The Slow Season - And How to Survive (and Thrive) In It

"Success is peace of mind, which is a direct result of self-satisfaction in knowing you made the effort to become the best of which you are capable." - Dan Miller

(A quick thank-you to the reader: Hello, Isaiah here. If you're reading this, you're likely a business owner looking to grow in your niche...in which case, great. You're in the right spot, you're learning, you're doing what 90% of business owners skip once they start.

If you want a fast-track to learning and handling almost everything mentioned here in-depth, I plan on creating a course that will go in-depth on these topics, the problems they bring and more solutions...I also have software in place that takes care of almost all of your online marketing and outreach problems. You can read up on that here - but besides that, thank you for taking the time to read here. I appreciate every minute you spend with me.)

If you’ve been in the landscaping business for any length of time, you already know the pattern. Spring hits, the phones blow up, so many leads are coming in that you don't know what to do with them and the money is flowing like nobody's business.

Then fall fades, winter creeps in… and suddenly revenue slows to a trickle. The work that was easy to find in April becomes nearly impossible in January.

Bills don’t stop, of course. Insurance, trucks, fuel, payroll, loans, equipment financing, storage, business software, etc. all still has to be paid for during the slow seasons. And if you’re like most landscapers, the roller coaster cash flow cycle creates the most stress out of anything in the business.

Here’s the good news:

Unsteady cash flow during slow seasons is completely fixable.
And once you fix it, your business becomes predictable, profitable, and actually enjoyable.

In this blog, you’ll learn the most effective ways landscaping companies create steady cash flow all year—no matter the season.

1. Build a Recurring Revenue Base (Your Business’s “Income Floor”)

Almost every healthy, scalable landscaping business has one thing in common:

They don’t rely on big one-off install jobs to survive.

Yes, design-build work is profitable. Yes, it’s fun.
But installs alone create a dangerous business model because:

• Weather delays shut down income instantly

• You only get paid when a project is complete

• Winter hits and there’s nothing on the calendar

• It’s impossible to keep staff long-term

To fix the cash flow roller coaster, you need a recurring revenue foundation. A framework that can be implemented in order to supplement your business year-round. This way, you no longer have to save and panic, wondering how you're going to keep overhead costs from crushing you before next spring.

The best recurring services for landscapers:

1. Weekly or bi-weekly mowing
Consistent work that is easy to staff and much easier to sell a potential client on than a full-on landscaping project.

2. Monthly landscape maintenance
Bed maintenance, pruning, weeding, edging, general upkeep. Most clients who hire landscapers do not want to perform these duties themselves, so it's a very nice upsell. The project gives them a solution, then a new problem...then you give a new solution.

3. Seasonal cleanups billed in advance
Spring cleanups, fall cleanups, leaf removal packages. Billing in advance helps to solve the problem of customers being slow to pay.

4. Fertilization & weed control programs
Typically sold in annual plans with 6-8 visits, these can be extremely lucrative ways to create consistent, reliable income spaced out over an entire year.

5. Irrigation maintenance plans
Spring start-up + backflow + mid-season check + winterization. These prevent freeze damage that could lead to repairs as well as saving water, so they can be highly useful to any customer with sprinklers installed.

6. Snow removal contracts (commercial or residential)
Huge stabilizer for cash flow during the cold winter months, especially if billed monthly. Unfortunately, this is a more conditional option though, as it obviously won't sell in places that do not regularly get snow in the winter.

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The goal is to have at least 30% of your annual income originate from recurring revenue. This creates an income floor; something reliable to cover fixed expenses even when install work dries up.

2. Sell Seasonal Prepay Packages Before Slow Months Hit

One of the fastest cash-flow fixes is to collect money before the season begins.

Landscaping companies do this all the time for:

• Fertilization programs

• Seasonal cleanups

• Lawn care bundles

• Snow removal services

• Holiday lighting

  

Prepay discounts often look like:

• 5% off when paid by February 1

• 10% off when paid by January 1

• $50 off if paid today (effective for residential services)

Even a modest prepay campaign can generate:

• A surge of early-season cash

• Predictable scheduling

• Fewer late payers

• More loyal customers

Pro tip:

Send prepay offers via email AND text. Text has a much higher open rate, especially with homeowners...if you aren't using it to at least ask, you're doing yourself and your business a huge disservice.

3. Add Off-Season Services That Create Winter Revenue

Landscapers often believe there’s no money to be made in the off-season. They are completely wrong.

There are dozens of profitable winter services that require minimal equipment or can be handled with what you already have. There is always money to be had and work to be done...it simply takes looking through a different lens sometimes.

Here are the best off-season add-ons that landscapers successfully sell:

1. Snow plowing + ice management
The gold standard for winter income if you live in a cold area with frequent snow, sleet or ice.

2. Holiday lighting installation
Highly profitable, low overhead, recurring every year. Campaigns can also be made around this service.

3. Firewood delivery
Simple, predictable, great for cash flow. Also very easy to fulfill and pitch to customers on top of being a good way to re-purpose the spare wood that would be discarded otherwise.

4. Gutter cleaning & roof clearing
Another quick, easy upsell for existing clients. It's possible that this can create recurring revenue as well.

5. Winter pruning or dormant pruning
Great for arborists or maintenance-heavy companies.

6. Hardscape repair & maintenance
Stone resetting, paver resealing, drainage fixes. All easy ways to earn extra money and prevent customers from needing repairs.

7. Interior plant care
Niche service with monthly contracts. Great for customers who love organic interior decor but don't love taking care of it properly.

8. Equipment repair / small engine repair
Especially useful if you have skilled mechanics.

These services won’t replace spring revenue, but they will significantly smooth out the dips.

4. Fix Your Billing System (Cash Flow Dies When Billing Is Slow)

Many landscapers unintentionally create cash flow problems because they:

• Invoice too slowly

• Wait until month’s end

• Don’t bill until the job is complete

• Forget to invoice small add-ons

• Don’t require deposits

• Have clients who routinely pay late

These habits create the “feast or famine” cycle that keeps so many small businesses small. It's impossible to grow beyond where you are now if your cash flow is dictated by your customers deciding to pay you, and not a system that makes it more predictable.

To fix this, implement the following:

1. Bill at the time of service.
Or even better, bill automatically. This takes away headache from both you and the customer, as the moment that they receive their desires outcome (the perfect yard) is when they are most willing to pay. Now, you don't have to remember to do that on top of the mountain of work you already have a business owner.

2. Require deposits or progress payments.
Typical structure:

• 50% deposit

• 25% mid-way

• 25% upon completion

This commitment on the customer's end also keeps them engaged in the process and helps to mitigate the issue of a customer ghosting you mid-way. If customers seem reluctant to pay you before you've started on a job, simply make the initial deposit refundable if they wish to do so before the project starts.

3. Use autopay for residential maintenance clients.
Monthly recurring billing removes 90% of headaches with the money portion of these plans. You get your payment on time, the client barely even notices the bill after some time. It feels much less committal than getting a separate invoice every time.

4. Charge late fees.
You deserve to be paid on time. As such, you should penalize any customers dragging their feet on payments. This will make late payments much less of a problem, as no one wants to pay a late fee (obviously) and you will now either get paid on time, or paid more.

5. Set up automated reminders.
Software can chase invoices for you (Jobber, Service Autopilot, LMN, etc.). Just like the systems that we use at Hi-Roller Solutions, most of these softwares have a feature that allows you to send out reminders for pretty much everything you'd need to, with little to no effort put in on your end. You may feel that you will annoy your customers, but chances are they will actually appreciate the communication, rather than having a payment they forgot about sneak up on them.

5. Create a 12-Month Marketing Engine Instead of Seasonal Bursts

Most landscapers market reactively:

• They advertise heavily in spring

• They get overwhelmed

• They stop marketing

• Fall comes, work slows

• Panic sets in

• Marketing restarts...but it's too late

This creates the exact cash flow problem you’re trying to avoid. Good news though, you just have to switch from being reactive to being proactive in order to fix this. Have a plan set for each coming month, execute it, and now you're controlling the business, rather than the business controlling you.

Here’s a simple annual framework:

January–February

• Promote prepay bundles

• Sell snow, pruning, spring cleanups

• Run Google Local Service Ads for annual maintenance plans

March–April

• Heavy ads for lawn care + season-long maintenance

• Push recurring contracts, not one-time jobs

May–June

• Upsell mulch, pruning, planting, landscape enhancements

• Market design-build at premium pricing

July–August

• Promote irrigation, drainage, mid-season cleanups for the hot summer months

September–October

• Push fall cleanups, aeration, overseeding

• Sell winter service contracts with a pre-pay discount, if possible

November–December

• Holiday light installation

• Pre-sell next year’s packages

• Build next year’s marketing plan

Marketing should never shut off.

Predictable leads = predictable cash flow. If you have too many customers, awesome. That means your business is ready to grow and make more money...it does NOT mean that you should decrease the customers you get.

6. Track Job Costs So You Stop Underpricing Work

Cash flow often suffers not because work slows, but because the work you do get isn’t profitable enough.

If you’re not tracking:

• Labor hours

• Equipment cost

• Materials cost

• Overhead %

• Actual vs estimated

• Job profitability

Then you’re guessing.

And guesswork kills margins.

The fix:

Track every job. Adjust pricing quarterly.

Winter is the best time to:

• Audit last year’s margins

• Raise prices

• Remove low-margin services

• Fix your estimating system

Better profit = better cash flow. Both of them mean that you are no longer wasting time on jobs that earn you very little profit, if any. After you fix the "no consistent projects" problem, the next step is to get more profitable projects.

7. Build a Cash Reserve (Your “Winter Survival Fund”)

Your business should operate with at least 2–3 months of operating expenses saved as cash.

This prevents:

• Late payroll

• Stress during winter

• Relying on credit cards

• Equipment repo or insurance lapses

• Panic hiring or panic discounting

How do you build the reserve?

• Add 3–5% margin to your prices

• Save all deposits (or as many as possible) instead of using them for bills

• Reduce unnecessary subscriptions

• Stop underpricing small jobs (!!!)

• Move to auto-billing to improve collection speed

Build your reserve at the height of the busy season. Again, the goal is to be proactive and tackle these problems before they crop up. That is what successful businesses do, and you want your business to be successful.

8. Sell High-Margin Winter Projects During the Summer Rush

A powerful strategy used by top landscaping companies:

Sell winter work during the summer.

Most landscaping business owners tend to focus on the now. Since you'll have the "now" planned out in advance, you have time to focus on the future and get projects for the slow season before other businesses even think about it. While you're busy installing patios and retaining walls, book:

• drainage installations

• tree removal

• grading work

• winter-time hardscape repair

• lighting system installation

• irrigation expansions

These jobs can be scheduled for November, December, and January. Again, use prepay discounts and pay structures as leverage to get these done and ease pain for your business and your clients.

Why this works:

• Customers don’t care when the work is done = easier to meet deadlines

• Your crews stay busy

• Your cash flow stays steady

• You avoid winter layoffs

• You don't rely solely on snow income or savings

When the leaves fall, you’ll already have revenue booked. While other businesses struggle and die, you will thrive in the winter and grow richer year-after-year.

9. Analyze Your Expenses to Plug Hidden Cash Flow Leaks

You can’t create consistent cash flow with unpredictable expenses.

Most landscapers overspend on:

• Fuel

• Dump fees

• Equipment repairs

• Materials waste

• Over-ordering

• Labor inefficiencies

• Insurance policies they don’t use

• Subscription bloat

Every winter, perform a “Profitability Audit.”

Look at:

• What services produced the lowest margins?

• Which clients had the most callbacks?

• Which crews were least productive?

• Which equipment cost the most to maintain?

• Where did hours disappear?

Fixing these leaks can increase net profit by 10–30% without adding a single new customer, yet so many business owners see these tasks as tedious and unimportant, so they simply allow themselves to lose money by not optimizing their systems. Don't be one of those business owners.

10. Create a Winter Production Plan Before the Slow Season Arrives

Most landscapers don’t fail because winter comes.
They fail because they don’t plan before it comes.

If you wait until November to think about winter cash flow, you’re already too late.

Your winter plan should include:

• Services you’ll sell

• Pricing & margins

• Crew sizes

• Roles during slow months

• Prepay promotions

• Lead-generation strategy

• Cash flow forecast

• Expense-cutting plan

• How long your cash reserve will last

• Projects scheduled for slow months

Run your winter plan by July or August.

Because planning creates stability.

Final Thoughts: The Slow Season Doesn't Have to Be Stress Season

Unsteady cash flow is one of the top reasons landscaping businesses stay small, struggle to keep employees, take on debt, underprice work, burn out, and fail to scale. But when you build recurring revenue, improve billing, diversify seasonal services, and plan ahead, something incredible happens:

Your revenue becomes predictable. Your business stops feeling chaotic. You keep employees year-round, you scale faster than your competitors, and you finally take control of your time and money. But most importantly, The business becomes stable enough to grow.

A prepared business is a business that is not only successful, but predictable. An un-prepared business leaves things up to luck and hopes for the best. If you want the former, than take the information here and run with it...future you will thank you.

- Isaiah S., Owner of Hi-Roller Solutions