Trading Khakis for Dickies


Another clothing item I never thought I’d own.

Note: This piece is about a decision I made pre-pandemic. I’ve saved any Covid-centric content for a separate entry so this one could stand alone regarding career change. Whether you’re still working or you’re looking to make your next move, I hope this brings you value.

After a decade in an office I needed change. It had been a good run working at the local college, starting in a temporary position, then getting hired part-time, and ultimately full-time. In that span I managed to marry my girlfriend, buy a house, have a baby girl, adopt my step-son, and have a baby boy.

The employment benefits were incomparable. I could almost always take time off to play gigs, and the hours were normal enough that I could comfortably do “Live from Stadium Drive” episodes during the week. (Won’t embarrass us by dishing on how demanding our silly show can be.) I also got incredible paternity leave. And it only took 10 minutes from my driveway to my desk whether I drove or biked. Most of all, the insurance rates were unbeatable.

How could I walk away from all that?

I’d hardly walked “toward” it to begin with—I’d just wanted a paycheck to supplement what I earned from music. Being a full-time musician at the level I was at meant agreeing to every possible gig, which started to suck the art and excitement out of performing. (To this day I’d rather play a quality concert for free than treat a show like an uninspired shift of work.)

Of course I liked the idea of helping students achieve their goals, but the job was ultimately means to pursue music and, later, to support my family. My opinion of higher education would change, but even if it hadn’t, I felt urgency to expand my skill set—even if it meant switching to an “unskilled” field.

After years of handling college enrollment, graduation, customer service, records, and some marketing and event planning, I had learned as much I could and effectively hit my ceiling. Since I’d always worked on and studied arts and communication, I considered becoming better rounded and learning a trade—something more tactile, while I was still young enough to devote the necessary hours.

After high school I worked three summers doing landscaping and lawn care, and in recent years had done all the random projects home ownership required, but I’d never really worked a trade full-time. Could I even hack it? I’m the sole financial provider for my family of five, so any kind of career switch would be risky. Humbling, too—I’ve got a Bachelor’s degree (double major: English and Film) that I’d more or less be admitting was a mistake, not to mention I’d suddenly be working with younger people who knew a lot more than me. I’d need to jump in, catch up, and succeed. But which trade?

I started calling friends who worked in carpentry, electricity, plumbing, and metal work. Trying to narrow things down, every answer raised more questions: In- or outdoors? Union or non-? Commercial or residential? Traveling or stationary?

A family friend suggested painting. I hadn’t considered it, though I’d done it a decent amount, and my late grandfather was a painter, and I had a friend from the music scene who was a full-time (and then some) painter. I reached out to that friend and by chance, the custom builder he works for was looking to hire another full-time painter. I picked his brain for over an hour, and beyond the demanding schedule (6am-4:30pm, Monday-Friday) I really couldn’t find a red flag. After a few days I decided I’d submit my resume, if only for the potential chance to chat with someone from the company and glean some insight. Since I was still employed I had no pressure or fear of rejection; I was just hoping for advice.

When I dropped off my resume I happened to catch both owners at the shop, which apparently rarely happens. They offered to talk right then, and I had time, so we sat in a conference room together, chatting while they looked over my resume. We got along very well; my gut told me this could be a good fit. One owner had left an accounting position to start this business, so he could relate to the type of change I was seeking. After a good 15 minutes they stepped out for a second, giving me time to think of any other questions. When they returned we talked a bit more before they told me they’d like to hire me(!), but wanted me to think about it some more, especially since I’d be taking a modest pay cut. They gave me their business cards, we shook hands, and I left, taking a moment to sit in my car before starting it. What just happened?

This was freaky alright. Directly from there I had to head into the college and work as if that meeting hadn’t just happened.

My head swirled that day. I knew everything about the job I’d be leaving, but couldn’t really know what full-time painting would be like until I was immersed. I’d be swapping known for unknown, and getting paid less to do it, though if it worked out I’d eventually earn more than ever. I had my wife’s support, but still, the risk would be one of the biggest I’d ever taken. This opportunity had come much faster than I’d anticipated, if I’d anticipated any opportunity at all.

…I had to seize it. The next evening I called one of the owners to accept the job and confirm a start date. The next morning I solemnly submitted my two-week notice to the place I’d worked for almost ten years—just eight days since I even considered painting! I could hardly believe what I was doing. My co-workers were shocked, too, but they understood, and even threw together a couple farewell parties for me. Until then I’d felt a peculiar assurance. Leaving on such good terms, though, I couldn’t help doubting the decision I made.

But now, two months into my new job, I know I made the right move.

At least for now. (Check back after I’ve scraped [paint off] a few more millionaires’ floors.) A job is a job, but here’s what makes the grass greener:

  • Physicality  — I’d rather be physically tired or even sore compared to the exhaustion from working with people. I hated the idea of draining all my politeness having to be “on” all day, and coming home tight-lipped or crabby to my family when they’re excited to see me. I also burn many more calories during the day, and suddenly spared my body from 40 hours of sitting a week.
  • Simplicity  — The work is refreshingly straight-forward. Emotion is rarely a factor. And there aren’t any meetings, e-mails, or seminars.
  • Accountability — There’s not much room for interpretation. We’re all just expected to get our work done well and efficiently. There’s no hiding incompetence, no defensiveness, and no shifting blame.
  • The vibe — I’m a pretty sensitive guy—I blog, even!—but in an office I felt like a business-casual Andrew Dice Clay. Working a trade I still mostly keep to myself, but it feels so much better to not walk on eggshells. The communication is also refreshingly direct.
  • The learning — Can’t say I’ve mastered painting, prep work, caulking, and sanding yet, but already these are skills I’ll carry forever, that I didn’t have before. (I cringe at the walls I painted in my house as an amateur.) If I ever wanted or needed, I could do this work independently for cash. I’m also trying to glean what I can about the other trades I work around—carpentry, electrical work, plumbing, masonry, flooring, etc.
  • Changing locations — From sitting in the same cubicle every day, to working at different sites in different towns every couple of weeks if not days.
  • Tangible, aesthetic results — There’s little sense of accomplishment from clicking a spreadsheet or list closed once it’s finished. But seeing a skeletal frame evolve into a unique, finished home will never get old.
  • Much more sunlight/fresh air — I still work almost entirely inside, but I’m usually surrounded by windows, and there are plenty of trips in and out of the houses.
  • No screens — Typing this blog has constituted more time staring at a computer screen than I’ve spent in the last two months combined, whereas dual monitors used to assault my eyes eight hours a day.
  • No fluorescent lights — Everything I’d hoped it’d be.
  • No dress code — Ditto!
  • Team work/collaboration — Modern offices like to pride themselves on their collaborative environment, but even with cubicle walls removed, workers are still essentially atomized. In trades, workers are like members of some savage symphony.
  • Leaner schedule/life — After a long day of work, then dinner and family time, it’s pretty much time for me to hit the hay, so without noticing I’ll go days without spending money or having a drink. It’s also got me valuing my free time more than ever, and I somehow do more because I’ve got less time.
  • Job security — The inherent insecurity in any trade is whether a given company can find work to do, so that goes without saying. But as long as I show up and do what I’m supposed to do, I’m set. The beauty of trades work is it will always be needed, it cannot be outsourced overseas, and it cannot be automated.
  • Improvisation — As opposed to micromanagement.

In the interest of fairness, here are the things I don’t like:

  • Early/long hours — I’ve been a night owl forever, so this isn’t natural for me. I’m also worried what this earlier schedule will mean for my social life and creative endeavors, which usually burn midnight oil.
  • Beating up my hands — Lots of scrapes, nicks, and broken nails. Working with caulk, putty, paints, and stains means scrubbing all that stuff off my hands and fingernails every night. Going to be a battle not to wreck my mitts (though my hands are stronger than before).
  • Port-a-potties — Self-explanatory.

In all ways this is rougher work than I’d been used to. I’ve been preferring it, but it’s going to take extra effort to keep it that way. This means a routine of stretching and light exercise every morning and night, but also keeping my mind and heart in good condition, detoxing daily with poetry or philosophy, and sweet, sweet family time.

I needed a lot of encouragement to make this switch, so I wanted to write this and pass some onto others. If you’re not liking your line of work (or lack thereof) I hope this offers some insight. If you’ve got some coordination, brain cells, discipline, and humility, you just might be happier taking on a trade.

Holler if I can help. Or just watch “Office Space”.




Seen here with a Sherwin-Williams HANDy Paint Pail®, somehow happy at 7am.