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"Maybe you should move back to LA and get a job," my accountant Dave said as we did my taxes in September.
"That's the meanest thing you've said to me in 17 years," I replied.
Dave remembers when I had a six figure tech salary and a condo. He doesn't understand why I choose to make less money and live as a vagabond. Only I know why I do it.
This was my first calendar year running this exact subscription and sponsorship model.
I've worked for myself since 2019 but my underlying business model has changed four times. It's a lot to explain to people who are better at picking a lane than I am but...it's working. It has always worked and it continues to work, feeding my delusion that I'm good at this and can teach others how to do it.
One key to my successful pivots is a deep review process every year and every quarter. What am I working on? How is it going? What have I achieved?
It sounds boring as hell and I hated doing it in a corporate setting but now that I'm on my own, I get to decide exactly how I do quarterly and end of year reviews.
As I prep to do my 2025 recap, I've been saving every year-in-review I could get my hands on just to see what questions and data other entrepreneurs are digging into. And I thought you might appreciate what I found in case you're putting together your own review.
Here's what seasoned entrepreneurs include in their year end reviews.
Audit of how time was spent
This is something I never would have included in my performance review days, but I spotted a time audit in both Matthew Fenton's Strategic Plan and Kat Schmoyer's 32 question worksheet.
I've run through Matthew's whole process before, which is super comprehensive and I think one of the best end of year (or anytime of year) plans you can find. The section on time includes several questions about what your actual hourly rate is and how much billable (or revenue-generating) time you have per week. You may think you know these answers but calculating them every year is insightful.
Kat Schmoyer's worksheet starts with questions about how you're using your time with a focus on the daily rhythm of work and life. She asks about ideal work days and how many of those you had in the past year.
I've been thinking a lot about how much of my time turns into money, because as a full time publisher, it's not that correlated. There's lots of days I generate no additional income. I need to be smarter about how I use my time next year so more of my hours spent pay off.
Leading indicators of success
Most year in review write ups include revenue or profit and loss, but many are missing this important question of what's starting to show promise?
Jessica Lackey calls this "The Sprouts You’re Tending," and in her review template, asks questions like "How many inquiries did you receive?" and "What kinds of earned media did you get?"
I've rarely seen this in a yearly reviews, because usually people write up binary successes or failures. Taking a deeper look at what signals are showing that people are paying attention and WILL BUY can move you into the next year with more momentum.
The easiest way to capture leading indicators is to map your funnel or growth model and put numbers or names to it. Newsletter subscribers, inbound DMs, inquiries about your offers, trials or other activities that demonstrate there's meaningful interest in what you're doing can all be signals that you have soon to be functional pipelines.
Successful and failed strategies
You don't just want to capture how much money you made. You want to know exactly how you made it.
What offers worked? What sales activities closed deals? Which promos failed?
IFS practitioner and coach Jennifer O'Sullivan told me she uses Racheal Cook's Plan Your Best Year Ever (and attends her planning retreats) which includes questions on what worked and what flopped. Racheal recommends capturing specific marketing strategies that led to the best sales results and distractions that cost money or time.
Devin Lee, who used to run Quarterly Planning Party for online entrepreneurs, has a similar approach. Devin's process identifies which successful parts of your operation could be systematized or automated and which parts of your business you need to shelve or stop altogether.
Revenue and expenses
Of course, whenever we're looking at other people's year in reviews, we want to know how much money they made because we're nosy as hell.
Hanna Raskin did the most incredible job at this in her 2025 Annual Report for The Food Section. She laid out subscription revenue by month, including labeling abnormal spikes and explaining them. She compared the free vs paid audience and added survey quotes about why some readers cancelled their subscription.
Graphic designer Brent Galloway hand draws his revenue and income stream breakdowns, which is worth seeing even if it's hard to replicate.
Max Read, who publishes Read Max, ran a year over year comparison of his revenue and paid subscriber count, writing "My longstanding belief, elaborated many times in these yearly reports, is that 'year over year' is the only proper way to judge the growth of a digital-media business"
Pretty sure that's true for all businesses and that's why Dave wants me to get a job.
On the expense side, I love that Anna Burgess Yang includes what software subscriptions you are cutting in the new year in her quarterly review checklist. The longer you run a business, the more those expenses creep up. You could take this even further and slash through the entire L side of your P&L. What else could you cut?
Life and work (but mostly life) highs and lows
End of year reviews aren't just about work. A lot of entrepreneurs include life highlights and lowlights in their recaps.
Dan Mall wrote the beefiest section on the life he wants to live and how his year stacked up, including photos and videos of how he spent his year. Creator Jay Clouse flipped the order but shared work and personal highs and lows like becoming a dad and how much stress it added to his schedule.
Sarah Jutras captured a month by month snapshot of both work and life highlights in her Freelance for Life newsletter. She also ran an extensive workshop on year in reviews last year that I participated in, and if she offers it again, you should snag a ticket because it was a super visual and artistic reflection that's hard to replicate yourself.
Writer Kara Detwiller put highs and lows in one simple list along with some stats about her year. And lest you think this is just for service providers and creators, tech founder Brennan Dunn from RightMessage included lots of updates about the company in his 2024 review but several personal moments too.
Client success stories
You had successes, but if you work with clients or sponsors, hopefully you generated some successes for them too.
I loved how government tech consultancy Compiler opened their 2024 year in review by shouting out a bunch of their client wins. This is a sneaky good lead gen strategy if you're emailing your yearly recap to your list (where potential clients might read it.)
Including testimonials in a year end review could be a simple way to capture this for those of us who aren't working with clients.
Biggest lessons
Once you've asked yourself the many questions about how your year went, you'll (probably) have cemented what you've learned this year. Some entrepreneurs include lessons or takeaways in their review recap.
Freelance writer Sam Lauron made this the bulk of her review last year, capturing lessons in a journal entry and pulling out a few themes.
Future plans
Almost everyone includes some wrap up about what will happen next for them but how far you go into the future seems to depend on whether you roll this review process into next year's planning.
Writer Kaleigh Moore included a simple takeaway on the future without much detail in her 2023 review but Anna Burgess Yang wrote out specific goals for the following year like launching a course and increasing income from subscriptions and digital products.
I personally like to separate these activities, but if I don't go into the new year with concrete, measurable goals that I can turn into projects, I'd be a goddamned mess.
Is your review for you or for someone else?
A whole lot of us publish these reviews publicly. I paywall mine and think you probably should too, but either way, it begs the question—what changes when we write our year in review for a public audience?
Who your audience is determines what you include in your review process. For some of us, that pressure might make us more rigorous. For others, it might make us less honest. You can always do one version of the review for yourself and another for your public audience, but in my experience, that audience judgement is always in the back of your mind.
I will be publishing my 2025 year in review and my 2026 plan here on the blog for paid subscribers this month. We'll see how openly vulnerable I decide to be.
Are you doing a review? What are you including in yours?
Templates and workshops for your year end review
I found lots of useful templates and live sessions while researching year end formats. Here's a few of them:
- Matthew Fenton's Freelance Strategic Plan
- Anna Burgess Yang's Quarterly Review Checklist
- Kari Ginsburg's End of Year Reflection Session on December 18
- Jennifer O'Sullivan's New Year Edition Spark Sessions (1:1 sessions)
- Rachel Cook's Plan Your Best Year Ever
- Kat Schmoyer's 32 Question End of Year Worksheet
- Chelsea Quint's Deep 3 Day Virtual Business Retreat (over for this year but follow for future ones)
