#3: Can you really teach yourself shoe cobbling?

4 days learning that shoe cobbling should be an all-immersive experience. Buckle up.

How did I get to “apprentice” with a shoe cobbler?

Welcome to the third installment of Modern Cobbler, a particularly exciting issue after spending a week as an “apprentice” at a shoe repair shop in Portland.

As a general disclaimer, I had the immense privilege of being able to dedicate a couple of hours a day at George’s Shoe Repair, working for free outside of my 9-5 marketing job. I understand the inherent privilege in “working for free”, and I am so grateful to have had this opportunity.

Last Friday, I stopped by George’s Shoe Repair, a family-owned and operated establishment in the Portland community since 1961. With a spark of courage, I told Joshua, the owner of the shop, that I was interested in learning about leather-working and shoe repair and asked if I could ever observe or learn from him as he worked. I noted that I had absolutely no prior experience. To my delight, he invited me to come in on a couple of days the following week. Before delving into my experience as a 4-day shoe cobbler “apprentice” (next week’s topic!), I explore the idea of being “self-taught” in the age of information.

Can (or should) you be self-taught in the digital age?

We live in a time where amidst hustle culture, being “self-taught” carries a frequency of (excessive) pride and accomplishment. Learning from Joshua this week was a humbling reminder that while I probably could teach myself how to repair shoes just fine on my own, it would take much more time and lose the art of it along the way.

As I’ve spent the past couple of weeks absorbing bits and pieces of shoe repair manuals and videos online, I had a prescribed perception of what it would take to learn the art of shoe cobbling. To give you insight into how my brain works, I keep a growing database (in Notion, for those curious) with shoe cobbling resources including everything from videos, to PDFs, to online courses, and even people. I was prepared to work chapter-by-chapter, take copious notes, practice bit-by-bit, accumulate materials and supplies as I went. A week in an actual shoe repair shop was a forced break in my bleak studying regime and a nudge that some lessons can’t be found in a Google Search (however extensive your search may be).

In an artisan trade that is so hands-on, I am unresolved on whether you can be completely self-taught. I do believe it is possible, though even more, I believe that it is an example of where there is unequivocal value in community and the passing down of knowledge, demonstrated beautifully in a commonly generational trade - starting with George’s Shoe Repair. Joshua, the current owner of the shop, is George’s son. George was self-taught in an era when “self-taught” nevertheless enlisted the help of others, the connection to local tradesmen. He passed down the practice to two of his sons like an heirloom and eventually, Joshua took over the shop, where he’s now teaching his daughter.

So yes, even with the scarcity of information on shoe cobbling available, I could absolutely teach myself how to repair shoes. But for the purpose of capturing the essence and roots of the trade, I’ll be enlisting experts in the field, like Joshua, to provide a holistic and largely untapped perspective on the art of shoe cobbling.

What did I learn in 4 days at a Shoe Repair shop?

I learned how to use machines, like the Master Finisher. I learned how to resole a pair of suede desert boots, which I observed Joshua do from start to finish. I learned what types of nails to use on a heel (clenching nails), how to replace the heel on a stiletto, what to use to clean suede (and when it’s not worth it), that friction is what makes shoe polish shine. What I learned most, however cheesy, was the value of learning from someone, including trade secrets & troubleshooting ideas that are not disclosed in “How to Repair a $1M Pair of Shoes” on YouTube.

With that, I’ll end with reiterating and re-evaluating the mission of this newsletter. The intended purpose of this newsletter is to directly share my experience in learning the shoe cobbling trade. Indirectly, my mission is to bring shoe cobbling into the digital age - to provide a firsthand account and create a space online to cultivate interest, intrigue, and passion in the trade - attempting to to bring with me its ancestry of wisdom and generations of knowledge.