Everything you need to reflect on 2023 (questions, templates, and prompts)

And a breakdown of my entire yearly reflection process from this year

Dec 31, 2023

Happy (almost) new year!

I hope you are enjoying some quiet time as we head into 2024.

For me, this end-of-year period is typically my most creative time of the year.

I use the extra time and space to reflect on the past 12 months, distilling what happened and what I learned.

So for today’s newsletter, I wanted to send over some resources you might find helpful in conducting your own yearly review.

Below you’ll find:

A full guide to doing your Yearly Review
My personal 2023 reflection video & recap post
My business 2023 reflection video & recap post
23 questions to reflect on as we end the year
The Dickie’s Digest “Best Of 2023 Curation”
A special discount for anyone looking to kickstart 2023 by building a daily writing habit

Let’s dive in.

1. The Yearly Review Guide

Inside this document, you’ll find everything you need to:

Reflect on 2023
Distill what you learned
Make a game plan for 2024

It’s the exact process I’ve used for the last few years and follows a simple structure you can follow in just a few hours.

So far, over 5,000 people have used it to complete their reflection process. I hope you find it useful!

Click here to download The Yearly Review

2. My 2023 Personal Recap & Lessons

I spent 12 days in the Austrian Alps reflecting on 2023.

This is the third year in a row I’ve done a trip like this. I head off to somewhere unfamiliar, toss my phone on airplane mode, and read through all of my journals to recall everything that happened.

Once I’ve distilled the entire year into a handful of bullet points, I try to summarize my lessons and realizations so I can double down on what’s working and avoid repeat mistakes in the year ahead.

Since this year was so eventful for me, I wanted to document it in as many different ways as possible.

You can watch the 100-minute-long video here
You can read the shortened lessons & realization post here
And next week I’ll publish the long-form blog post recap

I spent 50+ hours on this review, mostly because I know future me will look back on this year as one of the more pivotal ones of my life.

I hope you find my takeaways valuable!

Watch the full 2023 personal recap video here

3. My 2023 Business Recap & Lessons

This year I broke out my personal reflection and business reflection into two different videos/recaps.

So much happened in both my personal life and business life that there was no way I could cram them into one video.

I follow the same process for the business review as I do for the personal review. I recap what happened, then distill what I learned.

Watch the full 2023 business recap & lessons video here

4. 23 Questions To Reflect On 2023

Anyone who knows me knows I’m a fan of collecting high-quality questions.

And during the slow end-of-year period, I love to pull a random question from this list and reflect on it over my morning espresso.

You can find the full list of questions here

I’ve also put them all into one graphic you can download below!

5. Dickie’s Digest “Best of 2023” Curation

I asked my entire 375k Twitter/X following for their “best of” recommendations from 2023.

Books
Podcasts
Blog posts
Habits they built
YouTube channels
Sub-$250 purchases
Lessons they learned

Then, I combined the top responses into a master curation for anyone looking for some vetted recommendations as we head into 2024.

There’s plenty of here to keep you busy reading & learning in the 12 months ahead.

*Download the Dickie’s Digest 2023 Curation here*

6. Kickstart 2024 by writing & publishing every day for 30 days

And lastly, we are just a few days away from the 20th (!) cohort of Ship 30 for 30 which sets sail on January 1st.

If “building a writing habit” or “starting to write online” is something you’ve wanted to do for the last few years but have struggled to stick with, then Ship 30 for 30 is you.

I put together a special code for Dickie’s Digest readers to join for $250 off. Just add code DICKIE at checkout and it will auto-apply.

Click here to hop aboard the January Ship 30 for 30 cohort

7. The future of Dickie’s Digest heading into 2024

For the year ahead, I plan on upping the publishing cadence of this newsletter.

I’m not committing to weekly or monthly or anything like that, but I will be posting more long-form content that is best suited for a newsletter like this.

So stay tuned for my name popping up in your inbox more and more throughout 2024 and beyond.

Thanks for reading! I wish you a strong start to 2024.

If you have any questions about my yearly review process, please leave a comment here on Substack or hit reply to let me know. I read and reply to every one of them!

Dickie’s Digest