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Five Decisions to Make in October Before January Makes Them

October 19, 2026

There are nine weeks left in the year and four of them are already gone.

Thanksgiving week nobody answers. The week after is catching up on Thanksgiving week. Then there are two weeks in December where everybody is present but distracted, and then it is over.

So the real number is closer to five working weeks, and every year I watch people, myself very much included, spend those five weeks doing the urgent thing and then arrive in January with a set of decisions that got made by default.

This is the short list. Not a planning framework. Five specific decisions that are cheap this month and expensive in eleven weeks.

One. What you are charging in 2027

If your prices are going up on January 1, the people paying them need to know before the middle of December, and you need to have decided the number before you tell anybody.

Two things go wrong here and they are opposites.

The first is not deciding, which means January arrives and you charge the old rate for another year because raising it mid-year feels worse than raising it at a turn. That is a decision, it just got made by the calendar instead of by you.

The second is deciding in a hurry in the last week of December and then having the conversation while you are tired and it is a holiday and the client is on vacation. I did a version of that this year. I had a price increase drafted and ready to send to somebody who was out of office for two weeks, and if I had sent it, it would have landed on top of a week of backlog and taken effect three days after she got back. That is an ambush, and it does not read as a price change, it reads as a business you cannot rely on.

I moved it. It cost me a month of revenue and it bought a month of notice for somebody who has paid on time without complaint since the beginning, and it was worth it.

Decide this week. Communicate by mid-December. Effective date at least thirty days out from when they read it.

Two. Which client you are not keeping

Everybody has one. The account where the hours have quietly doubled and the number has not.

The honest test is not "are they difficult." Plenty of good clients are difficult. The test is arithmetic. Take what they pay you, divide it by the hours actually spent last month, and look at the number. Then compare it to what you would need to charge a new client to do the same work.

If the answer is embarrassing, you have three options and only three: rescope the work to fit the number, raise the number to fit the work, or end it. Doing none of those is the fourth option and it is the one everybody picks, and it is why the same account is on this list next October.

I ran this on my own book earlier in the year. One account was netting me under eight dollars an hour once I paid for the help doing it. Not a bad client. A scope that had grown and a price that had not, for long enough that nobody remembered it had ever been different.

Rescope, reprice, or end. Written down, with a date, this month. If the keep-or-not part is what is sticking you, this is how I think about client retention.

Three. The thing you built that nobody has seen

Go make the list. Finished proposals that were never sent. A service page that was written and never published. A case study sitting in a folder. An automation that was built and never connected to a trigger.

I did this in August and the list was long enough to be genuinely uncomfortable. Everything on it was ninety five percent done. Not one item needed a new idea, they needed the last five percent, which is always the part that involves telling somebody it exists.

That list is your cheapest available revenue in Q4, by a distance, because the work is already paid for. Nothing you start in November will be finished and delivered before the year ends. Something you finished in June and never sent can go out on Thursday.

Pick the three highest-value items and put a send date on each one. Not a work date. A send date.

Four. What you are not doing next year

This one is the hardest and it is the one that actually protects the other four.

Write down the three things you spent real time on this year that produced nothing you can point at. Not the things that failed loudly, those already stopped. The ones that quietly did not work and that you are still doing because stopping would mean admitting the time is gone.

Then decide, in writing, whether each one gets a defined test with a number attached or gets stopped.

The rule I use, because I need a rule or I will keep everything: if I cannot say what result would make me stop, I am not running a test, I am maintaining a habit.

Five. The one number you will run next year on

Not a dashboard. One number, that you check on the same day every week, that tells you whether the business is getting safer or not.

For most service businesses it is recurring revenue, because it is the only number that answers "what happens if I get sick for three weeks." For some it is cash collected. For a couple of people I know it is billable hours, which is a fine number if you are honest about the ceiling built into it.

The specific number matters less than the fact that there is one and that looking at it is a five-minute read rather than an hour of hunting. If checking your number takes an hour, you will not check it, and by March you will be flying blind again and calling it being busy.

I check mine on Friday. It takes twenty minutes and it exists because the alternative, which I ran for most of a year, was finding out about a problem in month four.

What this is not

This is not a planning retreat and it is not a strategy exercise. Five decisions, each of which can be made in an afternoon and written on one page.

The reason to do it in October rather than the first week of January is not discipline. It is that every one of these gets more expensive as the year closes. A price change needs runway. A client conversation needs to not happen during a holiday. A finished thing that gets sent in November lands on a desk. The same thing sent on December 22 lands in a pile.

If you want a hand with it

The 5-Minute Ops Quiz is free and it will tell you which of the five above is the one costing you most right now. It takes five minutes.

If you want somebody else to do the arithmetic on the client list and the unsent pile and hand you the answer, that is the Operations Audit, it is a fixed price, and the price is on the pricing page.

Either way, decide the five. January is going to decide them otherwise and it has worse judgment than you do.

Frequently asked questions.

What should a small business decide before the end of the year?

Five things while they are still cheap to decide: your 2027 pricing, which client you are not keeping, the finished work nobody has seen, what you are not doing next year, and the one number you will run on. Each one can be made in an afternoon and written on one page.

When should I tell clients about a price increase?

Decide the number this week, tell them by the middle of December, and set the effective date at least thirty days out from when they read it. A price change that takes effect three days after someone gets back from vacation reads as a business they cannot rely on, not as a price change.

How do I know if a client is worth keeping?

It is arithmetic, not whether they are difficult. Take what they pay you, divide it by the hours you actually spent last month, and compare that to what you would charge a new client for the same work. If the number is embarrassing, you have three real options: rescope the work, raise the price, or end it. Doing none of those is the fourth option, and it is why the same account is back on the list next October.

Why make these decisions in October instead of January?

Every one of them gets more expensive as the year closes. A price change needs runway, a client conversation needs to not happen during a holiday, and a finished thing sent in November lands on a desk while the same thing sent on December 22 lands in a pile.

What is the one number I should track?

One number you check on the same day every week that tells you whether the business is getting safer. For most service businesses that is recurring revenue, because it answers what happens if you are out for three weeks. The specific number matters less than it being a five-minute read instead of an hour of hunting.

Take the free 5-Minute Ops Quiz

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