Finally sat down and figured out what my time is actually worth, and wow

This hit close to home. I spent nine years at a two man shop doing mostly old farmhouses, and by year six I was doing the estimates, ordering the lumber, and running every job while the owner played golf on Fridays. My breaking point was when I found out the apprentice he hired to help me was making three bucks less than me, which sounds fine til you realize I was training someone at a rate I should have been making a decade earlier. One thing I did differently was talk to a couple of the finish carpenters I met on a church job, just casual conversations over lunch about what they were making. Nobody wants to share exact numbers at first, but once one guy opened up the rest did too. That gave me a real range for my county instead of some national average that meant nothing.

When I finally sat down with my boss I made the mistake of leading with how loyal I'd been. Big error. He heard 'loyal' and thougt 'cheap.' Second attempt I just laid out the jobs I'd run and what those skills go for elsewhere, same as you did, and that worked.

Only regret is waiting as long as I did. I calculated afterward that I'd basically worked two years for less than I was worth, and no retroactive goodwill makes that up.

My story went the other direction, so take this for what it is. I was the restoration guy at a three person crew outside Providence, doing window sash and clapboard repair on colonials, and I did the same math you did about four years ago. Brought my list in, made my case, and the owner told me business was too thin to match what I was worth. He offered forty cents an hour and a pat on the back. I stayed almost another year out of loyalty before it finally clicked that loyalty runs one direction in a lot of small shops. What changed everthing for me was getting on the books with the local union hall. I tested in, took a pay cut for about eight months, and then blew past what the small shop could ever have paid me. The benefits alone were worth more than my whole raise whould have been. Pension, health coverage, and a training fund that paid me to learn timber framing from guys who have been at it forty years.

I do miss the variety of small shop work, and some union job sites are more rigid than I'd like. But if your negotiation goes sideways like mine did, know that the union route is a real option for someone with your skills. The hall here was short on people who could do sash and millwork matching, and they practically rolled out the carpet.

Agreeing with the guy who said leading with loyalty backfires. I made the exact same mistake at a millwork shop years ago, opened my pitch with fifteen years of sticking around and watched my boss's eyes glaze over. What actually moved the needle was bringing a printout of a help wanted ad from another shop in the next town over, the pay range right there in black and white. He stopped arguing real quick. One page, one number, no speeches.