"When I've been doing one thing or staying in one place for a while, It actively feels harmful to keep doing the same thing I've been doing." - Derek Sivers

Derek is a unique human who consistently pushes the edges of convention, tests his assumptions, and embraces the new realities he finds on the other side. His identities have included musician, circus ringmaster, traveler, entrepreneur, father, programmer, speaker, and author. Derek gave three TED Talks in 2010, which have amassed 23 million views. His latest book, "Useful Not True" will be released in 2024. Although American, he is a world citizen living in New Zealand and is true to his word regarding answering email.

Derek delves into his experiences with questioning assumptions, pushing boundaries, and the role of journaling for self-reflection. The conversation encompasses topics like the importance of reframing perspectives, cultural differences in questioning, and Sivers' embrace of minimalism. He advocates for reframing situations and adopting beliefs that are useful over what is "true." Practical advice and anecdotes underscore the value of curiosity and inquiry, offering valuable insights into leading a more examined life through the transformative power of questions.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

Episode Notes:

Discovering the power of questions [1:42]

Reframing and journaling [6:06]

A circus boss builds Derek's confidence [7:50]

Derek's journalism practice [9:20]

The benefits of daily journaling [12:08]

Journals as a tool for remembering and decision-making [16:45]

The benefits of an electronic journal [23:13]

Derek's only recurring question [25:28]

Sherlock Holmes [26:18]

Questions that should be asked more [28:22]

A primary value that drove selling his company, CD Baby [30:46]

Cultivating a growth mindset [35:34]

Doing the scary thing [38:19]

Changing identities [43:47]

Questions in other countries [49:12]

Language and living abroad [59:57]

Pet rats: a surprising joy [1:02:18]

Favorite books that engage questions [1:07:16]

Derek's new book Useful Not True [1:10:11]

Minimalism and life choices [1:14:52]

The power of questions in conversations [1:20:36]

Where to find Derek [1:25:19]

Resources Mentioned

Awaken the Giant Within by Tony Robbins

O.J. Simpson

Michael Jackson

Useful Not True by Derek Sivers

Anything You Want by Derek Sivers

Hell Yeah or No by Derek Sivers

The Courage to Be Disliked by Ichiro Kishimi

SUM Tales of the Afterlife by David Eagleman

StudioBricks

Alicia Souza

Beauty Pill

Producer Ben Ford

Questions Asked

Why am I such an idiot?

What's great about this?

Why am I so confident?

How do questions inform journaling?

why am I upset?

What am I confused about?

How am I going to make this decision?

What's the real point?

What are my options here?

What am I really after?

How else could I think about this?

Why am I doing that?

Is that just leading to something else?

Why is that upsetting?

What's another way to think about this?

What else could it be?

Do you come back to the journals?

Do you do any kind of review process?

Why is this bothering me?

What's another way I could think about this?

Is that what's really bothering me about this?

How could I have reacted?

How would I like it to be in a perfect world?

What would be my ideal scenario?

What would be the most generous way to look at this?

Am I being too generous?

Have I been not selfish enough?

Have I not been doing enough self-care?

What else could it be?

What questions do you think should be asked more or ignored?

What's another way of looking at this?

What's a better way of looking at this?

Any other thoughts or encouragement about how questions might be used that we haven't touched on already?

Where's the best place for folks to engage with you and learn more about what you're excited about?

Why am I stuck?

Why am I not stuck?

Why is this not working out for me?

How can I make it work out more?

How can I make it work out less?

What would be a worse way of doing this?

What would be the stupidest thing I could do right now?

What's the opposite of this?

What's almost the opposite?

Why am I such an idiot?

Why do things never work out for me?

Why do I keep sabotaging myself?

Why am I stuck in this awful place?

What would be the uncomfortable thing?

What's another way to see this?

What's best for your family?

What's best for others?

Would buying this thing give me more status?

Would this job give me more status?

Why am I limiting myself to saying I'm an introvert?

Why do I think that person's being rude?

Could it be that they have different values?

Are they acting in a way that they're proud of right now?

Do they want to be this way?

Are they at their wit's end and short-circuiting and acting in a way they don't actually want to be acting either?

Any particular books that handle questions in new or creative ways?

Why are you saying you believe this?

What the hell is true anyway?

What questions do you ask of an item in order to become one of your things?

Am I really going to want to take care of that for the rest of its life for the rest of my life?

Do I really want that in my space?

Will that complicate my life?

Will that take up room?

Will that make it harder for me to leave on a moment's notice?

Would that hold me back?

Does this ever happen to you?

Why do you think we love a particular song?

What do you want more of?

What do I need less of?

Why do I think I need more?

Is more the solution?

Is less the solution here?

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