The Startup Ideas Podcast

Episode: Make 2026 the Best Year (Answer These 7 Questions)

Host: Greg Isenberg
Guest: Sahil Bloom, NYT Bestselling Author & Investor
Release Date: December 15, 2025

Overview

In this special end-of-year episode, Greg Isenberg is joined by Sahil Bloom to share a powerful framework to help listeners deeply reflect on 2025 and set up for an extraordinary 2026. Sahil introduces his “Personal Annual Review”—a set of seven questions designed to create real clarity, reset priorities, and foster actionable insights both personally and professionally. The episode is highly practical and invites listeners to reflect along, making it ideal for those wanting meaningful change in their work, startups, or daily life.

Key Discussion Points & Insights

1. The Importance of Reflection Before Goal-Setting

• Many people rush into new goals for the year without truly processing the learnings from the past twelve months.
• Quote: “We do not learn from experience, we learn from reflecting on experience.” – Sahil Bloom (03:02)
• Reflection is critical for meaningful progress and avoids repeated mistakes or unfocused ambition.

2. Sahil’s 7-Question Personal Annual Review Framework

• Listeners are encouraged to write down answers in real-time during the episode.

Question 1: What Did I Change My Mind On This Year? (05:00)

• Intelligence and growth often come from the willingness to update your beliefs.
• Reinvention is celebrated—changing your mind is not “flip-flopping” but evidence of growth.
• Tactic: Go through your calendar from the past year, recall your mindsets then vs. now, and identify moments that make you “cringe”—these are often key to spotting real change.
• Quote: “The things that make you cringe about your younger self—that’s where you’ve grown.” – Sahil (08:00)

Question 2: What Created Energy This Year? (11:33)

• Life outcomes follow your energy: boosting energizing activities yields better results.
• Separate analysis into three buckets: professional, personal (habits/health), and people.
• Consider how you feel after the activity, not during it—a draining task can energize you in the end (e.g., working out, podcasting, writing).
• Quote: “When you are working on… things that create that lift, that’s when you create the best outcomes.” – Sahil (11:33)

Question 3: What Drained Energy This Year? (18:58)

• Explicitly identify what people, behaviors, or routines sap your energy.
• Recurring meetings and back-to-back calls/wasteful Zooms topped the list for both hosts.
• Memorable Moment: Discussion of “shower people”—people who drain you so deeply you need to “take a shower” afterwards.
  • Quote: “Identify the people that make you feel like you need to take a shower after spending time with them.” – Sahil (24:40)

Question 4: What Were the Boat Anchors in My Life? (25:05)

• Boat anchors = things (people, beliefs, self-talk) holding you back from “full speed.”
• Most high performers look for new habits, but real progress often comes from cutting what drags you down.
• Do this with a trusted friend or partner if possible—ego often blinds you to your own anchors.
• AI Angle: Suggestion to use ChatGPT as an “intellectual sparring partner” to audit for boat anchors.
  • Sample Prompt: “Boat anchors are mindsets, beliefs, behaviors, and habits holding you back… What would you say are mine?”
• Quote: “The fastest way forward is to cut something that’s holding you back.” – Sahil (25:32)

Question 5: What Did I Not Do Because of Fear? (33:04)

• Fear thrives in the dark; shine a light on it via analysis.
• Often, inaction isn’t due to incapability, but inexperience.
• Use Tim Ferriss’s “fear setting”: Assess both downsides and upsides if you acted—downsides are usually overestimated.
• Both hosts shared personal fears: fear of failing publicly, fear of committing fully and not succeeding, or fear of thinking too small.
• Quote: “Self-protection becomes self-rejection.” – Sahil (35:36)
• Memorable Story: Greg’s recounting of being told his ventures “weren’t big enough” by an admired entrepreneur, leading him to re-validate his own choices. (36:13)

Question 6: What Were Your Greatest Hits and Worst Misses? Why? (39:49)

• Lay out both; ambitious people often focus too much on failures, optimists focus only on wins—neither leads to growth.
• Key: Analyze why victories and failures happened.
• Sahil’s hit: Book launch—succeeded due to total, all-in commitment, confronting fear, and an athlete-like intensity.
• “Are you really all in?” is the crux—most aren’t, even when they think they are.
• Quote: “You get a couple of these missions in your life—you pick and choose really well.” – Sahil (43:36)

Question 7: What Did I Learn This Year? (44:04)

• Synthesize learnings from the above into 3-10 clear lessons to carry forward.
• Greg’s big miss: Turning down a now-billion-dollar startup because of focusing on the idea, not the entrepreneur. Major learning: identify 3-5 exceptional people and attach to them, ideas may pivot, talent matters most.
• “Hang around the hoop”—be in the room when great founders or ideas emerge.
• Quote: “When I focus on the idea, I’m wrong 10 out of 10 times.” – Sahil (46:42)

Notable Quotes & Memorable Moments

• “We do not learn from experience, we learn from reflecting on experience.” (Sahil, 03:02)
• “The things that make you cringe about your younger self—that’s where you’ve grown.” (Sahil, 08:00)
• “Identify the people that make you feel like you need to take a shower after spending time with them.” (Sahil, 24:40)
• “Self-protection becomes self-rejection.” (Sahil, 35:36)
• “If you’re proud of the work, you should be happy to talk to your friends about sharing it... If you’re not willing to shamelessly self-promote, why should anyone else be willing to share it?” (Sahil, 42:40)
• “When I focus on the idea, I’m wrong 10 out of 10 times.” (Sahil, 46:42)
• "Hang around the hoop." (Sahil, 48:54) – Meaning: Be present and ready when opportunity arises around great people.

Timestamps for Key Segments

• 00:00-02:52 — Episode intro, overview of annual review
• 03:02 — The power of reflection over blind experience
• 05:00 — Q1: What did I change my mind on?
• 10:10 — Separating personal and professional reflections
• 11:33 — Q2: What created energy this year?
• 18:58 — Q3: What drained energy this year? (“Shower people” concept)
• 25:05 — Q4: What were my boat anchors?
• 28:08 — Using AI/ChatGPT to spot blind spots (boat anchors)
• 33:04 — Q5: What did I not do because of fear?
• 39:49 — Q6: Greatest hits and worst misses—and why?
• 44:04 — Q7: What did I learn this year? (Synthesizing lessons)
• 48:54 — “Hang around the hoop”: being ready for opportunity

Episode Tone

The conversation is candid, practical, and focused on self-improvement—balancing tactical self-help with reflective, vulnerable storytelling. It’s designed to empower listeners with tools, not just motivation.

Additional Resources

• Show notes will include: Sahil’s Personal Annual Review PDF, links to his book and social media, and templates for listeners to use.
• Idea Database: For more startup inspiration, visit gregisenberg.com/30startupideas.

Takeaway

By systematically answering these seven questions, listeners can reflect deeply on their past year, cut out what’s holding them back, and set themselves up to “operate at full power” in 2026. “Get your pen and paper out”—the transformation starts with reflection.