5 Step Strategic Planning Day: A Must for Entrepreneurs
If that sounds like you, take a deep breath. Today, we're making strategic planning so simple that anyone can follow it. This is your blueprint for planning without the overwhelm—so you can stop winging it and start feeling confident again.
If your business growth is unimportant to you, you’ll be stuck in your online business. Put on your CEO hat and be the person your future self will be proud of. (:
It may be me, but I think it's a good idea to go refill that coffee mug, and let's dive in.
Why You Need a Strategic Planning Day
Your business growth depends on strategic thinking. If you're serious about your business success, a Strategic Planning Day should be on your calendar every quarter. This focused time allows you to step into your CEO shoes.
I think you'll agree with me when I say that business leaders set time aside for strategic thinking. When you have a set process for your strategic planning meeting, you won't miss any important steps.
The Struggle is Real, But So is the Solution
If you're anything like me, you're juggling a million things simultaneously, trying to keep the wheels on the bus. At the end of the day, you fall into bed exhausted from running an online business, taking care of your family, and creating consistent, organic content marketing. It's a lot.
But here's the good news: You're not alone, and the solution is dedicating time to your strategic direction.
Your Free Planning Workbook
As an Online Business Manager (OBM), I've helped business owners set up strategic planning processes that drive real results. I set aside time with the owner every quarter for a business strategy meeting.
I understand that your small company may not be ready for a dedicated OBM as one of your team members. With that in mind, I created my most popular free resource—a planning workbook. It's like a one-day strategy meeting in a box.
It is 50 pages chock-full of all the prompts you need for strategy planning in your business. With the workbook and accompanying email series, you can create your repeatable strategy process.
Grab your copy of the planning workbook here!
Create a Distraction-Free Zone
Do you want to know what you must do first? You should put time on your calendar for your successful strategic planning session. While you are at it, why not set aside time for the whole year of strategy sessions and, of course, time at the end of the year for your annual plan.
If you cannot get through it all in one day, no worries, friend. Break it up into days, or maybe you want to stay at a hotel for a weekend. What is essential is that you focus on your business and where you're going in the next 12 weeks.
Before you start, make sure you're setting yourself up for success. Turn off notifications, close unnecessary browser tabs, and silence your phone. This is your time to focus solely on your business, so make it count.
Here is your strategic planning agenda:
- Reflection and Self-Assessment (15 minutes)
- Your Vision
- Goals (One, One, and One)
- Project Planning
- Content Planning
Step 1: Start with Reflection—Your 15-Minute Reset
Let's start with reflection. Before you roll your eyes, stick with me. This doesn't need to take an hour. Give yourself 15 minutes with a notebook and answer these three questions:
- What worked?
- What didn't work?
- What did I learn?
That's it. Even big companies pay thousands of dollars for this step. You can do it in 15 minutes with a quiet cup of coffee.
Grab your journal and jot down:
- What has worked well for you
- Areas that need improvement
- Lessons learned (the good, the bad, and the ugly)
Remember, you're amazing, and acknowledging your wins is a crucial part of the process.
Self-Assessment: How Happy Are You, Really?
While you have your journal, let's also do a self-assessment. How happy are you, really? Not put-on-a-show fake happy, but like real, real happy.
Rank your happiness (1-10) in these areas:
- Money
- Personal Growth
- Self Care (Mind, Body, Spirit)
- Family and Friends
- Love and Relationships
- You Time (Fun and Leisure)
- Home Environment
- Business
SWOT Analysis
A previous client won a two-day strategic planning day with Cameron Herold in a silent auction. One of my key takeaways was the importance of conducting a SWOT Analysis—assessing your Strengths, Weaknesses, Opportunities, and Threats.
While larger companies use this often, small business owners rarely take the time for this kind of deep analysis. It's crucial for identifying what's working, where you need to improve, and what external factors could impact your business growth.
I highly recommend incorporating a SWOT Analysis into your quarterly planning process. We used different color sticky notes for each of these areas. Remember that every idea is a good idea when you're having a brainstorming session, until it's not.
If you want to go deeper, you can use the self-assessment in my free planning workbook, but the simple version is more than enough for today.
Step 2: Revisit Your Vision
Your vision is your North Star. Read it out loud and ask yourself one question: Does this still excite me?
If the answer is no, there's no failure. That's clarity.
I used to be ashamed of pivoting, but honestly, God uses pivots. Sometimes they're his nudges to move us down the right path. Give yourself permission to adjust your vision if it no longer matches the season or the assignment that you're in.
Your vision is the North Star of your Strategic Planning Day. Read it out loud and ask yourself:
- Does it still align with your current vision?
- Does it evoke feelings of happiness, pride, and achievement?
- What needs to be adjusted?
If your vision no longer excites or motivates you, this is your opportunity to refine it.
Step 3: Simplify Your Goals (One, One, and One)
This is the step where so many women get stuck because we overthink everything. So let's make it simple:
- One big goal for the year
- One clear focus for the next 90 days
- One small focus for the next 30 days
One, one, and one. If you only remember that, you are ahead.
What strategic goals did you set on your last strategy day? I'm curious: Were you able to reach the desired outcome you've set for yourself in the past quarter?
Now, let's break your vision down into actionable goals. Think about:
- Your top 3 business, personal, and financial goals
- What you're fully committed to achieving
- How to turn those commitments into results
The 12-Week Year Method
If long-term goals make you lose steam, use the 12-Week Year method. Treat the next 12 weeks like it's its own year. It keeps you moving because the finish line is closer.
Have you read the book The 12-Week Year? This approach allows you to accomplish more in less time by focusing on 12-week cycles instead of traditional annual goals. The idea is to treat each 12 weeks as a full year, increasing urgency and execution.
If you find that a year plan doesn't work for you and you lose steam, why not give this a try?
Goal Breakdown:
- One-Year Goals (Big-picture milestones)
- 90-Day Goals (Quarterly objectives that feed into your one-year goals)
- 30-Day Focus (Immediate steps to move your business forward)
- 12-Week Sprint (A focused plan to drive real momentum in a short time frame)
What Are You Truly Committed To?
Always step back and ask yourself: What are you truly committed to?
If you are not committed, it won't happen. That's the truth. I had to learn that one the hard way, and I talk about it with my clients as well.
Do you want to know why I believe in this question of true commitment? It is because I've found myself chasing someone else's dream for my life. I'm sure you can guess how this turned out for me.
Maybe, like me, you've doubted your vision for your life and somehow following someone else's dream felt a little less scary.
Remember, God puts dreams on our hearts for us to follow. I think almost as a way to challenge us to release the outcome into his hands.
Step 4: Break That Goal Down into Tiny Steps
This is where your plan becomes real, but let's keep it simple.
Start with the end result and work backwards. Ask yourself what needs to happen right before that, and then what needs to happen before that? Write it all down. Don't judge. And don't organize it yet. Just get it out of your brain—what you think needs to happen step by step.
Then—this is the part where people skip—you actually need to set dates to all of those small steps.
If It's Just You and Your Business
If it's just you in your business, great. That makes assigning tasks so much easier because you know you are the one that's gonna be doing the work.
Friend, make sure you are honest about your time bank.
- How many days are your kids home?
- What holidays are coming up?
- When are you taking time off?
Don't plan your quarter in a fantasy world. Plan it for the life you actually live.
Your time bank is part of your strategy. It's not an obstacle.
Map Out Important Dates
As I mentioned, you must understand your time bank for the quarter. How many hours do you have to work on the goals and projects in your business? Do you have a realistic amount of time to get everything done in the timeframe your brain tells you?
It is essential to take the time to map out the dates and the actual chunks of time that you'll work on your goals and projects. When you do this, you're not sitting at your desk wondering what you must do today. It is all planned out for you in advance, thoughtfully.
Be sure to start by marking all the out-of-office dates on your calendar:
- Vacation Days
- Important Kid Events
- No School Days
- Holidays
Add all the out-of-office dates to your Google Calendar. Everything else is mapped around those dates on your calendar.
Who, What, and When
Sit down and do a whole mind sweep of every step you think you must do to achieve that goal. Once you have it, you want to map it out with who's responsible.
Suppose it's only you in your business. Well, you'll be the only one doing the work. If you have an entire team working with you, who are the team members that will be doing the work?
You need to know all the action items. No more flying by the seat of your pants. You need to have the who, the what, and the when documented, preferably in a project management tool like Asana, Trello, or Notion.
All the action steps are assigned a date by knowing the end date and reverse engineering the time frame.
We tend to underestimate the amount of work and time something will take to get done. Make sure to give yourself grace.
One Major Project at a Time
Depending on your goals, you may have a couple of goals in the quarter. However, if you have something big, like a launch, then you only want one goal for that entire quarter.
Here are the ground rules that I set with my clients: During a set period of time, you get only one major project to focus on. Why? You have a finite amount of time and energy.
A great way to add stress, overwhelm, and anxiety is by thinking it is a good idea to, let's say, be remodeling your house while prepping and executing a new course launch.
Here is an example of how to set up an Asana Board for Goals and Quarterly Planning:
Show Up Consistently—Without Doing It All Yourself
Your Podcast, Repurposed into a Full Marketing Strategy
A done-for-you repurposing service where we turn one piece of content into 5 Days of Marketing Content so you can grow your audience and impact in less time.
5 Days of Content from 1 Podcast Episode
- 2 vertical video clips
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- 4 Additional Social Media Captions
Step 5: Your Content Planning for 90 Days
Your content has to match your goals. If you are launching something, your content needs to lead towards that. If you are list building, your content should support that as well.
But I want to simplify this for you:
Plan one type of content per week for the next 12 weeks.
You do not need Pinterest, email, Instagram, YouTube, a blog post, a podcast, and five reels every week. That's where burnout happens.
Start with one. When that feels solid, add another.
While not directly related to strategic planning, your content calendar is crucial for the long-term organic marketing of your business. Plan out your content for the next three months, week by week. This will help you stay consistent while keeping content aligned with your revenue goals and strategic objectives.
What to Do With All That Content
Once you do this planning day, you'll notice something. Having clarity makes content so much easier, but creating that content can still feel like a lot.
That's why my done-for-you repurposing exists. You stay focused on your clients and I make sure your wisdom doesn't get buried inside your podcast episodes or videos. That way, you're visible, consistent, omnipresent—I think I've heard that before—and not stretched too thin.
Don't Forget to Track Your Numbers
And track your numbers, even if it's messy.
- Website traffic
- Email subscribers
- Social media engagement
- Number of Clients
- Number of Leads
- Number of Sales
What you measure actually will improve.
If you do not already have a stat/metric tracker in place, do that. Here is a link to my other popular free resource, a Google Sheet to keep track of all your business metrics or key performance indicators (KPI).
Time to Wrap This Up
So friend, head to the blog for all the details from today's episode and the link to my free quarterly planner so that you can walk through each one of these steps every quarter on repeat.
You don't have to figure it out alone. Everything is already in there. Yes, it's like 50 pages long. Sorry about that. Sorry, not sorry. Maybe.
But friend, you don't have to be great at planning or time management to build a business that honors your calling. You just need a simple system that works for the season that you're in.
Strategic planning isn't just about setting goals—it's about having a proactive approach to business growth. Whether you dream of leading an executive team, collaborating with board members, or keeping it simple as a solo entrepreneur mapping out your next move, sufficient time spent on planning can be the most important time you invest in your business.
By treating this as a strategy away-day, you'll align your mission statement, address key issues, and generate new ideas that fuel new investments. With a clear vision and a collaborative effort, your strategic planning sessions will become a roadmap for continued success.
Now, take a moment to reflect on the main benefits of this approach:
- Are you still in alignment with your vision?
- What are you actually committed to doing?
- Have you scheduled your strategy discussions?
- Are you tracking your progress?
The right people and different teams thrive when there's clarity and a plan in place.
You are doing better than you think. I pray this brings you clarity and peace in your business today.
Thank you so much for your time. I appreciate you and I hope you make it a wonderful week.
Ready to Take the Next Step?
- Grab your free Planning Workbook here
- Book a 1-Hour Virtual Strategy Session
- Learn about Done-For-You Repurposing Services
New Year Planning! Annual Plan for Online Entrepreneurs
Can you believe another year has flown by? I don’t know about you, but this year has been a journey of ups and downs. I frequently have to remind myself that the LORD's plan is always greater when things do not go exactly how I planned. With that said, an annual plan provides a compass so you don't lose sight of what's important when you hit the bumps in the road.
Successful online business owners understand that business ebbs and flows. What you need to hold tight to is your why. That is what will keep you going during the struggles and thankful in times of prosperity. Understanding what drives you towards your goals or why you are so passionate about taking yourself on this unknown journey of entrepreneurship. Your why, along with your what or the vision you have of where you want to go in the next year, three years, and even five years. Does this mean that every detail is planned? Nope, not at all. It's important to plan your year as a small business owner. But, even more essential is to plan each quarter. That’s when you dive into the details.
Let's start the new year strong by creating a purposeful success plan. I'm sharing everything that's in my annual planning process. Download the Free Quarterly Planning Guide for Small Online Business Owners. It will be a resource that you will use time and time again. https://misstask.com/free-planning-workbook
If you’d like this in a Google Doc, I’ll put the link to get your hands on the Annual Toolkit for only $27! Here is the link to buy it now!
Why Create an Annual Plan?
Are you thinking, NOOOO, Michele, I am not a planner. It feels overwhelming, so I'll stick with flying by the seat of my pants. I get it. In the past, I've flown by the seat of my pants and felt that worked well. However, if you intend to grow your business and become a CEO, you must act like a CEO. What has worked in the past to get you to this point will not be what scales your business to the next level.
You see, an annual plan provides many benefits:
- It lets you set goals and work towards achieving them
- Keeps you focused on what matters most to you
- Reduces the chance you'll lose sight of your priorities,
- Provides direction and alignment for the year ahead
- Helps you feel in control and on top of your business
- Allows for less hustle to get everything done
Map Out Your Year
When we map out the year, this is our roadmap of where we want to go in the upcoming new year it allows you to focus on the big picture.
Creating your full-year roadmap lets you schedule important events and commitments around your life by blocking out vacation days.
When you map out the year, you begin to understand your time bank—knowing what you can take on and still allowing yourself three-day weekends and spending time with your kids during the summer.
It provides direction without getting stuck in the details. When you create your annual budget. Plan your launch schedule around your life and not your life around your business. Decide what major initiatives to undertake for the year, not only with your business but with your life, too.
Because whether it is a business project or a personal project, it is important to keep it to one major initiative at a time. When you take on too much, you’ll not have enough time in the day to do all the things in the end, leaving you feeling like you’re failing.
Begin With Reflection
Take a moment to reflect on what has happened in the past year before planning. Allow yourself to identify successes and areas that need improvement. This will help you focus your energy on the initiatives that will have the most impact. Your wins and failures can teach you a lot. Take some time to reflect on what is most important to you. Write about the life you envision for yourself in the future.
Here are a few journal prompts to get you started:
- What went really well that you want to repeat?
- What are you most proud of?
- What challenges did you face?
- What changed you?
- What do you want to do differently next year?
- Remember, there is no failure, only feedback. What feedback did you receive?
Not much of a journaler? Don't worry; instead, write out an exhaustive list of key points and things you’d like to improve. As with everything, it has to work for you.
How Happy Are You Really?
Inside Notion, I have a daily journal. One of the fields is my daily happiness. By keeping track of this daily, I’m able to go into my monthly and yearly roll-ups and see how happy I really am in my day-to-day life.
Next, let's do a self-assessment to determine how happy you are with your life and online coaching business. Let me break this down for you, how happy are you with each of these categories in your life? One is not happy at all something must change, and ten means you’re over the moon happy.
- Money
- Personal Growth
- Self Care (Mind-Body-Spirit)
- Family and Friends
- Love and Relationships
- You Time (Fun and Leisure)
- Home Environment
- Online Business
Reflect On Your Assessment
- What scored high in your self-assessment?
- Why do you feel these things are working?
- What is not working in your life and online business?
- What scored low on your self-assessment?
- Why do you feel these things are not working?
- Where do you need to give yourself grace?
Vision Planning for the New Year
If you have a journal, now is the perfect time to get it out to dream about your future life. Really, let your mind wander as you think about what you’re aspiring to achieve in the new year. Step into your future self and what is different in your future life. In one year, where do you hope to be? I believe this is very important; what do you want your feelings to be one year from now?
I’m not stopping there; here is a list of questions for you to journal on in order to gain even more clarity.
- Where are you now in your present life?
- Who do you want to become in the new year?
- Where do you want to be in your life and online coaching business?
- Where do you hope to be one year from now?
- What does your ideal life look like?
- What does your ideal schedule look like?
- Where are the gaps between who you are now and who you want to become?
- What's holding you back? Let go of limiting beliefs.
- Looking back at your self-assessment, where are you not in alignment?
- What matters most in life to you?
- What makes me the happiest?
- What is one word to describe your focus for the year? Is it family, consistency, joy, growth, or health?
- I haven't fully decided on my word for the upcoming year yet. But, gratitude has come to mind on more than one occasion.
What is holding you back? Be honest with yourself; what beliefs or shoulds are you holding on to that are no longer serving you?
Once you have answered the following questions, go to Canva or Pinterest and create your vision board. On Pinterest, make a secret board and pin those images you want to embody in the new year. As for Canva, design an image for your desktop to keep your vision board and goals front and center!
Create a vision board featuring images that represent your ideal future. Keep it visible as motivation.
Another thing I do in Notion is my vision board. I find an image to represent one thing I envision in my life. Then, I write down why I want this and how it will make me feel.
Once I have my vision and goals inside of Notion, I create a vision board for my desktop. I have two monitors. One that has my vision board for the year. My primary monitor has my vision board for the month. Yes, I create a vision board each month to focus on one thing.
Here is a previous YouTube video that I did on annual planning.
Long-Form Content Planning
What is your content strategy for the year ahead? Does your long-form content lead up to your live launches? Does your pillar content support your revenue stream?
The long-form content in your business is a door away to working with your business; it should be given the proper amount of time. Does your long-form content showcase your skills and the benefits of your services?
Do you have a process for refreshing, reusing, and repurposing your content? If you take the time to create the content, make sure you have a plan to spread the word without leaving you feeling exhausted and overwhelmed.
If part of your yearly plan includes being more consistent with your long-form content, or you want to refresh, reuse, and repurpose what you already have… this is where I can support you. My done-for-you repurposing services give you strategic content that actually sounds like you, without the overwhelm. Check it out here: Content Repurposing Services
Yay! Goal Planning
With your vision in mind, set goals for the year. Do you know what motivates you to accomplish your goals? Do you need outside accountability? If that’s the case, find yourself an accountability bestie. What if you’re not really sure?
In the past, I’ve mentioned Gretchen Rubin's book The Four Tendencies; here is a link to the quiz to find out your tendency: https://gretchenrubin.com/quiz/the-four-tendencies-quiz/. What, I know, right? It boils down to this: what drives you to take action to achieve your goals?
UPHOLDER: “I do what others expect of me—and what I expect from myself.”
QUESTIONER: “I do what I think is best, according to my judgment. If it doesn’t make sense, I won’t do it.”
OBLIGER: “I do what I have to do. I don’t want to let others down, but I may let myself down.”
REBEL: “I do what I want, in my own way. If you try to make me do something—even if I try to make myself do something—I’m less likely to do it.”
Gretchen Rubin, The Four Tendencies
Set Your Goals
- What do you want to achieve this next year?
- Launch a new service or product.
- Hit your ideal income amount.
- Achieve important business outcomes.
- Make commitments to what you'll achieve.
- Address expected challenges
- Get the resources you'll need (team, tools)
Are your goals in alignment with your vision? Be committed to achieving them. If you’re not committed to achieving your goals, who will be? I’ve mentioned this before: Is it the right goal if you’re unwilling to dedicate time to your goal?
Plan Your Budget
An essential part of annual planning is creating a budget for the year ahead.
Determine:
- What are your financial goals for the new year? Not sure what financial goals to set? Here is a list:
- Revenue goal
- Spending goal
- Savings goal
- How much do you want to pay yourself this year?
- Make sure your products and services are priced right to hit these goals. Have you done the math on your revenue goals versus the price of your offer?
Do you know if it is even possible to hit your revenue goals with how you have your services priced?
I have a free resource, Know Thy Number. It has a bonus tab to Price for Profit. If you’ve not created a budget or do not have a clue how to price your services for profit, grab that free resource here: https://misstask.com/know-thy-numbers
Map Out Your Launches and Promotions
The final piece to include in your annual planning is your launches, promotions, and time off:
- Block out vacation days and regular days off first
- Decide your quarterly focus areas
- Schedule promotions and launches
- Allow time for new offer creation
One of the key reasons you map all of this out at a high level? It gives you a 10,000-foot view of your year. It allows you to avoid planning promotions or launches during your scheduled time off. I promise you, your family does not want to go on vacation while you’re in the middle of a launch. That would not be a vacation for anyone.
What more planning read this next!
Time To Wrap Up New Year Planning
Wow, we made it to the end! You have everything you need for annual planning success! Download the FREE Quarterly Planning Resource to get started.
Or, for $27, get the Annual Planning Google Doc template to use again and again. Feel free to reach out with any questions. Here is the link to buy it now! Cheers to a fabulous New Year ahead!
Happy planning!
Thank you so much for reading. I appreciate you and hope you have a wonderful week!

