Happy Monday 🌞

And happy December! I love this time of year because December is my cue to start going into reflection mode for the current year to better help me plan for the upcoming year.

There are two stages to how I use this time I want to share today: 1. reflecting on the last year, and 2. pre-planning for the next year.

1. Reflecting on the last year

If you haven’t done a reflection on the last year before, I highly recommend it. Reflecting helps me clarify what were the part of this year that went the best for me, and see more of a bird’s-eye-view of how the year truly went.

This is an important step in annual planning for me because we’re often biased with the most recent events. If I happened to have a particularly difficult November and December, I might think “Wow 2023 was hard.” Whereas when I take the time to reflect I have the opportunity to reflect on all of the great things that happened even if they were back in January.

It’s a useful exercise and I usually start thinking of the year as a whole in December, and then closer to mid-to-late December I take the time to write down my answers to a few end-of-year reflection prompts. The list is:

• How did the year go overall?
• What were my accomplishments and causes to celebrate this year?
• What could have been improved?
• Was there a theme for this year that you can see in retrospect?
• What was the highlight of the year?
• What was a lowlight of the year?
• What did you want to happen this year but didn’t?
• What was the most positive unexpected thing to happen this year?
• What would you do differently if you could do this year over?
• What were the biggest lessons from this year?
• If you had to describe the past year in a few words, what would they be?

I don’t always answer the questions to this whole list, but it’s a helpful starting point to make sure I have a complete picture of the last year.

(I originally shared this in a MakeWorkWork blog post here.)

2. Pre-planning for the next year

Before I sit down to dig into what I want the year to look like and what my priorities are, there is something I’ve started doing that I think of as “pre-planning.” It’s a time when there’s no pressure to immediately come up with what’s top of mind for me, there’s just room for it to flow organically.

The way I do this is simple, and as the best systems are, it’s also stolen.

One of my favorite podcasters, Myke Hurley, spoke once on his show Cortex about how for his yearly theme he keeps a note open he opens a note on his phone and keeps a record of things that are frustrating him or that he wants to do better or that are going well.

Last year for the first time, I did the same thing with a Notion page throughout November and December ahead of setting my goals, and it meant I was extremely prepared when it came time to plan out my goals for the year — I loved it.

I once again have a page in Notion just called “2024” where I am starting to drop how I want to feel next year and some things that are top of mind. This seemingly scattered note becomes an anchor for setting specific goals later on.

As much as I always want to make it straightforward, the process of reflecting on the past year and starting to think of priorities for the year ahead simply takes time. I usually give it most of December to simmer, and then write everything down before the end of the year to help me with the next stage: goal setting.

More on that over the next few newsletters as I have a few new resources on goal setting that should be coming out soon.

I hope you have a lovely week ahead. As always, feel free to reply if this sparks any thoughts or questions.

See you next week,

Hailley

• I recently had the chance to chat with someone I’ve loved interacting with over the internet for years now, Kat Boogaard. She has an amazing freelance career and is just as great live as in-person. Here’s a piece for Buffer about how Kate made $300,000 in one year as a freelancer and then chose to scale back.
• Learning to properly delegate tasks is something I still don’t consider myself an expert at, but I was lucky enough to be asked by Rochi Zalani (another amazing freelancer), to contribute my approach for this blog post about how to delegate on the Doist blog. It turned out great and I loved reading quotes from other leaders on the tactics they use.
• This 30-second tactic for how to overcome mental resistance by Chris Bailey is something that’s been very top of mind for me as I try to squeeze too much into the end of the year.

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