Which Are You Actually Planning For, the Business New Year or Calendar New Year?

Brittney Simpson
13 hours ago
8 min read

Every December, the planning emails start rolling in.

You see goal-setting frameworks, strategic planning templates, and year-end review guides everywhere. They all assume your business year starts on January 1st. But does it really?

Before diving into the planning frenzy, take a moment to assess your own business cycle.

Consider these quick questions:

When is your busiest season?
When do you naturally find time to plan and strategize?
When do major contracts or projects kick off?

Jot down your answers in a dedicated space or worksheet—this will make your reflection more actionable and memorable. Keep these insights at hand as you continue reading with your business's unique rhythm in mind.

But for many companies, that just isn’t true.

Your actual business doesn't run on a calendar year. It runs on a fiscal year, a contract cycle, a seasonal rhythm, or whatever pattern actually governs how work flows through your organization.

Still, since everyone else plans in January, you do too. You pull your team into goal-setting sessions while many are still in vacation mode. You're setting new priorities as you wrap up Q4. You start new projects during your busiest time just because it’s a new year.

And then you wonder why nothing sticks.

From working with founders, I’ve seen that the calendar year is more about culture than strategy. Treating it as your business’s reset button can cost you momentum, clarity, and follow-through.

The calendar year trap

Let me give you an example.

I worked with a founder last year who runs a construction-focused business. His busiest season is May through October. That's when projects are happening, when his team is maxed out, when revenue is flowing.

November through February? Slower. Planning season. Time to breathe.

And yet, every January, he'd gather his team for a big strategic planning session. New goals. New priorities. New initiatives to launch.

He did this during his slowest revenue period, just before his busy season started.

When May arrived, and work picked up, the January goals were forgotten. The new projects didn’t take off because the team was too busy to remember what they had agreed to months before.

Each December, he felt like the year slipped away, and he never really got a handle on the strategy.

The problem wasn't his strategy. It was his timing.

His business year didn't start in January. It started in November, when things slowed down, and he actually had the mental space to plan. His peak execution period was May through October. His planning period was November through February.

When we adjusted his planning to better align with his business’s real rhythm, things improved. He began planning for the busy season in November. By May, the team knew what to do. Goals stuck, priorities stayed clear, and the year felt organized instead of chaotic.

The business and team stayed the same. Only the timing changed.

That’s the trap of following the calendar year. You end up planning based on expectations, not when your business is actually ready.

Your business has a rhythm.

Every business has its own natural cycle. The real question is whether you’re noticing it.

For some companies, the fiscal year doesn't align with the calendar year. Your year ends in March, June, or September, but you're still doing "new year" planning in January because that's when everyone else does it.

For others, it's contract cycles. If you're a government contractor and your major contracts renew in October, your strategic year begins then. Planning in January is planning in the middle of your year.

For seasonal businesses like retail, hospitality, construction, landscaping, or anything affected by weather, your business rhythm depends on when customers buy. Planning in January could mean planning just before or after your busiest time, when you have the least energy for strategy.

And for professional services firms, it's often client cycle-driven. If your clients do annual planning in their Q4, that's when your pipeline builds. If they're quiet in summer, that's your planning window.

None of these business cycles takes January 1st into account.

But here’s what happens if you ignore your business’s real rhythm and plan by the calendar instead:

You end up planning at the wrong time. You’re either too busy to think clearly or too far from the work to plan well.

Your team can’t follow through. You set goals in January, but then head straight into your busy season with no time for new projects.

Nothing sticks. By the time you have space to act on your plans, the priorities already feel outdated.

You always feel behind, because you are. You keep trying to fit your business into a schedule that doesn’t match how it really works.

How to find your business's new year.

This isn’t complicated, but you do need to stop defaulting to January and start looking at how your business really runs.

Ask yourself these questions:

When does your business naturally slow down? That’s your planning window. It’s not when you’re busiest or in the middle of projects, but when you actually have time and space to think ahead.

When do your major contracts, projects, or revenue cycles renew or restart? That's often the real start of your business year, regardless of what the calendar says.

When does your team have time to focus on new projects? If you’re in the middle of heavy work, you won’t have space for strategy. Look for times when your team can actually take on and apply changes.

When do you typically make your biggest hiring or investment decisions? That's a signal about when you're actually thinking ahead, not when you're just trying to survive the current workload.

For many founders, once they look at this, the answer is clear. Their business year doesn’t start in January. It starts in April, July, October, or whenever their real business cycle begins.

Still, they’ve been trying to fit their planning into January just because that’s what others do.

What changes when you plan at the right time?

Here's another example.

I work with a healthcare consulting firm. Their clients, mostly hospitals and health systems, do their strategic planning in fiscal Q4, from July to September. This means the firm’s pipeline grows in late summer, and their busy season is October through June.

For years, the founder was doing traditional January planning. Setting goals, launching initiatives, and rallying the team.

Every year, those goals fell apart by March because the team was swamped with client work and had no time for internal projects.

We shifted her planning cycle. Instead of January, she now does strategic planning in July. Right before her pipeline builds. When she can look ahead at the upcoming busy season with clarity.

Now, her team starts October knowing exactly what they’ll work on for the year. Client work doesn’t disrupt their priorities because those priorities fit the client cycle.

She's not fighting against her business rhythm anymore. She's working with it.

The result is better follow-through, less confusion, and more trust from her team that priorities really matter.

She does the same amount of planning, just at a better time.

What if you're stuck with calendar year planning?

Some of you might be thinking, "That’s great, but my board wants a January plan. My investors expect calendar year reporting. I don’t have a choice."

Fair enough.

But here’s the thing: you can report on the calendar year without planning around it.

You can give your board or investors the January update they want while still running your internal planning cycle on a rhythm that makes sense for your business. The key is to separate what you need for external reports from your internal planning rhythm. They don't have to match. To kickstart momentum, take a simple step this week: schedule a two-hour 'cycle audit' in your calendar to analyze your business's real cycle. This involves reviewing sales patterns, ongoing projects, and team workload to identify your actual business flow.

Alternatively, you could send out a short survey to your team to gather their insights. These small commitments can transform insight into action. If you need to make a calendar-year plan for outside stakeholders, that's fine. Just don't confuse that with the real work of getting your team ready for what's next.

Then, turn that plan into whatever format your external stakeholders need.

The uncomfortable truth

Most founders don’t like to admit it, but a lot of January planning is just for show.

You do it because it feels expected as a leader. Everyone else is sharing their goals and visions for the year. There’s pressure to start fresh when the calendar changes.

But deep down, you know it’s not the right time. Your team is tired from year-end and doesn’t have the energy to start new projects. You know the plan you make in January won’t last past February.

And you do it anyway.

Not planning in January feels like falling behind.

But here’s the truth: skipping January planning doesn’t put you behind. You get ahead by planning when it really matters.

The companies that succeed aren’t the ones that plan when everyone else does. They plan when they’re actually ready to act.

Permission to ignore January

If January isn’t your business’s new year, it’s okay to ignore it.

You don’t have to set new goals just because the calendar changed. You don’t need to start new projects just because it’s Q1. You don’t have to reset everything just because everyone online is talking about fresh starts.

You need to plan when your business is ready to plan.

For some of you, that's January. Great. Plan in January.

For others, it’s April, July, October, or whenever your business cycle gives you the space and clarity to plan.

There’s no prize for planning in January. What matters is whether your plan moves your business forward or just gets forgotten by March.

What to do instead

If you’re reading this in early January and realize your planning cycle is off, here’s what I suggest:

Don’t push for a big strategic plan now if it’s not the right time. You’ll just waste energy on something that won’t last.

Instead, use January to get settled. Wrap up last year’s loose ends, figure out what’s working and what’s not, and let your team recover if they need to.

Figure out when your business’s new year really starts. Examine your operations and identify your natural planning window.

Do your real strategic work then, when you have the clarity, time, and context to make decisions that will last. In contrast, for external stakeholders, keep the planning light. Focus on high-level priorities and directional goals. Avoid overcommitting to a plan you know won't survive the year.

Save the real planning for when it counts.

The shift

When you stop planning by the calendar and start planning by your business's schedule, things change. You stop feeling like you're always behind. You stop dropping goals after a few months. You stop pushing your team into strategy talks when they're already overwhelmed. It's like sailing; you tack the sail when the wind changes, not when the calendar flips. This approach harnesses the natural momentum of your business, aligning your strategy with the real conditions you face.

You start planning with purpose, not just out of habit. You make decisions when you have the right information and time. You build momentum that lasts all year, instead of losing steam by spring.

That's not laziness. That's not a lack of discipline.

That's strategic thinking.

Your business’s new year might be January, or it might not. If it isn’t, the smartest move is to stop pretending it is.

Plan when your business is ready. Don't plan your business's readiness just because the calendar says so.

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