Redesigning New Year’s Resolutions

Chris Castiglione
Dec 29, 2014 · 4 min read

I start at the end.

I ask,

“One year from today, who will I be?”

With that question in mind I mindmap the year onto a large piece of white paper. Anything goes: If I were free of money, power, age, and limiting beliefs what would I dream up for myself?

In my first draft I imagine all possibilities of who I could become. Who do I want to spend my time with? What do I want less of?

It’s fun. I play.

This is the first step of my three step process for writing New Year’s resolutions.

1. Explore:

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The first draft of my mindmap for 2015.

Then, I write a journal entry to myself. From the future...

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I ask myself, “Future Chris. How’s he doing?”

I’ll write something like, “Today is January 1st, 2016 (one year from today). I can’t believe the years keep coming at me!…” I’ll include a note to myself about how amazing the past year was, sights, smells, images, etc.

Here are some prompts I like to use to open up my mind:

  1. Three things I’m most proud of in 2015 are: ____________
  2. Three things I’m glad I did less of in 2015 are: ____________
  3. I spent more time with: ____________
  4. I traveled to: ____________
  5. Words to describe 2015: ____________

2. Choose Projects

  1. What do I really want? (Vision)
  2. What is important about it? (Values)
  3. How will I get it? (Methods)
  4. What is preventing me from having it? (Obstacles)
  5. How will I know I’m successful? (Measurements)

3. Execute

  • Monthly Checkin (to check overall progress) — I schedule time on the first Saturday of each month to review my yearly resolutions. I set these dates for the entire year.
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  • Project based checkin: I add projects to Asana and Evernote. If a project is too big (as many of them are), I like to break them down into tasks no bigger than 1–4 hours.
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A screenshot of my Project in Asana
  • Reoccurring task checkin (i.e. the gym and yoga): I use a paper calendar. It’s on my wall and I put an X for each day that I complete the task. You an print out these free wall calendars at
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My wall calendar for reoccurring tasks like going to the gym and yoga

Recap: A Three Part Process

  1. Explore — consider all possibilities for next year by drafting a journal entry from the future
  2. Choose Projects — decide on the most important projects
  3. Execute — set up a process to schedule your projects, and keep yourself in check throughout the upcoming year

Your turn! Who will you be one day from today?

How do you keep your resolutions?

PS. Resources to Help You Succeed:
Essentialism (2014) by Greg McKeown
The First 20 hour (2014) by Josh Kaufman
“A Kinder, Gentler Philosophy of Success” [TED TALK] (2009) by Alain de Botton
Remember Your Goals — Receive free reminders and tips on how best to achieve your goals.
One Month Writing Prompts, one writing challenge a day, for thirty days

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