Ten Steps To Plan This Year (or How To Run a Useful & Enlightening Yearly Review)

How to plan the year and run a yearly planning process

Every year around this time you'll find me alone in a cabin in the woods.

The reason is I like to take a day or two, clear space in my calendar, and plan the year ahead.

The goal is to get perspective on where I've been, recenter myself on where I'd like to go, and then use the resulting high-altitude perspective to plan out the route I'll take for this next year.  

I’ve refined this process over the last few years and it's incredibly useful for me.  I'd love for you to try it out and let me know how it goes.  

So here goes: 

What you’ll need: blank white paper, pencil, pen, colored markers or pencils, tape, a stapler, a file folder, your preferred journaling system (either digital or paper), and any notes from previous “Year In Review”s.

Here are the ten steps: 

  1. Set Aside Time
  2. Clear Distractions
  3. Do a Year In Review
  4. Complete the Previous Year
  5. Review Where You've Been
  6. Clear Space Ahead
  7. Plan Your Whole Life (Provisionally)
  8. Set 5 Year Goals
  9. Set 1 Year Goals
  10. Create Your Support System

Let's go through the steps: 

Step 1: Set Aside Time

To do an effective yearly review process it's important to set aside time where you won’t be distracted. It's possible to do this process in a few hours, and if that is the only option, go for it. But setting aside an entire day (or two) where you will be alone and undistracted is best. 

I like to rent a cabin somewhere and go there alone. I prefer this option because new surroundings bypass our procedural memory, meaning we’re more likely to get new ideas and new perspectives in a new location. 

Step 2: Clear Distractions

Reviewing your past, present, and future is deep work, and you want to be able to really sink into it. To do this you need to squash all distractions. Block out your calendar, turn off the internet, put your phone in Airplane Mode, etc.

If you are at home or with people, let everyone know a few days in advance that you’ll be in Deep Reflection Mode on your chosen day and that they should leave you alone unless there is an emergency.

You need to clear space for this process to work it's magic so do whatever you need to do to be free of distractions. Put a “Do not disturb” sign on your door, change your voicemail to say you are off the grid, and get a baby-sitter.

Step 3: Year In Review

Ok now you have space: physical, mental and emotional. With this space you are going to do a Year In Review for the last year. Lay out some blank paper on your desk, or (as I like to do) on the floor. Use as much paper as you want. You are going to be drawing and writing, circling and connecting, so give yourself a big canvas.

Know that all this paper is going to end up in a little booklet called "20xx Year In Review”. You'll use this booklet in future years, so make it something that will be fun to return to. 

Ok, once you have your canvas of paper ready to go, here are the steps: 

a) Map the Year. Start writing or drawing everything that happened in the last year. Do this in words, pictures, colors, bullet-points, arrows, whatever feels right. Just start and take it from there.

This Year in Review can be free-form and artistic, or it can be super organized with bulleted lists and sub-lists. The point is to get everything that was significant over the last year out of your head and down onto paper.

You are essentially making a free-form mind-map of your experience of the last year. Address your physical, emotional, mental, analytical, romantic, financial, creative, and athletic realities over the last 12 months. Add in any other realities or experiences that were important. 

Here are some prompts to use as you go through this process: 

  • Peak Experiences - What were the highlights of last year? how can you get more of them in your life? When in the last 12 months did you feel exhilarated in a good way? When were you most bored.  
  • Relationships & Love - How does your love life occur to you right now? What are you grateful for? What are you challenged with? 
  • People - Who are the people in your life you are most grateful for? Which relationships deepened this past year? Which relationships are on the way out? Which relationships do you want to deepen moving forward? Which relationships are you willing to let fall away to make room for newer deeper ones? 
  • Home - How does you home and home life occur to you right now? What are you grateful for? What would you do differently? 
  • Work - How does your work and work life occur to you right now? What are you grateful for? what do you want to be different? 
  • Creativity - How does your creative life occur to you right now? What are you grateful for? What did you create this year? What do you really want to create in the future? 
  • Health - How does you health occur to you right now? What are you grateful for? What are your challenges? 
  • Service & Contribution - How does this area of your life occur to you right now? What types of service did you love this year? 
  • Adventure - What adventures did you have this year? What adventures do you want to have next year? Before you die? 
  • Internal Reality - What was it like inside your head this year? What thought patterns did you build? what thought patterns did you let go of? what thought patterns would you like to let go of? 
  • External Reality - What got accomplished out in the world this year? 
  • Challenges - What were your biggest challenges this year and what did you learn or get from them? 
  • Jems & Lessons Learned - What were your biggest learnings this year? 
  • Regrets - What are your regrets from this year? What did you learn from them? 

When your head feels empty, do some light organizing with arrows and circles, connecting things together and summarizing themes. Once everything is out of your head, move on to the next step. 

b) Review Yearly Goals. If you set goals at the beginning of last year, pull them out and on another piece of blank paper, make a list of the ones that got accomplished and why. Make a separate list of the ones that didn’t get accomplished and reflect on why not. Reflect on your goal setting process and the quality of your goals from last year. Did you set too many or too few goals? Were your goals specific and measurable? How do your goals from last year occur to you now? Do some evaluation and jot down some notes and then move on to the next step. 

c) Do an Infrastructure Inventory. On another piece of blank paper make a list of the infrastructure in your life that helped make the past year the year that it was.

(note: when I say infrastructure I mean set processes that you do on a regular schedule and that help you in your life. For example, for me the following regular processes are infrastructure: brushing my teeth twice per day, meditating every morning, doing a weekly review on Sunday, going to bed by 10pm, having a monthly life dinner with Kati, keeping our kitchen free of sugary snacks (unless we're having a party), filling out my habit tracker daily, tracking my time daily, doing a weekly date night, holding quarterly retreats, and moving my body every day. For you the list will be different).

Address and list daily infrastructure (habits), and weekly, monthly and quarterly infrastructure. Address infrastructure around spirit, love, relationship to self, wealth, creativity, and contribution. What infrastructure was super helpful this year?  Are there places where you’d like to add more infrastructure or need more support? What infrastructure was missing or didn't work?

Take a minute to look at your goals that didn't get accomplished from last year and ask yourself what infrastructure could have supported you in getting those goals met. When you are done with infrastructure, more on to the next step. 

d) Do an Accountability Inventory. On another piece of paper list the things in your life that keep you accountable. Notice that accountability is a special and powerful kind of infrastructure. It involves using relationships with others to hold us to account and help us get where we want to go, even when the journey is uncomfortable or outright painful. 

Accountability can come from friends, business partners, coaches, community members, groups, programs, family, mentors, advisors or other places. Take an inventory of what relationships you have in your life that keep you on track. What accountability relationships are working well? where could you strengthen your accountability relationships? Would stronger accountability relationships help you to realize your goals and dreams? if so how could you put them in place? Jot down these questions and answer them.

e) When you are done with your accountability inventory, the last step of Year in Review is to review everything you've drawn or written. Organize and circle themes and accomplishments that are meaningful to you. Add anything else you want to record for posterity. 

You are now finished your Year in Review! This process can be done in 30 minutes, or it can take an hour or more. Once you're done, it's time to move forward to officially Complete The Previous Year . 

Step 4: Complete the Previous Year

Now that everything about last year is out of your head and down on paper, it's time to declare last year complete.  By declaring last year complete we open up intellectual, emotional, and spiritual space. This space makes room for next year to unfold with new energy, unencumbered by the past.  

To complete last year, get present to everything that happened and everything you experienced and learned over the past 12 months. Feel deep gratitude for the gift that was last year. Take a moment to feel gratitude for all the experiences, lessons, moments and love you received last year. Feel gratitude for everything you had the opportunity to give and that you gave to yourself. 

This is a good time to summarize and make any other additional notes or insights you have about the last year. At this stage I like to make a highly condensed digital "20xx Year In Review" note in Evernote to refer to throughout the year. 

Finally, when you are ready to say goodbye to last year, collect all the paper and notes in front of you, staple them together or put them into a file folder, and go ahead and declare last year officially, finally, Complete. 

Step 5: Review the Last Few Years

Before looking ahead, I find it helpful to look back a little further. If you have any previous “Year In Review”s, get them out and have a look over them. You'll see how you've changed and evolved. You'll also see what hasn't changed, and what has remained important to you over time. 

Another way to review the past, is to draw your "life story" by mapping out the various chapters of your life, what it was like to be you in each chapter, what each chapter means to you, and how they all fit together.

I did this once for my entire life and it provided me with a lot of perspective. It actually pointed out an area of life I had been silently suffering through since early adult-hood.  It showed me how building things, and making music have been consistently important to me for as long as I can remember. Both these learnings informed my goal setting for the next year. 

As you look back, feel gratitude for all the life experience you’ve been given. Remember how lucky you are. 

Step 6: Clear Space Ahead

Before looking to the future, it's useful to take a minute to clear even more space ahead by getting rid of clutter. Clutter is stuff that is no longer useful, but that is still hanging around.

Clutter comes in many varieties: physical, digital, emotional, relational.  This step is about getting the clutter out of your life. Ask yourself the following 4 questions: 

  1. What could I simplify, get rid of, or stop doing? 
  2. What am I doing that is wasting my time and life energy and how can I stop doing it? 
  3. What can I unsubscribe from? 
  4. What is in my life but that I don't use, or that makes me feel bad?  

Take some time to make a list of all the clutter in your life, and book some time in your calendar to get rid of it. Clutter consumes energy. Less clutter means more energy for the year ahead. 

For me, decluttering includes:

  • Unsubscribing from everything that isn't “tip of the spear” important to my life right now.
  • Deleting all the tasks from my task manager that have gone stale
  • Clearing out my physical and digital inboxes
  • Unsubscribing from calendars I no longer use,
  • Getting rid of clothes and toiletries I didn't wear or use over the previous year, and 
  • Making a list of things I hate doing and setting aside time to delegate them (ex. opening mail, grocery shopping, email, and anything to do with facebook).

It’s a fact of life (and in fact a property of the universe) that things tend to get cluttered. The end of the year is a good time to intentionally declutter your life. Schedule time to throw stuff away, organize anything that is taking up mental overhead, and simplify. 

Step 7: Plan Your Whole Life (Provisionally)

I got this trick from my friend Jamie Thompson. The process here is to take out more paper and plan in broad strokes, your entire life from now until you die. To do this, pick the year of your death.  Remember that medical research is proceeding at an exponential rate so it's entirely possible some of us will live to 120, 150 or beyond

Personally, I plan to live to be 150 and die on my birthday so that’ll take me to Apr 23 2130. I’ve got a little over 110 years left. 

Whatever year of death you choose, plan out the chapters of your life from now until then. You aren’t committing to this future, but you are sketching it out for the purposes of getting perspective. 

When planning your entire life, it’s useful to look at the various chapters you have planned and ask yourself what capabilities you’ll need to make them real. This next year would be a good time to start building those capabilities. 

If planning in chapters doesn't resonate for you, it can be helpful to speak in terms of decades. Like “In my 30’s I’m going to X, then in my 40’s I’ll Y, so that in my 50’s I can Z, etc.”

When you are satisfied with your blocked out life and feel that you might die feeling complete at a ripe old age. It’s time to move on to the next step. 

Step 8: Set 5 Year Goals

Based on where you’ve been (Year in Review), and where you are going (the future you just mapped out), where will you be in 5 years? What will have been accomplished?

Close your eyes and go to today's date 5 years from now in the future. From there, root yourself in gratitude and possibility and imagine everything has gone swimmingly these past 5 years. Feel into what has been accomplished and jot down the three big accomplishments or experiences that are most meaningful to your life story. These are your 3 five-year goals. 

When setting 5-year goals, it's important to make sure your goals are specific and measurable, and also that they stretch you, so that you’ll need to grow and learn to achieve them. This will make the next 5 years fun and meaningful. As Dan Sullivan says, "Goals are the Fuel for Growth”.

Lastly, what capabilities do you need as a human to achieve these goals? How can you start working on those capabilities now? 

Step 9: Set 1 Year Goals

Now that you have 5 year goals, it's time to translate them into 1 year goals. Ask yourself, what are the three things you could accomplish this year that would give you the greatest sense of achievement, growth, happiness, and fulfillment at the beginning of next year? What new capabilities will it be challenging yet enjoyable to build? If you died next year on New Year’s Eve, what would you want to have accomplished in your last year? 

When setting your yearly goals it’s important to only have 3 of them. As Steve Job’s said “focus is saying no”. With only 3 goals, it’ll be way way easier to obsessively focus on them and give them the quarterly, monthly, weekly and daily attention they need to become real. 

I used to make a list of ten goals every year, but then I noticed at the end of the year I never felt happy about what I had accomplished, since invariably I didn't achieve some of the goals on my list.  Setting three goals makes it easier to underpromise, and over-deliver. 

To set your 3 big goals, look through the different areas of your life (personal, spirit, professional, creative, relationships, health, contribution, etc.), and pick 3 specific, measurable, goals to focus on achieving this year. Make them all "needle movers” that will make a big impact on your life when they become real. They should be big enough so that if you accomplish nothing else, you would still be stoked at the end of this year.  

Then, for each goal, do four things: 

  1. Write out the goal in very specific unambiguous language. Make sure the goal accurately describes in it's entirety the achievement and experience you desire. Goals have a funny way of coming true, and so language matters. Anything you leave out of the goal might kick you in the butt later. For example, when I set the goal to pass the CEO role at Kindara on to another person, I didn't specify how long that person would remain CEO in the goal. The goal was achieved, but when our CEO resigned a few months later it caused stressful disarray at the company. I wish I would have specified at least 3 years in the goal. So language matters. Specify in your goals the exact result you are aiming for, how you want to feel as you achieve the goal, and any details that could be relevant. 
  2. Map out each goal in your notes: what are your reasons for wanting to achieve the goal? Why is it a must for you? What are the obstacles? What strategies can you use to overcome the obstacles? And most importantly, what are the specific next actions you can take to get started? Write it all down for each goal.  
  3. Schedule the specific next actions in your calendar. This step is of critical importance. By scheduling your next actions you are getting yourself on the court and moving towards achieving your goals. This motion can continue all year long.  
  4. This might seem silly, but write the three goals in big letters on a piece of paper and tape the paper to the wall. If you are doing your yearly review away from home, I recommend still doing this step. When you go home you can take this piece of paper home with you and stick it on the wall of your office. Sure, you can design a nicer-to-look-at version of it and replace the hand-drawn one at some point in the future, but it's important to get these three goals on the wall now so you start to see them every day. If you have two offices, make two signs. If you travel a lot, make a nice wallpaper image for your computer or phone with your three goals on it. Get them where you will see them every day. Trust me this is magic. 

When you're done setting your three big goals for the year, there's only one final step. 

Step 10: Create Your Support System Infrastructure

The last step is to identify the infrastructure you’re going to put in place to support you this year, and make it highly likely that you will accomplish your 3 goals. Some examples of infrastructure are, quarterly reviews, monthly reviews, weekly reviews, joining a mastermind group, signing up an accountability buddy, or participating in an ongoing personal development program. Basically you want to give yourself nowhere to hide from these three goals. You want people in your life who will remind you of them constantly. 

The ultimate infrastructure is a coach, because you can explicitly tell him or her “Hey coach, here are my three goals for the year. I’m going to take 100% responsibility for achieving them. However, your job is also to take 100% responsibility for me achieving them. I want you to do everything in your power to make sure I achieve these three things”. This is a powerful commitment to your goals, and this kind of infrastructure will make a huge difference.   

Whatever infrastructure you put in place, make sure some of it involves people. We’re much more likely to do things we’ve committed to in the context of our relationships with others. 

Last Step - Make It Real and Enjoy The Ride

You are done! Congrats! This process can be done in a few hours, or stretched over a few days depending on what feels right for you. I hope once you start doing it as a ritual every year you’ll wonder how you ever existed without it. 

Please let me know how this goes for you, and if you’re building something cool and want help making it real, please get in touch


Will Sacks