Annual Planning Workbook
By: Janine Sickmeyer
Tags: New Year, New Year Resolution

To say that 2020 was a tough year is an understatement. We experienced loss in many areas of our lives and were forced to adapt to a new way of living. But 2021 is coming and with that comes more possibilities. A new year is a time to take some time to reflect on where we’ve come and move forward to a new beginning!

The reflection part is so important because it allows us to identify what went right and what went wrong. In my experience, reflection has always been a catalyst for change and has encouraged me to make goals and better decisions.

Now that we’re on the cusp of a new year, it’s also the perfect time to set intentions. You’ve probably set dozens of New Years Resolutions and abandoned some of them by mid-February (or earlier). It’s easy to make some mistakes when making New Year’s goals like holding yourself to an impossibly high standard. We’ve all done it, but let’s make 2021 different. Instead of setting cookie-cutter goals that are hard to keep, create thoughtful and achievable ones that’ll allow you to stay true to yourself in all aspects of your life (professional, personal, family, etc.)

As an entrepreneur, you probably have a million things you want to accomplish in 2021 because that’s just who you are. Members of the startup community are hungry for change and growth both in business and as an individual. Before the start of the new year, take a day out of your busy schedule to plan out what you want your 2021 to be so that you can hit the ground running on January 1st.

Every year my husband and I (both entrepreneurs and business owners) unplug and go on our Annual Planning Retreat. Don’t let the name fool you. We spend a day away at a hotel and/or doing activities we enjoy in order to reflect and recenter our goals for ourselves and our family. For example, a couple of years ago we spent a Saturday at a local float spa where we immersed ourselves in a morning of relaxation and took the afternoon to look into the year ahead. This year we are planning to escape to a cabin for two days to focus on our future and listen to the sweet sound of nothingness while hiking in the cold forest.

When you’re planning for the new year, it’s hard to know where to begin so that’s where I come in!

I created the Annual Planning Workbook to help YOU reflect, reset, and plan for the new year WITH INTENTION!

The workbook contains four parts: reflection, visualization, action plan, and one word. Each section walks you through questions and activities so you will have a deeper understanding of yourself, plans, and intentions. Ideally, you (and your partner, if relevant) will unplug and follow the workbook to plan for 2021. Download the workbook here.

In order to have a deeper reflection, I encourage you to print out a copy (and maybe a second) of this workbook. Leave your laptop or computer behind and limit any distractions so you can fully focus on your goals. I usually go to a cabin or a secluded place to unplug for this exercise and spread it out over two days.

Part 1: Reflection

Resist the urge to dive in and start listing out your goals. In order to look forward, you must look back. Even if 2020 was messy or complicated, it’s necessary to reflect so that you can identify what you’d like to improve. When thinking about your year, it’s just as important to recognize and celebrate your wins, even the small ones. The workbook prompts you to answer several questions to spark reflection like:

Who inspires you to grow?

How did you practice kindness to yourself and others?

What new skills did you learn or master?

What risks did you take and what were the rewards?

What were your biggest failures and what did you learn from them?

Who or what did you lose? How did you handle that?

and more!

These questions serve as reminders of what you experienced and accomplished in 2020. But I want to challenge you to go deeper. With a reflection framework, you can analyze each area of your life such as career, mental health, and relationships. The framework table gives you space to rank each category from 1–10. One being “not fulfilled” and ten being the “exceptional” Also list out your greatest success, areas for improvement, and how to change. This way, you are targeting exactly what you want to change and springing into action.

But before you move on, it’s important to have a final reflection that puts everything into perspective. Ask yourself: What do you I want to remember most about 2020?

Don’t forget to review your reflection and share it with those who are most important in your life — like your partner, a family member, or even a best friend.

Part 2: Visualization

Picture what you want out of 2021. As Amit Ray says, “visualization lets you create your own reality so that the universe will reflect back to you.” I’m not an expert in meditation, and you don’t have to be to complete this exercise. Find a quiet place to be alone and imagine next year. Start by thinking of who and where you want to be at the end of 2021. Then, think of every detail that will get you there. Some questions to get you started:

What do you want to achieve?

Where do you want to live?

What do you want to do for work?

What do you want to do with your free time?

After thinking about 2021, write all your thoughts down. Don’t hold anything back, let it all flow out. Then, circle what stands out and what resonates. These words and phrases will turn into your top goals for the year.

Part 3: Action Plan

Once you’ve reflected on 2020 and visualized 2021, it’s time to create an action plan. Whether you are doing this exercise with another person or are doing it alone, list out your values and how they will fit into the next year. Your values could be health, happiness, advancing in your career, etc. Listing out these values should give you an understanding of what you need and what you don’t in 2021. Now, turn your values into actions: things you want to invest in, save for, or spend time doing. For example, if one of your values is to advance in your career, you might want to take a professional development course or work with a business coach.

Letting go of things that don’t serve you is just as important as creating action items. Write out what you’re leaving in 2020 and walking away from.

In one of my favorite books, Atomic Habits, James Clear says “all big things come from small beginnings.” List out three habits you want to start, three you want to continue, and three you want to stop next year. Remember, habits are little improvements you can commit to every day.

Part 4: One Word

What do you want to live by in 2021? Choose one word that will guide you through the year, no matter what challenges come your way. This word will also help you stay focused. Embrace your word for guidance and strength. When feeling lost, you can use your word as a way to recenter you. One year my word was “Growth” while the next was “Rest”. It is a personal choice so be sure it is meaningful to you and can honor what you need in your life.

2021 will only be “your year” if you take the time to reflect, set your intentions, and create an action plan. Let’s go!!

Download your Annual Planning Workbook now 📆 ✍️ 🚀