Following Your Dream Even When the Going Gets Tough

American-made artisanal footwear

I followed my dream only find out I’m a serial failure and bad businessperson – and I keep going anyway

With the new year, my Facebook feed is overflowing with motivational messages about embracing the unfamiliar, following your dream and taking bolder steps toward living our dreams. I was once one of those searchers, dreaming of finding my true calling while slaving away at a desk job that felt like it was killing my soul. I longed for the opportunity to quit my career as an architect and start my own business crafting pretty things with my hands.

One day in 2005, a friend sent out an open call to share a booth with her at a craft fair. I decided that this was my opportunity – I should design something that would sell so well, I’d have no choice but to quit my career in order to keep up with demand. Then it came to me in a flash: shoes! Everybody likes shoes, right? I envisioned a pair of simple slip-on sandals made from wood, a naturally sustainable material. I knew nothing about shoemaking, but even cavemen made shoes for themselves… with my background in design, surely it’s something I could figure out?

I spent that summer working mad-scientist style in my basement, making prototype after prototype using tools from an ongoing home renovation. I often worked 18 hour days, a full shift at the office and then a full shift in the workshop. But I was having so much fun, teaching myself to use tools that used to intimidate me and making tons of mistakes but exciting discoveries. I ended up creating a sandal design, now patented, where the shoes are tied with interchangeable ribbons that provide a comfy fit and customizable styling.

The day of the fair arrived and after a final marathon of sandal making, I arrived late and bedraggled, but with nearly 100 pairs of my new sandals. Almost immediately, a line formed out of our tent. Sizes were selling out fast. I had a hit!

But the following Monday was one of the worst days of my life. One by one, emails trickled in from my customers. Their shoes broke.

I was devastated and humiliated. My error was that I tested the shoes for comfort, without realizing that just because shoes are great for a stroll around the block doesn’t mean they’re durable for miles. I wrote hysterical apologies to each customer, promising to make them better shoes. I did more research and consulted shoemaking and woodworking experts. And I experimented. And experimented. And experimented.

A year later, I finally made a pair of shoes that I wore 100 blister-free miles. All of my original, wonderfully patient customers were sent new shoes.

In the meantime, some buzz started building around my business. In 2006, Al Gore’s movie “An Inconvenient Truth” came out, and as the green movement grew, suddenly sustainable footwear became trendy. The rapidly growing publicity was a lucky break. I realized that maybe my business could be something much bigger!

So I dug in. I went to small-business classes, found mentors and assistants, and moved out of my basement into a bigger workshop. I continued improving my designs and shipped shoes to customers and shops all over the world. I had close calls with major media coverage that I usually deflected for fear of “catastrophic success”. I was still just a girl making shoes and I getting in over my head.

I tried to outsource the production some of the components, with a focus on keeping things as local as possible. But because the construction of my shoes is so unusual, there are no existing factories set up to produce anything like them. Every year, every penny I made went into trying to grow the business, yet I couldn’t actually make a profit due to the costly learning curve of figuring things out as I go.  The stress started outweighing the fun.

But I couldn’t quit! I was living my dream and nobody said it’s supposed to be easy. Demand continued to grow and everybody said that being unable to keep up is a “good problem” (except for customers, late deliveries are not a good problem for them). I was letting people down and copycats started popping up – time was running out for me to figure out how to grow.

A pair of sourcing agents, a Chinese woman and American man, had been urging me to produce in China, but I was concerned about labor conditions. Then I learned of a new copycat who not only mimicked my shoe designs, but also my website, photography style, verbiage – everything. Adding salt to the wound, they even started working with my retail partners, who had grown frustrated by my late deliveries. Fueled by anger at the copycats who had practically stolen my identity, I immediately contacted the sourcing agents, booked a flight to China and was in Shenzhen 10 days later.

Arriving by oneself in China is intimidating, but I was on a mission. After a few days of muddling around at a footwear tradeshow unsuccessfully seeking alternate leads, I met up with the sourcing agents. They introduced me to a factory that produces quality footwear for reputable international high-end brands.

I had tea with the factory owner and met the employees. The workers seemed to be happy and healthy, light and ventilation was great, and scrap materials were reused or recycled. I was excited that my shoes could be produced to the same standards as the thousand-dollar Italian shoes they produced.

Upon returning home, I found investors and made final prototypes for the factory to reproduce. After several back-and-forths, the factory sent a great set of final samples that I tested thoroughly.

I also researched other people’s experiences manufacturing in China and, despite the factory’s shining reputation and our convivial meetings, was concerned that things could still go terribly awry. I asked the sourcing agents to thoroughly examine each pair of shoes as they came off the assembly line. With their promise, I gave the go-ahead for production and paid for my first batch of mass-produced shoes. A few months later,  the finished shoes arrived.

It was incredibly exciting – in a single day, more shoes arrived than I could make in two years! I tied a pair on and walked outside. Suddenly,  I felt a snap and the shoe dramatically loosened on my foot. My heart sank. I limped back to my workshop, sat down, and willed myself to look at my feet.  The nails holding the shoes together had pulled out. I burst out crying. I’d put $100,000 of investors’ money into shoes that fall apart nearly immediately. I was devastated and humiliated.

“You’re a bad businessperson,” an investor informed me. Another layer of failure and heartbreak. I had spent years trying so hard to grow my business, working around the clock and sacrificing nearly everything for what?  The factory accepted no responsibility; my tiny shoe line was never important to them so they took substantial shortcuts that differed from the approved samples. My sourcing agents apologized for not monitoring  production as promised but admitted that I had zero recourse.

I didn’t know what else to do but carry on. Those shoes were promised to customers and shops. I hired several helpers to take the shoes apart and rebuild them from scratch. Over the next couple years, we remade every pair, and it was the experience of systematically assembling each pair that taught me not just to approach shoemaking in a much simpler way, but also to reclaim my love of making things.

Recently, I’ve developed new styles that we make completely from scratch in my workshop, utilizing my own little robot army. So now I’m expanding my own factory, on my own terms. But there is no guidebook.  I’m doing this because I have genuine curiosity about this adventure of running a business, and I love to experiment with the intersection of technology and craft.

Yet doing anything remotely innovative requires a high percentage of failures, and finding the right path for my business will always be a process of trial and error. I’ve come to learn that the biggest challenge isn’t about finding the stamina to overcome the daily roadblocks in my path to growth, but succeeding in my internal fight to overcome the fear and stigma of failure and the sting of other people’s judgment when things don’t go exactly to plan (and they rarely do). I’ve found that true success, for me, is reclaiming the simple joy of crafting pretty things with my hands and sharing those things that I made with love.

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