Want an interactive version of this annual review in Notion?
Click here to download it for free.
•••
Why an Annual Review Matters for Entrepreneurs
As entrepreneurs, we live in a world of constant demands, so reflecting on our journey often takes a backseat to chasing the next goal. An annual review isn’t just an opportunity to evaluate your year; it’s a chance to understand the deeper patterns shaping your decisions, actions, and results. By reflecting thoughtfully, you can uncover insights that help you align your efforts with your values and set a foundation for sustainable success.
This process is especially useful for entrepreneurs because our professional and personal lives are deeply intertwined. Success in one area influences the other. This guide focuses on cultivating clarity, identifying growth opportunities, and using reflection as a tool for both personal and professional transformation.
The theme for this annual review is simple: Reflect on the Past to Succeed in the Future.
•••
How This Process is Unique
Unlike other annual reviews that present endless lists of generic prompts, this review is intentionally focused, practical, and rooted in psychology.
Here’s what to expect:
- You’ll reflect on the past year’s achievements and challenges.
- You’ll uncover what worked, what didn’t, and why.
- You’ll identify the fears and patterns that held you back (and what to do about them).
- Most importantly, you’ll leave with a plan that aligns with your values and sets you up for a year full of alignment, authenticity, and impact.
This approach ensures that your reflection is meaningful, actionable, and rooted in your unique journey.
By the end of this process, you’ll have a clear picture of where you’ve been, where you want to go, and how to get there.
•••
1. Understanding Expectations
The expectations you set for yourself can be a double-edged sword.
On one hand, they drive you to aim higher. On the other, they can become a source of frustration when you fall short. The gap between expectation and reality is often where the most valuable lessons lie.
This section is about examining that gap without judgment and uncovering what it reveals about how you set goals.
💡 Reflection Exercise:
Overall, how well did you live up to your own expectations this year?
We’ll dig into this more in the next few steps, but for now, consider your overall impressions on this question. Do you feel like you fully lived up to your potential, or did reality not quite live up to what you know you’re capable of achieving?
•••
2. Achievement Inventory
Now that you have a general impression of how well you lived up to your own expectations, let’s dive in to specifics to get a clearer understanding of how much you achieved (or didn’t) this year.
💡 Reflection Exercise:
Think back to this time last year and consider everything you planned to achieve throughout the last 12 months.
Step 1:
List out everything you wanted to achieve this year.
Step 2:
Organize each of them into one of two categories:
- Things you achieved
- Things you didn’t achieve
•••
3. Analyzing (and Celebrating) Success
How often do you actually stop to celebrate your wins? If you’re like most ambitious people, probably not enough.
Recognizing your achievements isn’t just about feeling good—it’s about learning what led to your success so you can replicate it.
These insights can be applied to future goals, ensuring you’re building on your strengths while also enjoying the process of achievement itself.
Otherwise, what’s the point of all this sacrifice if you never take time to enjoy and learn from everything you’re doing?
💡 Reflection Exercise:
For each thing you achieved, ask:
- What contributed to your success? Break down what worked and why.
- How did you celebrate this achievement? And if you didn’t, why not?
🛑 Don’t Skip This Question
If you didn’t celebrate your achievements, deeply consider why.
- Was it because you just did what was expected of you, so you don’t feel right celebrating?
- Was it because you were so busy focusing on achieving the next thing, you didn’t stop to enjoy the small milestones along the way?
- Was it because you’re used to being hard on yourself to the point you don’t think you deserve to celebrate your accomplishments?
Most of the entrepreneurs I work with absolutely suck at celebrating their achievements in the moment, then wonder why they constantly feel overwhelmed, inadequate, and dissatisfied despite everything they’ve achieved.
If you’re anything like this, don’t skip this question. It might seem like a waste of time, but you’ll learn a lot about yourself by deeply reflecting on why you don’t celebrate more often.
•••
4. Understanding Missed Goals
Not achieving a goal can feel like failure, but it’s often an opportunity to learn. Goals that remain unmet usually fall into two categories: those that were unaligned with your true values and those that were hindered by fear or other psychological barriers.
Sometimes we abandon a goal because our priorities have changed, we realize achieving this goal was never a good fit for what we actually want to achieve, or we gain clarity on what truly matters which means creating new values-aligned goals.
Other times, we deeply want to achieve a goal that’s aligned with our values, but fear (especially the Four Horsemen of Fear) pops up, self-doubt creeps in, or Imposter Syndrome stops us in our tracks.
Reflecting on these distinctions will help you approach future goals with greater clarity and intention.
💡 Reflection Exercise:
Step 1:
Organize everything you didn’t achieve into one of two categories based on why you didn’t achieve them:
- Unaligned
- Fear
Step 2:
For unaligned goals, ask:
- Why did you set this goal? Was it truly yours, or was it influenced by external pressures?
- What did not achieving or pursuing this goal teach you about your real priorities?
For goals held back by fear, dig deeper:
- What specific fear held me back? (Name it.)
- How did this fear show up in my actions or lack of actions (procrastination, analysis paralysis, perfectionism, etc.)?
- What would it look like if fear wasn’t holding you back?
Step 3:
Write a short reflection on the biggest lessons learned from your missed goals and how they will inform your goal-setting process for the upcoming year.
•••
5. Insights for Growth
Reflection is only useful if it leads to action. The insights you’ve gained from this process are your blueprint for growth. By identifying patterns, shifting beliefs, and refining systems, you can step into the next year with intention and clarity.
💡 Reflection Exercise:
Step 1:
Answer these questions:
- What patterns showed up in my successes and challenges?
- What habits or systems served me, and which ones didn’t?
- What beliefs about myself, what I want, and what I’m capable of shifted this year?
Step 2:
Summarize your top three insights from this year. For each, describe how you’ll use them to build a more fulfilling and aligned life next year.
•••
6. Planning for the Future
With clarity from your past, it’s time to look forward. Setting aligned goals rooted in your values and applying lessons from the past creates a powerful framework for the year ahead. This is your chance to envision what success looks like and map out how to achieve it.
💡 Reflection Exercise:
Step 1:
Define your top three goals for the upcoming year. For each goal, ask:
- Why is this goal important to me?
- How does it align with my values and what I truly want?
- What could get in my way?
- What steps do I need to take to make it a reality?
Step 2:
Write a one-page manifesto for the upcoming year that includes what you’ll achieve, why it’s worth committing yourself to, the impact you’ll have by achieving these goals, and what will be different about you and how you show up in the work you do (like your mindset, your habits, your authenticity, etc.).
•••
Conclusion
The past year was full of lessons—some hard, some incredible.
By taking the time to reflect, you’ve gained clarity on what matters most and how to move forward with purpose. Remember: every experience, whether it felt like a win or a setback, was data.
Use that data to make the next year even better.
•••
Next Steps
If you found this guide helpful, stay connected by subscribing to the Creator Alchemy newsletter.
You’ll receive exclusive resources, tools, and insights to help you build a fulfilling life and thriving business aligned with your values.
When you subscribe, shoot me an email with your one-page manifesto.
I’d love to read it.
