October 28, 2026 – The Potential Headaches to Anticipate When Hiring a Contractor

Do you ever develop a knot in your stomach that just won’t go away? That’s the present situation I find myself in. And it’s all due to what I can best describe as an ongoing communication breakdown or lack of mutual understanding with our landscape contractor. Is it just me, or is that the norm when you hire a contractor? Because, let me tell you, it seems like it happens at least 50% – 75% of the time. And why is that?! After getting burned enough times, I made sure to cross all the T’s and dot all the I’s. I looked for a reputable company, I went over my expectations with the owner in detail, he provided a contract and after reading it thoroughly, I signed it. But as soon as the work began, despite all the effort I put forth to ensure that THIS TIME would be unlike all the others, it still went south. 

What does that mean? Well, let me explain. What I learned after this latest snafu is that the devil’s in the details. I thought I did everything right by making sure (as the famous TV judges, Judge Judy and Judge Milian, often vigorously reminded their plaintiffs, defendants, and TV audience) to ‘GET IT IN WRITING’. Evidently, if you follow this sage advice and have a contract drawn up, it’s supposed to save you a whole lot of grief and guarantee a meeting of the minds. Unfortunately, as so often happens when my husband or I hire anyone to do work on our home or property, nothing goes according to plan. And the word I will use to best help you understand why (in this particular case) is AMBIGUITY.

Yep, I had a contract written up by the owner of the company we were hiring and at first glance everything seemed fine. And I can’t tell you whether it was intentional or not, however, I did notice that the wording was extremely ambiguous (but not enough to set off alarm bells). Four separate projects were listed on the contract; each contained a short, approximately 2-sentence description of the work that was to be completed, some of the materials that would be utilized and what the cost would be. There were no sketches or drawings or visual references provided. With all that taken into account, because my husband and I had spent a sufficient amount of time with the contractor, describing in detail what we wanted to have done, we thought he had a pretty good idea of our expectations and would proceed accordingly. Boy, was I WRONG!

Now, while I have your utmost attention, can I give you a word of advice? When you have a discussion with someone (i.e.; someone that’s going to charge you a sizable amount of money in exchange for a service) and they do a lot of nodding and/or repeatedly indicate that they are in agreement through a variety of affirmative remarks or gestures, if you believe that that verbal/non-verbal exchange means you’re both on the same page, you’re probably going to wind up in the same predicament I’m in…with a sizable knot in your stomach, BEYOND FRUSTRATED and DEAD WRONG! Sad to say but that’s simply not enough. You have to get it in writing, DETAILED writing. And I could kick myself for not insisting that this latest contractor provide a better description of what he intended to do along with photos or sketches. Had I done that, I’d be sleeping soundly right now rather than anxiously ranting at two o’clock in the morning.

And I’d be remiss if I didn’t provide further clarification as to why I’m feeling so anxious and frustrated and outright lousy at the moment. I also feel bad because after multiple texts and phone calls trying to clear up misunderstandings with the contractor, especially after what transpired yesterday, I reached my limit and told my husband (in order to preserve what’s left of my mental and physical health) that I needed to tap out and asked if he could handle any/all future communications related to the current landscaping project. He RELUCTANTLY agreed. I know it seems like a pretty wimpy thing to do but I’m so angry, I’m seeing red. I’ve also developed a knot in my stomach, my head hurts AND I can’t sleep. I’ve had enough! I just don’t understand why it keeps happening. Honestly, is it me or is that just how it is? I’m SO OVER hiring people to help with projects and winding up utterly disappointed.

If this was the first time something had gone awry, it’d be one thing. But as I said (at least I think I did?), this has been ongoing. Are you ready for this? Here’s another great example. About two years ago, after spending considerable time vetting concrete contractors, I (with great confidence) chose one. I was convinced that EVERYTHING would go smoothly because not only had I checked out the company’s reviews on Google, but I’d seen their work with my own eyes while walking my dog through the neighborhood. At first, everything appeared to go well. The owner showed up with his crew on the date and time we agreed upon and they started to frame out two slabs we contracted to have poured in our backyard (for workshops).

All went according to plan until the day the concrete/cement mixer truck showed up. Wouldn’t you know, that’s when things (as usual) went south. I had no concerns at first and thought the job would be completed in a matter of hours, and completed CORRECTLY. I assumed (BIG MISTAKE) they’d pour and smooth out the concrete, give it a few hours to dry, remove and load up their materials, I’d hand over a check, and they’d be on their way. Nevertheless, after a couple of hours, the doorbell rang. When I opened the door, I was greeted by the owner of the company who had some rather unpleasant news to share. It’s difficult to accurately describe the look on his face, but his words were crystal clear. “I’m so sorry,” he stated grimly, “Of the 30 years I’ve been in this business, this has never happened before, but the concrete truck ran out of concrete before we were able to complete the job.”

ARE YOU KIDDING ME?! Expletive! Expletive! Expletive! If you’ve ever hired someone to pour a slab and they run out of concrete in the middle of the job, you’ll know this is no small matter.

And then there was the gutter guy. What could possibly go wrong, you ask, when you hire a gutter guy? Oh, let me tell you, my friends! PLENTY! We had asked around and were referred to a guy in town who owned his own seamless gutter company. Since he was referred, we errantly believed we were in good hands. And apart from the one long-ish piece that came out remarkably wavy when it was formed on-site, I thought we’d made a sound choice as far as gutter guys go. Once all the gutters were installed, we paid the man and off he went. Two months later, they started pulling away from the house. After my husband went to do some investigating, he discovered that the guy we’d had so much confidence in used too short of screws to attach the gutters to the flashing; hence, they quickly began to detach themselves from what once held them ‘firmly’ in place.

Before the gutter guy, there was the painter. Dear Lord! This was another time I thought for sure I had selected someone who we’d unfailingly leave a 5-star review with once the job was said and done. “No way this guy’s going to let me down!” I assured myself. Famous last words. And once again, I did my research. I looked up his company online and even had an opportunity to see his work up close and personal on another day I happened to be walking my dog. It was impressive! There were several company trucks parked on the street with the logo emblazoned on the side(s) of each vehicle and an ample crew busily working utilizing different implements (brushes, rollers and sprayers). But when I contracted with this same company to paint our home, it was a different story. On day one, I KID YOU NOT, some yahoo (on the company payroll) literally rolls up on a bicycle and proceeds to ask if he could borrow some of my husband’s tools so he could start prepping the house. I thought it was joke. It wasn’t. It went downhill from there.

And, unless you want to witness what someone looks like when their blood pressure increases rapidly to a dangerous level, don’t get me started on the drywall guys! You know, I think I understand now why people don’t readily offer up their restrooms when contracting out work. In our particular case, we became all too familiar with the ‘give an inch, take a mile’ approach. The company we hired consisted of two guys, Huey and Louie. I’m not sure of Dewey’s whereabouts but he never made his presence known. Anyhow, Huey was the owner and Louie was his apprentice and most of the time, Huey was nowhere to be found. But Louie? He made an appearance daily for the two to two-and-a-half weeks it took to complete the job. That in itself isn’t terribly noteworthy. What sets this apart and makes it truly stand out was the way he chose to make himself at home in our home each and every morning, minutes after walking through the front door.

I should have known better, but on the first day when he asked if he could use our restroom, I readily agreed. He only lived about ten minutes away but I didn’t think much of it. When you’ve got to go, you’ve got to go, right?! Not in Louie’s case. I thought he was just going to zip in, empty his bladder, and hightail it back to work. But that’s what I get for thinking. No, once Louie had our permission to use the restroom the one and only time, he never asked again. And Louie had a routine. Each day, after arriving at our home, within a matter of minutes he’d make his way to the nearest restroom, shut the door behind him, and reemerge about 30 minutes later after taking a nice, satisfying dump in our toilet. I surmised this not only by the smell that emanated from the bathroom once he’d done his business, but also by the wide grin on his face. There’s no denying the look of satisfaction.

Listen, when considering what took place yesterday along with all of the other stress-inducing past contractor mishaps I’ve endured over the years, I’m seriously considering giving up on them entirely. Not only is it expensive to hire out work, it’s rarely done right. Most of the time, my husband and I do the work ourselves for a fraction of the price the ‘professionals’ charge but there are some things I’m no longer eager to do. Once upon a time, I’d be willing to assist my husband with reroofing a building or installing drywall (by holding it steady while he screwed it into position and then mudding and taping afterwards) or retiling a kitchen. But I have to admit, I’m not a young chick anymore and all the physical labor has taken its toll AND I don’t bounce back as quickly as I used to. So, as much as I don’t want to ever have to deal with another contractor, because I am convinced it will never end well, I can promise you this. If it ever happens, it’s going to be a L-O-N-G time from now, a VERY LONG TIME. A VERY extensively, astronomically, titanically LONG TIME. I think you get my point.

And on that note, I bid you farewell. Until we meet again!

Peace, love and blessings to you and yours…