2022 Annual Planning for Founders

Janine Sickmeyer
5 min readDec 28, 2021


With just a few days left of 2021, there’s no better time to look forward into the new year than now. 2021 was the second year of the COVID-19 pandemic and although life started to get back to normal, it was filled with uncertainty from new variants. It’s no secret that 2021 was difficult, but we adapted to the challenges. 2022 is just around the corner, and the new year brings a whole new set of possibilities, a chance to reflect on the past 365 days, and set goals.

We’ve all set ambitious New Year’s Resolutions, some of which we abandoned before the Spring. It’s easy to do it. This year, take a different approach to New Year’s Resolutions. Avoid cookie-cutter goals and instead create thoughtful and achievable goals that allow you to stay true to yourself and do what is important to you.

As a founder, you are ambitious, hard-working, and love the hustle. That means you probably have a ton of items on your list that you would like to accomplish in 2022. But before the new year, it’s important to take time out of your busy schedule and disconnect from work so that you can rest, recharge, and plan for the year ahead.

A great way to set the stage for 2022 is to take a day or two away from the hustle for an annual planning retreat if you’re able. Your retreat can be anything you want it to be. Spend a day away at a hotel or doing activities you love such as a spa day. While you’re unplugging, the Annual Planning Guide is a great companion for outlining the year ahead.

The refreshed 2022 Cobble Annual Planning Workbook will help you reflect and plan for the new year with purpose!

We created the Annual Planning Workbook with entrepreneurs in mind. It contains four parts: reflection, visualization, action plan, and one word. Each of these sections contains questions and activities that challenge you to think deeper and understand what you want out of 2022.

My preferred way to use the Annual Planning Workbook is to print out a copy and put pen to paper. This limits distractions and helps you fully focus on your goals.

Part 1: Reflection

When you think about new year planning, the first thing that comes to mind is goal setting. Resist the urge to write down a bunch of goals. Before you look forward, you need to look back. Reflection allows you to identify places to improve and what you did well. It’s just as important to recognize and celebrate the wins. The workbook helps you do this by asking questions such as:

  1. What new skills did you learn or master?
  2. What challenged you the most? (Example: work-life balance, a missed opportunity at work, etc.)
  3. What did you invest in? (Example: relationships, health, your startup)
  4. What risks did you take and what were the rewards?
  5. What were your top three peak moments?

These questions act as a guide to remind you of your experiences and accomplishments of the prior year. Next, you’ll dive deeper using a reflection framework so that you can further think about 2021. The framework table gives you space to rank areas of your life based on who much they fulfilled you, as well as list out your greatest success, area for improvement, and how to change. This table gives you the tools you need to spring into action.

The last part of the Reflection section encourages you to put your year in perspective with a final question. “What do you want to remember most about 2021?”

Part 2: Visualization

Amit Ray says that “visualization lets you create your own reality so that the universe will reflect back to you.” You don’t need to be an expert in meditation to complete this exercise. Find a quiet place to imagine your next year. Think of who and where you want to be at the end of 2021 amd 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. Circle what resonates and these words and phrases will turn into your top goals for the year.

Part 3: Action Plan

After reflection and visualization, create an action plan for 2022. Start by listing out your values and how they will fit into the next year. Doing so will give you an idea of what you need and what you don’t in 2022.

Next, turn your values into actions. What do you want to spend your time, energy, and money doing? For example, if one of your values is to have freedom in your career, then think about turning your side hustle into a full-time job! On the other hand, letting go of things that don’t serve you is just as important as creating action items. Write out what you’re walking away from in 2022. It’ll be a relief.

In this section, you’ll also list out some habits you’d like to start in 2022. In one of my favorite books, Atomic Habits, James Clear says “all big things come from small beginnings.”

Part 4: One Word

What do you want to live by in 2022? Choose the one word that you’d like to guide you through the year. Whenever you face challenges, this word will serve as a reminder. If you’re feeling lost, use your word to recenter. A couple of examples for your word are “Growth” and “Rest.” 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”.

The 2022 Annual Planning Workbook is a great piece for entrepreneurs who want to reflect, learn from their mistakes and successes from the previous year, and plan the next 365 days intentionally.

Grab your copy of the Annual Planning Workbook on Cobble, an app for entrepreneurs planning their business. You can sign up free at https://app.gocobble.com/signup and access the Annual Planning Workbook in the Founder’s Library, along with dozens of other templates for entrepreneurs.