Annual Planning & Goal Setting

A lot of people have been asking me about how I approach planning, goal setting, and thinking about the year ahead. For my own benefit, and for the ease of sharing with others, I created this structure to share. I’d love to hear about what you do, what you like, and what has been most sticky and impactful for you over the years.

I like to start by batching the different parts of my planning into categories so that I’m pairing things that are connected to each other. This allows me to move through a natural progression. Then I split each part up into days and I keep track each year of how much time each part requires, so I can properly block my time for the following year. In addition, I always give myself an additional 30% buffer on top of that in case something new sneaks in or I get side-tracked.

In addition, I try to keep these two thoughts front and center through all of my planning:

1. What’s one decision I can make to remove 1,000 decisions?
2. What’s the work I can do once that keeps working for me perpetually into the future? (think zero cost of replication)

And lastly, take whatever is relevant and leave the rest. Everyone’s process and focus is different. Flexibility > rigidity.

Day 1 – Personal Goals:

Part 1 – Personal Goal Setting – Current Year, 3-Year, 10-Year & Lifetime

1. 20-30 MINUTES – Complete your Personal Year Review – the purpose of this is highlight what people, places, activities, and moments were energizing and which were draining. Keep a list of both as you go through your calendar week by week, and then aim to get as many things on the calendar that will be energizing for the upcoming year and avoid the draining ones at all costs. I split these into people (the relationships I want to focus on deepening), activities (the things that were the most fun & inspiring), and personal time (how I want to allocate my free time).

2. 2 HOURS – Create a list of categories in which you want to set goals and then set a MAXIMUM of 3 goals in each category. Here are the ones I use: Relationship, Health, Giving, Not to Do, Financial, Areas of Growth, Time Management, & Other Personal Items.

3. 30 MINUTES – Reread my 10-year remarkable life letter. Reflect on it. Make adjustments if you like. And cherry-pick items that require action where you can move the needle in the upcoming year. If you haven’t done this, click the link and I strongly encourage you to spend 3-4 hours writing this letter to yourself. It is one of the most impactful writing exercises I have ever done in creating a vision for the life I want to create.

4. 1 HOUR – Review & update your 3-year, 10-year, and lifetime goals document. If you haven’t done goals on these timelines, I also encourage you to consider. You can use the same categories outlined above, or whatever is relevant to you. The research around writing your goals down is really powerful and what gets written seems to find a way of getting done a lot of the time. 25% of people abandon their NY resolutions within 1 week and 60% within 6 months. Plant the seed in your subconscious and let it sprout plants and trees whose shade you’d like to sit under in the future.

5. 1 – 3 HOURS – Ideal Calendar & Scheduling – I will create on a blank piece of paper what does my idea schedule look like every year. And then I will block my calendar using a version of this. Show me your calendar and I’ll tell you your priorities. This is the first best step to getting me to spend more time doing the things that are most important, even if it’s not perfect. Additionally, I will block the time for all anticipated travels and potential trips, even if I don’t have the exact dates or details yet. This makes it so I have the time pre-blocked and almost ensures that I end up getting the most important stuff planned—time with friends, family, and new experiences.

6. 5 MINUTES – Bonus / Fun – I like to look back on the year and identify what the theme(s) of the year was and keep a running record over time. I also like to identify what I believe the theme for the upcoming year will be and include that at the top of my personal goals list.

7. PIECE OF ADVICE – Keep a running list of to do’s that arise as you’re going through your goal setting so that you have a clear list of action items and don’t get overwhelmed. For example, I will block my entire calendar for the year and then keep a running list of each travel item that will need to be sorted out along with a target date to have it completed by. Then I may block out 3 hours one day in the next few weeks and knock out everything on the list in one shot. Another example, I typically reboot my exercise, fitness, & nutrition plan each year, so I will block time for specific items like this so that I’m not sitting here on January 30^th with no plan because I got busy and the month got away from me. Remember, Memorial Day will be here before you know it.  

Part 2 – Personal Goals Review For the Year

1. 30 MINUTES – Score each category 0 – 100% based on your level of completion. Copy/paste your goals from the previous year into a word document where you can make notes and comments to yourself.
   • Side note – I start with this, however I included the goal setting as a preliminary starting point in case you are setting goals for the first time and will be reviewing goals for the first time in the upcoming year

2. 15 MINUTES – Write a short blurb to yourself about what went right, what went wrong, and what were some key realizations from your goal review.

Day 2 – Cash Flows & Finances:

1. 30 MINS – 1 HOUR – Update your net worth tracker—if you are not doing this yet, or are unfamiliar, here are some tools that are worth considering:
   • Budgeting, Account & net worth tracking — Monarch, Co-Pilot, Personal Capital
   • Financial projections – Kubera
   • Advanced planning & taxes – Holistiplan

2. 1 – 3 HOURS – Finalize cash flow tracking, make tax payments (if applicable), and send preliminary tax information/considerations to tax team (if applicable)

• There are two main takeaways here…1) having a system for tracking your cash flows—savings & expenses—is a necessary discipline for most to hit their goals—what gets measured, gets managed, and 2) being strategic, thoughtful & thinking ahead about things that may impact your tax situation helps you avoid having any last minute issues in April when the year is already going and you’ve forgotten a lot of what happened the previous year

3. 15 – 30 MINUTES – Review your monthly subscription fees, credit cards with annual fees, bank account fees, and anything else that you’re paying for on auto-pilot or is “out-of-sight-out-of-mind.” These have a way of eating a way at you little by little and then all at once. They also often get forgotten about and we just throw money down the drain. Little things like eliminating unnecessary credit card fees, subscriptions, bank fees, etc. might add up to a few thousand dollars per year. I like to keep a running excel on this simply because I always want to know at any moment, how small of a monthly budget could I live on and maintain my quality of life.

4. 1 HOUR – Review your investment allocations

5. 1 HOUR – Game plan for how you will track and manage cash flows in the upcoming year

Day 3 – Writing, Reflections, Lessons, & Favorites:

1. 15 – 30 MINUTES – Read my previous ‘Annual Letter to Self’ – this is a letter I write each year and save, to open 10 years later. There are no rules for this letter and every year I believe I have done something different. This year, I asked myself the following questions:
   • What made this a challenging year?
   • What were your favorite memories from the year?
   • What are you most proud of yourself for?
   • What do you envision the next 5-10 years will look like and what surprised you this year?

2. 30 – 45 MINUTES – Write your Annual Letter to Self

• Make sure you have a consistent place where you save these documents and can easily find them in the future when it’s time to review (I use Notion)

3. 30 MINUTES – Soliciting Feedback – I do this every 2 – 3 years, otherwise I think it becomes excessive. I will send an email to a maximum of 10 people (expecting only half will reply), with very specific questions, seeking feedback. I will include some very specific notes about the responses I get around what I want to enhance and what I want to bring awareness to based on these communications.

4. 1 – 3 HOURS – Jotting my favorite things in whatever categories bring me joy—quotes, movies, shows, books, lessons learned, experiences, places visited, whatever. It’s a fun way to memorialize the year and distill your most important lessons and favorite things to come back to down the road.

Day 4 – Bonus Items & Fun Activities:

1. Yearly Photo Book – using the application Printastic, I create a physical photo album with all my favorite memories from the year that I keep on my coffee table. It’s tons of fun and since most of us never go back and look at any of the gazillion photos in our phones, this is a fun way to memorialize them–I think about it like my physical cloud backup
2. House Purge – I love to go room by room in my house and get rid of anything I haven’t used in the last 3 months or anything that I really don’t love. It’s a great practice to become skilled in letting things go. If you haven’t been through this before, Marie Kondo has a good blueprint that a lot of people swear by.