How I Plan for the New Year: Your High-Level Planning Guide
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“Give me six hours to chop down a tree and I will spend the first four sharpening the ax.”
— Abraham Lincoln
What does this quote mean to you? Your plan is your axe. Your mind is your axe. Your goals are your axe. It's no secret that I believe in planning as a tool for any endeavor: Project management, grocery shopping, a lifelong bucket list, getting Christmas shopping completed on-time. That's why December has seen more of me face down in my notebook more than any other month.
I originally intended to publish a near replica of my 2017 post of the same name and content, only to realize while comparing the piece to my present-day notes, that I am still planning to the exact rhythm, with a few refinements.
January 1 is an arbitrary day.
The idea of new year's resolutions has long passed me. I find that setting lofty expectations for new habits and personality traits to materialize in a single day cheapens what's possible when the year turns anew. While January first is an arbitrary day, it marks the turning of a cycle: a year. In business, we divide our expectations by year, quarter, month, week, and beyond. It's less the date and more the cycle that matters.
My year moves seasonally: Winter, Spring, Summer, Fall - with milestone dates in-between. Those dates are:
My birthday, February 25
The completion of my first one-hundred days, April 10;
Mid-year review at the start of July;
and the start of the holiday season on November 1.
If planning in great detail doesn't thrill you, these activities might drive you insane. You may think it's too much to think deeply about what you want to accomplish, who you want to be, where you want to go, and how you want to live. But, if you've either never tried it or find yourself wishing for more fulfillment this year, give planning a try.
Each of these activities can be done separately, in groups, or all-together. This is how I plan for a new year.
Year-in-Review: Take time to rediscover your year
Here are some suggestions for completing your year in review:
Grab a pen and paper and write it all down.
After you've exhausted your memory, go back through your social media posts, journal entries, and calendar entries to see what you may have missed.
Be sure to write down everything, no matter how big: Trips, work accomplishments, special surprises, new foods and experiences, major purchases or sales, goals accomplished, skills learned or tried, milestones, events attended, charitable giving, good books + movies you enjoyed, creations, commitments, instances of luck or happenstance.
Don't skip over the sad, disappointing, not-very-nice, unacceptable, and "I never want that to happen again" items. See your whole year for what it was: beautiful. Because it brought to you the moment you're in right now.
Circle favorites, get out some colored markers or pencils and make notes, see patterns, and celebrate!
Vision Casting: Do a possibilities brain dump
A brain dump is typically timed, but an otherwise unstructured outpouring of ideas, thoughts, hopes, dreams, and information from your brain. Set a time for 5 or 10 minutes (any longer and you may lose steam!) and write with reckless abandon for your upcoming year.
Do not worry if something you're thinking about or writing down is impossible, ridiculous, expensive, weird, a pipe dream, unimaginably difficult to attain, something you know nothing about, a place you've never been, or a thing you don't even know exists.
Let these questions serve as mini prompts to help you complete that brain dump list. Take as many 5 or 10 minute increments as you need but be sure to give yourself breaks in-between.
What do you want the most right now?
What did you want last year but didn't attain, accomplish, or acquire?
What did you need last year that you didn't get?
What do you need right now? This can be items, support from a loved one, advice, a new job, anything.
Have you been idolizing, loving, or admiring someone or something on social media? How would that look in your life?
What would make this your best year yet?
What do you want to accomplish?
Where do you want to visit or explore?
What do you want to learn, try, or experience?
Goal Setting: Take your big dreams into consideration
I have seen firsthand that the power of planning can help big dreams become a reality. Travel to Europe? Check. Buy + sell my first home? Check. Start a successful marketing business in a new state? Check. Planning a month to work and live abroad this year? In-progress.
Take this opportunity to indulge your BIG DREAMS. Use this list below to help you review, adjust, or start your big dreams bucket list:
Who do you want to be?
How do you want to be?
What do you want to have?
Who do you want to be with?
Where do you want to go?
Where do you want to be?
What impact do you want to make?
What do you want to create?
What do you want to learn?
What do you want to see?
How do you want to be remembered?
How do you want to leave a legacy?
Your "big dreams" are your priorities. When you're making decisions, setting goals, and preparing for a new year, be sure your choices are in-line with your priorities.
Create Boundaries: Assess what's concrete
As I've aged, I've had more things become concrete in my life. While anything can change at any moment, there are some aspects that I consider "set in stone" that I can rely on: My relationship with my partner, my pets, the fact that I need food-air-water to live, my burgeoning career as a writer, my long-distance relationship with my parents, and my growing career.
What's concrete in your life? It's scary to assess the big commitments: our relationships, our jobs, our families, our teams or clubs, our education, our house and town, our physical health. Just as well, assess the more peripheral aspects: wardrobe, habits, hobbies, possessions, indulgences, diet, preferences. Take a half-hour and journal about any of these that stand out to you. Is it time for a change? Is it time to invest more in one area?
Word: Establish the year's theme
bloom, verb
to become more apparent or fully expressed.
In 2019, my theme was "Consistent." My whole life, I’ve been told by others if I’d “just been consistent” I’d have this or that or be this or have that. I felt that so much of what was missing from my life was due to being consistent. On the contrary, I quit when something didn’t work, I pivoted and switched gears, I moved on, and often rather quickly.
Yet, focusing on being consistent and cultivating more routine, ritual, and reliability in my life completely changed my perspective of myself. Yes, I was inconsistent in some areas, and with focus, I made improvements: Taking supplements each morning, daily skincare, morning and night routines that didn’t involve screens. What I truly gained was confidence in my personal approach to choice and commitment: I will stand by my word until I no longer can, and in the event that I can’t, I’ll take every necessary action to right the ship for the next sail.
When giving this advice to others, I often phrase it: “Making the best decision you can with the information you have at the time.”
In previous years, my themes have included:
2016 - Authenticity
2017 - Patience
2018 - Grace
2019 - Consistent
And now, bloom. Having cultivated and grown so much, I am ready to step into my power and to be fully expressed. In the year of my Saturn return, more rooted than I’ve ever been, I’m ready to bloom.
Goal Setting: Working backwards from your destination
When I plan a road trip, I set my destination point first. I see how long it'll take me to get there and estimate how long I actually have for the trip. How many stops can I make? How much time do I truly have?
Goals, milestones, and big dreams are your destinations.
Each time you endeavor toward one of these beacons, you're on a road trip. You'll have stops, challenges, and changes along the way. You'll also have beautiful scenery, exciting developments, and special surprises throughout your journey. It's up to you to take that destination and make the most of the journey. Here's an exercise for establishing a milestone backward:
Destination: Publish my professional writing portfolio. → What I'll need to make that happen:
Know who will be reading my portfolio and what they'll need → List potential audience of portfolio such as magazine and blog publishers, book publishers, and businesses • Outline what they're looking for in a writer they want to work with
Curated works for display → Collect all of my published works in one place for review • Choose 12 - 15 that best represent my style, range, and desired projects
Portfolio design → Research and curate my favorite examples, 3 - 5 maximum • Create my portfolio within Squarespace and publish.
After you've worked backwards to determine what is needed to reach your destination, schedule those activities in your 2018 planner where most appropriate. I'm giving myself January + February to complete my portfolio for publishing on March 1, 2020.
Calendar + Schedule Setup: Setting your plans in (official) writing
It's important to tell the difference between your brainstorming practices and your actual plans. Give yourself the same formality and attention you'd give a work project or professional commitment. Schedule your milestones AND the steps it will take to get to each of them in your planner, giving them ample time for creation. Most importantly, give yourself time to reschedule.
If I've learned anything about planning this year, it's to give yourself space to stop, rethink, and reschedule. Don't fall prey to the satisfaction of a full-planner or a structured year. Life will happen as it deems fit and all we can do in the moment is be flexible. Set yourself up for success by making room for failure.
This may look like a monthly half-day or bi-weekly afternoon where you review what's fallen off of your to-do list or what commitment has been left behind.
How do you plan for a new year? Do you plan at all? Share in the comments or on Instagram where the magic is happening!
