Question 6: Greatest hits and worst misses

I’m joined by Sahil Bloom for a throwback episode where he walks me through his “personal annual review,” a 7-question framework to reflect on 2025 and set yourself up to crush 2026. We talk about why reflection beats raw experience, how to use your calendar to surface what you’ve actually changed your mind on, and how to identify what creates vs. drains your energy. We dig into “boat anchors” (the hidden drag holding you back), what fear kept you from doing, and how to learn from both your greatest hits and worst misses. By the end, you’ll have a practical set of questions you can answer on paper to extract real insights from the year and carry them forward.

Get the Personal Review Template: https://www.sahilbloom.com/annual-review

Timestamps

00:00 – Intro

02:54 – Why Reflection Matters (The “Annual Review” Setup)

04:12 – Q1: What Did I Change My Mind On?

11:29 – Q2: What Created Energy This Year?

18:58 – Q3: What Drained Energy This Year?

25:05 – Q4: What Were The Boat Anchors In My Life?

33:06 – Q5: What Did I Not Do Because Of Fear?

39:51 – Q6: Greatest Hits & Worst Misses (And Why)

44:04 – Q7: What Did I Learn This Year? (Synthesize 3–10 Learnings)

Key Points

• You don’t learn from “having a year,” you learn from reflecting on it, and that reflection becomes usable data for the next year.

• Your outcomes follow your energy, use your calendar to identify what creates energy and what drains it, then adjust accordingly.

• For “draining” activities, evaluate how you feel after (not during), because many high-value things feel hard in the moment.

• The fastest progress often comes from cutting what holds you back (“boat anchors”), not adding new habits or protocols.

• Fear is often inexperience (not inability); shine a light on it with deconstruction exercises (e.g., upsides vs. downsides) and take action.

• “Hits vs. misses” reflection prevents bias, overly critical people only see misses; optimists only see wins, both lose learning.

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