The Introverted Entrepreneur’s Guide to Annual Planning

The transition from one year to the next is not just a calendar change. It’s a period for deep reflection, especially for us introverts and ambiverts. This makes it the perfect time for annual planning!

The key is to ask useful questions that will help us set ourselves up for success in the New Year. So let’s do that! 

Below you’ll find two series of questions. The first are thought-provoking questions designed to help you take a constructive look back at the previous year. Following that, you’ll find a series of questions that will help you step into your annual planning as you look intentionally and strategically into the year to come.

The questions are designed to build upon each other so I recommend you take each in turn. As you get to each question, take a moment to think about it and write your thoughts down someplace where you can reference them easily.


1. What went well?

As you reflect on your business and your marketing this past year, ask this question: "What went well?"⁠

Was it a particular marketing campaign, a new service you offered, the way you connected with your clients, or something else?⁠

Take a moment to celebrate these successes! Write them down so you remember them.

Understanding what went well is not just about feeling good; it's about building on your strengths and carrying these successes into the year to come! 


2. What did you do right?

As you look back on last year, ask: "What did I DO right?"⁠

This is a very different question from, "What went well?" Here, you're focusing on your specific actions that generated positive results. ⁠

This reflection is about recognizing your agency in your own success. Whether it was a bold decision, a consistent effort, a system you put in place, or something else 👉 it's empowering to recognize and acknowledge your active role! 🌟

This can be a difficult question to answer because we aren't used to thinking this way. We often overlook our own contributions to our successes, writing them off to luck or chance. Let's break that habit! Claim your victories! 🙌

Be sure to document these moments of triumph so they’ll be easy to reference when you start planning for next year. ⁠


3. What did you learn? 

As we continue reflecting on the previous year, let's ask another key question: "What did you learn?"⁠

When things don't go the way we want them to, we're tempted to write them off as "failures." But there's a more empowering approach: Choosing to learn from the experience. This is a mindset shift that can transform those so-called failures into lessons!

So take a moment to ask: What lessons did you learn last year? Perhaps there was a marketing tactic that didn't go as well as you'd hoped, or a client that taught you something valuable.⁠

As you jot your answer down, ⁠remember: Every lesson is a step towards the success you're looking for.⁠


4. How did your introversion benefit you?

As an introvert, your unique strengths can play a vital role in our business and marketing success. As you reflect on the previous year, ask: How did these qualities help you in your business and your marketing?⁠

Perhaps your listening skills helped you connect with a client? Or maybe your self-awareness helped you tune into your need to rejuvenate, which helped you manage your energy more effectively, leading to greater productivity and creativity? ⁠

Think back and notice. Write it down so you can remember the strengths you bring to the business. This isn't just about acknowledging your past successes; it's about planning how to leverage your introverted qualities for even greater impact in the year to come.⁠

5. Where in your marketing did you find JOY?

I firmly believe: If you aren't finding joy in your marketing, you're doing it wrong.⁠

Not everything has to be joyful, but there should be moments that genuinely light you up. After all, if there's no joy in what you're doing, it will be difficult to sustain the energy and enthusiasm you'll need for the long haul… and marketing and running your business is a long haul!

So as you reflect back on the previous year, consider this key question:⁠ Where in your marketing did you find JOY? ⁠

Perhaps it was in the creative process, or the interaction with a client you enjoy, or the success of a particular campaign?⁠

Recognizing the joyful aspects of your marketing can provide valuable insights into what works best for you and what you might want to focus on in the coming year.⁠

Capture these joyful experiences in your notes so you can celebrate the parts of your work that bring you happiness and inspiration.

Remember: Finding joy in your business & your marketing isn't a luxury; it's a necessity. It's in the joy that you'll find success.⁠⁠


I hope that the "looking back" portion of these questions have helped you gain a clearer understanding of your recent journey. Next, we'll get into your actual annual planning as you explore what you want for your business and yourself in the New Year. We'll be building on the insights and joys we've uncovered from last year and applying them to your overall strategy.⁠


As you step into the New Year, this is the perfect time to set your intentions for what you want the year to bring. This is a little different from your typical annual planning beause we’ll be taking in mind your introverted, ambiverted, or naturally quiet nature.

Below you’ll find a series of thoughtful questions aimed at helping you envision and strategically plan for your business and marketing in the New Year. 🚀 Each question is crafted to ignite your imagination and to align your plans for your business and your marketing with your authentic self.⁠

The questions listed below are more than just prompts; they are invitations to dive deep into what truly matters to you and your business. By reflecting on these questions, you'll be able to craft an annual plan that is not only aligned with your vision for your business, but also resonates with who you are.⁠

Let’s choose to approach this New Year with intention, insight, and a bit of introspective wisdom. Your answers to the questions below will lay the groundwork for a year that feels authentic, fulfilling, and successful on your own terms.⁠

1. What are your aspirations for the New Year?

As an introverted small business owner, it's important that the goals or intentions that you set for your business resonate deeply with your authentic self. ⁠So start with this question: What are your aspirations for the New Year? 

As you set your sights forward, I invite you to think beyond the conventional metrics of success. Your aspirations could be about making a meaningful impact, finding a balance between work and life, or growing in a way that aligns with your values and strengths.

Visualize them! ⁠How would it feel to achieve them? Put yourself in that moment. This will help you set aspirations with which you feel emotionally aligned.⁠⁠

This is your opportunity to set intentions that truly matter to you.⁠


2. What is something different that you want in your business?

Here's your next key question: What is something different that you want in your business?⁠

Change can be a great catalyst for growth, and the beginning of a year is a wonderful time to introduce change. ⁠

A great way to think of this is:⁠
- What is something you want to add?⁠
- What is something you want to subtract?⁠

Perhaps you want to diversify your services, take on a new marketing tactic (or stop one!), or even integrate more of your introverted qualities into your business practices. (I'm a huge supporter of that last one!)⁠

Think about changes that would resonate with you personally and professionally. What shifts can you make to not just grow your business but also enrich your experience as an entrepreneur?⁠

Writing down these ideas is your first step towards making them a reality. 


3. What will you DO differently in the New Year?

"If you want something different, you have to DO something different." This is a mantra that I repeat to myself often. If you want change in your business, I hope you will draw on it as well.⁠

As you look ahead to the New Year, ask: What do you want to do differently? ⁠

This isn't just about setting goals. It's about showing up differently and taking different types of actions. ⁠

Perhaps you want to honor your introversion more in your business, or show up more authentically in your marketing? Maybe you want to ensure that you take more time off to recharge your energy? Each of these actions can significantly shape your business journey and personal well-being.⁠

Change is hard! So capture the actionable changes you want to make into your notes where you can remind yourself of them.


4. How will you incorporate your introversion into your marketing?

Your introversion isn't just a trait; it's a strength, especially in your marketing. ⁠

As you look ahead to the New Year, answer this question: How do you want to weave your introverted qualities into your marketing strategies?⁠

Think about the aspects of introversion that you can leverage. Maybe it's your ability to create thoughtful, deep content, or your knack for building strong one-on-one relationships with clients, or your preference for more reflective, less aggressive marketing tactics. Each of these qualities can become a unique and authentic part of your marketing approach!⁠

When you embrace your introversion, you can transform the way you connect with your audience and show up in your marketing. ⁠

Remember, marketing doesn't have to be loud to be effective. As introverts, our power lies in authenticity, depth, and meaningful connections. ⁠


5. What’s your plan for balancing work & rest in the New Year?

A crucial aspect of success for introverted entrepreneurs is finding the right balance between work and rest. ⁠

With that in mind, consider this question: What's your plan for balancing work and rest in the New Year?⁠

Consider setting clear boundaries that prioritize your well-being. It might be about carving out dedicated 'me-time' in your daily routine, adjusting your work hours to better suit your energy levels, or planning downtime before and after engaging events. Each of these steps can play a significant role in maintaining your energy and preventing burnout.⁠

Remember, self-care isn't just a luxury; it's an integral part of your journey to success. When you proactively manage your energy and time, you set ourselves up for a more productive, fulfilling, and sustainable year.⁠ So write down your plans for balancing work and rest so you can go back and reference them when you feel off track.

As you embark on your journey into the New Year, it’s important to remember that your past experiences are the foundation upon which you build your future. When we draw upon your past experience to help you plan for where you want to go next, you draw upon powerful tools that help you shape your journey as a business owner. When you embrace your unique qualities, learn from your past experiences, and set meaningful intentions, you set the stage for your own success.

🥂 Cheers to the New Year where you not only achieve our business goals but also thrive in your personal well-being!⁠

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