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Growing up Rural: Roofing with Dad

Posted on Saturday 14 June 2025Friday 20 February 2026 by Joshua

Papa knew I loved Boston Creme donuts and he always hooked me up.

Dad’s company started out as Earthworks Landscaping in the early days. As he did more work on basements, pouring concrete, building additions, garages, and remodels, it became Earthworks General Contracting. I always loved his logo… dark green, all lowercase letters, and how the “h” became a plant. His business card was printed on heavy cream stock with raised ink and it had a beautiful texture. He told me a lady in Albany designed the logo, which sounded impressive to me at the time. And honestly, she did a great job. When I look at it now, I still think, “That’s a cool logo!”

In the summer of 1986, when I was thirteen, I began working with Dad, “officially.” Of course we had been working since we were kids — doing chores and jobs around the house — that was expected as part of our family life. But this was work for money. The first house I recall working on was the Singer house on Coolidge Road in Amsterdam. It was a beautiful white one-story house with two big chimneys and an immaculate lawn, and it seemed like a mansion to me. We were installing cedar shingles on the roof — first tearing off the old, dried-out, brittle shingles and then installing the new golden brown cedar shakes that smelled so amazing. Stripping off the old created a huge mess. We had tarps over the bushes and over the grass, and most of the mess found its way there. It was our job (Justin Ashley, my brother Matt, and I) to do clean up. Dad, Papa, and Bob Ashley were up on the roof. I remember it was a hot week and a ton of work. Working with Dad and Bob was a trip. They were always joking and telling crazy stories. Bob would joke — “So I says to my wife with the wooden leg — Peg, how you doin’?” Papa was the organizer, always making sure nails were picked up, and tools and boards were not in the way to cause someone to stumble. The best part was that he always brought donuts and soda — for two teens and an 11 year old, that was bonus. — we definitely scarfed those down!

The house on Coolidge.
The window on the left is where the ladder went through. The bush below is where I landed. I guess I didn’t do any damage as it is still there 40 years later.

One day, we were working on the side of the house and the ladder had been set up at a shallow angle as there was a large bush in the way. I came down the ladder incorrectly, and the bottom kicked out and I went down into the bush and the other end of the ladder went through the window. Dad was pretty fired up and yelled at me for going down the ladder wrong, but Papa said it was his fault setting the ladder shallow. Dad said it would come out of my pay… but Papa, being Papa, whispered to me, “Don’t worry about it, I’ll take care of it.” Looking across those golden shingles at the end of the job was so satisfying. In time, they would turn a beautiful silver.

Life was never dull in the roofing business and believe it or not, upstate NY still gets plenty hot in the summer months. Dad was a very hard and fast worker because the quicker you could do a roof, the quicker you got paid. I remember some days when it was so hot on those roofs, looking down on the neighboring yards and seeing those beautiful swimming pools and wishing we could jump in.

Picture I found of Galway Lake. ©Galway Lake Rental, LLC

We got our wish at one house. It was up on Galway Lake. It was not a large house, just a simple summer camp. When we pulled up I thought, “This one will be easy.” Only a simple gable, no dormers, no valleys. I could not have been more wrong. First of all, the roof was a 12:12 pitch, meaning it was very steep and we had to use roof jacks. Roof hooks hold long pieces of wood like a shelf to stand on while you work on the roof. It is a flat metal piece with holes for nails (into the roof decking) and the end has a J-shape bracket used to hold a board – typically a 2×8. Secondly, Dad did not ever do lay-over roofing. We always stripped the shingles down to the decking, put new paper and then fresh shingles. He did not believe in shingling over existing because he said, “How can you know if there is any rot under there or what kind of shape the decking is in if we dont strip it.” At any rate, we got up on the roof and began using shovels and flat bars to remove the shingles. One layer, two layers, three layers, fours layers, five layers… all normal three tab shingles (architectural shingles had not been invented yet). Needless to say, I was amazed at how many layers there were. The sixth layer was the diamond shingles (which became popular in the 1920s). The SEVENTH LAYER, much to our chagrin, was roll roofing. You would think that would be easy to remove as it is wide swaths of asphalt, but it was so melded to the roof and was nailed every 2” across each seam that it took forever to get off; and… it broke into tiny pieces. (This is burned into my memory, can you tell?!) And remember, you are doing this all on these narrow boards at a steep angle. However, the one redeeming thing about this job was the fact that it was on the lake. So you know that as soon as we were done, we took off our shoes and shirts, ran down the dock and jumped in. Pure bliss on a summer day.

Roof hooks (stock image)

At some point, (and maybe Sara remembers why better than I do since she frequently brings it up), Dad started calling me “The Great Shing-a-lini” which got shortened to “Hey, Shingalini, I need some more bundles up here!” Honestly that was the worst part of the job — hauling shingles to the roof. Being a skinny kid with literally no padding on my body, and hoisting a 50lb bundle of shingles over my shoulder (literally half my weight) and climbing up a ladder while loose asphalt pieces ground into my sweaty skin… ugh! Meanwhile, Dad would demonstrate the proper shingle lifting technique and tell us how easy it was, because you know, he could pick up a fridge. In the meantime… the cry of “Shingalini! I need another bundle…” still haunts me, haha! Now I am wondering if Matt had a nickname, because I can’t remember. Also, I am a little amazed by the fact that nowadays, they literally have a crane lift that can place all the shingles for the whole job up on the roof at one time.

The George Street house. You can’t tell how steep this hill is until you drive it.

Another notable house was located on George Street. Amsterdam is built on a hill, and there are some significantly steep hills throughout the city, which certainly made life interesting as a Domino’s Pizza delivery driver in my college days. But it also made things challenging with Dad parking his dump truck. The George Street house was quite a challenge as it is a very steep curving road. The house was near an intersection and a curve and also had a sloping driveway. The roof was easy though — a typical Cape Cod with two dormers. We got the roof stripped off quickly and were cleaning up the mess; throwing it into the back of the dump truck. The front of the house was tar-papered but the back was down to the bare wood. It was cloudy and we heard thunder in the distance. I asked why we would even start a roof if there was a chance of rain, and Dad said, “Listen, if I didn’t work every time they said it might rain, I would be sitting around twiddling my thumbs on a nice day. You work until it starts raining because we have too much to do to be lollygagging around.” At the time (in all my teenage wisdom) I thought he was crazy. But as an adult, I subscribed to his philosophy and I still hold to this view of work and life! Well, the rain clouds gathered and it started sprinkling, but the paper was not on the back of the house yet. Dad was a machine trying to get it on, so in the meantime we grabbed this massive tarp that was big enough to cover the entire roof and hustled it up on to the roof. We got it draped over the whole house and Dad was underneath it, nailing down paper while the rains came. After he was done, he felt better about the whole thing and we went to Tulio’s for lunch. Another benefit of working with Dad. I had my usual open faced Turkey Manhattan with fries; gravy on the fries. So good.

The Bostitch compressor looked like this one.

One day, this amazing new invention came into our lives — the Bostitch roof nailer. They were very expensive in the early 80s, but eventually Dad and Papa decided it would be a good investment so they bought one. It was a double tank compressor with handles, a wheel and long air hoses. They bought a couple roof nailers and a framing nailer. And oh how that changed things! Dad was a fast nailer with a hammer, to be sure. We did not staple shingles ever — it was five roof nails to a shingle. (Dad had definite opinions about people who used staples to secure shingles.) But when he got that nail gun, as fast as I could hand him a shingle, he had it nailed. Bam bam bam bam bam! The pace could get pretty frenetic, but it definitely saved so much time on those jobs.

Another house I recall doing was a flat-roofed three story place in the city. I just remember Matt and I hauling buckets of tar up all those flights of stairs and then sealing the joints and mopping the whole roof with tar (which got everywhere) on a sweltering summer day. I was definitely glad to be done with that job, but it was cool looking over the city from that rooftop.

Dad was working on the place to the right of the Masonic Temple. The ladder jacks were up the front of it above the sidewalk and street.

At one point Dad was doing a job in Broadalbin, right on the main street. It was a two story brick building and he had ladder jacks up the front of it to reach the eaves. I remember standing two stories in the air, on this narrow plank with my back to the street, holding on to the edge of the roof and contemplating my life choices. I was just helping him out for an hour or so on that job as I was working at Perth Bible Church by the time and I was very glad to not have to do that roof.

There were so many house roofs that were done in the years I worked for Dad and Papa. I remember the various houses we worked on as I open Google maps and virtually “walk” down the streets of Amsterdam. Of course we did work in many other surrounding villages and towns, on all kinds of buildings. Dad built houses and garages, dug basements, poured concrete, mortared block walls, hewed beams, excavated trenches and driveways, and even dug ponds. He remodeled kitchens, built additions, put siding and cedar shakes on, built decks and stairs and porches, and put up lots of paneling (in the 80s!). He put in a huge septic and sand filter field system for the church (Sara helped with that one and got to drive the big machines), and later he remodeled the entire auditorium and built a porch on the church as well. There are many stories that could be told, I am sure.

I still have one or two of Dad’s old shirts!

Roofing was fast work. Hard work. Dirty work. I look back on those formative years and know that is a time when I learned to work hard, fast, and finish the job well. But it was satisfying to complete a job and step back at the edge of the yard, look at the new roof and say, “Wow, that turned out great!” Also, Papa knew I loved Boston Creme donuts and he always hooked me up.

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