
Stop Overthinking and Start Deciding with Derek Sivers
From All the Hacks: Money, Points & Life by Chris Hutchins
April 8, 2026 · 1h 59m · Episode 273
About this episode
Chris and Derek discuss strategies to stop overthinking and improve decision-making.
#273: Learn to stop overthinking and make better decisions. Chris and Derek discuss how optimizing can go wrong, a coin flip trick for making decisions, journaling as a superpower, how your actions might reveal what you actually want, and more. Derek Sivers is an entrepreneur, writer, and self-proclaimed "slow thinker" best known for founding CD Baby, which he sold for $22M and gave the proceeds to charity. He’s since dedicated his life to creating, learning, and writing books like Hell Yeah or No. Link to Full Show Notes: https://chrishutchins.com/derek-sivers-stop-overthinking-make-better-decisions Partner Deals Mercury: Help your business grow with simplified finances Superhuman: Free month of the fastest and best email with code ALLTHEHACKS Upwork: Free job posting to find, hire, and pay top freelance talent Gusto: Free 3-month trial of the #1 payroll software Copilot Money: Free 2 months access to my favorite personal finance app with code HACKS2 For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals Resources Mentioned Derek Sivers: Website | X Book: Hell Yeah or No: what's worth doing Articles: My Heroes | Actions, Not Words…
People in this episode
Host: Chris Hutchins
Guest: Derek Sivers
Topics covered
- decision making
- overthinking
- entrepreneurship
- journaling
- self-improvement
Keywords
- decision making
- overthinking
- Derek Sivers
- entrepreneurship
- journaling
- self-improvement
- CD Baby
- Hell Yeah or No
Sponsors
Mercury, Superhuman, Upwork, Gusto, Copilot Money
Mentioned in this episode
Organizations: CD Baby
Books & works: Hell Yeah or No, The Paradox of Choice, Brain Rules for Baby
Places: New Zealand, Staglands Wildlife Reserve
More episodes of All the Hacks: Money, Points & Life
- Saving Money and Optimizing is My Kryptonite · June 10, 2026 · 53 min
- Taking My Health Into My Own Hands: Tests, Records, and What Actually Worked · June 3, 2026 · 1h 5m
- The Hidden Rules of Credit Card Approvals · May 27, 2026 · 51 min
- How Long-Term Investors Actually Think About Risk with Ben Carlson · May 20, 2026 · 1h 1m
- The AI Tools I'm Building to Replace My Spreadsheets with Anish Acharya · May 13, 2026 · 1h 11m
- The Japan ER Visit That Changed How We Travel (& Tokyo Disney) with Amy Fox · May 6, 2026 · 52 min
Explore listener stats, chart rankings, contacts and more on the All the Hacks: Money, Points & Life podcast page.