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Transition, Work And Motherhood – In Search Of The “Ninth Path,” And Things That Make My Heart Pound

Sydney Chaney Thomas

Ed: Sydney Chaney Thomas is a Moraga-based writer and businesswoman with three books to her name, all currently available on Amazon. She is also co-founder of a sustainable sailing apparel company called Ocean SF, and operates a nonprofit that works to reduce plastic waste called the The Trident Project.

Sydney teaches entrepreneurial marketing at UC Berkeley in their International Diploma Program and, in addition to this column, she writes a popular lifestyle blog, which can be found at sydneychaneythomas.com.

Transition, Work & Motherhood
March 23, 2018

When I was young I wanted to be a fashion designer, and of course, I wanted to be a writer too. So, I spent most of high school, in the small town I grew up in, either reading Vogue, or buried in books. And I’ve always loved clothes. Beautifully made clothes.

So now, I am a writer and a clothing designer. I don’t do fashion, I do performance wear for sailing. While I was in LA last week, I stopped in at our factory on Maple Avenue in the Fashion District. This may sound glamorous, but it is anything but. The factory sits under the freeway and every window of every building on Maple Avenue has bars on it. The streets are littered with dumpsters. I’m thinking twice about even getting out of my car when I get a phone call, instructing me to park, and come in the alley entrance. I find the alley, and walk in.

Inside, the factory is completely different than you might expect from the outside. The large rooms are painted a crisp white, there are soft benches and sofas to sit on, a station to make tea or coffee, and everyone who works there is warm and welcoming. People are sewing, and there are bolts of fabric, zippers, and racks of clothing everywhere.

I’ve come to the clothing design world late, but I can tell you this: anyone can design clothing, it’s the making the clothing and what comes after that is difficult. There is much more to it then I could have ever imagined. I use every business skill I’ve acquired, and still, it is anything but easy, and yet there is nothing I would rather do.

When I return home, I meet up with a former colleague of mine at the Berkeley Yacht Club, affectionately referred to as BYC. I often meet friends there as it is central to Contra Costa County where I live, and San Francisco where many other people live.

On this day, and many others, I’m asked how I got into sailing, or more importantly, how I came to make sailing clothing. In both instances, it was literally out of necessity.

I am passionate about the outdoors. I don’t just need it, I crave it, and can’t live without it. I get a feeling of happiness and freedom when I am sailing that I get nowhere else. I love the heart-stopping moment the engine is turned off, and the boat turns into the wind, and it is loud but silent at the same time.

So, that is why I sail.

I make clothes because it’s bone chillingly cold on San Francisco Bay. I am very sensitive to both heat and cold and I am someone who likes to be comfortable. When I began sailing, I was hit by a wave that went down the back of my ski jacket and through three layers of clothing. I then had to spend the next four hours in the wind, soaked to the skin. When I got to shore, my teeth were chattering, and I was shaking so badly I couldn’t drive.

After that, I bought my Gill Foulies, but would get my midlayer wet and be shivering for hours. When Andrew Lacenere told me he was making sailing clothes, I went to the boat he was living on, appropriately named, “Dreamer,” where he had a sewing machine and bolts of 100 percent Merino from New Zealand. Now, mind you, I have made better clothes for my Barbies, but the fabric felt like cashmere, and after launching software companies, I thought how hard could it be to make clothes? Well, as it turns out, it’s plenty hard.

After agreeing to help Andrew, he sent me a link to the famous letter written in 1958 by writer Hunter S. Thompson (see excerpt below). I still love being a teacher at Cal, a writer, and a painter. I remember fondly my marketing days in the financial district, but none of this compares to making clothes.

In the summer of 2016, I met with a pattern maker in LA and explained my vision, and handed her a drawing and a bolt of orange fabric. This is where my most charming personal characteristic comes in handy, my naivety. Had I known then what I was getting into, I might not have done it. A few weeks later, a box arrived on my doorstep, ironically, I was in the middle of a sailboat race that day, so my beautiful daughter Paris put on the first prototype for our mid-layer jacket and sent me a photo. With frozen fingers, I opened her text and saw it on my phone, and it was at that moment that knew I had found my ninth path.

The Ninth Path
by Hunter S. Thompson

“To put our faith in tangible goals would seem to be, at best, unwise. So we do not strive to be firemen, we do not strive to be bankers, nor policemen, nor doctors. WE STRIVE TO BE OURSELVES.

“We must make the goal conform to the individual, rather than make the individual conform to the goal. In every man, heredity and environment have combined to produce a creature of certain abilities and desires—including a deeply ingrained need to function in such a way that his life will be MEANINGFUL.

“Let’s assume that you think you have a choice of eight paths to follow (all predefined paths, of course). And let’s assume that you can’t see any real purpose in any of the eight. THEN—and here is the essence of all I’ve said—you MUST FIND A NINTH PATH.”


Did you like today’s column? Have something you wish to ask Sydney or perhaps suggest as a future topic? Drop it into the comment stream, below!


  1. Honestly, I spend most of my time writing or working on my sailboat and clothing line. It’s very fun and enjoyable for me, and I’m very thankful.

  2. I saved this for when I had time over the weekend! Good read but I’ll ask the tough question: as a woman in business, have you ever met any resistance or bias from male counterparts?

  3. Yes, constantly. Even women. It’s hard to follow your dreams. It’s important to surround yourself with positive people who believe in your vision.

  4. I enjoy the column. Always interested in how peers meet and hopefully overcome challenges in their business lives — and you seem like the type to do that. I also know things don’t always go well and I’m interested in how you overcome those times when nothing seems to be going right!

  5. I’m happy you enjoy the Column. It’s rewarding to share my experiences.

    As for being an entrepreneur, I’ve had to be very determined. My business partner and I have faced many challenges, but we decided early on not to give up no matter what. Having a loyal, encouraging and calm business partner is key. He always has my back and we are very like minded. We also sail together and have fun together which is also key. I’ve worked for several start ups and expected obstacles, and that has also helped.

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