The Continuum...

...and how my career path unfolded

In November of 2016 I was on a plane flying home from my sister’s wedding in Colorado when I did the math that told me I was done.

Not done immediately. Likely by February, March at the latest. The home mortgage payment and the shop overhead couldn’t both get paid from what I had, and I had been telling myself for months that something would change before it came to that. On that plane, I stopped telling myself that.

The business I had built over six years was a good one in the ways that I understood how to measure “good” at the time. I loved the work. The clients were wealthy and demanding, but satisfied. I had accumulated the kind of specialty tools and equipment that serious craftspeople spend careers building toward. I was doing historic restoration and architectural woodworking in the Hudson Valley, working on estates and churches and private homes in Millbrook and Manhattan, the kind of work that many carpenters envy.

What I didn’t have was any real understanding of what I was doing.

I had started the business in 2011 with insurance money that I received after my brother was killed in a workplace accident. I used it to buy equipment and set up a shop and begin the slow work of becoming self-employed. That money gave me a runway that I didn’t know how to use correctly, but I used it anyway, and by the time I was sitting on that plane doing the math in my head it was essentially gone. Converted into tools, rent, insurance and the thousand other small costs of keeping a shop running that I had never fully accounted for. When I eventually closed the business, the equipment I sold was enough to even the books. I didn’t lose everything in a dramatic sense. I lost everything in a slow quiet sense, which is harder to talk about but so much more common.

The thing I’ve come to understand about the years between 2011 and 2017 is that I was confusing proximity to excellent work with building a business. For much of that time I was essentially a quasi-employee of a large private estate in Millbrook. I was showing up, doing beautiful work, getting paid well and covering my costs. What I wasn’t doing was learning how to run anything. I was perfecting my craft and pleasing my client and not once looking at the horizon.

When the estate stopped spending money almost overnight in 2016, spooked like a lot of wealthy people by the uncertainty of that election year, I didn’t have the business infrastructure to absorb the loss. I had clients and some ongoing work and I figured I could sort it out. And then I did what I now recognize as the first move of a business that is bleeding out: I started selling tools.

Not all at once. If you have ever hit hard times you know that’s not how it works. You sell the things you know you can get full value for, the specialty items, the things only another “real craftsperson” would pay good money to have. You tell yourself you’re being strategic, liquidating assets, making smart decisions. What you’re actually doing is dismantling what you built, piece by piece, to buy time that you don’t know how to use.

Then you go back to work that feels safe. Handyman carpentry, small jobs, familiar tasks for people you already know. Not because it’s profitable. Because when you feel like you’ve lost control of everything, work you’ve done a thousand times feels like control. It isn’t. It’s just the illusion of forward motion.

And then, if you’re me in late 2016 and early 2017, you do the opposite — you take on work you’re not confident in, projects outside your expertise, because you’re desperate enough to think that a big score will fix what careful accounting would have told you couldn’t be fixed that way. The handyman work and the long-shot work aren’t opposites. They’re the same fear expressing itself in two different directions.

By the time I got on that plane, I had been doing all three of those things for the better part of a year. My wife, who was sitting next to me on the plane, didn’t know the full picture. She knew things were hard but I really did not have the right words to have a real conversation about it. When I told her I was going to close the business and go back to work for someone else, she was supportive. She understood that we needed the income. When I told her I needed to sell the tools, she pushed back. She didn’t want me to. I understood why, but I also knew that what she was trying to protect was the version of the future where this still worked out, and I had already let go of that somewhere over the Great Plains.

Going back to work

In February of 2017 I went to work for a company doing high-end residential work and I walked out of my shop for the final time that July. On paper this should have been the right move. The work this company performed was serious. I set up my own woodworking shop on site, built doors and millwork by hand, the kind of thing I’d spent years getting good at. I tell people sometimes that it should have been my perfect job. Maybe it was, in terms of the work itself.

The company managed its people by keeping them uninformed. Not maliciously, I think, just as a habit of control and the assumption that workers perform better when they don’t know too much about what’s happening around them. But I had just spent six years as my own boss, making every decision, knowing everything there was to know about my operation even when what I knew was bad news. I couldn’t work that way. I lasted maybe five months.

Both that move and the one that followed — going to work as a lead carpenter for Hudson Valley Preservation — were made out of financial desperation more than anything else. I think there’s a version of this story where I make the pivot sound deliberate, like I saw something clearly and acted on it. I didn’t. I was trying to keep the household intact and running on instinct.

I found that I enjoyed working at HVP alongside the owners of the company who still worked in the field every day. HVP did work that aligned with my estate work and about a year into my time at HVP the company hired Andy Engel.

Andy was a longtime editor at Fine Homebuilding and JLC, the kind of person who had spent decades in and around the trades and understood them at a level that went beyond technique or business. He was looking to get back in the field after working the trade show circuit and HVP brought him on as lead carpenter, and from early on he took an interest in what I thought about things. He wanted to talk shop and life. He wanted to know where I’d come from and what I’d seen and what I believed about the work.

We talked about my apprenticeship, about what it had meant to have teachers who actually grabbed hold of you and wanted to help you make something of yourself. About developing apprentices on my own crews in those years, the family tree of people I’d worked with and watched grow that I still keep up with today. About the idea of the trades as something you receive from the people ahead of you and pass forward to the people behind you. Andy called it a continuum and the word fit exactly what I’d been trying to say.

Andy was a people developer at heart. He was one of those people who wanted to see those around him be seen, even people he barely knew. He had momentum. He knew people, he generated goodwill, and he used both to help others find their footing. He told me I should be writing. Not someday. Now.

When Andy told me I had something worth saying, I published a few pieces tied to the projects that we were doing at HVP and the ideas about leadership and career paths learned during my apprenticeship. Then at the beginning of covid we sold our house in NY, moved back to Wisconsin and built our house on my family’s farm. I wrote about the build and the financial and emotional costs of being an owner builder but I was still writing from the perspective of a tradesperson.

Trading the hammer for the pen

I took a Project Developer role at TDS Custom Construction in Madison in the summer of 2020 a few months before a change in ownership that saw a 20 year employee, who moved from laborer to GM, purchase the business from the owner of 30+ years. It was a genuinely inspiring story arc for me to witness. Soon after the ownership change I found myself part of a five-person leadership team working to run the business. We were a decision-making collective, figuring out how to run something that had just changed hands during a pandemic while the broader construction market was doing things none of us had seen before.

Some of what I experienced in those two years felt familiar. Not identical to what I had lived through during my shop years, but recognizable. The patterns of a business under pressure have a recognizable choreography to them once you’ve seen them up close. I started calling things out, decisions or directions that matched patterns I associated with businesses in trouble. Sometimes I was right. Sometimes I was wrong. Sometimes I was overruled and the outcome proved me wrong or right in unexpected ways. It was not clean. It was a complicated mix of partial knowledge and imperfect communication and collective decision-making under stress, which is what it actually looks like to try to apply hard lessons inside a real organization.

What the pressure of those years drove us toward was better tools. The coaching work and lifelong learning. VPW, GP/Day and how to apply it. Financial forecasting and modeling. Crabtree’s Simple Numbers framework specifically landed the way it did because I recognized myself in the failure cases. The owner who couldn’t read a P&L. The business that confused revenue with health. The person staying busy and going broke without understanding why.

I had been that person and now being at TDS talking about gross profit and labor efficiency ratios and what the numbers were actually telling us, I understood what I had not understood during the shop years. I hadn’t been running a business. I had been running a craft practice with overhead I couldn’t see and no real mechanism for knowing whether any given week of work was moving me forward or backward.

That’s not a character flaw, though I spent a long time treating it like one. It’s a knowledge gap. The trades do an extraordinary job of teaching people how to build things and a remarkably poor job of teaching people how to build businesses. The skills transfer. The frameworks for profitability rarely come with them.

The continuum

The instructors that I had at the Southeast Wisconsin Carpentry Training Center were the first people in an educational setting who grabbed hold of me and wanted to help me make something of myself. I came from a small rural high school. I hadn’t gone to college. I was in my early twenties and I had no particular map for what came next. And then there were these instructors who saw something worth developing and decided to develop it.

That experience shaped everything that followed. Not in ways I could have articulated at the time. But when I found myself developing apprentices on my own union crews a few years later, I was doing a version of what had been done for me. When Andy Engel told me I should be writing, he was doing what that instructor had done. When I meet someone who came up through the tools and is trying to figure out how to think about the business side of what we do, I am trying to do the same thing.

Andy died suddenly in 2023. Heart attack, no warning. We had stayed close after I moved to Wisconsin. We’d done some writing together and I was honored when he asked me to help with some financial work for the business he’d started back in Connecticut, we’d kept up in the way that people do when they’ve found something real in each other. When he died I thought a lot about what he’d given me in that one year at HVP, and his ideas of the trades being a continuum.

The trades, at their best, work this way. Someone ahead of you sees what you can’t see about yourself and transfers something; knowledge, confidence, momentum, a framework, a name for something you already knew was true. You receive it and you use it and eventually if you’re paying attention, you pass it forward.

While my brother never got to see any of this, his death in 2010 sent me down a path. And the money that came along became the equipment that became the business that became the lessons that became everything I’ve written since. I don’t know what he would have made of the writing or the framework or the consulting practice I’m slowly building. I know that the money he left me bought me the education I needed even though it didn’t feel like education at the time. In that way I’m still trying to spend it well.

The person on that plane in November of 2016 couldn’t see what was still possible. He could only see what was ending. He was doing math that confirmed what he already knew and dreading the conversations that would follow and trying to figure out how to hold it all together through what came next.

If I could say something to him I wouldn’t give him the framework. He wasn’t ready for the framework yet. I’d just tell him that the thing he was most ashamed of — not the failure itself but the not knowing, the years of not understanding what he was actually running — that was going to become one of the most useful things about him. That the cost of not knowing was going to be exactly what made him credible to the people he would eventually try to help.

And that there were still people ahead of him on the road who would grab hold of him and help him make something of himself. And others still who would gain something from his experience.

He would have found that hard to believe. But it was true.