterizes modern education.