The secret to making this year amazing

Photo by Jamie Fenn on Unsplash

I’ve been doing some form of annual life planning for 15+ years, and it wasn’t until the last few years that things began to take off.

There are lots of planning tactics I hope to share, but the game-changing activity to unlocking the year ahead is looking back.

Plato stated that “The unexamined life is not worth living.” Making plans in isolation of reflection ignores the richness of the life you’ve just experienced, and we risk repeating all of the same mistakes.

Have we been really living the last ten years, or have we just been living the same year over and over for ten years? If it’s true that over 90% of the thoughts we have today are the same thoughts we had yesterday, we desperately need to make a habit of breaking out from those rhythms if we’re seeking to grow.

Here’s what I do.

Create time

Set aside 2–3 hours. You may want to break this up over a few days to allow thoughts to surface.


Look through your calendar(s) and jot down noteworthy activities. Your phone’s camera roll may help as well. It’s mind-boggling how quickly we forget significant events.

If you have a journal or any sort of life log, skim through your notes. Jot down any highlights, especially things you may have underlined or asterisked — now’s your chance to make sure you don’t lose it before closing the books on the year.

Review any goals, plans, and values you may have had coming into this past year. It’s helpful to do this after reviewing calendars and journals to avoid judging goals just as a series of hits and misses. Instead, review your goals within the context of everything else that happened in life.

Whether you had goals or not, review the different spheres of your life. Mine are self, family, creative, work, health, finances, and connections. You might have broader categories or want to split yours up further. List activities. My annual life plans also follow these categories.

With the above as cues, let yourself in free form fashion fill out any other gaps from the year that was — this might include experiences, books read, courses taken, people met, occasions celebrated, etc.


These are the five questions I reflect on each year with the above in mind.

  1. What went well & why? It’s always best to open with gratitude as it’s so easy to be self-critical. Go wild here. It may have been your most difficult year ever, but it may have been the simplest of things you can find joy in. Were there moments you laughed till you cried? Was there a situation you handled well? What were you most proud of? Even if there were setbacks where was progress made?
  2. What was hard this year & why? Name it. The things that didn’t go your way. The disappointments. The regrets. The unresolved. Some of this you’ll need to find ways to let go. Some of this may need processing later. Circle the ones you want to revisit so that you’re not mentally ignoring it but giving it a spot down the road to be addressed when appropriate.
  3. Who mattered this year & why? It could be a partner, a friend, an author, even a challenging coworker. When it comes to people who held space in your heart and mind?
  4. What might have made this year even better? Being real here is important — i.e. not winning $ millions. What was in your control, or what decisions you could have made differently? Were there things you could’ve cared for less or different ways you could spend your time? What would you do differently in hindsight?
  5. What did you learn this year? What did you discover? About yourself, others, or the world around you? What do you now know that you didn’t truly understand the previous year? What insights are worth carrying into the new year?

The more detailed you can be the more it will serve you. For example, I had broken out my daily routine at the beginning of the year; however, a recurring issue I had was whenever I started intermittent fasting for periods it would throw everything off. It seems simple, but it wasn’t until reflecting that I discovered there was a number of workflows and alternative routines I needed to construct as well. Lists can be helpful, but the value will be in the details.

Rewrite your year

The last thing I do to close out each year is to sum it all up. You may have all sorts of loose thoughts about how the year went, but after going through the reflection, I find it helpful to distill it down to a paragraph. I include my year-end paragraph in one place for reference, and it helps me see the overall arc of my life before I begin planning out my next year.

Bonus tip — I was able to get my kids to do this as well.

I framed it as a creative activity that we would turn into a game (they’re 12 and 8). First, each family member did a solo reflection based on these questions as best as they were able. Then, we simply did our own form of year-in-review battleship guessing what was on each person’s list, enriching one another’s review in the process. Let me know if you try it.


You can take all of this a lot further, but this sets the foundation before diving into new dreams and plans. One of the greatest injustices is being granted a year of life and not acknowledging it for all it’s worth. Do yourself a favor and wring out every bit of insight from the year you just had.

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