Year-End Reflection Routine for Entrepreneurs
Every year around this time, I used to sit down with a notebook and try to make sense of everything I’d done over the past twelve months. I’d write down wins, frustrations, goals, things I wanted to “do better,” and whatever else came to mind.
But when the new year started, the list didn’t actually help me.
I went right back into the same patterns: working harder than I wanted to, juggling too many projects, reacting more than planning, and feeling like my schedule was full but not productive. The reflection felt meaningful in the moment, but it didn’t translate into anything practical.
It wasn’t until I shifted my approach and started using a planning system — not just reflection prompts or journaling — that things actually changed. Looking at the year through the lens of 90-day cycles made everything clearer. It helped me see what was working, what wasn’t, and what needed to shift so I could step into the next quarter with a plan I could actually follow through on.
This routine is the same one I now use in my business every year, and it’s the foundation of both the SYS Planner™ and the Profit Planning Challenge. If you want a simple, structured way to review your year without spending hours on it, this is it.
ONE || Review What Worked
Start by looking at your year in four sections instead of one long blur. This keeps the process objective and helps you spot patterns faster.
You’re not reviewing everything… just the things that actually moved your business forward.
Ask yourself:
Which offers or projects produced revenue?
What marketing habits created consistency?
Which routines made your week more manageable?
Where did you feel most aligned with how you want to work?
What tasks supported your time and energy?
A few years ago, I noticed that anytime I did a weekly planning session on Friday, my entire week felt smoother. I made better decisions. I didn’t waste time figuring out what to do next. That single pattern became a key part of my planning system, and it came directly from reviewing my quarters instead of relying on memory.
Look for those simple, repeatable strengths. They’re easy to miss in the day-to-day, but they matter.
TWO || Identify What Didn’t Work
This isn’t about listing mistakes or “fixing your weaknesses.” It’s about noticing what created friction so you can stop repeating it.
Consider:
Which routines you couldn’t maintain
Where projects stalled
Offers that required more time than they returned
Patterns that kept pulling you into reactive weeks
Tasks you kept avoiding or procrastinating
Things that consistently felt heavy or disorganized
For months, I tried to fit my content batching into one single block on Wednesday. It sounded efficient, but it consistently collided with client work and unexpected tasks. It wasn’t that batching didn’t work… the timing didn’t work.
Understanding why something didn’t work prevents you from copying the same plan into the next year.
THREE || Clarify What You Want Next Year to Look Like
Instead of asking yourself big-picture questions like “What do I want this year to feel like?” focus on what you want your business to actually do.
Here are some examples of clear statements:
I want dedicated time each week for CEO tasks.
I want predictable lead generation instead of last-minute posting.
I want my client workflow to be simple and repeatable.
I want my schedule to reflect my actual capacity, not my ideal capacity.
I want space in my week for planning, not just working.
When I shifted into this kind of clarity, my planning process changed. I stopped trying to create a perfect year and started aiming for a functional quarter… one that supported the reality of running a business and having a life at the same time.
FOUR || Turn Your Reflection into a 90-Day Plan
This is where your reflection becomes actionable.
Look at everything you’ve written and choose the top three outcomes you want to focus on in the next quarter.
Then use my Plan → Prioritize → Protect framework:
PLAN:
Create a clear 90-day direction and build a weekly schedule that lines up with it so that you’re not guessing what to work on each week.
PRIORITIZE:
Focus on the actions that move your most important goals forward so that your time isn’t pulled in ten directions.
PROTECT:
Build routines and boundaries that support your priorities so that your week stays aligned with what matters most.
One quarter, my focus was improving customer experience for my planner buyers. That meant specific weekly tasks: updating tutorials, refining the order flow, and planning touchpoints. Because it was a 90-day focus — not an annual goal — it fit into my life and became something I could actually maintain.
FIVE || Set Up the Routines + Boundaries that will Support Your Next Quarter
This is where the “fresh start” actually comes from… the routines you will carry into the year, not the goals you write down.
Some examples:
Weekly routines:
Weekly planning session
Daily startup time
Content creation block
Finance check-in
One admin block
Boundaries:
When you check email
When you stop work for the day
How many client calls you schedule each week
What days you commit to deep work
When you don’t take meetings
One thing that helped me was actually checking + responding to emails first thing in the morning so that I didn’t find myself getting distracted with emails throughout the day. I delete anything I don’t need and use the snooze button for things I need to get back to that I might not have time for (or isn’t a priority) at the moment. That decision supported my goals more than any new planner or new routine ever could.
Reflection is Only Useful if it Leads to Action
People spend a lot of time reflecting at the end of the year, but very few turn that reflection into a plan they can implement. When you use a system — not just prompts — your reflection becomes direction (see what I did there?!).
This is why the SYS Planner™ is structured around 90-day cycles. It doesn’t ask you to create a perfect year. It helps you build a functional quarter, one week at a time. And if you want guided support, the Profit Planning Challenge walks you through this same process step by step.
Ready to start your next quarter with structure?
If you want to use the same system I rely on in my own business and teach my clients:
>> Check out the SYS Planner™ — it’s designed around the exact 90-day routine outlined above.
>> Join the Profit Planning Challenge if you want hands-on support with your next 90-day plan.
Both options give you the structure you need to step into the new year with direction, not overwhelm.
