Year-End Review Questions Every Woman Entrepreneur Should Answer Before 2027
20 Year-End Review Questions Every Woman Entrepreneur Should Answer Before 2027
As we’re closing in on the end of the year, there are evolved parts of myself that I barely recognize. It’s so cool looking back at the things I’ve done over the last few months that the 2025 version of myself would not have expected.
It’s so important as a founder to take the time to do a year-end review so that you don’t grow into the next version of yourself without noticing.
Why Do a Year-End Entrepreneur Review?
We have no shortage of tools to track the progress in our business: measuring our KPIs, AOVs, P&Ls, you know where I’m going with all the acronyms.
But beyond chasing ROIs and CACs (promise I’ll stop now), when’s the last time you intentionally dedicated just as much time as you pour into your analytics into checking in with how you feel and how you’ve grown as a founder? A year-end review for an entrepreneur is a look back at how you grew as a founder, not just how the business performed.
That’s the why behind the Pearl Spark Pages brand: creating an opportunity for female founders to focus on how they feel about themselves as a founder. It’s not that I don’t care about your business, but what I care about more is creating an opportunity for women to explore their inner narrative, celebrate every win along the way, and to feel truly confident from the inside out while building their business.
I'm guilty of frequently moving the goalpost forward. The Gap and the Gain by Dan Sullivan and Dr. Benjamin Hardy was a huge help for that, so now I remind myself to stop and review backwards instead of constantly planning forward.
How to Use These Questions
I like to tackle one category every few days to keep the process feeling manageable without overwhelm. I’ll also get out of my office and change my environment when I’m doing this review. It’s a nice energy shift. Here in Toronto, a number of hotels will offer a reduced day rate, so you can book a room for the day and get full access to the hotel amenities.
More than once I’ve booked a local hotel room, holed up to do my review along with some other work, and then capped the day off with some spa time! It’s a nice treat to myself after completing the reflection.
My mind works in categories, so when I was coming up with these 20 entrepreneur self-reflection questions, I looked back at my own quarterly reviews for the last year. They’re all handwritten in my daily planner and reviewing them helped me get a better understanding of the personal development areas I’m keeping score on as a founder, totally removed from my business KPIs. Those five key areas are:
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Personal Growth
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Relationships
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Focus
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Feelings of Satisfaction
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Future
Personal Growth
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What did you learn as a founder? This could be a concept like angel investing or something tactical like building an AI agent.
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What limiting beliefs can you let go of? Being bad at math is my big one, and I paid the self-doubt tax for it.
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What’s the hardest thing you’ve done?
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What’s something about yourself currently that the version of you a year ago would be surprised by? (The 2025 version of Lisa would be SO surprised to know that now she’s done five in-store author events at Canada’s largest bookstore chain!)
Relationships
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Who created the most direct business value for you this year? Your network really does have an impact on your net worth!
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How did you actively grow your network / community? For example virtual or in-person conferences, workshops, networking events, dinners, etc.
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Who have you outgrown?
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Who would you like to build a more meaningful relationship with? The book Rich Relationships by Selena Soo is a great read to support you in this category!
Focus
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Review your January goals. Did you follow through on their execution? Why were you successful or unsuccessful? An audit of what didn’t work helps inform what to change next time around.
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If a prospective investor shadowed you for a day, would they say that you spend your time wisely?
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What three apps distract you the most?
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Can you block these apps during the workday? A tool like Brick helps with distractions!
Feelings of Satisfaction
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How do you want to feel in your business? I struggled with this one since I’m so often in my head. Danielle Laporte’s book, The Desire Map, has a helpful list of Core Desired Feelings.
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Where do you feel that way now?
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How can you intentionally cultivate more of that feeling?
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Outside noise removed, what feels like ‘enough’ for you? This question helped me realize where I was seeking approval, instead of listening to my inner-voice.
Future
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What feeling do you want to carry into next year? This is a good word to put up on your vision board!
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What do you want to do more of?
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How do you want people to describe you?
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What do you want to be proud of yourself for? Reverse-engineer your big 2027 win!
Frequently Asked Questions
How long does a year-end entrepreneur review take?
Anywhere from two hours to a full day, depending on how you like to work. Usually I’ll do just one category of questions at a time so that I don’t end up feeling overwhelmed. There have been other years where if I have the capacity to take a full day to indulge in this, I will!
I always find it helpful to review the entries in my Female Founders Journal, in my Simplified Planner, and my Google calendar so I can recount all the events and experiences from throughout the year.
What should be included in a year-end review for an entrepreneur?
I think the biggest thing that makes a year-end review for an entrepreneur different from a year-end review for a business is all about YOU as a founder. Ask the questions that get away from the business metrics and dial into you as an entrepreneur, as a leader and as a visionary.
The 20 questions listed above will give you a great starting point.
When is the best time to do a year-end review?
The time when it will actually get done is the best time. Whether that means while on a plane flying to a holiday destination or quietly at 6:00 a.m. with a cup of coffee while the family is still asleep. Done is better than perfect so whenever works for you is the perfect time!
Where to Write Your Answers
This is not a time for loose leaf paper.
A big miss that I see when people start writing is they simply grab the nearest piece of paper and start their stream of consciousness. This makes it near impossible to revisit at a later date. It’s way more likely you’ll lose them in a pile and the effort will eventually become forgotten.
Of course I love having my Female Founders Journal to write my thoughts in. The Female Founders Journal is a 90-day guided journal for women entrepreneurs with more than 180 prompts, reviewed by a licensed therapist. Between each weekly set of prompts and at the end of the journal, we were sure to include some blank pages so that you’re able to keep all your founder progress in one beautiful book. There are also Reflection Pages every 90 days so that you’re doing a quarterly reset as part of a simple planning routine!
Give Yourself the Space to Answer These
You just did the hard part. Treat yourself to a copy of the best-selling Female Founders Journal that has 90 days of guided prompts built for exactly the kind of thinking you just did here, and the Reflection Pages bring you back to it every quarter.
Buy one for yourself and gift one to a founder friend who talks about her wins like they were luck.
