Can You Pursue Two Goals at Once? Ryan Holiday on Conversations with Tom

TL;DR

Ryan Holiday argues that creators should avoid pursuing contradictory outcomes with one product, but can pursue different kinds of work when each has a distinct purpose. He and Tom discuss fiction, nonfiction, audience overlap, intellectual honesty, and why passion must be balanced with the ability to make a business profitable. Read on for their practical distinctions between creative ambition and conflicting goals.

Transcript

conversations with Tom I am here with none other than Ryan holiday dude thank you for joining me course so this is gonna be the hopefully most laid-back and then laid-back strong word it's gonna be far more informal as I was explaining before I want to push my own thinking in real time yeah which means I'm a [ __ ] up your flow which on impact theo... Read More

Key Insights

• 🥺 Changing perspective can lead to greater self-awareness and opportunities for growth.
• 🍉 Momentum is essential in achieving long-term goals, starting with small, achievable steps.
• ✋ Balancing high standards with realistic goals can prevent perfectionism from hindering progress.
• 🤗 Acknowledging personal limitations and biases can open doors to new opportunities and perspectives.

Questions & Answers

Q: Can you pursue two goals at the same time?

Ryan Holiday says the problem is not simply having two goals, but having two contradictory goals for one product. Trying to create literary fiction for a selective audience while also seeking broad fame, or trying to maximize both sales and awards, can require different outcomes and be very difficult.

Q: Why is Tom creating both nonfiction and fiction?

Tom wants his nonfiction work to teach people how to think and act, while his fiction work includes comic books, movies, and TV shows. He hopes fiction will capture people emotionally and eventually lead some of them toward the nonfiction side.

Q: Does Ryan Holiday consider Tom's fiction and nonfiction goals contradictory?

Holiday says he is not sure they are contradictory because they involve different products rather than two incompatible outcomes for one product. He relates Tom's approach to his own experience writing different types of books.

Q: Do different kinds of creative work attract the same audience?

Not necessarily. Tom says people drawn to his nonfiction may not also want his fiction, and Holiday says his book “Conspiracy” succeeded almost exclusively with people who had not read his other books.

Q: How can reaching a different audience benefit a creator?

Holiday says limited crossover can initially feel disappointing, but it can also be additive. A different work may reach new readers instead of relying only on the audience for earlier projects.

Q: How should creators balance passion and business considerations?

Holiday says artists, creators, and entrepreneurs must care about business and success because money provides operating fuel. At the same time, they should work on subjects that get them out of bed in the morning and should not automatically discard projects that deeply interest them.

Q: Why does Tom say passion alone is insufficient for entrepreneurs?

Tom says a meaningful purpose can be powerful, but entrepreneurs also need to learn how to run a business. Someone who wants to help people or build an audience may still fail to progress if they cannot make the work profitable.

Q: Would Ryan Holiday simplify his books to sell more copies?

Holiday says he could probably write simpler, less nuanced books that might sell more copies. He resists that approach because he believes it would not be intellectually honest.

Summary & Key Takeaways

• Ryan Holiday and Tom discuss how to push personal thinking boundaries in real-time conversations.

• They explore pursuing contradictory goals simultaneously and how they affect creative endeavors.

• The importance of balancing business acumen with personal motivation for successful endeavors.