Annual reflections

I don’t think there’s one “perfect” way to do an annual reflection. I like to try different ways of thinking through things so I’ve managed to pick up various resources as I go.

The Year Compass has been the most used tool in my kit, but I’ve also used some of the others listed here. I’ve got my own quick reflection template as well, which I’ve added below.

This list is presented with no particular opinion—just a collection of tools I’ve found. Take what is useful to you, leave the rest behind.

The Resource List

  • Year Compass A free, downloadable booklet that helps you close out the past year and plan the next.

  • My Plucky Path A career-focused planning guide that helps you reframe your professional narrative. Great for those wanting to focus specifically on their work life for the year ahead.

  • Steph Ango’s 40 Questions A simple but deep set of 40 questions to ask yourself every year. It’s less about planning and more about capturing a snapshot of who you are right now.

  • Year-end reflection tools/frameworks It encourages you to review habits/projects that worked and decide what to build next.

  • Alex Vermeer’s 8760 Hours A comprehensive guide for planning the next 8,760 hours (one full year). It’s highly detailed and perfect for anyone who loves data, productivity, and optimization.

  • HBR: Planning When the Future is Foggy An article for when you feel paralyzed by uncertainty. It offers strategies for “micro-planning” and focusing on what you can control when the big picture is unclear.

  • Tessie Tracy’s Goal Setting A “Back from the Future” approach that encourages projecting forward to gain clarity, then working backward to set specific, written goals and deadlines.

  • The Community Collective Review Focuses on “best practices” like identifying true feelings, reviewing goals against specific blockers, and incorporating peer or manager feedback for a holistic view.

  • Townsend House: Word of the Year A resource dedicated to the concept of “Intentionality.” It focuses on picking a single guiding word to help filter decisions throughout the coming year.

  • Wide Lens Leadership Exercise A “Gap Analysis” for both work and personal life. It asks you to rate your current success on a scale of 1-10 and identify what is missing.

  • Intelligent Change: Best Year Journal A physical journal focused on gratitude and structured planning. Good if you want a tactile artifact to keep you on track all year.

  • MacSparky’s Reflection Prompts For mid-year check-ins. Based on a “roles-based” system. You audit your different life roles (e.g., parent, worker, friend) to see where you are meeting your ideal standards and where you aren’t.

Year-End Reflection

A 30-Minute Check-In With Yourself

Grab your coffee or tea. Find a quiet spot. Be honest - this is just for you.

How To Use This

  • You can do it in one sitting or break it into three 10-minute sessions across a few days
  • Write by hand or type or dictate your answers - whatever helps you think
  • Keep it or share it - this is yours, for however you’d like to use it
  • There are no wrong answers - be honest with yourself
  • Skip questions that don’t resonate or make up new ones - this isn’t homework

I’ve also created a Google Doc to save you some copypasta.

Part 1: What Actually Happened (10 minutes)

The Highlights Reel

What are 3-5 moments from this year that made you feel most like yourself?

The Hard Stuff

What were 2-3 things that genuinely sucked or challenged you this year?

The Unexpected Turn

What’s one thing that happened this year you didn’t see coming? (Good, bad, or just… different)

Part 2: Who You Were This Year (10 minutes)

Authenticity Check

When were you most genuinely yourself this year? What were you doing?

The Things You Made

What did you create/build/fix this year that you’re proud of? (Big or small, digital or physical, public or private)

Time & Energy Audit

Where did your time actually go this year?

  • What got most of your energy:
  • What deserved more of your attention:
  • What took energy it didn’t deserve:

Relationships That Matter

Who brought out the best in you this year?

Part 3: What Matters Going Forward (10 minutes)

The Non-Negotiables

What are 2-3 things about how you lived this year that you want to protect and carry forward?

The Stuff to Leave Behind

What’s one pattern, habit, or way of thinking you’re done with?

The Seeds You Want to Plant

What’s one thing you want to start, build, or explore in the coming year? (Just one. Don’t overcomplicate it.)

Your North Star

Complete this sentence: This year taught me that I need more _____________ and less _____________ in my life.

More:

Less:

Final Thought

If you could tell yourself one thing right now - something true, something kind, something you need to hear - what would it be?

That’s it. You’re done!