I don’t write about failure often. Not because I don’t experience it — anyone running a small business in a seasonal industry like lawn care does — but because it’s easier to write about the jobs that went well, the lawns that recovered, the customers who sent nice messages.
But I’ve been thinking about a particular season for a while now, and I think there’s more value in writing about it honestly than in pretending it didn’t happen. Because the things I got wrong that year, and what I learned from them, have shaped how I work more than almost anything that went right.
This is the story of my worst season since I started Cutting Edge Lawn in 2020. I’m going to be direct about what happened, why it happened, and what’s different now because of it.
How the Season Started — and Where the Problem Began
The season started well, which is part of why it went sideways. Spring came early that year — warmer than normal, ground dried out fast, homeowners were calling in early May wanting to get started. I took on more customers than I should have. Not dramatically more. But enough that my schedule was tighter than it should be from the beginning of the season.
I told myself it would be fine. I’d managed a full schedule before. I knew Greater Sudbury — knew the routes, knew the properties, knew what to expect. I thought I had enough buffer to handle the inevitable complications of a busy spring.
I didn’t.
By late May I was running behind consistently. Not badly — a day here, a day there. But in lawn care, consistently behind by a day on every property means consistently cutting grass that’s slightly longer than it should be, which means taking off slightly more than a third of the blade per cut, which means accumulating stress on every lawn on my route. I knew this. I was doing it anyway because the alternative was telling customers I’d be there Thursday and showing up Friday, which I also knew was a problem.
This is the kind of compounding mistake that doesn’t look dramatic in the moment. Each individual decision seems manageable. The cumulative effect of making it across forty-plus properties for an entire season is significant.
July — When Everything Showed Up at Once
By July, Sudbury’s summer conditions were doing what they always do — heat, dry stretches, lawns going dormant or showing stress. In a normal year, I manage this by raising cut heights, adjusting schedules, communicating with customers about what’s happening. This year, I was already behind before the heat arrived, and the heat made everything harder.
Three things went wrong in July that I’m still thinking about.
First: I cut a lawn I should have skipped. One property — a regular customer in Hanmer — had gone into drought dormancy. I knew it. I could see it when I pulled up. But I was behind on the schedule and I told myself a quick cut wouldn’t hurt. It did hurt. The dormant grass doesn’t need cutting, and cutting it adds stress to crowns that are already conserving energy. That lawn was brown and patchy through August in a way it hadn’t been before. The customer noticed. So did I.
Second: I missed a problem I should have caught. Another property had a section that was showing early signs of grub damage — the spongy feel underfoot, the grass pulling away slightly at the edges of the affected area. In a normal year I would have caught it on a routine walkthrough and flagged it. This year I was cutting and moving, not walking and looking. By the time the customer called me about brown patches in early August, the grub damage was significant. Earlier intervention would have made the recovery simpler and cheaper.
Third: I had a difficult conversation I handled badly. A customer who’d been with me since my first season called to say the lawn didn’t look the way it usually did and she wasn’t sure I’d been cutting at the right height. She was right — the schedule pressure had led to some cuts that were lower than they should have been because a slightly lower cut meant faster mowing. I knew it, she sensed it, and the way I handled that call was defensive rather than honest. I fixed the cutting approach but the conversation left a crack in the relationship that didn’t fully heal before the end of the season.
What I Did Wrong — The Honest List
After that season, I spent some time writing down what had actually gone wrong. Not to punish myself, but because I wanted to be specific rather than vague about it. Vague lessons don’t change anything. Here’s what I came up with.
I took on too many customers relative to my capacity. The growth was real and the demand was there, but I didn’t have the crew capacity to service that many properties at the standard I wanted to maintain. Revenue went up. Quality went down in ways that were hard to see in the short term and visible in the long term. That’s a bad trade.
I let schedule pressure change how I cut. The right cut height for Sudbury lawns isn’t a suggestion — it’s the foundation of a healthy lawn through the season. The moment I started adjusting that for convenience rather than for the lawn’s needs, I was making a choice I’d have to answer for. And I did.
I stopped walking properties and started just cutting them. The thing that catches problems early — grub damage, drainage issues, sections that need different treatment — is being present enough to actually see what’s happening. That year I was moving too fast to see much. Paying attention is most of the job, and I’d stopped paying attention the way I should have been.
I was defensive when I should have been honest. When that customer raised concerns, the right response was to acknowledge what had happened and be direct about it. Instead I got slightly defensive, slightly explanatory, and the conversation didn’t go the way it should have. She stayed through the end of the season but didn’t call back the following spring. I understand why.
What Changed the Following Season — and Every Season Since
The following spring I made a specific decision: I was going to take on fewer new customers and do better work for the ones I had. Not a little fewer — meaningfully fewer. Enough that I had actual buffer in the schedule for the complications that always come up in a Sudbury season.
I went back to walking every property before I started cutting, not just at the beginning of the season but through it. Fifteen minutes on a property before you start the equipment running tells you things you’ll miss if you just show up and cut. A section that’s changed since last week. Something that needs flagging before it becomes a problem. The kind of thing that separates a service that maintains lawns from one that improves them.
I got stricter about following the right approach for each point in the season — raising heights in July regardless of schedule pressure, skipping cuts on dormant grass rather than cutting to stay on schedule, doing the core aeration and spring cleanup work properly rather than rushing through it because the cutting backlog was building.
And I got better at the honest conversation. When something goes wrong on a property — and things go wrong sometimes, even when you’re doing everything right — the right response is to say so directly, explain what happened, and tell the customer what you’re going to do about it. Not defensively, not with excessive apology, just directly. People can handle that. What they can’t handle, and what erodes trust, is sensing that something is being managed rather than addressed.
The season after the bad one was the best I’d had. Fewer customers, better results, almost no difficult conversations. That’s not a coincidence.
I write about what I’ve observed cutting the same Sudbury street for three years — how the right approach compounds over time into genuinely better lawns. The same principle applies in the other direction. One season of doing things wrong doesn’t ruin everything, but it leaves marks. And the cost of those marks shows up in ways that are harder to see than a declined lawn — a customer who doesn’t call back, a relationship that has a crack in it, a property that needs an extra season to recover.
I’d rather learn those lessons early, on my terms, than keep repeating them. That season was uncomfortable. I’m glad it happened.
— Ryan Lingenfelter
Cutting Edge Lawn & Landscaping, Garson, Ontario
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