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Why I Love October

October is my favourite month of the year. Ok - except for maybe December because I do love Christmas.

Why do I love it so much? Is it because of Thanksgiving, the pumpkins and decorations, or the great food? All of these factors help, but I love October because I take the month - and I mean the whole month - to create my business plan for next year.

Right now, I am about halfway through my planning for 2021 - right on schedule. I’ve tried planning in many different ways and during different months, but I’ve found the most successful to be dedicating October for this venture. I’ve been planning this way for the past 4 years, and it has worked so well that I wanted to share my strategy with you!

Why is October the best time to create your business plan for the following year?

Many people will plan a month at a time, a quarter at a time, or maybe annually, and they typically do so in January. They come back from holidays and realize “it’s January 10th, I want to have a good year” - so they create a plan in one day that includes a variety of things they want to achieve, but they don’t necessarily have a clear direction and they don’t have a battle-tested plan to help them achieve those goals.

While their goals may appear to be well-organized, they haven’t taken the time to consider how they will reach those goals and what challenges may arise along the way. They haven’t reviewed their plan with colleagues to ensure any gaps are filled and issues are avoided.

In my experience with business consulting and creating plans for my own business, I have developed a 7-step strategy that has helped both me and my business become more organized, efficient, and successful with each passing year. Let’s break down each step into detail:

Step 1: Establish A Vision

The first question you need to ask yourself is “Where do I aspire to be at the end of next year?”. It is important to ensure that your vision for the year is big enough to keep you excited and motivated, but still within reach of being attainable.

As business owners, we all have an entrepreneurial spirit inside of us. Having a big goal will keep that spirit alive and drive you towards success. Your vision for the year is very important as the short-term annual goals that you set for your plan will help you reach your long-term goals too.

Step 2: Identify Your Targets & Set Up Milestones

To reach your year-end goals, you will need to set targets throughout the year to stay organized and hold yourself accountable to the plan you are creating. The milestones you create must be defined clearly with an exact due date.

Without these milestones, your business plan will lack direction and many of the planned tasks will not be completed. This will likely result in your year-end goals not being attained. Think of milestones like a recipe. If you follow a cake recipe, you will end up with a delicious cake. So by setting up and following your milestones, you will reach your annual goals!

Step 3: Determine the Tactics Needed

Milestones & targets are difficult to attain. Once you have created your milestones for the year, you need to consider what tactics you will need to use to reach them.

If your milestone is related to revenue, you will likely need marketing and/or sales tactics to achieve it. If your target is to increase efficiency within your business, you may consider training tactics.

The tactics vary greatly depending on what the milestone entails. Once you have identified the tactics that will be used, consider how these tactics will be executed to achieve each milestone.

Step 4: Understand Who Needs to Be Involved

This may be the most crucial step towards the success of your business plan. You may be the one in charge, but your plan cannot succeed without the people around you. You will need certain people in your life such as colleagues, friends, mentors, and family for specific aspects of your plan to succeed.

Make a list of the people you need to execute your tactics and figure out their roles in the process of achieving them. Not everyone will consciously know that they are helping you, however the role they play in your plan’s success is crucial.

Step 5: Identify where you will fail

It’s time to be honest with yourself - nobody is perfect. It is important to have the self-awareness to analyze yourself in relation to your business so that you can plan for challenges you may have throughout the year.

Ask yourself: “Reflecting on my own work, what are the reasons why I would historically fail at hitting these targets or executing on certain tactics?” Every person has strengths and weaknesses. By identifying where you could potentially miss your goals you will be able to get back on track faster.

It is very easy to give up on your plans when you hit a series of misses, but identifying your problems, and planning to react to them accordingly. The next step will help you get over these challenges and remain focused.

I started using this step 3 years ago and it has made a massive change in my ability to reach my milestones.

Step 6: Create A Plan to Avoid Failure

Now that you have identified the potential problems you may encounter; you need to create a plan of action to identify and solve them as quickly as possible.

Will you call a team member and ask them to help you execute a tactic when you are having difficulties? Maybe you can plan to reach out to a mentor when you need advice on a situation?

Some of the action plans you come up with may not work as well as you originally planned, but as you gain more experience and try different methods, you will find what helps you overcome your challenges.

It’s alright to run into these problems and challenges, it will inevitably happen to everyone - but creating a preconceived plan to get past them will allow you to get back on track faster.

Step 7: Create A Reward System

We all love a good reward when we do something successfully, so reward yourself!

I added this step last year and it really helped me stay motivated and on-task. I filled my Pinterest with a variety of prizes that I used as rewards for meeting deadlines and it worked very well! With this strategy, your plan succeeds and you get rewarded with the things you want. It’s a win-win!

Conversely, you also need to set up a punishment system for instances where you do not reach your milestones. Examples of some punishments could be not eating out for a month or doing 100 burpees. It is all subject to what will motivate you to stick to your plan.


These are the steps I use in my annual business planning strategy. I'm still working on refining the process and putting it all together, but every year gets better and more efficient. Maybe your annual planning doesn’t need to take 4 weeks. However, that is what I find works best for me, and you will find a timeline that works for you as well.

The important part is starting in October. I use many tools to help me plan: whiteboards, notepads, iPads, Google Docs and I put it everywhere. Then I bring it all together to come up with my plan.

As you follow these steps and plan your next year, you will find different organizational & time management tactics that optimize this process for you. If you have any tactics or strategies that you find work for you already, please share them in the comments below! I would love to hear about what works for you.

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