Dear Crabby, Should I Hire a Snowplow Guy?

Dear Crabby,

I hate shoveling my driveway when it snows. Would you recommend hiring a snowplow guy to do it for me? Will it be worth the money?  Will I be happy with that decision?

Sincerely, Lazy Lou

Dear Lou,

I’m not sure about your happiness Lou, but I can tell you about my experience with this. One winter after I threw my back out for a second time, I broke down and hired this fella to plow my driveway. He left a flyer on my mailbox that said he would plow my driveway for $25 each time and would give me the first plow for free just for calling on this ad. I figured I might as well give it a try. The first time it started snowing, I heard him come down the drive and sure enough he cleared the whole thing in seconds. However, the next morning when I went out to inspect, I could hardly tell he had been there! There was another 3 inches of snow covering my driveway! I did see a snow bank as evidence that he came, but what good was that as I found myself out there shoveling a path for the missus and myself. Later that day, the guy called and asked if he should come back and clear it again. I said, “Yes, please keep it clear whenever it snows.” He then told me that was his premium service and he would have to charge me $45 each time if I wanted that kind of service. I said “No, you promised to clear the driveway for $25 whenever it snows!” He replied that’s what he did, but that if I wanted it clear all the time, it was extra. I protested, “What’s the point of having you clear it whenever you feel like it, if I’m still required finish it later when it has snowed more?” He just stated that that’s how it works. Shortly after this conversation, I got his first bill. He charged me for 4 plows at $25 each time! I called and calmly asked him to clarify. He explained that he had cleared it a couple times in the middle of the night while it was still snowing to make sure it was clear for me! Frustrated, I then asked about my one free plow for calling from his ad. His response did not make me happy!  He had the audacity to say that he had a tough year last year and really didn’t want to honor that offer anymore! So I grumbled and whined as I paid the bill and went out to shovel my driveway once again since it was still snowing. Later that night, I asked Mrs. Crabby for some wisdom on how I could handle this situation, and of course her answer was, “Fire this guy and hire someone who will actually clear the snow for us when we need it cleared!”  It always seems so simple when she says it.  So, I guess we live and learn.  Somehow, I still end up clearing my own driveway every year, so I wish you the best of luck. Let me know if you figure out the secret.

Sincerely, Dear Crabby

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Stuck in a rut? Need some biased advice from a crabby old baby-boomer? Read regularly by thousands and loved by some, Dear Crabby answers questions weekly to life's challenges. Send him a note at

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