Business · Book club
Anything You Want book club questions
Here are 11 book club questions for Anything You Want by Derek Sivers, ordered to open easily and end somewhere worth arguing about. Copy them, print them, or bring them up one at a time.
Anything You Want is Derek Sivers' account of building, running, and eventually selling CD Baby, the independent musician distribution company he founded accidentally in 1998 when a few friends asked him to sell their CDs online.
Derek Sivers · 2011 · 1h 15m
Full summary and key takeaways →The 11 questions
- 1.
Sivers defines success entirely by his own criteria. How do you define success for a business or project you care about, and where did that definition come from?
- 2.
The book is essentially an argument against raising outside funding. What would you lose, and what would you gain, by building something without investors?
- 3.
Sivers says he stayed too long running CD Baby after it stopped being fun. How do you recognize that moment in a project or role you've built?
- 4.
The company grew without a formal business plan. Is that a feature of Sivers' specific situation or a generalizable lesson?
- 5.
Sivers gave the sale proceeds to charity. Does that decision make his business philosophy more or less credible to you?
- 6.
He argues that most business advice assumes you want the same things everyone else wants. Which pieces of conventional business advice don't apply to what you actually want?
- 7.
The book was written quickly and is explicitly short. Does the format reinforce or undercut its argument about simplicity?
- 8.
CD Baby succeeded without a marketing strategy in the conventional sense. What does that suggest about the role of luck versus intention in small business outcomes?
- 9.
Sivers describes the moment when managing employees stopped feeling meaningful and started feeling like a burden. Have you had an equivalent moment in work you've done?
- 10.
What would it look like to apply Sivers' approach—serve your own definition of what you want—to a career path rather than a business?
- 11.
The book's core audience seems to be people who want to do something small and good rather than something large and scalable. Is that a coherent market, and is Sivers the right person to speak to it?
How to run the discussion
- Pick six to eight, not all of them. An hour of real discussion covers fewer questions than anyone expects, and racing the list is what makes a book club feel like homework.
- Open with what people noticed, not what they concluded. Asking for a verdict first hardens opinions before anyone has heard each other.
- Let the disagreement run. The questions below that split a room are the ones worth the time; the ones everyone answers the same way can be skipped.
- Ask the quiet person a specific question. A direct, narrow question is far easier to answer than an open invitation to contribute.
Themes worth steering toward
If the conversation stalls, these are the threads that usually restart it.
Common questions
What are good book club questions for Anything You Want?
Here are 11 book club questions for Anything You Want by Derek Sivers, ordered to open easily and end somewhere worth arguing about. The strongest openers ask what each reader noticed rather than what they concluded, and the discussion usually turns on entrepreneurship, business philosophy, simplicity.
How long should a book club discussion of Anything You Want last?
Most groups run 60 to 90 minutes of actual discussion. That is roughly six to eight questions, not all of them, so pick the ones that suit your group rather than working down the list in order.
What are the main themes in Anything You Want?
Entrepreneurship, Business philosophy, Simplicity, Values, Independence. Those are the threads most likely to divide a room, which makes them the useful places to steer a discussion that has gone quiet.
Picking the next one? See books like Anything You Want or questions for other book club picks.
