As Fractional CFOs and firm owners, we spend the entire month of December acting as the strategic brain for everyone else.

We’re finalizing their budgets, cleaning up their balance sheets, and calming their anxieties about the year ahead.

But in the midst of the year-end close chaos, it's easy to neglect the most important client on your roster: your own firm.

We often suffer from "Cobbler's Children Syndrome"—our clients get our best strategic thinking, while our own businesses get whatever energy is left over (which, by December 31st, isn't much).

Before you dive headfirst into January deliverables, I want you to pause...

Stop with the spreadsheets, forget the forecasts, and pick up a pen.
(For those of you who love alliteration, you're welcome!)

I’ve put together a few "non-obvious" journal prompts to help you reflect.

I'm not talking about revenue goals or firm profitability targets; we’re looking at the structural and psychological hurdles that will determine if next year is just busy, or if it’s actually scalable.

Let's dive in... 

1. "If I had to sell my firm tomorrow, what is the single biggest 'deal-killer' a buyer would find during due diligence?"

Why this matters: We spend so much of our time focused on our clients' businesses that we can easily ignore the fact that our own operations run on duct tape and institutional memory.

If your firm’s success relies entirely on you being in the room, you haven’t built a business; you’ve just built a high-paying job. No shame, but maye 2026 is the year you do something about that.

This prompt forces you to look at your firm as an asset, highlighting weak systems, key-person dependencies (this is a big one!), or messy internal financials that need to be cleaned up in the new year.

2. "Which client am I secretly hoping churns in Q1, and what does that say about my boundaries?"

Why this matters: Revenue is a vanity metric if it comes at the cost of your sanity. Most firm owners hold onto "legacy clients" who pay too little and demand too much, simply out of a scarcity mindset.

Identifying that ONE client you dread hearing from helps you pinpoint exactly where you are undercharging or over-delivering.

Sometimes, the best way to grow in the new year is addition by subtraction.

3. "Am I selling 'data' or am I selling 'decisions'?"

Why this matters: Data is a commodity; you can find someone to produce accurate financial statements for cheap.

But decisions are premium.

If your clients only hear from you when you send the monthly reporting package, you are selling data.

If they call you before they hire a VP of Sales or sign a new lease, you are selling decisions.

The shift from "reporter" to "strategic advisor" is the single biggest lever you have to increase your pricing in the new year. 

4. "If I were forced to double my profit next year without adding a single new client, what would I have to do?"

Why this matters: Most firm owners default to "more clients" as the only path to growth.

This constraint is uncomfortable because it forces you to look at operational efficiency. It demands that you consider raising prices on existing contracts, upsizing scope, or productizing your knowledge.

Often, the path to a healthier bottom line isn't about finding more leads; it's about mining the gold you already have.

As an added bonus, spending time here makes running your firm SIGNIFICANTLY easier.

5. "Did I act as a CFO for my own business this year, or just a Controller?"

Why this matters: A Controller looks backward at what happened; a CFO looks forward at what could happen.

The irony of the Fractional CFO industry is that we are often so busy executing for others that we only do "historical accounting" for ourselves.

This year, challenge yourself to stop merely recording your history and start designing your future:
Set personal and firm goals 
Put together forecasts and projections
Set quarterly "rocks" or projects to help you get there
Set aside time each quarter to reflect and plan for the future
(You know, do the CEO stuff you've been talking about)

6. "What is the one conversation I avoided having with a client this year that cost me money?"

Why this matters: Whether it was avoiding a scope creep conversation, skipping a price increase, or failing to push back on an unreasonable deadline, avoidance is expensive.

This question exposes the "soft skills" gap that prevents many technical financial experts from scaling.

Your ability to hold a difficult conversation is directly correlated to your profit margin.

And, if you haven't noticed yet, putting these conversations off only makes things harder and more expensive over time. 

Identify the conversation and rip the bandaid off in 2026.

7. "How many times this year did I say 'I'll just do it myself because it's faster'?"

Why this matters: This sentence is the "Scaler’s Trap." It feels efficient in the moment, but it is the primary reason firms hit a revenue ceiling.

For your firm to grow, you must stop being the best technician in the room.

This prompt shines a light on the specific bottlenecks where you need to either hire support or build better SOPs immediately.

One of the hardest lessons I've had to learn is that being the best at multiple things in the firm isn't a badge of honor. It's just a neon-lit indicator that I'm the bottleneck for scale. 

This is the way; ego be damned.

8. "If my firm grew by 5x overnight, would my current lifestyle break?"

Why this matters: Many of us started this journey for freedom, yet we end up building a machine that requires our constant inputs to survive.

If scaling your revenue means destroying your personal life, the business model is broken. This prompts a necessary check-in on capacity planning to ensure you are building a firm that serves your life, not the other way around.

The Roadmap is in the Discomfort

It is tempting to read through this list, nod your head in agreement, and click away. But the real value comes when you actually sit down and write the answers.

You might find that some of these questions make you squirm.

Good.

If I'm being honest, they made me squirm, too.

That discomfort is a signal. It is telling you exactly where your firm has outgrown its current systems, or where your boundaries have become too porous, or where YOU are choking out your own scalability.

The answers to these questions aren’t just journal entries; they should be your strategic roadmap for next year.

Take the time to get clear now so you can hit the ground running in January. Not just busy, but focused.

Enjoy the rest of your downtime.
You’ve earned it.

See you in the New Year.

-Michael